Negotiating your salary in 2025 in tech isn't just about knowing your worth. It's about understanding the hidden strategies that recruiters and hiring managers use. I saw these from both sides of the table landing up to Sr. Director, VP, and CPO offers from big tech down to Series B startups.

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Find the written summary of our discussion below.

Quick aside: My upcoming live workshops

We’re running (free) live negotiation workshops to help you apply these strategies in real time. Pick the session that best fits your situation or attend all of them.

📌 Handling Salary Expectations Questions (Tue, Mar 18 @ 6:00pm PST)

📌 Negotiating Big Tech Offers (Wed, Mar 26 @ 11:00am PST)

📌 Negotiating Startup Offers (Mon, Mar 31 @ 9:00am PST)

📌 Mock Negotiation Practice with Annie (Tue, Apr 8 @ 5:30pm PST)

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The Current Market

The market is just one component of negotiation, but it's an important one. Amazon L6 offers, for example, have seen periods of compression and expansion, but exceptions above band are now rare.

That said, top-of-band offers still exist, and positioning yourself as a "market of one" (someone uniquely suited for a role) can significantly increase leverage. This could be due to your network, sector experience, specific skills, or all the above.

Types of Leverage and the Role of Information

There are two primary types of leverage: external leverage, which comes from tangible factors like competing offers or a strong current job, and internally created leverage, which is based on how you present yourself and frame your value.

Many candidates assume that leverage only exists if they have multiple job offers. While external leverage is powerful (having a competing offer from a high-paying company can immediately shift negotiations in your favor), it's not the only way to negotiate effectively.

Internally created leverage is just as important and is within your control. This includes how you frame your expertise, your unique fit for the role, and the way you align with the company’s pain points. If you can position yourself as the ideal candidate who will solve their specific challenges, the company may be more willing to stretch their budget to secure you.

Recruiters and hiring managers typically have more data about compensation ranges, internal budget flexibility, and competing candidates than you do. But strong candidates close this gap by doing market research, networking with others who have negotiated at the company, and strategically withholding information until the right moment.

Step-by-Step Negotiation Process

1. Before You Hit Apply

   • Start preparing early. Practice interviews and refine your narrative.

   • Line up company options strategically: high-paying, high-leverage companies, core companies, and ideal companies.

   • Time your offers to maximize leverage.

   • Keep in mind that opportunities can sometimes serve as better leverage than actual offers—except at places like Google, where written offers matter most.

2. Handling Salary Expectations Questions

   • Recruiters often ask about salary expectations early.

   • Avoid anchoring too soon. Use price discovery later in the process.

   • A strong response: "Compensation has many factors; I’d love to understand more about the role first. What’s the range for this position?"

   • Stay neutral when receiving information.

3. Handling Recruiter Pressure

   • If a recruiter pushes for a number, repeat your stance.

   • Use follow-up objections like "I just started my search."

   • If necessary, fall back on: "Everything looks good, and I’m sure we’ll find something that works for everyone."

   • If you mistakenly disclose a number, use the Recovery Method: Any new information (internal or external) can justify reopening negotiations.

Building Leverage with the MERIT Framework

• Market: Understand the company’s financial position and hiring outlook.

• Expertise: Position yourself as a "market of one." Showcase how your skills solve the company's pain points.

• Results: Quantify past achievements.

• Inventory of Options: Know your alternatives, but don't reveal them too soon.

• Tactics: Focus on rapport-building and strategic communication.

The Offer Call: Best Practices

• Express excitement about the role but stay neutral about the offer details.

• Never make a decision live on the call.

• Buy time to evaluate by saying you need to discuss it with family or mentors.

• Acknowledge their timelines, but prioritize your decision-making process.

Using a 30-60-90 Day Plan to Strengthen Negotiation

After receiving an offer, scheduling calls with the hiring manager and even the skip-level leader can be strategic. A 30-60-90 day plan shows:

• Your vision for the role

• Strategy and impact

• Key metrics and assumptions

It also serves as a reverse interview, allowing you to validate if the role is the right fit. Often, hiring managers clarify expectations or adjust job scopes during this process.

4 Ingredients That Can Make or Break a Negotiation

1. Likable: People fight for candidates they like. Be appreciative and professional.

2. Deserving: Justification for higher pay comes from a strong interview performance.

3. Justified: Companies need to internally justify a higher offer, so frame your request with clear impact and scope.

4. Winnable: They must believe you’ll accept. If they suspect you’re shopping around, they may not advocate for you.

Negotiating Even When They Say It’s the Best Offer

• Even if they say it's the "top offer," you can still ask for more.

• More than 50% of the time, candidates get a higher offer after pushing back.

• The risk of an offer being pulled is low, especially at the top of the band.

• Sometimes, they will find a way to increase the offer significantly.

Going Beyond Your Hiring Manager

Sometimes, hiring managers and recruiters don’t have full decision-making power. Getting support from a skip-level leader can make a big difference, especially if:

• The hiring manager lacks political capital.

• They’re at too low a level to push for a higher offer.

• The company is hesitant to stretch the budget.

Considering Layoff Risks When Negotiating

Some candidates hesitate to negotiate for fear of being laid off later. While this is a valid concern, layoffs usually target:

• Poor performers.

• Those with massive equity appreciation (due to company stock growth).

Given that layoffs now focus more on performance rather than cost-cutting alone, negotiating for what you deserve remains a good strategy, especially if you believe in the company.

The Importance of Negotiating

Many candidates fear negotiation, worrying about burning bridges. In reality, a well-handled negotiation earns respect. There is significant variance in pay not based on merit but on negotiation skill. Some key takeaways:

• Most top tech employees negotiate: it’s expected.

• Long-term financial impact: increases of 15-40% are common, which can translate to millions over a career.

• Advocacy matters: if you can’t advocate for yourself, how can you advocate for a team or product?

• Women especially should negotiate to keep pace with male counterparts.

Wrap-up

Negotiation is a skill, not a one-time event. It’s about positioning, strategy, and confidence. The more you practice, the better you get. Whether you're negotiating salary, title, or team resources, advocating for yourself is key to long-term success. It’s worth trying even if you’re scared.

Quick reminder: If you have any questions about negotiating or want feedback on your approach, sign up for one of our free live workshops below:

• Handling Salary Expectations Questions (Tue, Mar 18 @ 6:00pm PST)

• Negotiating Big Tech Offers (Wed, Mar 26 @ 11:00am PST)

• Negotiating Startup Offers (Sat, Mar 22 @ 9:00am PST)

• Mock Negotiation Practice with Annie (Tue, Apr 8 @ 5:30pm PST)

See you there!

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"When a company does run a great recruiting process, it's such a rare bird. Candidates will choose a company based on that."
—Andrew Abramson, Co-founder of Fusion (ex-Riviera/Korn Ferry)

Welcome to Top Tech’s “How to Hire” Series

This is the first in a series on hiring great tech executives and leaders. In coming weeks, I'll be featuring insights from some of the most respected executive recruiters, VC talent partners, and top executives in the industry who specialize in product, engineering, and other technical leadership roles.

• TODAY: Andrew Abramson (Co-founder at Fusion Talent, ex-Partner at Riviera)

Coming up…

• Chris Johnson (CEO & Managing Partner at Artisanal Talent)

• Jodi Jefferson (Founder, Managing Partner at People Project)

• Hillary Mager (CEO at Sterling Strand, ex-Flatiron Health/Citadel/Bridgewater)

• Lauren Ipsen (VC Talent Partner at Decibel Partners, ex-Daversa Partners)

(My VC, exec, and exec recruiter friends! Message me if you have a unique take to share)

This series is for founders, hiring executives, recruiters, and even job-seeking leaders to gain insights into how to hire great talent and how recruiters and hiring leaders think.

How To Hire Great Product Leaders With Andrew Abramson

Finding the right product leader can make or break your company's trajectory, but the search process is filled with complexities that even experienced founders struggle to navigate effectively.

For this inaugural article, I spoke with Andrew Abramson, co-founder of Fusion Talent and widely regarded as one of the best executive recruiters in the product leadership space.

Andrew has built an impressive track record working with companies across all stages - from Series A startups to industry giants like:

Airbnb, Chime, Atlassian, Character.ai, HubSpot, Webflow, Checkr, Lyft, PagerDuty, and more.

Andrew co-founded Fusion with Alex Zakupowsky (a top recruiter for CTs and other engineering leadership searches) with a vision of building a partner-led firm delivering exceptional outcomes through highly-specialized focus areas.

Andrew conducts Product Leadership searches (CPO, VP, and Head of) and has placed over 100 product leaders throughout his career.

Prior to Fusion, Andrew spent five years as a Partner at Riviera Partners, focusing exclusively on Product Leadership roles, and has over a decade of experience in Executive Search at Safire Partner and Korn Ferry.

He also used to be a sports agency Director of Analytics, helping rep NBA, NFL, NHL, MLB, and Olympic athletes!

In our wide-ranging conversation, he shared invaluable insights on how to identify, attract, evaluate, and successfully close top product talent.

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What You'll Learn in This Executive Hiring Guide

This deep dive into product leadership hiring covers everything founders, executives, and board members need to know about finding the right product leader. Here's what we'll explore:

1. Andrew's Journey in Executive Recruiting - How Andrew built his expertise in product leadership recruitment

2. When Do Companies Need a Product Leader? - Five clear signals it's time to make this critical hire

3. Determining the Right Level of Seniority - How to match leadership level to your specific needs

4. Can Product Leaders Help Find Product-Market Fit? - When this works (rarely) and when it doesn't

5. The "Up and Comer" Pattern - Why first product hires often come from unexpected backgrounds

6. Evaluating "Up and Comers" - How to distinguish true contributors from passengers on rocket ships

7. The Art of Back-Channeling - Getting honest feedback without burning bridges

8. Why Use an Executive Search Firm? - The ROI calculation for professional help

9. Running an Effective Search Process - Step-by-step guidance for a rigorous yet efficient process

10. The Importance of Cultural Fit - Why this matters more for product leaders than almost any other role

11. The Art of Closing Top Candidates - Starting from your very first interaction

12. Managing Internal Team Dynamics - Navigating existing teams and passed-over internal candidates

13. Measuring Success - How to tell if your product leader hire is working out

14. Why Product Leader Hires Fail - The misalignment trap and how to avoid it

15. Real-World Examples - Stories from Andrew's work with top companies

Whether you're hiring your first product leader or looking to upgrade your existing leadership, this guide provides actionable frameworks and insider knowledge from one of the industry's most respected executive recruiters.

Andrew's Journey in Executive Recruiting

Andrew began his executive search career at a large publicly traded firm called Korn Ferry, where he worked on searches across diverse industries including commercial real estate, oil and gas, and consumer packaged goods. While he appreciated the foundational skills he developed there, he found himself gravitating toward the tech sector.

"I knew that I wanted to be in search at that point. I liked the job and what it entailed, but I wanted to work with clients that I could resonate with a bit more, that I was a bit more excited to work with."

This led him to Riviera Partners, where he joined the product practice in 2018 and spent about five years focusing on Chief Product Officer searches. Then, just over a year ago, he launched his own firm, Fusion, alongside his partner Alex Zack Kupalski, who specializes in engineering leadership recruitment.

Their vision for Fusion reflects a quality-first approach: "Our kind of view is that we're trying to stay small and focus on quality - the quality of the clients that we work with, the quality of the searches that we do, of the candidates that we interact with, and make sure that founders have the absolute best experience when they work with us."

When Do Companies Need a Product Leader?

One of the most common questions founders ask is when they should bring in dedicated product leadership. Andrew has identified several clear signals that it's time to make this critical hire:

1. Short-Term Roadmap Orientation

"The roadmap might be very short term or quarter-to-quarter oriented. And the primary features being shipped up to this point are all from customer requests, as opposed to building towards kind of this longer term vision or goal."

When companies can't prioritize between immediate customer requests and strategic long-term initiatives, it often indicates they need experienced product leadership to establish a more balanced approach.

2. Communication Breakdowns

"Communication is starting to break down and you see this more towards Series C, Series D when a number of other execs and different functions have been hired. Product, the communication is starting to break down kind of cross-functionally like engineering and/or go-to-market. They're not sure why certain things are being prioritized over others."

This issue becomes particularly acute as the company scales and hires more executives. When teams don't understand the reasoning behind product decisions, it creates friction and inefficiency.

3. Over-Involved Founders

When founders find themselves "needing to be way too involved in the details of the day-to-day of the product decisions," it's a clear sign they need to bring in leadership that can take ownership of the product organization.

4. Lagging Recruitment

"Recruiting or hiring might be lagging behind other functions. The current most senior product person, if they have a head of product, has been having trouble hiring or attracting senior talent. Their bar for talent isn't as high as it needs to be."

Product teams need talent magnets who can attract and retain top performers. If your product organization isn't growing at the same pace as other departments, it might be time for new leadership.

5. Founders Without Product Management Experience

"If it's the founders still running product, they might be getting to a point where they have, call it like, three to five PMs in the org and they're probably not a product person themselves. They're probably doing this for the first time. And so they'll admit, 'I'm not the best person to be managing product people. I'm not the right person to be firing product people. I don't know how to manage and how to grow PMs, how to put the right incentive structures in place.'"

Many founders reach a point where they recognize their limitations in developing and managing a product team, which signals the need for experienced product leadership.

Determining the Right Level of Seniority

Once you've identified the need for a product leader, the next question is what level of seniority is appropriate. Andrew emphasizes that this decision should be driven by the specific pain points you're trying to address:

"It really kind of comes back to what are the real pain points that exist. What are you kind of trying to solve for here? If the PM team and the role wants to own is going to own design too, and it's already at like six or seven people, you're going to need a head of product who's managed teams of probably like 12 to 15, I would think."

The key principle Andrew emphasizes is to "hire someone that the company can kind of grow into as opposed to having them kind of grow into and learn on the job too much." This approach reduces the risk inherent in the hire.

Different challenges call for different profiles:

• If communication is breaking down, you need someone who "has been through hyperscale and has worked in more complex environments and worked with other senior leaders cross-functionally."

• If you need more creativity and innovation, "you need someone who really spikes more on zero to one might be a former founder themselves."

Can Product Leaders Help Find Product-Market Fit?

Many founders hope to bring in a product leader who can help them find product-market fit, but Andrew has observed this rarely works well, especially for consumer products:

"If it's a consumer product, no, like you should not be hiring an external head of product to find product market fit for your consumer product. If you need that, it's already too late, most likely."

However, he notes two important exceptions:

1. B2B Products Transitioning from Open Source to Monetization

"If it's a B2B product and maybe like an open sourcey type product where the go-to-market motion so far has been about user adoption, not about monetization... That doesn't necessarily mean that you have product market fit because no one's paying for your product yet. And so having someone who understands how you can transition from open source to a strong kind of go-to-market monetization muscle... Having a product person who understands how to do that can come in and make an impact in an earlier stage."

In these cases, the technical foundation exists, but the product leader adds value through monetization strategy, pricing, and packaging expertise.

2. AI Startups with Research-Focused Founders

"So many founders of AI startups now are coming from research backgrounds, especially if it's foundational models company, and they might not understand how to even like ship commercially viable products before they just understand the models themselves and the AI around the models... When it comes to actually putting the processes in place, experimenting, testing and learning, scaling, things like that, I'm seeing product people add a lot of value to founders who aren't even like software engineers, they're researchers."

For AI startups with technically brilliant but commercially inexperienced founders, the right product leader can bridge the gap between technological capability and market viability.

The "Up and Comer" Pattern for First Product Hires

Interestingly, Andrew has observed a consistent pattern in successful first product leader hires - they're typically not individuals who have already held the top product role multiple times:

"The odds are it's going to be someone who has not been a head of product before. It's someone who has seen a lot of success going through hyperscale at another company where they learned a lot of amazing lessons. They saw things that work that didn't work. They've seen a level of scale beyond where that company is today, but they haven't been in the number one seat before, and now they're ready to do that for the first time."

This "up-and-comer" profile is not just common but often more viable than recruiting someone who has already been a head of product. Andrew explains why:

"Probably more than 50 percent of the people who've been a head of product before, or just coming off of a head of product stint, they don't want to do that again right away. It's a very draining job to be a head of product, to be working so closely with a founder all day, every day or founders all day, every day can be very demanding. It can be a very soul-sucking job."

Many experienced product leaders follow a pattern: "They took a swing on something early stages, they did it for a year to two and a half or three years. And they're like, 'That was fun. I need to go do something later stage. I have a family now, I need liquid comp, and then I'm going to kind of take another swing in four or five years.'"

Evaluating "Up and Comers" vs. Passengers on Rocket Ships

With "up and comers" being the most viable candidates, how do you distinguish between someone who truly contributed to a company's success versus someone who was "just along for the ride" on a rocket ship? Andrew acknowledges this is challenging but offers practical advice:

"The best way to find out is through back channels, understanding is what they're saying and what they're telling me about their impact lining up with what other people at the org feel that their impact actually was."

He emphasizes that you're not necessarily looking for someone who "set the vision" for a major company like Airbnb. Instead, you want to understand:

• Incremental metrics they improved

• Net new ideas they contributed

• How they navigated the organization to bring ideas to fruition

• Their ability to convince others that something was the right thing to build

The ultimate question: Were they providing the fuel, or were they just along for the ride?

The Art of Back-Channeling

Back-channel references are essential for effective evaluation, but they require finesse and relationships built on trust:

"Back-channeling is definitely an art, not a science. And it can go very wrong if you go about it the wrong way. I think that the biggest thing with back-channeling is it just kind of comes through relationships and building up a network of people who will trust you, who will know that you will keep this hyper confidential."

Andrew offered several key principles for effective back-channeling:

1. Build trust over time: "There's really no substitute for that other than just time in the market and doing this job and doing it for a number of years."

2. Don't overuse references: "You don't want to overuse one person too frequently for back-channel requests."

3. Never cold back-channel: "Never ever cold message to someone to try and get a back channel on a candidate. That's the surest way of having it blow up in your face. That could put their job in jeopardy."

4. Avoid current colleagues: "Back-channel someone with a current employee of the company that the candidate is employed at - that's another kind of no-no."

5. Time it right: The timing varies by situation - sometimes it's before introducing candidates to clients, sometimes it's further along in the process.

Andrew's bottom line: "I don't think you should ever make a hire without getting a back-channel read from someone somewhere."

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Why Use an Executive Search Firm?

For founders weighing whether to conduct searches themselves or engage professionals, Andrew points to several key benefits of working with experienced search firms:

Access to Passive Candidates

"The best candidates are not the ones who are actively seeking jobs. The best candidates are ones who are happily employed or being paid really well, have great scope, have great impact, and it's about like, how do you get to those people? And again, that's just through the network and through relationships."

Efficiency and Quality

"It's about efficiency in your search and not spending time with unqualified candidates or candidates that aren't A+, which is a huge drain of time for a founder or CEO. And it's about getting access to people that might otherwise be out of reach."

Domain Expertise

Internal recruiters working across all functions can't possibly match the depth of knowledge that specialists have: "There's just going to be this knowledge that the recruiter should have on the candidates, on the candidate ecosystem, that even an internal recruiter at a company, if they're working in doing searches, recruiting across all the different functions, there's just no way that they could have."

While search firms represent a significant investment, Andrew notes that once founders have a positive experience with a retained search, "they tend to get religion around that and then money doesn't really become the barrier."

When comparing different search firms, Andrew likens it to any service:

"Just like any service, the more that you pay, the better the outcome that you'll probably get. Just like with consulting, with a design agency, with a branding agency, et cetera, the best firms just charge more because they're better at the job."

Running an Effective Search Process

Andrew emphasized that how you run your search process significantly impacts who you'll attract:

"When a company does run a great recruiting process, it's such a rare bird in the wild that candidates will choose a company based on that, rather than a company that might be better, that might pay a little bit more, that might look sexier, but it was just such a jumbled process and a bad candidate experience."

Here's his step-by-step approach for running an effective product leader search:

1. Define Your Interview Panel Upfront

"At the front end of a search, you need to determine who you want to have on your interview panel, whose buy-in on the leadership team that you want to make sure that you have, and who is going to be kind of like the veto votes of 'if this person is a no, I just can't really see a path to hiring them.'"

2. Align on Evaluation Criteria

"You need to sit down with them in a group setting and say, 'Okay, here's the context. Here's what we're looking for. Would love to get all of your input,' and have a very open dialogue with the team on what they think is going to be needed in this person and what the founder wants each person to be evaluating for in the interview process."

3. Assign Specific Focus Areas to Each Interviewer

"Each person should be tasked with evaluating for a specific attribute or attributes. You don't want multiple interviewers asking the same questions to candidates. That's a bad candidate experience."

4. Involve Investors Early

"If you're doing an exec search, you should probably always loop in your investors because your investors not only will provide their thoughts, but they also will have a network or they'll have talent partners who work with them at their shop who will probably make some intros for you, who can help with back channels."

5. Create a Detailed Scorecard

A comprehensive scorecard should cover two key areas:

General product leadership criteria:

• Strategic thinking

• Process orientation

• First-principles thinking

• People management capabilities

• Communication style

Company-specific requirements:

• Commercialization expertise

• Technical depth for engineering collaboration

• Domain knowledge (e.g., marketplace dynamics)

• Experience with similar end users

• Stage-appropriate scaling knowledge

By defining these criteria upfront, you create alignment and reduce the likelihood of making decisions based solely on charisma or gut feeling.

The Importance of Cultural Fit

For product leaders especially, cultural fit is absolutely critical:

"For product, you're such a kind of a cultural bellwether at a company. It's such a cross-functional role in nature. You're interacting with so many different departments that the cultural fit has to be there. You cannot make a hire that's not going to be a good cultural fit for your company. The cultural fit of the hire is just P0 in my opinion for product."

To assess cultural fit, Andrew recommends looking beyond the companies on a candidate's resume:

1. Consider timing at previous companies: "If they grew up in Uber in the early days, they probably are going to operate a bit differently than someone who spent the last two or three years at Uber. You always kind of have to understand the years or the point in time when someone was actually at Uber and what the culture of that company was like because cultures of companies change over time."

2. Use back-channel references: Ask specific questions about "what does this person like to work with? What are they like when they disagree with someone? How strongly held are they in their opinions? Are they a jerk?"

3. Arrange out-of-office interactions: "Spend time with your team as well outside of just the standard interview process... What is this person like when they're not working? Could I be stuck with this person for five hours in the airport? And like, I would actually enjoy that time spending that time with this person."

Andrew shared an illuminating example of how cultural fit can influence decisions:

"There was an example of a search that I did a few years ago where it was a really hot company and they had amazing candidates that they were talking to. And one of the candidates came in to interview. It was after the workday. So he came in at like six o'clock to meet the founder. And as he was walking out, the company was setting up to do a full company all-hands or something at seven o'clock on a Wednesday night. And he was like, 'Great company, great founders. I can't like that's not good for my lifestyle. I just can't do that.'"

His advice to companies: "As a company, you shouldn't apologize for that if that's how you operate and that's how you've been successful. But you also shouldn't obscure that fact that that's who you are either just to get the person because that comes back to misaligned expectations."

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The Art of Closing Top Candidates

When it comes to closing candidates, Andrew advises that the process starts with the very first interaction:

"Closing really kind of starts in the very first conversation that you have with the candidate. It's not like you're interviewing, interviewing, interviewing, decide you want them, and now it's time to close. You are continually, ideally if a process is being run the right way, building the candidate's interest with each interaction that they have with your company."

Here are his key strategies for effective closing:

1. Build Rapport from Day One

"If it's a great candidate and that's a great conversation, you should send a thoughtful follow-up. 'Thank you so much for the time. Here's what I liked about the conversation. Here's like what I would propose as next steps.' You should start establishing that direct line of communication with a candidate as soon as you possibly can."

This is especially important for product leadership roles:

"Candidates at this point are savvy enough and they've heard enough horror stories about working with founders to know that the success of your job as a head of product is going to all come down to fit with the founder. And so building comfort and rapport between candidate and founder is so critical to do from the outset of a process."

2. Create Multiple Touch Points

Andrew recommends several ways to keep candidates engaged:

• Making yourself available for questions outside formal interviews

• Meeting in person when possible

• Sending materials like decks or demos

• Walking them through what you're currently working on

3. Only Make Offers When You Know They'll Accept

"You shouldn't make an offer unless you know that the candidate wants to join the company. You have to spend political capital, social capital, all that to get a very strong offer green-lit. You might have to go to comp committee, etcetera. You should only do that if you have conviction that this person, this candidate wants to make it work too."

4. Watch for Red Flags in Negotiation

When candidates focus exclusively on compensation without showing genuine enthusiasm for the company and role, it's concerning:

"If it just comes down to numbers for them, then that might be a red flag to me because it's not necessarily clear that they're doing this for the right reasons. Maybe it's not something that's a super big passion area for them. Or they, the team doesn't stand out to them over all the other teams."

5. Encourage Clear Communication During Negotiation

The most effective candidates are direct about their requirements:

"Where I've seen candidates have the most success when negotiating is if they're honest and transparent and then if you do want to negotiate with your counter being like, 'Okay, if you can get to this number, I'm in.' If you're just very explicit to a founder of like, 'I want this. If you can meet this, I sign tomorrow,' that will then, even if it's a big ask, the founder will then be more incentivized to go back to their board, to go back to their comp committee, to try and move mountains to make it work because they know that doing that results in a yes."

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Managing Internal Team Dynamics

When bringing in a new product leader over an existing team, you'll need to navigate complex dynamics, especially if you're passing up internal candidates for promotion:

"If you're passing up people for a promotion in order to hire someone externally, or there's a team of people who came in to work for one person, that person's no longer there, you have to hire someone with credibility. Like it has to be someone where it's like, okay, it's obvious why they'd want to hire this person. 'Oh yeah, that makes sense. Like that person is a lot more senior and more accomplished than I am.'"

Andrew's approach to involving the existing team depends on your specific situation:

If You're Looking to Upgrade the Team:

"Maybe you don't care as a founder CEO or as a VP of product, what your team thinks, because maybe you feel like your team's underperforming. And a big reason why you want to hire this person is because you want them to be very critical and evaluating how's my PM team doing? Can we uplevel this team? Is it okay if people leave?"

If You Value Your Current Team:

"Including them in the process, not necessarily as a critical, evaluative part of the process, but a like, 'Hey, we're getting towards the end here. We have one or two people that we're seriously considering, would love for you to just spend a session with them, whether it's a lunch, whether it's a group zoom, just kind of getting to know this person, asking about their background, their leadership philosophies, et cetera, and just kind of making sure that you would be good reporting to this person.'"

Andrew advises against having candidates formally interviewed by their potential direct reports:

"You don't put candidates in there to be interviewed by their subordinates or the people that they're going to be inheriting necessarily. It's much more making sure it's not going to be some organ rejection, cultural type, asymmetrical fit at the end, making sure that your team feels like they were at least included and consulted as part of the process."

Measuring Success of a Product Leader Hire

How do you know if your product leader hire was successful? While it's difficult to attribute company success to any single hire, revenue growth is typically the North Star metric:

"Nine times out of 10, I would think that it would probably be revenue as the biggest thing that you're looking to in terms of like, is this a successful hire or not? How did revenue, what shape did revenue take in the time that this person was in the chair?"

However, Andrew candidly acknowledges the challenge of attribution:

"It's hard to know, would that have happened with the next best hire that they could have made? Was the company already going to be on that trajectory regardless? As an exec recruiter, I will never claim to say that I have that all-knowing power of like, 'Yeah, this never would have happened if you had hired the second, the backup candidate as opposed to this candidate.'"

Success can manifest in multiple ways:

"There's plenty of examples that I can speak to where it's like made a hire at a series B or series C. And that person was still the CPO at series E series F and company had raised three or four rounds and revenue was three X."

But even when quantitative metrics look good, qualitative factors matter:

"The company does great and person's been in the chair for that long and they won't reference well. And you'll be like, what the heck? Maybe they were really difficult to work with. Maybe the founder was really the CPO. And so that person is not really granted the credit that they think they should be getting. And they have an outsized opinion of themselves and their impact on the product relative to what other people at the company thought their impact was versus the founder."

Why Product Leader Hires Fail

The biggest reason product leader hires fail is misaligned expectations:

"There was a misalignment of expectations on day one of what the founder and/or team was expecting out of this person versus what this person felt like they were walking into and what their strengths really are."

This is particularly challenging for product roles because:

"Everyone at the company has an opinion about the company's product and therefore the company's product leader. I don't know if everyone at a company is going to really deeply care about the CFO, but product is something that is very, there's a lot of opinions that exist and a lot of different opinions at the company about how the product should look and how it should feel and how it should be used."

Andrew advocates for the "anti-sell conversation" to prevent misalignment:

"Something that I've seen work really well is before you hire a CPO, you need to kind of have the anti-sell conversation with them and just be super honest and transparent about 'these are the things that are broken right now. If you're scared of this, if you're not excited about jumping into these challenges, if you don't feel like you're good at solving these types of problems, you should probably not come.'"

He cautions against prioritizing closing the deal over finding the right fit:

"Sometimes founders can get so wrapped up in trying to close and trying to get the person that they'll do anything in order to make it happen. But hiring someone is not the goal - hiring someone who's going to actually make a great impact and be a great fit is the goal."

Real-World Examples

Throughout our conversation, Andrew shared several illuminating examples from his extensive experience:

1. The After-Hours Culture Shock: A candidate for a hot company came in for an evening interview, only to discover the entire company was setting up for a 7 PM all-hands meeting. Despite liking the company and founders, he immediately knew the culture wouldn't work for his lifestyle.

2. The Public Company Searches: Andrew has worked with companies like "HubSpot, PagerDuty, Atlassian" on the public side, and seen how different their search processes are compared to early-stage startups.

3. The AI Researcher Founders: He's observed founders from research backgrounds building AI companies who understand the models but struggle with productization - making them perfect candidates for bringing in product leadership.

4. The Series B to Series F Journey: He's placed CPOs who stayed through multiple funding rounds and saw companies triple their revenue, demonstrating long-term value.

5. The Black War AI Company: He recently completed a head of product search for an AI company called Black War at the seed stage, showing his range across company stages.

Conclusion

Hiring great product leadership is both art and science. It requires understanding your company's specific challenges, creating a rigorous yet flexible evaluation framework, and running a process that builds candidate interest from day one.

The best product leader hires often aren't the most obvious ones on paper - they're the up-and-comers ready to step into their first leadership role, with the right combination of experience, potential, and cultural alignment. As Andrew emphasizes, "Just hiring someone isn't the goal. Hiring someone who's going to actually make a great impact and be a great fit is the goal."

For founders navigating this critical hiring decision, Andrew's parting advice is to focus on alignment of expectations above all else. The clearer you are about your challenges and what you need, the more likely you are to find a leader who can truly transform your product organization.

This interview has been edited for clarity and organization.

If you're a founder, executive, or board member looking to hire great product leadership, you can reach Andrew at andrew@fusiontalent.com or connect with him on LinkedIn.

Andrew's LinkedIn

About This Executive Hiring Series

This article is part of a series on hiring great technical leaders. In upcoming articles, I'll be featuring insights from other expert recruiters including:

• Chris Johnson (CEO & Managing Partner at Artisanal Talent): One of the most highly sought-after search consultants in the field who placed Yukhi who became CPO at Figma and has completed searches for elite tech companies including Airtable, Databricks, DocuSign, GitLab, Loom, Superhuman, and Zuora. Chris quickly rose from Analyst to Partner at SPMB before co-founding Artisanal.

• Jodi Jefferson (Founder, Managing Partner at People Project): Conducts C-Level, VP-Level, and Director-Level searches across Engineering, Product, AI & Data for major companies like Dropbox, Oscar Health, Weight Watchers, Audible, and Grubhub Seamless. Her clients include companies backed by Bain Capital, Tiger Global, Union Square Ventures, Thrive Capital, and dozens of other top-tier VC firms.

• Lauren Ipsen (Talent Partner at Decibel Partners): Previously a top performing executive recruiter at Daversa Partners and talent partner at General Catalyst, Lauren has placed over one hundred product and engineering leaders at high-growth companies including Airbnb, Canva, Discord, Reddit, Twitter, and Snap. Her recent portfolio includes build-outs for Grammarly, Hippocratic.ai, Reddit, Nextdoor, and Opendoor.

• Hillary Mager (Founding Partner & CEO at Sterling Strand, ex-Flatiron Health, Citadel, and Bridgewater): Hillary built Flatiron Health from 30 to 1000 employees in five years, working directly with the founders, leading all executive searches herself and building all hiring processes and operations along the way. She’s also spent time at top hedge funds, including Bridgewater and most recently Citadel, as MD, Global Head of Technical Recruiting. She started Sterling Strand because she wanted a search firm to exist that would serve the needs that were most pressing for her as an in-house recruiter. “Hiring is a science. Not an art.”

My Top Tech Newsletter typically focuses on job search strategies and salary negotiations. This series explores the other side of the table - helping founders and executives build world-class leadership teams.

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Are there specific executive hiring topics you'd like to see covered in this series? Drop a comment below!

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Recruiters negotiate for a living. You don’t.

If you go into salary discussions without a strategy, you’re handing over control before the conversation even starts. Annie Murray and I have spent years on both sides of the table: hiring at top tech companies and helping candidates secure 5, 6, even 7-figure increases.

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This video breaks down 37 lessons we’ve learned from negotiating 300+ job offers. Find the written summary of our discussion below.

Next Step: Learn It Live

We’re running free, no-fluff negotiation workshops to help you apply these strategies in real time. Pick the session that fits your situation. Or better yet, attend all of them.

📌 Handling Salary Expectations Questions (Tue, Mar 18 @ 6:00pm PST)

📌 Negotiating Startup Offers (Sat, Mar 22 @ 9:00am PST)

📌 Negotiating Big Tech Offers (Wed, Mar 26 @ 11:00am PST)

📌 Mock Negotiation Practice with Annie (Tue, Apr 8 @ 5:30pm PST)

Free Live Workshops

Lesson 1: Recruiters Are Trained To Negotiate

• Recruiters are not simply facilitators; they are often trained professionals with specific negotiation strategies. They understand common candidate responses, and they have tactics to influence your decisions. It's important to recognize that while they may want to fill the position, their role involves negotiating the best possible outcome for the company. Being aware of this training helps you anticipate their strategies and prepare your own.

Lesson 2: Don't Fear Negotiations

• Don't let fear prevent you from negotiating. Many candidates avoid negotiation due to concerns about jeopardizing the job offer. However, negotiation is a standard practice in the tech industry, and companies often expect it. With the right approach and preparation, the risk of losing an offer is often low. Fear can lead you to leave money on the table, so it's essential to overcome it.

Lesson 3: Negotiating is Expected

• Companies generally anticipate candidates will negotiate. It's not seen as aggressive or unusual; in fact, it's a standard part of the hiring process. Companies often build negotiation ranges into their compensation plans. Failing to negotiate may signal a lack of confidence or an unfamiliarity with industry norms. Embracing this expectation empowers you to advocate for your worth.

Lesson 4: Embrace Discomfort

• Negotiation can be uncomfortable, but this discomfort often indicates you are advocating effectively for yourself. If you feel too comfortable, you might not be pushing hard enough to achieve your goals. It's a sign that you're stretching beyond your comfort zone, which is often necessary to secure a favorable outcome. Discomfort is a natural part of the process, and accepting it can lead to better results.

Lesson 5: Negotiating Improves Your Reputation

• Professional negotiation can enhance your reputation and demonstrate valuable skills to potential employers. When done correctly, it showcases your ability to communicate effectively, advocate for yourself, and understand your value. Hiring managers often respect candidates who negotiate confidently and professionally. It can set a positive tone for your future interactions within the company.

Lesson 6: Negotiate Your Level

• In addition to salary, consider negotiating the job level or title to ensure it aligns with your experience and career goals. Sometimes, a higher title can open doors to more opportunities and higher compensation in the future. It's a crucial aspect of negotiation that goes beyond immediate financial gains. Negotiating your level demonstrates your ambition and long-term vision.

Lesson 7: Uplevels Anchor Compensation

• Achieving a higher job level can significantly influence your overall compensation and future earning potential. Companies often have salary bands associated with different levels, so securing a higher level can lead to a substantial increase in your earning power. It also establishes a higher anchor for future salary negotiations and career growth.

Lesson 8: Title Isn't Everything

• While titles are important, evaluate the entire opportunity, including company growth, reputation, and overall compensation potential. Don't fixate solely on the title; consider the bigger picture and the long-term impact on your career. Sometimes, a less prestigious title at a high-growth company can provide greater opportunities for advancement and financial gain.

Lesson 9: Step-Downs for Long-Term Gains

• Sometimes, accepting a slightly lower title or position can lead to greater long-term career advancement and earning potential. This strategy is particularly relevant when transitioning between different types of companies (e.g., startup to FAANG). A temporary step-down can provide access to better opportunities, resources, and career growth in the long run.

Lesson 10: Don't Give A Number

• Do not disclose your salary expectations prematurely in the negotiation process. It's crucial to gather more information about the role, the company's compensation structure, and your own value in the current market before discussing salary. Providing a number too early can limit your negotiating power and potentially undersell your worth.

Lesson 11: Protect Information

• Control the flow of information during negotiations. Information is a valuable asset, so be mindful of what information you share and when. Avoid giving away unnecessary details that could weaken your negotiating position. Be prepared to answer questions strategically and thoughtfully.

Lesson 12: You Never Know If Your Number Is High Enough

• You might be able to negotiate a higher offer than you initially expect. Companies often have some flexibility in their compensation packages. Don't assume the first offer is the final offer. Research salary ranges for similar roles and be prepared to justify your request for a higher compensation.

Lesson 13: Prepare For Aggressive Recruiter Tactics

• Be prepared for recruiters to use various negotiation tactics, and develop strategies to address them. Recruiters may use techniques like creating a sense of urgency, emphasizing other candidates, or downplaying your contributions. Understanding these tactics allows you to remain calm and focused during negotiations.

Lesson 14: Show the Best Photo of the House

• Focus on highlighting your strengths and the value you bring to the company. Emphasize your accomplishments, skills, and how you can contribute to the company's success. Present yourself as a highly desirable candidate and clearly articulate the value you bring to the team.

Lesson 15: Framing Other Opportunities

• When discussing other job opportunities, present them in a way that maximizes your leverage. You can use competing offers or interest from other companies to demonstrate your value and create a sense of urgency. However, be honest and avoid exaggerating your situation.

Lesson 16: Interviews Can Be Better Than Offers

• Early-stage opportunities can be used effectively as leverage in negotiations. Even if you don't have a formal offer from another company, expressing interest from other potential employers can strengthen your negotiating position. It indicates that you are in demand and have options.

Lesson 17: Control The Narrative

• Maintain a consistent and compelling narrative throughout the negotiation process. Your story should align with your career goals and demonstrate why you are a strong fit for the role. Consistency and clarity in your communication are essential for building trust and credibility.

Lesson 18: Beyond Base Salary

• Consider all components of the compensation package, including equity, bonuses, and benefits, not just base salary. Total compensation encompasses more than just your base salary. Explore and negotiate other elements like equity, signing bonuses, performance bonuses, benefits, and perks. A holistic approach will help you maximize your overall compensation.

Lesson 19: Don't Underestimate Equity

• Equity can be a significant part of your overall compensation, especially in startups or high-growth companies. Understand the equity structure, vesting schedule, and potential value of the equity offered. Equity aligns your interests with the company's success and can provide substantial financial upside in the future.

Lesson 20: Negotiate Equity Protections

• In addition to the amount of equity, negotiate terms that protect your equity in various circumstances. This can include things like accelerated vesting in case of acquisition or change of control, or extended exercise windows for stock options. These protections ensure that you are fairly compensated for your contributions, even if unforeseen events occur.

Lesson 21: Pre-Negotiate Severance/Separation

• Discuss and negotiate severance or separation terms before accepting a job offer. While it might feel uncomfortable to discuss the possibility of leaving before you even start, it's a responsible and proactive step. Having a clear severance agreement in place provides security and clarity in case of unexpected circumstances.

Lesson 22: Stop Talking

• Silence can be a powerful tactic in negotiations, encouraging the other party to provide more information or make concessions. After receiving an offer, pausing before responding can prompt the recruiter to elaborate or improve the offer. It's a way to create space and allow the other party to fill it.

Lesson 23: Step Back Under Pressure

• Don't feel pressured to accept an offer immediately. It's essential to take time to review and consider all aspects of the offer, including compensation, benefits, and the overall opportunity. Rushing into a decision can lead to overlooking important details or accepting less than you deserve.

Lesson 24: They're Just Psychological Manipulation Tactics

• Be aware of common psychological manipulation tactics used in negotiations. Recruiters may use techniques such as creating artificial deadlines, emphasizing other candidates, or downplaying your contributions. Recognizing these tactics allows you to remain objective and avoid being pressured into making a hasty decision.

Lesson 25: Kill Them with Kindness - Excitement Sandwich

• Even when faced with aggressive tactics, maintain a professional and positive demeanor. Respond calmly and confidently, focusing on the facts and your value. Avoid getting drawn into emotional responses, as this can weaken your position.

Lesson 26: Be Likable

• Being likable can significantly influence the outcome of negotiations. Building rapport and maintaining a positive relationship with the recruiter and hiring manager can make them more willing to work with you and meet your requests. Likability fosters a collaborative environment, even during negotiation.

Lesson 27: Be Neutral But Excited On The Offer Call

• On the call where you receive the offer, express excitement about the opportunity but remain neutral about the offer itself. This approach allows you to acknowledge the offer positively without committing to it or revealing your immediate reaction. It sets the stage for further discussion and negotiation.

Lesson 28: Don't Negotiate When You Receive An Offer

• Do not begin negotiating the offer during the call where it is presented. Instead, express gratitude and request time to review the offer thoroughly. This allows you to gather your thoughts, research, and prepare a well-reasoned counter-offer.

Lesson 29: Buy Time To Plan Your Counter Offer

• Take time after receiving the offer to plan and prepare your counter-offer strategy. Research salary ranges, gather data to support your requests, and determine your priorities. A well-prepared counter-offer demonstrates your professionalism and strengthens your negotiating position.

Lesson 30: Get the Hiring Manager On Your Side

• Having the hiring manager as an advocate can significantly strengthen your negotiation position. Building a strong rapport with the hiring manager and demonstrating your enthusiasm for the role can encourage them to support your requests. Their advocacy can be invaluable when negotiating with the company.

Lesson 31: 30-60-90 Action Plan Call

• Have a conversation with the hiring manager about your plans for the role to demonstrate your understanding and commitment. Discussing your 30-60-90 day plan or your vision for the role can showcase your initiative and enthusiasm. It also provides an opportunity to align your goals with the team's objectives.

Lesson 32: Involve Your Skip Manager

• In some cases, involving the skip manager (the hiring manager's manager) can be beneficial. The skip manager may have more authority to approve higher compensation or make exceptions to company policies. This is a tactic to consider if you're encountering roadblocks with the hiring manager or recruiter.

Lesson 33: Ride The Momentum Of The Negotiation

• Time your counter-offer to capitalize on the momentum and enthusiasm of the hiring team. There's often a peak in excitement after successful interviews, and it's advantageous to make your counter-offer while that enthusiasm is high. Delaying too long can allow that momentum to fade.

Lesson 34: Warm Up Cold Negotiations

• If there are delays in the negotiation process, re-engage with your advocates to maintain their support. Stay in touch with the hiring manager and recruiter, providing updates and reiterating your interest in the role. This keeps you top-of-mind and ensures that your advocates continue to support your requests.

Lesson 35: Internal Leverage Is Gold

• Internal support within the company can be a significant advantage in negotiations. Having advocates like the hiring manager or skip manager on your side can greatly increase your chances of success. Building these relationships is a valuable aspect of the negotiation process.

Lesson 36: Don't Let Fear Drive Decisions

• Do not let fear dictate your negotiation strategy or decisions. Fear can lead to missed opportunities and accepting less than you deserve. Approach negotiations with confidence and a clear understanding of your value.

Lesson 37: Avoid Offers Being Pulled

• Negotiate in a way that minimizes the risk of the offer being withdrawn. While it's rare for offers to be rescinded, it's important to be professional and respectful throughout the negotiation process. Avoid making unreasonable demands or being overly aggressive, as this could potentially jeopardize the offer.

Quick reminder: If you have any questions about negotiating or want feedback on your approach, sign up for one of our free live workshops below:

• Handling Salary Expectations Questions (Tue, Mar 18 @ 6:00pm PST)

• Negotiating Startup Offers (Sat, Mar 22 @ 9:00am PST)

• Negotiating Big Tech Offers (Wed, Mar 26 @ 11:00am PST)

• Mock Negotiation Practice with Annie (Tue, Apr 8 @ 5:30pm PST)

See you there!

Free Live Workshops

Negotiating soon?

Get 1-on-1 Negotiation Support

I got the chance to interview Annie Murray, a negotiation expert who's helped secure over $10 million per year in added compensation for over 200 tech professionals. I wanted to challenge the common views on negotiating in today's market.

Find the article form of our discussion below.

Our conversation revealed why 30% of candidates are leaving money on the table, how to spot the signals that your offer might get pulled, and the surprising insight about what really drives successful negotiations.

Drawing from hundreds of successful negotiations she's coached at Valued and her experience as a recruiter at Amazon and Microsoft, we explored how internal leverage, built throughout the interview process, often drives larger increases than external factors like competing offers.

Topics:

• The real story behind rescinded offers in 2025's market

• Why traditional negotiation advice is failing candidates

• The Risk Thermometer framework for reading company signals

• How to save an offer that's about to be pulled

• The 5 proven tactics of successful negotiators

• Why pre-offer preparation matters more than the actual negotiation

• What really makes companies willing to go above band

• The truth about "final" offers

Article below…

Want to go deeper? Annie & I are running a negotiation bootcamp live on Maven
$250 OFF only for Top Tech readers

📘 Maven Live Course: 1 Week Salary Negotiation Masterclass

Exclusive early bird: Get $250 off the course if you enroll this week!
Use code TOPTECH250

• Live sessions

Learn More

The Current State of Tech Negotiations

"It's kind of hard to know exactly because we hear so many conflicting things," Annie explains when I ask about the current market. "For a moment there, it seemed like layoffs were on the decline. But then Intel and Dell happened. And we saw them lay off, unfortunately, quite a few people."

Despite the uncertainty, Annie emphasizes that negotiation is still very much possible. The key is understanding how the market has evolved.

The Truth About Rescinded Offers

When I ask about the real story with pulled offers, Annie shares some surprising data. After combing through extensive data on platforms like Blind, they found that while offer rescissions peaked in early 2022 to early 2023 with about four offers pulled monthly, we're now seeing closer to one per month.

More importantly, Annie explains that offers typically get pulled for just three reasons:

1. Market conditions and hiring freezes (outside your control)

2. Unprofessional behavior during negotiations

3. Overly aggressive compensation demands

"It's not so much of, oh, they asked for a reasonable number in a reasonable way and the offer got pulled," Annie emphasizes. "It's more like these outlier behaviors that are causing these offers to get taken away."

The Risk Thermometer: Reading Company Signals

I've heard Annie talk about this concept of a risk thermometer when approaching negotiations. She explains it's about looking for specific signals from companies that indicate your negotiating position.

"There are signals that we call red flags, aka things that might indicate you don't have that much leverage here, versus green lights, which are signals that companies can send that are indicating, 'Oh, we really like you. We're going to do what it takes to get you to sign.'"

Green Lights:

• You're the only/top candidate

• Recent funding or strong earnings

• Rising stock performance

• Recruiter indicates compensation flexibility

• No pressure on timelines

• Internal referrals

• Skills exceeding requirements

• Strong interview feedback

Red Flags:

• Multiple final-stage candidates

• Recent budget cuts/freezes

• Declining stock performance

• Rigid salary bands

• High urgency to fill role

• Slow responses

• Vague role details

• Unwillingness to document details

The Emergency Toolkit: Saving a Troubled Negotiation

What if you get in one of those rare situations where they threaten to pull the offer? Annie shares her proven approach: "The best turn of phrase that I'd recommend using is 'I'm confident we can get to a number that works for everybody and money isn't everything.'"

This works because it:

• Returns to a collaborative position

• De-emphasizes financial impact

• Opens the door for continued dialogue

Even if things seem dire, Annie notes that offers can often be revived by talking directly to the hiring manager. "They are the one who has the authority here, not the recruiter."

The 5 Core Tactics of Successful Negotiators

When I ask about advanced tactics that help candidates succeed, Annie breaks it down into five key elements:

1. Avoid Number Fixation "The more you're married to a number, the more you're going to be fixated on trying to get it above everything else. And we really got to remember that the more we push back, the more we alienate the company."

2. Strategic Number Presentation Present a number that feels thoroughly considered with advisors and family. Hedging or frequently changing numbers undermines credibility.

3. Focus on Value Add "Talk to the hiring manager. Present your 90-day goals for your time in this role. That is really going to help them see that you are the best fit for this position."

4. Show Excitement and Willingness to Sign "A lot of people think that it's more strong to seem a little bit less interested, but recruiters get benefited in their metrics if they know that you're gonna sign."

5. Read the Room Pay attention to verbal and non-verbal cues. After 2-5 pieces of pushback, consider changing approach.

Success Story: Turning an IC Offer into a Director Role

Annie shares a fascinating case where a product manager received an individual contributor offer well below market rate. Through careful positioning focusing on stakeholder management and their 30-60-90 day plan, they secured a Director-level position instead.

The winning argument? They highlighted how their IC-level title would impact their ability to influence senior stakeholders effectively. The hiring manager called it "a really intelligent way of arguing this" – and approved the Director title with corresponding compensation.

The Four Essential Ingredients for Successful Negotiations

Annie emphasizes that every successful negotiation needs four critical elements:

1. They Have to Like You You must be someone they want to fight for internally, while still remaining firm about what you need.

2. They Need Internal Justification Companies need to justify exceptions, especially to compensation committees at bigger companies.

3. You Must Be Winnable They need to believe you'll accept if they meet your terms. Otherwise, why expend political capital?

4. You Must Show Excellence Your performance throughout the process needs to justify the ask.

Work-Life Balance: The Hidden Factor

Annie emphasizes looking beyond pure compensation. Using TikTok as an example, she notes how some candidates focus on compensation without considering the 80-hour work weeks some teams require.

"Are you comfortable working 80 hours a week for higher compensation, or is it worth taking a 10k pay cut for reasonable work-life balance?"

However, she notes it's very team dependent: "I was at Amazon, and a lot of times people ask me, 'Oh, you must have thick skin to work at Amazon.' I was in the recruiting department with a team of wonderful women who never gave me any issues."

Looking Forward: How to Navigate This Market

Annie's final advice focuses on balancing assertiveness with flexibility. "You have to be someone they want to fight for internally," she explains. But you also need to know when to stop pushing.

Remember her core principle: "The comp you accept today is the comp you're living with for the indefinite future."

Want to go deeper? Annie and I are running free live workshops on the topic:

→ Lightning Lesson: How to answer Salary Expectations questions without losing leverage (free recording)

→ How to negotiate Startup Offers (free recording)

→ How to negotiate Big Tech Offers (Thu, Jan 16th at 5:00pm PT)

To go even deeper and maximize your total compensation in your next offer—and throughout your career, you can check out my full negotiation course or work with Annie or me 1-on-1.

🤝 Valued: 1-on-1 Negotiation coaching

⚡️ $250 OFF: 📘 Maven Live Course: 1 Week Salary Negotiation Masterclass

Find the article form of our discussion below.

Our discussion uncovered why traditional negotiation advice fails, how successful candidates secure dramatic increases without competing offers, and why many top executives strategically quit in their first week.

Subscribe now

Drawing from 100s of successful negotiations we've coached at Valued and my experience as a senior director making hiring and compensation decisions, we explored how internal leverage, built throughout the interview process, often drives larger increases than just external factors like competing offers.

Topics:

• How candidates still secure $200,000+ increases without competing offers

• Why many top executives quit in their 1st week

• The 5 stages of outlier negotiations

• The 4 ingredients that make-or-break a negotiation

• Why pre-negotiating severance matters more than ever

• Protection strategies ICs & Executives should negotiate post-downturn

• Equity considerations that create 6-figure tax implications

• When to keep negotiating even at top of band

Article continues below…

Want to go deeper? Annie and I have been running free live workshops on the topic:

→ How to negotiate Big Tech Offers (Thu, Jan 16th at 5:00pm PT)

→ Lightning Lesson: How to answer Salary Expectations questions without losing leverage (free recording)

→ How to negotiate Startup Offers (free recording)

🤝 Valued: 1-on-1 Negotiation coaching

📘 Maven Live Course: 1 Week Salary Negotiation Masterclass

Exclusive early bird: Get $250 off the course if you enroll this week!
Use code TOPTECH250

Get Expert Negotiation Support

The New Reality of Negotiations for Professionals and Executives

Let me share something that might change how you think about compensation negotiation in tech. There's a persistent myth that's costing people hundreds of thousands of dollars in lost compensation—the idea that you need external leverage to negotiate. You know what I mean: competing offers, current employment, or a strong market position.

Here's why this conventional wisdom is wrong: based on hundreds of real negotiations and my direct experience as a senior director making hiring decisions.

Breaking the Leverage Myth

I recently worked with someone who challenges everything people think they know about negotiation leverage.

• They had been off the market for four months.

• No competing offers.

• No current job.

Traditional wisdom would say they had no leverage.

Yet they secured a $200,000 increase annually.

This wasn't a fluke or a lucky break. It was from knowing how to build leverage and, having the confidence to ask for what they were worth.

Understanding Market Evolution

To understand why this works, let me show you how the market has actually evolved. I did a detailed analysis of offers at the L6 Amazon level over time, and the pattern is fascinating:

Historical Pattern (Pre-2023):

• Enormous variance in compensation

• Frequent above-band offers for the right candidates

• Significant below-band offers for others

• Companies regularly making exceptions for the right talent

The 2023 Compression:

• Everything squeezed down to nearly nothing

• Far fewer exceptions made

• Bands became more rigid

• Companies became more conservative

Current State:

• Starting to expand again, but differently

• Fewer extreme exceptions above bands

• But top-of-band offers very much still happening

• More emphasis on internal equity

• Greater focus on justification

I'm seeing this play out in real time when candidates negotiate. What most people miss: it's all about playing the information game correctly.

The Five Core Stages of Strategic Negotiation

Let me walk you through exactly how top 10% negotiations actually work. There are five stages, and missing any one of them can undermine your position.

Stage 1: Strategic Preparation

Before you even start your search, you need three things:

1. Practice rounds on your interviews

2. Clear responses for early compensation questions

3. Strategic categorization of target companies

You need to organize your targets into three tiers:

• High-paying, high-leverage companies that might seem out of reach

• Your core target companies

• Your ideal companies that are perfect fits

Sometimes having an opportunity in process can be better leverage than an actual offer. Even with companies like Google that typically want hard evidence, I've seen early discussion opportunities help move the needle.

Stage 2: The Expectations Dance

This is where most candidates make their first critical mistake. The recruiter asks about salary expectations, usually in multiple early calls. Common advice says give a range or come in higher than your current position, claiming you can always adjust later.

Let me tell you exactly why this fails: If you anchor on something early, recovering from it is like pulling teeth. Even when we manage it - and we often do - it never feels as smooth as when you defer price discovery.

Instead, here's the exact language we found consistently works: "I haven't thought much about that yet. In my experience, there's so much more that goes into compensation than just the numbers. I need to find out more about the role and go through my other processes."

If they're persistent, then you be persistent - kindly repeat yourself. Don't feel like you need to give further justification because they are pushing. Your job is to get to the next round, not negotiate. So if you encounter the rare intense and pushy recruiter who just won't let you go without a number, tell them there's nothing you see that makes you want to stop the process and you trust you will come to something that works for both sides.

Stage 3: Building Strategic Leverage - The MERIT Framework

This is where we get into the real mechanics of building leverage throughout the process. I've seen this framework transform negotiations time and again, but it requires understanding each component in detail.

Market Understanding

First, you need to deeply understand what the company is going through. This isn't just about whether they're hiring - it's about their strategic position:

• Recent layoffs? This affects not just budget but approval processes

• Hiring freezes? Often these have specific exception processes

• New funding? This changes budget flexibility

• Strategic initiatives? These can override normal constraints

Let me give you a concrete example:

A Series B company struggling with fundraising has very different constraints than a growing public company. With the Series B company, cash compensation might be tight, but equity and scope flexibility could be significant. Understanding these dynamics changes your entire negotiation approach.

Expertise Positioning

This is where you become a "market of one" for the role. During the process, you're gathering intelligence about:

• Specific pain points they need solved

• Strategic initiatives that align with your experience

• Team gaps you can fill

• Unique combinations of skills they need

During that interview process, you need to be reading the tea leaves. Every conversation is an opportunity to understand what they really need - often beyond what's in the job description. You can use that to position yourself as a market of one. for the role

Results Quantification

You need to

• Quantify your impact in ways that matter to them

• Translate past achievements to their context

• Show scaling potential that aligns with their goals

• Demonstrate strategic thinking that matches their needs

One of the most powerful tools here is what I call "impact translation." Don't just say you grew revenue by 40% - explain how that growth model could apply to their specific situation.

Inventory Management

This includes everything in your negotiating arsenal:

• Current position

• Other opportunities

• Upcoming equity vesting

• Market alternatives

• Personal timing constraints

Don't reveal most of this until you're actually in final negotiations. Think of it like playing poker. You don't show your cards until the right moment.

Tactical Execution

This is about:

• How you communicate

• Building rapport with key stakeholders

• Managing the process timeline

• Engaging decision makers effectively

I've seen candidates with perfect qualifications fail here because they didn't understand the human element of negotiation. You have to be likable while being firm.

Stage 4: The Role Vision & 30-60-90 Plan

This is where you can really change the dynamics. After receiving an initial offer, create a detailed document that outlines:

1. Vision for the Role

• Strategic alignment with company goals

• Specific impact metrics you'll target

• Innovation opportunities you've identified

• Cross-functional collaboration plans

2. Implementation Strategy

• Key stakeholders you'll engage with

• Resource requirements and timeline

• Risk mitigation approaches

• Success metrics and milestones

3. Execution Framework

• First 30 days: Learning and assessment

• 60 days: Initial implementation and quick wins

• 90 days: Strategic initiatives and scaling

When you schedule a call with both the hiring manager and their skip level to discuss this plan, two things happen:

First, for reverse interviewing: About 50% of the time - and I'm not exaggerating this number - candidates discover the role is completely different than what they thought. Let me share a specific example: I had a candidate who was told they would own an important part of the ads platform. During the 30-60-90 discussion, the hiring manager said, "Oh no, you're totally not doing that - you're doing this other thing." Imagine discovering that after accepting the offer.

Lots of - especially senior - candidates push back on having these meetings. They think it's unnecessary or will be awkward. In 300+ negotiations, we have seen 0 candidate regret doing this. Even if the hiring manager doesn't read the document they walk away impressed and advocating for them.

Second, for leverage in negotiations: When you get things on paper and have leaders acknowledge your impact, you build powerful ammo for pay talks. I've seen this conversation turn "we can't go any higher" into significant increases because now they have concrete justification for compensation committees.

Stage 5: Counter Offer Strategy

We won't go into much detail. But, at the end of the 30-60-90 calls, or just with the recruiter, you will use elements from MERIT to make your case. Ideally, you will have buy-in from those conversations. Use the HM and Skip's words if you can about the importance of the role.

Negotiate up other offers first using these tactics before using them as competing offers in counters. This gives you higher offers with fewer counter rounds.

This is where the four essential ingredients of a successful negotiation become important. Every successful negotiation needs all four of these elements - miss any one, and you're likely to fail.

The Four Essential Ingredients for Success Negotiations

1. Likeability

You must be someone they want to fight for internally. This doesn't mean being a pushover - quite the opposite. When you're having that conversation with the recruiter, you say "Thank you so much. You're one of the best recruiters I've worked with. You got me this far. Thanks for advocating for me." But then you're still firm about what you need.

2. Demonstrated Excellence

They need to think you deserve it through the interview process. This comes through in your performance, your preparation, and especially that 30-60-90 day plan.

3. Clear Justification

They need to be able to justify this internally, especially to compensation committees at bigger companies. This is where objective things matter. That can mean your unique mixture of skills and experience, your competing opportunities, your role's target impact, or your on paper expertise.

4. Perceived Winnability

They need to believe you're likely to accept if they meet your terms. If they think you're using them as leverage or you're not super excited about the role, they're not going to fight for you. Why would they expend political capital and go to the compensation committee if they don't think you'll accept?

Advanced Strategic Considerations

Executive Level Considerations

As you reach these levels, the game changes dramatically.

Title Significance

I hear this all the time from hiring managers: "What does a title matter? We don't care about titles here." Let me tell you why this is completely wrong.

Except for firms like OpenAI or Stripe where everyone's just "head of" something, titles matter.

You can't get things done as easily as a principal as you can as a director. People will just go above your head to find decisions to be made.

This is actually the best argument I've seen for getting a title bump - you need it to win over these people and get things done effectively.

Protection Strategies

At executive levels, you need to think beyond just compensation. Here's what you should be negotiating:

1. Severance Protection The package typically varies based on your position:

• 3 months for senior individual contributors

• 6 months for directors

• 8-12 months for VPs

• Up to 18 months at executive level

You can actually pre-negotiate your severance. Do this in person, help them understand where you're coming from. Frame it as risk management rather than lack of confidence.

2. Equity Optimization Standard equity packages often don't align with the strategic risks executives take. You need to negotiate:

Extended Exercise Windows:

• Standard 90-day windows can force impossible choices

• Negotiate 5-10 year extensions

• Get tiered exercise periods based on tenure

• Include special provisions for voluntary departure

Early Exercise Provisions:

• Exercise unvested options immediately

• Start the long-term capital gains clock early

• Minimize AMT impact

• Create more favorable tax treatment

I've seen this make six-figure differences in after-tax outcomes: You need to negotiate this upfront. You can't add it later.

3. Acceleration Clauses Think about scenarios like:

• Company gets acquired

• Leadership changes

• Founder who hired you leaves

• Company IPOs

You want protection for your equity in these scenarios. Sometimes this includes additional triggers - like if your role changes significantly within six months of these events.

4. Scope and Resource Guarantees This is especially important in leadership roles with fast turnover like growth. You need guaranteed:

• Headcount commitments

• Budget allocations

• Decision rights

• Strategic ownership

Let me share a specific example: With growth leaders, you need a certain number of people to get things done. If you don't have them, you're just not going to hit your targets. Getting these guarantees in writing can make the difference between success and failure.

The New Reality of Offer Management

The relationship between companies and candidates has fundamentally changed. Let me show you why this matters more than ever.

In 2023, we saw companies rescind offers right before start dates - sometimes days before people were supposed to begin. Think about what this does to candidates who:

• Had quit their previous jobs

• Turned down other opportunities

• Relocated families

• Made financial commitments

This has created a new strategic imperative. Here's what the smartest career people I know do:

1. Maintain Optionality

• Keep interviewing until your first week

• Don't close other processes prematurely

• Maintain relationships with other opportunities

• Create backup plans for worst-case scenarios

2. Strategic Verification Use your first week to verify:

• Cultural reality vs. promises

• Role scope accuracy

• Team dynamics

• Resource availability

• Leadership support

Why Top Executives Quit In The First Week

Many of the most successful executives I know have done something that might surprise you - they've left in the first week when they saw red flags. This never makes it to their resume, and they saved everyone time by not dragging it out.

Let me share a specific example: I know a VP who joined a high-growth startup. Within the first week, they discovered the founder had misrepresented the company's runway and key metrics. Instead of trying to make it work, they left immediately. Six months later, they were in a much better role, and that startup had major layoffs.

Risk Analysis and Career Protection

Let's discuss a barrier to effective negotiation: fear of becoming a target. Here's how to think about this.

The concern is real but often misunderstood. Based on what I've seen, targeting typically focuses on:

• Long-tenure employees with appreciated equity

• Clear underperformers regardless of compensation

• Roles with unclear value alignment

• Redundant positions post-merger

Simply being highly compensated rarely makes you a target if you're delivering value. I've seen this play out in multiple layoff rounds - companies keep their top performers regardless of compensation level.

The Bottom Line

Remember this: If you can't advocate for yourself in compensation discussions, how will you advocate for your products, your promotions, or your team? This isn't just about this offer - it's about developing a important career skill that pays dividends throughout your journey.

Want to go deeper? Annie and I are running free live workshops on the topic:

→ Lightning Lesson: How to answer Salary Expectations questions without losing leverage (free recording)

→ How to negotiate Startup Offers (free recording)

→ How to negotiate Big Tech Offers (Thu, Jan 16th at 5:00pm PT)

To go even deeper and maximize your total compensation in your next offer—and throughout your career, you can check out my full negotiation course or work with Annie or me 1-on-1.

🤝 Valued: 1-on-1 Negotiation coaching

📘 Maven Live Course: 1 Week Salary Negotiation Masterclass

Executive search can be a mysterious process for many product leaders. In this article, we'll break down 5 key topics to help you navigate executive search and become a "job search magnet" based on insights from 20+ year executive recruiter Somer Hackley, author of Search In Plain Sight, and product leader Colin Lernell (myself), former product leader at Patreon, Noom, and Udacity.

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1. Understanding Executive Search: Learn how search firms operate, their relationship with clients, and how to effectively engage with different types of firms.

2. Becoming a "Job Search Magnet": Discover how to develop a compelling personal brand and create a memorable "Think of me when..." statement that resonates with recruiters.

3. Optimizing Your LinkedIn Profile: Understand how recruiters use LinkedIn and learn strategies to make your profile stand out in search results.

4. Engaging with Recruiters: Master the art of building meaningful relationships with recruiters, including effective outreach and ongoing communication.

5. Navigating the Interview Process: Prepare for recruiter interviews with strategies to articulate your value proposition and showcase your leadership experience effectively.

Interested in taking action on your job search? Consider applying to my intensive Maven program on the product executive job search starting Oct 29.

Learn more

1. Understanding Executive Search

Executive search firms are hired by companies to find top candidates for senior roles.

Some key points to understand:

• Recruiters find candidates for jobs, not jobs for candidates

• Their priority is to find candidates that make them look good to their clients

• They typically present only the top 5-10 candidates to the hiring company

• Different firms specialize in different company stages, industries, etc.

"We're working for the hiring company to find the top five, 10 people in the world for that job." - Somer Upload

How it works:

1. Company engages search firm for a specific role

2. Firm develops search strategy and target list

3. Recruiters create market map of potential candidates

4. Initial outreach and screening

5. Present top 5-10 candidates to client

Tips:

• Build relationships with multiple recruiters, not just one

• Understand a firm's specialization before reaching out

• Don't assume contacting one recruiter at a firm means you're considered for all their roles

• Research the different types of firms: big firms (e.g., Korn Ferry), mid-market tech firms (e.g., True Search), and boutique firms

Do:

• Research firms and individual recruiters to understand their focus

• Engage with recruiters at various levels, from associates to partners

• Ask your network for introductions to reputable recruiters

Don't:

• Spam generic messages to every recruiter you can find

• Expect recruiters to find you a job; instead, position yourself as a valuable candidate for their searches

• Ignore boutique firms; they often have strong relationships with specific clients

2. Becoming a "Job Search Magnet"

To attract opportunities, focus on:

• Developing a clear personal brand

• Cultivating relationships with recruiters

• Staying visible in your industry

• Offering value to recruiters

The key is to be memorable so recruiters think of you when relevant roles come up.

"It's all about realizing recruiters aren't helping you get a job. So how do you frame these conversations with them so that you're the person they think of in a month from now, three months from now, in a year from now, in three years from now?" - Colin Lernell

How to craft a "Think of me when..." statement:

1. Identify your unique combination of experiences and strengths

2. Consider the specific problems you've solved and transformations you've led

3. Think about the stage and type of company where you add the most value

4. Craft a concise statement that captures these elements

Examples:

• "Think of me when a SaaS product is growing beyond initial traction and needs to scale from $10M to $100M ARR with a team of 10+ PMs."

• "Think of me when a consumer product company is looking to transition into the enterprise space. I've led this transformation, building teams from scratch to 60+ across geos and landing Fortune 500 clients."

Tips:

• Be specific about your experience and value-add

• Highlight unique journeys/transformations you've led

• Include metrics and tangible outcomes

• Mention specific industries or company stages where you excel

Do:

• Focus on problems you've solved and value you've added

• Update your "Think of me when..." statement as your career evolves

• Practice delivering your statement succinctly in conversations

Don't:

• Use generic descriptions like "seasoned product leader"

• Make your statement too long or complex

• Forget to tailor your statement based on the recruiter's specialization

3. Optimizing Your LinkedIn Profile

Your LinkedIn profile is often the first thing recruiters see. Understanding how recruiters use LinkedIn can help you optimize your profile effectively.

"I love LinkedIn because LinkedIn is fresh and new and people keep their own profiles up to date. And it reminds me of who I already know a lot of the time." - Somer Upload

How recruiters search LinkedIn:

1. Use Boolean search strings with specific titles, keywords, and company names

2. Look for active LinkedIn users (they appear higher in search results)

3. Scan headlines and current roles quickly

4. Click through to read detailed experience for promising candidates

5. Check mutual connections and endorsements

Key elements to optimize:

1. Headline:

   • Use a specific headline, not generic terms

   • Include your current title, company, and key area of expertise

   • Example: "VP of Product at TechCo | Scaling B2B SaaS from $10M to $100M ARR"

2. About section:

   • Focus on your unique value proposition

   • Include a concise version of your "Think of me when..." statement

   • Highlight key accomplishments and areas of expertise

3. Experience:

   • Include details on team size, company stage, and specific accomplishments

   • Use bullet points for easy scanning

   • Start with a brief overview of your role and impact

4. Skills and Endorsements:

   • List relevant technical and leadership skills

   • Seek endorsements from colleagues and direct reports

Tips:

• Include metrics and specifics in your experience descriptions

• Highlight career progression and growth

• Make sure your industry and location are accurately tagged

• Regularly update your profile, especially after major accomplishments

Do:

• Use your headline to clearly state your current role/level and key expertise

• Include a professional, current photo

• Engage on LinkedIn by sharing insights and commenting on relevant posts

Don't:

• Use long narrative bios with fluffy language

• Leave large gaps in your work history unexplained

• Neglect to customize your LinkedIn URL

  Leave a comment

4. Engaging with Recruiters

When interacting with recruiters:

• Start by giving, not taking

• Offer market knowledge, referrals, or leads

• Be responsive and professional

"I think as a recruiter, I care so much about the gold stars that people are putting. If Colin sends me a candidate, I'm like, you know what? That's a good candidate. I can trust that's a good candidate." - Somer Upload

How to approach recruiters:

1. Research: Identify recruiters specializing in your area of expertise

2. Warm introduction: Seek introductions from mutual connections when possible

3. Initial outreach: Craft a personalized message highlighting your value

4. Follow-up: Be persistent but respectful in your follow-ups

5. Ongoing engagement: Stay in touch with periodic updates on your career

Example of a good outreach message:

"Hi [Recruiter Name],

I hope this message finds you well. [Mutual Connection] suggested I reach out to you given your expertise in placing senior product leaders in the B2B SaaS space.

I'm currently the VP of Product at [Company], where I've led the team through our growth from $5M to $50M ARR over the past three years. While I'm not actively looking, I'm always open to interesting opportunities that align with my experience in scaling product organizations.

I'd love to connect and learn more about the types of roles you're currently working on. Additionally, I'd be happy to share insights from my recent experience leading a major platform overhaul, in case it's relevant to any of your searches.

Looking forward to connecting,
[Your Name]"

Tips:

• Personalize your outreach

• Be prepared to discuss your career journey and motivations

• Always be polite, even if processes are frustrating

• Follow up after interviews with thank-you notes and additional insights

Do:

• Refer great candidates for roles that aren't a fit for you

• Offer valuable market insights or feedback on job descriptions

• Stay in touch periodically, even when not actively searching

Don't:

• Send generic "please place me" messages

• Pester recruiters with constant follow-ups

• Speak negatively about previous employers or other recruiters

5. Navigating the Interview Process

During initial recruiter calls:

• Be prepared to discuss your career journey succinctly

• Highlight specific examples of impact and leadership

• Ask thoughtful questions about the role and company

"If you're answering a question, answer it with something you did, not what you would do or should do in a specific situation. They need to give an example back to the client, not a hypothetical." - Colin Lernell

How to prepare for recruiter interviews:

1. Research: Study the company, role, and recent news

2. Reflect: Review your career highlights and prepare specific examples

3. Practice: Rehearse your "Think of me when..." statement and key stories

4. Prepare questions: Develop thoughtful questions about the role and company

5. Technical setup: Ensure a quiet environment and stable internet connection

Example STAR responses:

Situation: "At my previous company, we were struggling to expand into the enterprise market."
Task: "As the newly appointed VP of Product, I was tasked with developing a strategy to land our first Fortune 500 clients."
Action: "I led a cross-functional team to develop a new enterprise-grade feature set, implemented a pilot program with three target clients, and personally oversaw the onboarding process."
Result: "Within 18 months, we secured contracts with five Fortune 500 companies, increasing our ARR by 150% and positioning us as a leader in the enterprise space."

Tips:

• Practice articulating your key accomplishments

• Research the company and role beforehand

• Be clear about your motivations and career goals

• Prepare questions that demonstrate your strategic thinking

Do:

• Provide specific examples of past successes

• Ask about the company's challenges and how the role contributes to solving them

• Follow up with additional thoughts or questions after the interview

Don't:

• "Soapbox" or speak in hypotheticals

• Badmouth previous employers or colleagues

• Discuss compensation details too early in the process

By understanding these key topics and following the advice from experienced recruiters and leaders, you can position yourself to become a "job search magnet" and navigate executive search processes more effectively. Remember, it's about building long-term relationships and clearly communicating your unique value proposition.

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Colin shares key strategies for navigating the executive job market with Bobby Gormson, Partner at True Search and a seasoned executive recruiter with over 20 years in search firms and leading internal talent teams - including Etsy through their IPO and Frame.io through their Adobe acquisition.

Scroll below for Key Takeaways, Slides, and Examples!

⭐️ My Maven bootcamp on the executive job search starts next week!

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The session with Bobby covers:

1. The importance of reputation and networking

2. Crafting effective outreach messages

3. Interactively crafting your “Executive Blurb”

4. Creating compelling LinkedIn profiles

5. Leveraging your networks

6. Connecting with decision-makers

7. Differentiating between contingent and retained search firms

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The episode emphasizes strategic job search techniques, utilizing both warm and cold outreach, and refining profiles to attract recruiters, with interactive elements and Q&A sessions to address common challenges.

00:00 Introduction and Session Overview

00:29 Meet Bobby Gormson: Executive Recruiter Extraordinaire

03:34 Interactive Q&A and Audience Engagement

04:03 Agenda and Icebreaker Activities

07:17 Real-Life Job Search Success Stories

11:34 The Importance of Reputation in Executive Search

16:48 Crafting Your Executive Blurb

35:29 Leveraging Your Network for Job Search Success

36:27 Crafting Genuine Outreach

37:47 Leveraging Peer Networks

40:58 Understanding Executive Search Firms

43:47 Contingent vs. Retained Search Firms

45:20 Effective Networking Strategies

46:14 Q&A Session: Best Practices and Tips

53:19 Final Thoughts and Program Preview

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Key Takeaways:

1. Your reputation matters more than you think

Bobby revealed that every interaction with an executive recruiter is carefully tracked and documented in their systems:

"Every interaction that you have with an executive recruiter is tracked, okay? It's tracked within their system. All firms take notes, whether it's an associate, a principal, a partner. We all take notes and these notes are going to live with your profile within the system."

Colin added:

"Even if you're unresponsive, if you never even answer the message in the first place, that also comes up."

Action items:

• Utilize time with recruiters effectively

• Highlight quantifiable results and achievements

• Be professional and responsive in all interactions

2. Understand the difference between retained and contingent search firms

Bobby emphasized the importance of knowing which type of firm you're dealing with:

"There's two different kinds of search firms. And this is big. There's contingent and there's retained. And they work a bit differently on how they find and present candidates. All search firms are not created equal."

Key differences:

• Retained firms (e.g., True Search, Riviera Partners): Paid upfront, relationship-driven approach

• Contingent firms: Only paid if they place a candidate, more transactional process

3. Craft a compelling "executive blurb"

Having a concise, achievement-focused summary of your experience is crucial.

Example blurb:
"Senior director of product with 12+ years experience in B2B SaaS. Led LLM powered products at Twilio and Dropbox, managing teams of 30+ across US and EMEA, with GM style experience scaling from 1 million to 50 million ARR."

Bobby advised including:

• Your archetype as a product leader (e.g. technical, design-focused, business-oriented)

• Quantifiable results and revenue/growth numbers

• Specific transformations you've driven

"Any anecdote, any numbers, any quantifiable achievements that I can actually take in and then regurgitate to my client is going to be super helpful."

Colin added an important insight:

"If you use very subjective language or things that could be said about pretty much any product leader... So even if it is true for you, if it's also true for the next three people, then it's not useful."

4. Leverage your network strategically

Rather than cold outreach to every recruiter, focus on building warm connections through your network.

Bobby shared:

"I get a lot of warm outreaches from candidates that I have engaged with over the last 5, 10 years...If you're going to put your stamp of approval on this person, I've already built a relationship with you. I'm going to listen to you and feel free to intro."

Colin provided a surprising tip:

"This is a really good hack. If you're, you have a very dry network, and you don't know any executives who have talked to recruiters for some reason, or you're just in a very niche market, and so your network isn't relevant, I like to find people who are peer title peers to me."

Networking tips:

• Reconnect with former colleagues now at target companies

• Engage with industry peers at events or online

• Offer to help others before asking for favors

5. Persistence pays off in outreach

If you don't hear back from a recruiter initially, don't give up. Bobby advised:

"3 is probably my magic number. And it's pretty much spot on, with that 3rd outreach, people, executives are busy, recruiters are incredibly busy...I would say 3 outreaches...Nobody's going to get annoyed by your outreach. If anything, I really appreciate persistence."

Outreach best practices:

• Keep messages concise and tailored

• Reference specific roles or areas of expertise

• Follow up politely after a week or two

Less “credentialed” profile:

6. Optimize your LinkedIn presence

Bobby confirmed that recruiters heavily rely on LinkedIn and its algorithm.

LinkedIn optimization tips:

• Turn on "Open to Work" for recruiters only (not publicly visible)

• Regularly update your profile

• Engage with industry content and post thought leadership

Colin shared a surprising hack:

"If you turn off and on the LinkedIn Open To, does it actually send the pings again? I've heard from executive recruiters that this does work. I've noticed I did this with candidates cause I found out accidentally I told someone to turn it off and on. And the next day he got seven recruiter inbound." “Yes!”

The Hidden Job Market is Real

Perhaps most importantly, Bobby confirmed that for senior executive roles, much of the market is indeed hidden:

"Things have to be confidential at the top level. and honestly, the hiring managers only want to see five to ten candidates."

Colin emphasized the importance of networking:

"What they should do is about 75 percent networking. And that includes some semi cooled outreach, but Outreach with some warm connection, right? Actively going and finding connections into things. And what they actually do is about 10 percent that, and a lot of cold applying, cold DMing people with templates, that type of thing. And it's just completely backwards at this point in your career."

FAQ from the Audience

Q: How do we find out what reputation we may already have in the system?

Bobby: "If you build a relationship with the recruiter, you can just ask them. Hey, what's the word internally here at true or Riviera? How is my profile, internally there, is there anything I can do to bolster my profile with you all?"

Q: If you reach out to a recruiter and don't get a response, should you follow up? How many times should you try before giving up?

Bobby: "I would say 3 outreaches... Nobody's going to get annoyed by your outreach. If anything, I really appreciate persistence."

Q: What do you recommend for someone that doesn't have big brands on their resume?

Bobby: "Even if you don't have the brand names, there are other ways to bolster that, whether it's articles, blog posts, interviews, share ideas, thought leadership ideas, post on LinkedIn. And of course the videos that I just mentioned of, if you're a speaker at a conference or leading a small event."

Q: Should you always focus on the bigger ARR numbers in your blurb?

Bobby: "I think there's a different inflection point, 0 to 40, and I have a role that we're working on now from, it's a CTO role, that this company's at 40 million ARR. And they're looking for someone to take them from 40 to 100. And the person that is in the seat now took them from 0 to 40. And it's a different profile."

Q: How would one represent ARR if work experience has been at Fortune 25 companies?

Bobby: "The number is going to be big. What was your impact? I would just say here is what I did to either cut costs or to scale revenue from 250,000,000 to 350,000,000. You had to do something really well."

What's Coming Up:

Part 1: Understanding Executive Search (You are here)

Part 2: Positioning, Resume, LinkedIn, Pitch & Dossier for Product Leaders

Part 3: Networking Strategies

Part 4: Mastering Executive Interviews (Triple STAR)

Part 5: Negotiation and Picking the Right Role

📣 Exciting Announcement!

Join my upcoming Maven program:

"Product Executive Job Search: Land Hidden Roles, Interviews, and Top Offers"

• Tailored for Director, VP, and CPO candidates
• Hands-on workshops and projects from resume to negotiations
• Direct access to executive recruiters and product leaders

Please share this with any other product leaders you may know on the job hunt.

👉 Learn More and Apply Here

WATCH TWO FREE 60-MINUTE LIGHTNING LESSONS WITH TOP RECRUITERS

1) The Product Leader’s Guide to Executive Search

with Somer Hackley
CEO of Distinguished Search, CT Partners, Author of Search In Plan Sight

Wed, Oct 9, 12:00PM (PDT)

2) Unlock the Hidden Product Executive Job Market

with Bobby Gormsen
Partner at True Search, ex-Riviera, Etsy, Frame.io, and Google

Wed, Oct 9, 6:00PM (PDT)

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Now, let's dive into understanding the executive search landscape...

As a seasoned product leader eyeing Director, VP, or CPO roles, you're entering a different playing field. The best opportunities at this level often never see the light of day on job boards or LinkedIn postings. Welcome to the world of executive recruiting, where discretion, networks, and insider knowledge reign.

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The Hidden Job Market: Why It Exists

Before we dive into how to navigate this landscape, let's understand why it exists:

1. Confidentiality: Companies often need to replace underperforming executives or create new strategic roles without causing internal drama or tipping off competitors.

2. Targeted Searches: For critical leadership positions, companies prefer to headhunt specific, proven talents rather than sifting through a pile of resumes.

3. Network Leverage: At the executive level, it's all about who you know. Companies tap into their board members', investors', and executives' networks to find the right fit.

4. Quality Control: Public postings for high-level roles can lead to an avalanche of unqualified applicants, creating a time-sink for HR and hiring managers.

How Executive Searches Really Work

Understanding the mechanics of executive search can give you a significant advantage:

1. Retained vs. Contingent Search:

   • Most executive searches are retained, meaning the search firm is paid upfront to conduct an exclusive search.

   • This incentivizes them to find the best candidate, not just the first acceptable one.

     

2. The Process:

   • Briefing: The search firm works closely with the client to define the role, ideal candidate profile, and search parameters.

   • Research: They identify potential candidates through their database, network, and targeted research.

   • Outreach: Recruiters discreetly contact potential candidates to gauge interest.

   • Screening: Initial interviews to assess fit and interest.

   • Client Presentation: A shortlist of candidates is presented to the client.

   • Interview Process: Multiple rounds with various stakeholders.

   • Offer and Negotiation: The search firm often acts as an intermediary.

3. The Players:

   • Researchers/Associates: Build the initial candidate pipeline.

   • Consultants: Your main point of contact, conducting initial interviews.

   • Partners: Manage client relationships and often handle final candidate stages.

4. Timelines:

   • Executive searches can take 3-6 months or longer, especially for C-suite roles.

   • The process is thorough and often involves extensive backchannel referencing.

5. Exclusivity:

   • Once a firm is retained for a search, they "own" that search.

   • If you're introduced to a company through a search firm, that firm will represent you throughout the process.

Now that we understand the landscape, let's look at the key players and how to engage with them effectively.

Understanding the Executive Search Landscape

Executive search firms vary widely in size, focus, and approach. Here's a breakdown of the key players:

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Large Global Firms ("SHREK")

• Spencer Stuart

• Heidrick & Struggles

• Russell Reynolds

• Egon Zehnder

• Korn Ferry

These behemoths focus on all leadership roles for large corporations and Fortune 500 companies globally. They typically handle C-suite and board-level searches.

Mid-Market Firms

• True Search

• Daversa Partners

• Riviera Partners

• SPMB

These firms specialize in director to C-level roles for VC-backed to public companies, primarily in the US. They often have specialized partners for different sectors.

Boutique Firms

• Paradigm Search

• Fusion

• Artico

• Artisanal Talent

• Nucleus Talent

• People Project

These smaller firms are typically started by Partners of the larger firms who want to take on a select set of clientele and be more involved in the search. They focus on specific niches within product and engineering leadership roles, ranging from seed-stage startups to public companies.

Choosing the Right Firm for Your Search

Your choice of firm should align with your experience level and target companies:

1. For director-level roles in VC-backed companies, focus on mid-market firms like Riviera Partners or Daversa Partners.

2. For VP and C-level roles in high-growth tech companies, consider boutique firms like Paradigm Search or Fusion.

3. For executive roles in large public companies, target the SHREK firms.

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Strategies for Engaging with Executive Search Firms

Now that you understand the landscape, here's how to effectively engage with these firms:

1. Build Relationships Early:

   • Don't wait until you're actively job searching to connect with recruiters.

   • Engage with them when you're not looking, providing market insights or referrals.

2. Be a Valuable Node:

   • Recruiters thrive on information and connections.

   • Offer insights about your industry or refer strong candidates for other roles.

3. Clarify Your Value Proposition:

   • Be crystal clear about your expertise, achievements, and the types of roles you're interested in.

   • Quantify your impact wherever possible (e.g., revenue growth, team scaling).

4. Stay Top of Mind:

   • Periodically update your contacts with career milestones or industry observations.

   • Congratulate them on successful placements you hear about.

5. Be Responsive:

   • When a recruiter reaches out, respond promptly, even if the opportunity isn't right for you.

   • Your responsiveness and professionalism can keep you on their radar for future roles.

6. Leverage Your Network:

   • Seek warm introductions to recruiters whenever possible.

   • A referral from a mutual connection can fast-track you to their "high potential" list.

7. Prepare for the Long Game:

   • Building relationships with top search firms is a career-long endeavor.

   • Don't expect immediate results, but rather focus on cultivating trust and credibility over time.

Crafting Your Outreach

When reaching out to recruiters, be direct and highlight your most relevant experience. Here's a template:

Subject: [Your Level] Product Leader with [Key Experience] - Exploring Opportunities

[Recruiter's Name],

[Insert non-cringe reason you're reaching out - ideally through a shared connection, but okay if you engaged with their content, see they focus on specifically your domain/specialty/niche, or similar]

[X] years of product leadership experience in [Industry/Sectors] focusing on [specialties].
- [Key Achievement 1]
- [Key Achievement 2]
- [Key Achievement 3]

I'm exploring [target role] opportunities at [company stage/type] in the [specific industry] space. Would you be opposed to discussing how my background aligns with your current searches?

[Your Name]

Example based on the template:

Subject: Unicorn CPO and multi-time founder with AI/ML Scaling Experience - Exploring Opportunities

Hey Alex, Derek Johnson had great things to say about working with you on his last search and I thought I would reach out as I'm considering my next move.

15+ years of product leader in B2B SaaS and AI/ML applications, focusing on launching Enterprise and new markets within Consumer companies as well as LLM-powered products.

• As CPO of SaleyAI, scaled AI-powered talent platform from $1M to $50M ARR in 3 years

• As CPO and GM at EdCo, led Enterprise pivot, managing a 100+ person product org across 5 global offices

• Launched industry's first LLM-based procurement tool, capturing 30% market share in 18 months

I'm exploring CPO opportunities at Series C+ or public companies in the Enterprise SaaS space.

Available to discuss how my background aligns with your current searches?

Jacqueline

This LinkedIn connection request note worked very well for a VP Product I coach. But this is fairly generic and won’t work for many profiles that aren’t a clear fit.

Hi Sarah! I'm an experienced (15+ years) Product Leader in enterprise SaaS including VP of Product at Calm and helping scale a Series B startup to unicorn status. I know Riviera Partners works with consumer subscription companies. Would be great to connect.

Understanding the Recruiter's Perspective

To effectively navigate the executive search landscape, it's crucial to understand the recruiter's motivations and challenges:

1. Client-Centric Focus:

   • Recruiters are primarily serving their client companies, not candidates.

   • Their goal is to find the best fit for the role, not necessarily to find you a job.

2. Time Pressure:

   • Recruiters often juggle multiple searches simultaneously.

   • They prioritize candidates who are responsive and easy to work with.

3. Fit Beyond Skills:

   • At the executive level, cultural fit and leadership style are often as important as technical skills.

   • Recruiters assess how you'll mesh with the existing executive team.

4. Long-Term Relationships:

   • Top recruiters think beyond the current search.

   • Building a relationship with you could lead to future placements or referrals.

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Maximizing Your Visibility to Search Firms on LinkedIn

To increase your chances of being found by executive recruiters for inbound, optimize your LinkedIn profile with these targeted strategies:

1. Strategic Keyword Placement:

   • Use industry-specific keywords and job titles in your headline, About section, and job descriptions.

   • Include terms like "Product Leadership," "CPO," "VP Product," or specific areas like "AI/ML Product Strategy."

2. Detailed, Searchable Job Titles:

   • Use your actual title, but add specifics: "VP Product, Enterprise SaaS" or "Director of Product, Fintech Solutions"

   • In job descriptions, include alternative titles recruiters might search for.

3. Comprehensive "About" Section:

   • Front-load with key information: years of experience, industry focus, team size managed, budget controlled.

   • List specific domains, company stages, and specialties you've worked in.

   • Include a clear career summary with highlights.

4. Quantifiable Achievements:

   • For each role, list 3-5 bullet points with specific, measurable accomplishments.

   • Use numbers, percentages, and dollar amounts to quantify your impact.

5. Skills and Endorsements:

   • List relevant skills that match your target roles and get endorsed for them.

   • Prioritize skills that align with common recruiter search terms.

6. Recommendations:

   • Obtain recommendations from senior executives, focusing on specific projects or skills.

   • Ask recommenders to include keywords relevant to your target roles.

7. Activity and Engagement:

   • Regularly share or comment on industry-relevant content.

   • Participate in LinkedIn groups frequented by recruiters in your industry.

8. Profile Settings:

   • Ensure your profile is set to "Open to New Opportunities" in your career interests.

   • Allow your profile to be visible to recruiters at companies you're interested in.

9. LinkedIn URL:

   • Customize your LinkedIn URL to include your name and possibly your focus area.

10. Regular Updates:

    • Update your profile quarterly with new achievements or skills.

    • Each update increases your visibility in recruiter searches.

11. Premium LinkedIn Features:

    • Consider LinkedIn Premium to appear higher in recruiter searches and see who's viewed your profile.

12. SEO Optimization:

    • Use LinkedIn's search feature to find profiles similar to yours and note commonly used terms.

    • Incorporate these terms naturally throughout your profile.

Reverse Engineer the CAR

Candidate Assessment Reports and Dossiers are used by recruiters to help communicate candidates in the most relevant way to the hiring manager before putting them in front of them. You want to ensure your profile online meets the types of qualifications and search criteria they will be looking for.

CANDIDATE ASSESSMENT REPORT (CAR)

Position: VP Product, Enterprise at TechScale Solutions

Candidate Name: Alex Chenn
Email: alex.chenn@email.com
Phone: (415) 555-7890

GENERAL OVERVIEW

Should the Candidate Move Forward? YES.

Alex is an outstanding candidate! He has been working as the Senior Director of Product at EnterpriseCloud for the past 4 years, leading their core enterprise SaaS platform. Alex is actively pursuing opportunities to move into a larger enterprise software company with a focus on AI/ML integration. He was exceptionally well-prepared for our conversation, demonstrating in-depth knowledge of TechScale's product suite, recent AI initiatives, and competitive landscape. Alex considers himself a "product visionary with an execution mindset" and has a track record of successfully scaling both products and teams.

RESEARCH CRITERIA (OVERALL SCORE 4.7 OUT OF 5)

Seniority: Is this person at or near VP level in Product? Score: 4.5
Yes, we scored him 4.5 out of 5 because he is at the Senior Director level, just one step below VP, and is managing a $100M+ product line with a team of 15+ product managers and their managers.

Location: Can this person be onsite daily? Score: 5.0
Alex lives in San Francisco and is willing to commute to TechScale's office regularly. He expressed enthusiasm for in-person collaboration.

Experience: Does this person have experience at a large, well-known tech company? Score: 5.0
Alex has over 12 years of experience in enterprise SaaS, including significant roles at Salesforce and Oracle before joining EnterpriseCloud.

QUALIFICATIONS

Communication Skills: Alex communicates with clarity and confidence. He articulated complex product strategies and technical concepts with ease, breaking them down for non-technical stakeholders. His responses were well-structured, demonstrating strong executive presence.

Experience: Alex walked me through his product leadership journey:

• Started as a Product Manager at Salesforce, working on their Sales Cloud product.

• Moved to Oracle as a Senior PM, where he led the development of AI-enhanced analytics features.

• Joined EnterpriseCloud as Director of Product, quickly promoted to Senior Director.

• At EnterpriseCloud, he spearheaded the company's AI strategy, launching their AI-powered assistant that now processes 60% of customer queries.

Skills: Alex showcases a rare blend of strategic thinking and tactical execution:

• Product Strategy: Developed EnterpriseCloud's 3-year product roadmap, aligning it with market trends and customer needs.

• AI/ML Integration: Led the development and launch of EnterpriseCloud's AI platform, now a key differentiator in the market.

• Team Leadership: Implemented a mentorship program that improved team retention by 25%.

• Stakeholder Management: Successfully navigated complex organizational dynamics to secure buy-in for major product initiatives.

Motivations: Alex is driven by:

• Solving complex technical challenges at scale

• Building and mentoring high-performing product teams

• Creating products that significantly impact how enterprises operate

• Working at the forefront of AI/ML integration in enterprise software

Challenges & Adversity: At EnterpriseCloud, Alex faced significant resistance when proposing the AI initiative. He overcame this by:

• Developing a comprehensive business case with clear ROI projections

• Creating a prototype to demonstrate the potential impact

• Building a coalition of supporters across engineering, sales, and customer success teams

Interests & Cultural Fit: Alex is passionate about enterprise software and the potential of AI to transform businesses. He's an avid reader of tech publications and regularly attends AI conferences. Alex values a culture of innovation, continuous learning, and cross-functional collaboration – all of which align well with TechScale's ethos.

INTEREST

Role: Alex is highly interested in the VP Product role at TechScale. He sees it as an opportunity to:

• Lead a larger product organization and drive enterprise-wide product strategy

• Expand his impact in the AI/ML space with TechScale's resources and market position

• Shape the future of enterprise software by integrating cutting-edge AI capabilities

Company: Alex is excited about TechScale for several reasons:

• TechScale's strong market position and growth trajectory in the enterprise space

• The company's commitment to AI/ML innovation

• The opportunity to work with a talented team and influential enterprise clients

Potential Obstacles: While Alex is very interested, he did express two concerns:

1. Work-life balance: He wants to ensure the role allows him to maintain his commitment to his family.

2. Decision-making processes: Coming from a smaller company, he's curious about how quickly TechScale can move on strategic product decisions.

AVAILABILITY

Timing: Alex is currently employed but actively exploring opportunities. He would need to give a 4-week notice at EnterpriseCloud and would prefer a short break between roles. He could potentially start within 6-8 weeks of an offer.

Compensation:
Current: $250K base, $100K bonus, $500K equity (4-year vest)
Expected: $300K-$325K base, $150K-$175K bonus, $1.5M-$2M equity

Alex emphasized that while compensation is important, he's more focused on the role's potential impact and growth opportunities. He's open to discussing a package that balances cash and equity.

Next Steps: Schedule an in-person interview with the CPO and key stakeholders. Provide Alex with more details on TechScale's AI strategy and product roadmap to address his questions about decision-making processes.

RECOMMENDATION

Alex is an exceptional candidate who should absolutely move forward in the process. His blend of enterprise experience, AI/ML expertise, and proven leadership in scaling products and teams makes him an ideal fit for the VP Product role at TechScale. His strategic vision, coupled with his ability to execute and lead teams, could significantly accelerate TechScale's AI initiatives and overall product strategy.

Compared to other candidates, Alex stands out due to his direct experience in successfully integrating AI into enterprise products and his track record of driving significant revenue growth. His clear communication style and strategic thinking will be valuable assets in collaborating with C-level executives and board members.

I strongly recommend bringing Alex in for in-person interviews as soon as possible, as candidates of his caliber are likely to have multiple opportunities.

Navigating the Executive Search Process

Once you're in an active search process, here's how to navigate it effectively:

1. Initial Contact:

   • Respond promptly, even if it's just to schedule a call for later.

   • Do your homework on the recruiter and their firm before the call.

2. Screening Interview:

   • Treat this as seriously as you would a client interview.

   • Be prepared to articulate your leadership philosophy and key achievements.

   • Ask thoughtful questions about the role and company.

3. Interview Preparation:

   • Request a comprehensive brief on the role, company, and key stakeholders.

   • Research the company thoroughly, including recent news, financials, and competitive landscape.

   • Prepare specific examples that demonstrate your fit for the role.

4. Client Interviews:

   • Expect multiple rounds with various stakeholders.

   • Be consistent in your messaging across interviews.

   • Follow up with the recruiter after each round for feedback and next steps.

5. References and Background Checks:

   • Be proactive in managing your references.

   • Alert your references that they may be contacted.

   • Provide context about the role to help your references tailor their comments.

6. Offer Negotiation:

   • Leverage the recruiter's insights on the company's compensation structure.

   • Be clear about your expectations early in the process.

   • Remember, the recruiter can be a valuable ally in negotiations.

Handling Multiple Search Firms

As a senior executive, you may find yourself working with multiple search firms. Here's how to manage this effectively:

1. Maintain Transparency:

   • Always inform recruiters if you're actively engaged in other searches.

   • Be clear about your timeline and decision-making process.

2. Respect Exclusivity:

   • If a firm introduces you to a company, don't try to circumvent them, even if another firm approaches you about the same role.

3. Manage Information Flow:

   • Keep detailed notes on which firms are representing you for which opportunities.

   • Ensure your story and salary expectations remain consistent across all interactions.

4. Set Boundaries:

   • It's okay to limit the number of firms you're actively working with to avoid overwhelm.

   • Be polite but firm if you need to decline engagement with a particular firm.

The Power of Backchannel References

In executive searches, backchannel references play a crucial role. Here's what you need to know:

1. Anticipate Backchannel Checks:

   • Assume that recruiters and hiring companies will reach out to mutual connections, even if you haven't provided them as formal references.

2. Map Your Network:

   • Identify potential backchannel references in your industry.

   • Think about former colleagues, bosses, and even competitors who might be contacted.

3. Proactive Outreach:

   • Reach out to these contacts before they're contacted by others.

   • Update them on your career goals and refresh their memory about your work together.

4. Address Potential Issues:

   • If there's someone in your network who might not give you a glowing review, try to address it head-on.

   • Sometimes, a frank conversation can turn a potential detractor into an advocate.

Continuous Engagement Strategy

Remember, your relationship with executive search firms should be an ongoing part of your career strategy, not just something you activate when job hunting. Here's how to stay engaged:

1. Regular Check-ins:

   • Schedule brief, quarterly check-ins with your key recruiter contacts.

   • Update them on your recent achievements and any shifts in your career interests.

2. Industry Intelligence:

   • Share relevant industry insights or trends you're observing.

   • This positions you as a valuable source of market intelligence.

3. Referrals:

   • When you come across exceptional talent, consider referring them to your recruiter contacts.

   • This reinforces your value as a node in their network.

4. Career Milestones:

   • Hit a significant achievement or milestone? Let your recruiter contacts know.

   • This keeps you top-of-mind for potential opportunities.

5. Continuous Learning:

   • Keep recruiters informed about new skills or expertise you're developing.

   • This could open doors to opportunities you might not have previously considered.

By implementing these strategies, you're not just preparing for your next move; you're positioning yourself as a valuable asset in the executive talent ecosystem. This approach ensures that when the right opportunity arises, you're not just on the radar – you're at the top of the list.

In our next installment, we'll explore how to craft a compelling executive narrative that resonates with both recruiters and potential employers. We'll dive into storytelling techniques that highlight your unique value proposition and position you as the ideal candidate for top-tier product leadership roles.

Ever struggled to explain what makes you unique as a product leader? You're not alone. Whether you're gunning for a VP Product role or eyeing a CPO position, standing out in the crowded field of product leadership can be tough.

This article will help you build a clear picture of your product leadership strengths. We'll dive into a framework that covers your product management leadership archetype, superpowers, expertise areas, and product-culture fit. By the end, you'll have a sharper sense of what sets you apart - and how to position yourself for the right opportunities.

Let’s build your comprehensive product leadership profile.

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Table of Contents

1. Product Leadership Archetypes

2. Core Product Management Superpowers

3. Expertise Areas

4. Product Cultures

5. PM Culture Types

6. Synthesizing Your Product Leadership Profile

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Introduction to Archetypes

In product management, archetypes are different styles of leadership. Each archetype has its own strengths, skills, and ideal work environments. Knowing your primary and secondary archetypes can help you understand your natural abilities and areas for improvement. This lesson will help you identify which product leadership archetypes suit you best, so you can clearly communicate your value and find the right fit in a team or organization.

This article expands a framework for product leaders inspired by ’s article on PM archetypes, ’s work on PM Superpowers, and Reforge’s content on important career profile factors for product managers. Thank you to those creators.

I. Product Leadership Archetypes

As I coach more and more product leaders, I’ve found that there are a consistent set of archetypes. Some have a primary and secondary type. Some layer on superpowers and domain specialties. Some have very different product culture preferences. But we always tend to start with a pretty solid idea of their archetype.

Here is my adapted list of archetypes for product management Directors, VPs, and CPOs.

Growth Driver

• Focus: Scaling products and driving user engagement through data-driven strategies

• Key Skills: Advanced data analysis, A/B testing, user acquisition strategies, funnel optimization, retention modeling, marketing channel optimization, cohort analysis, predictive modeling

• Background: Often from data science, growth marketing, or analytics

• Favorite Metrics: CAC, LTV, retention rates, conversion funnel metrics, virality coefficient

• Ideal Environment: Companies with product-market fit, ready for rapid scaling

• Example: Sarah increased user retention by 40% through cohort analysis and targeted engagement campaigns at a SaaS startup.

• Challenges: Rapid user base expansion, improving key performance metrics, data-driven decision making, identifying and optimizing growth levers

• Blindspots: Prioritizing metrics over user experience, short-term gains over sustainable growth

• Tools: Mixpanel, Amplitude, Optimizely, SQL, growth modeling spreadsheets

UX Innovator

• Focus: Creating intuitive, user-centered product experiences

• Key Skills: User research, prototyping, information architecture, visual design, usability testing, interaction design, accessibility, design thinking

• Background: Often from UX design, interaction design, or cognitive psychology

• Favorite Methods: User interviews, journey mapping, card sorting, usability labs, eye-tracking studies

• Ideal Environment: Companies where product differentiation comes from superior user experience

• Example: Michael increased new user activation by 25% by redesigning an app's onboarding flow.

• Challenges: Solving complex user problems, creating delightful experiences, reducing friction in user journeys

• Blindspots: Over-designing or focusing too much on aesthetics at the expense of functionality or business goals

Internal Scaler

• Focus: Improving internal processes and operational efficiency

• Key Skills: Process optimization, cross-functional collaboration, change management, project management, team productivity tools and methodologies, workflow automation, resource allocation, organizational design

• Background: Often from operations, project management, or business analysis

• Favorite Frameworks: Agile, Lean, Six Sigma, OKRs, RACI matrices

• Ideal Environment: Rapidly growing companies facing operational challenges

• Example: Alex implemented a new project management system that reduced time-to-market by 30%.

• Challenges: Streamlining workflows, improving team productivity, managing complex cross-functional projects

• Blindspots: Focusing too much on process over product outcomes or user needs

General Manager

• Focus: Overall product strategy and P&L responsibility

• Key Skills: Strategic planning, financial management, leadership and team building, market analysis, stakeholder management, business model innovation, portfolio management, risk assessment and mitigation

• Background: Often MBA, management consulting, or business operations

• Favorite Metrics: Revenue, profit margins, market share, customer lifetime value, return on investment

• Ideal Environment: Established companies with multiple product lines

• Example: Jamie led a product division to 50% year-over-year growth by realigning the product portfolio with market demands.

• Challenges: Setting long-term vision, managing complex product ecosystems, balancing multiple stakeholder needs

• Blindspots: Being too removed from day-to-day product development or user needs

Commercial Leader

• Focus: Driving revenue growth and market expansion

• Key Skills: Go-to-market strategy, pricing and packaging, sales enablement, competitive analysis, partnership development, market segmentation, channel strategy, customer relationship management

• Background: Often from sales, marketing, or business development

• Favorite Activities: Pricing strategy, sales pipeline analysis, market sizing, competitor benchmarking

• Ideal Environment: Companies looking to monetize or expand market share

• Example: Casey developed a new pricing model that increased ARPU by 35%.

• Challenges: Identifying new revenue streams, optimizing pricing strategies, aligning product with sales goals

• Blindspots: Prioritizing short-term revenue gains over long-term product health or user satisfaction

Product Optimizer

• Focus: Continuously improving existing products

• Key Skills: Feature prioritization, A/B testing and experimentation, incremental innovation, user feedback analysis, performance optimization, technical debt management, product analytics, customer support integration

• Background: Often from product management, UX research, or data analysis

• Favorite Methods: Feature impact assessment, user surveys, usage analytics, customer feedback loops

• Ideal Environment: Companies with established products seeking ongoing improvement

• Example: Taylor increased product usage by 20% through targeted feature enhancements based on user feedback and behavior analysis.

• Challenges: Identifying and fixing pain points, optimizing user flows, balancing new features with performance

• Blindspots: Focusing too much on incremental improvements at the expense of disruptive innovation

Technician

• Focus: Managing complex technical products or platforms

• Key Skills: Technical architecture understanding, API design and management, system integrations, performance optimization, security and compliance knowledge, database design, scalability planning, DevOps practices

• Background: Often from software engineering or systems architecture

• Favorite Challenges: Solving complex technical problems, optimizing system performance, designing scalable architectures

• Ideal Environment: Companies building technical products or platforms

• Example: Sam led the development of a new API that enabled 100+ new integrations.

• Challenges: Bridging technical and business requirements, managing complex technical dependencies

• Blindspots: Prioritizing technical elegance over user needs or business goals

Zero-to-One Innovator

• Focus: Creating entirely new products or entering new markets

• Key Skills: Market validation, rapid prototyping, vision setting, risk management, storytelling and evangelism, design thinking, lean startup methodologies, disruptive innovation theories

• Background: Often from entrepreneurship, R&D, or innovation labs

• Favorite Activities: Ideation workshops, MVP development, pitch presentations, trend analysis

• Ideal Environment: Startups, innovation-focused companies

• Example: Jordan launched a new product category in the IoT space, generating $10M in first-year revenue.

• Challenges: Identifying unmet market needs, creating disruptive solutions, navigating high uncertainty

• Blindspots: Underestimating operational challenges of scaling or maintaining a product post-launch

New Market-Fit Expander

• Focus: Adapting existing products for new markets or use cases

• Key Skills: Market research, product localization, use case expansion, cultural sensitivity, adaptability, international business practices, regulatory compliance across markets, cross-cultural communication

• Background: Often from international business, product marketing, or anthropology

• Favorite Methods: Market segmentation, user persona development, cultural analysis, localization testing

• Ideal Environment: Companies looking to expand into new markets or verticals

• Example: Charlie adapted a B2C product for B2B use, opening up a new $50M market.

• Challenges: Identifying product-market fit in new contexts, balancing core product integrity with local needs

• Blindspots: Overestimating the transferability of product success across markets

Question for Your Profile: Which two archetypes do you most identify with? Choose your primary and secondary archetype.

II. Core Product Management Superpowers

Product management superpowers refer to the unique strengths and skills that a product manager brings to the table. These superpowers can greatly influence how a product manager approaches their role, solves problems, and drives product success. Understanding your superpowers can help you leverage them effectively in your career, ensuring that you are playing to your strengths and continuously developing areas that are crucial for your growth as a product leader.

Superpower 1: Product Crafting

• Description: Creating innovative, user-centric products that solve real problems

• Key Skills: Feature specification and prioritization, product vision and roadmapping, UX design principles, prototyping and iteration, user story development, product requirements documentation, balancing user needs with business goals, cross-functional collaboration in product development

• How It Manifests: PMs with this superpower excel at turning abstract ideas into concrete product features. They have a keen sense of what makes a product intuitive and valuable to users. They can articulate a clear product vision and translate it into actionable steps for development teams.

Superpower 2: Growth Expertise

• Description: Scaling products and driving user acquisition and engagement

• Key Skills: Data analysis and interpretation, growth modeling and forecasting, A/B testing and experimentation, user acquisition strategies, retention and engagement tactics, funnel optimization, viral loop design, marketing channel optimization

• How It Manifests: PMs with this superpower are adept at identifying growth levers and designing experiments to optimize key metrics. They have a deep understanding of user behavior and can develop strategies to rapidly scale user bases while maintaining engagement.

Superpower 3: Organizational Expertise

• Description: Managing complex, cross-functional projects and processes

• Key Skills: Stakeholder management, process optimization, change management, project management, cross-functional collaboration, organizational design, conflict resolution, resource allocation

• How It Manifests: PMs with this superpower are adept at navigating complex organizational structures and aligning diverse teams towards common goals. They can design and implement efficient processes that improve overall product development and delivery.

Superpower 4: Team Expertise

• Description: Building and leading high-performing product teams

• Key Skills: Hiring and talent assessment, mentoring and coaching, performance management, team culture development, conflict resolution, agile team management, fostering innovation and creativity, building diverse and inclusive teams

• How It Manifests: PMs with this superpower excel at assembling diverse, talented teams and fostering a positive team culture. They can identify and develop individual strengths, manage conflicts effectively, and create an environment where team members can do their best work.

Question for Your Profile: Which two superpowers do you feel are your strongest? Choose your primary and secondary superpower.

III. Expertise Areas

Identifying your areas of expertise is crucial for tailoring your job search, enhancing your resume, and excelling in interviews. This section will help you pinpoint your experience and strengths across various markets, business models, industry verticals, and technologies. By reflecting on these areas, you can better align your career path with your unique skills and knowledge, ensuring you are positioned for success in roles that best fit your expertise. Use this insight to highlight your strengths in your resume, articulate your value in interviews, and target job opportunities that align with your background and interests.

Markets:

1. B2B (Business-to-Business)

2. B2C (Business-to-Consumer)

3. B2B2C (Business-to-Business-to-Consumer)

4. C2C (Consumer-to-Consumer)

5. D2C (Direct-to-Consumer)

Business Models:

1. SaaS (Software as a Service)

2. Marketplace

3. E-commerce

4. Subscription

5. Freemium

6. Ad-supported

Industry Verticals:

1. FinTech

2. HealthTech

3. EdTech

4. E-commerce

5. AdTech

6. PropTech

7. AgTech

8. CleanTech

9. Social Networking

10. Gaming

Technologies:

1. Artificial Intelligence / Machine Learning

2. Blockchain / Cryptocurrency

3. Internet of Things (IoT)

4. Cloud Computing

5. Augmented Reality / Virtual Reality (AR/VR)

6. 5G and Edge Computing

7. Cybersecurity

8. Big Data Analytics

9. Robotics and Automation

10. Quantum Computing

Questions for Your Profile:

1. Which 1-2 markets do you have the most experience in?

2. Which 1-2 business models are you most familiar with?

3. Which 1-2 industry verticals do you have expertise in?

4. Which 0-2 technologies do you have deep knowledge of?

IV. Product Cultures

Understanding the culture of a product team or organization is crucial for aligning your personal strengths and working style with your work environment. Different product cultures emphasize various aspects of product development, from technical innovation to user experience and data-driven decision making. Identifying the type of product culture you thrive in can help ensure you are in an environment that best supports your growth and success.

These were drawn from ’s famous post on the topic.

Summary of Product Cultures

Engineering-Driven Culture

• Characteristics: Focus on technical innovation and problem-solving, products often start with a unique technical insight, high value placed on engineering talent and technical skills, decision-making often based on technical feasibility and elegance

• Strengths: Ability to create technically superior products, strong focus on solving complex technical challenges, often leads to breakthrough innovations

• Challenges: Prioritizing technical solutions over user needs, struggling with non-technical products or markets, risk of over-engineering solutions

• Examples: Google, Microsoft, Dropbox

• PM Role: Need to be technically proficient, focus on translating technical capabilities into user value, balance technical ambition with market realities and user needs

• Signals in Job Descriptions: Emphasis on technical skills or engineering background, mentions of working closely with engineering teams, focus on technical problem-solving

Data-Driven Culture

• Characteristics: Heavy reliance on metrics and A/B testing for decision-making, strong focus on optimization and incremental improvements, product decisions often based on quantitative analysis

• Strengths: Ability to rapidly iterate and improve products based on user behavior, clear definition of success through measurable metrics, reduced reliance on individual opinions for decision-making

• Challenges: Risk of short-term focus at the expense of long-term vision, struggling with decisions that can't be easily quantified, potential for over-optimization leading to local maxima

• Examples: Facebook, LinkedIn, Zynga

• PM Role: Need strong analytical skills and comfort with data interpretation, focus on defining and tracking relevant metrics, balance data-driven decisions with qualitative insights and long-term strategy

• Signals in Job Descriptions: Emphasis on analytical skills and data interpretation, mentions of A/B testing and experimentation, focus on metrics and KPIs

Design-Driven Culture

• Characteristics: Strong emphasis on user experience and aesthetic quality, products often differentiated by superior design and usability, high value placed on design talent and user research

• Strengths: Ability to create intuitive, delightful user experiences, often leads to strong brand loyalty and emotional connection with users, can revolutionize existing markets through superior UX

• Challenges: Prioritizing form over function, decision-making can be subjective and rely heavily on "taste", struggling with highly technical or backend-focused products

• Examples: Apple, Airbnb, Snapchat

• PM Role: Need strong understanding of design principles and user-centered thinking, focus on facilitating collaboration between design and other functions, balance design ambition with technical feasibility and business goals

• Signals in Job Descriptions: Emphasis on user experience and design thinking, mentions of working closely with design teams, focus on creating intuitive and delightful products

Sales-Driven Culture

• Characteristics: Strong focus on meeting customer demands and closing deals, product roadmap often influenced by sales pipeline and customer requests, high value placed on customer relationships and sales expertise

• Strengths: Close alignment with customer needs and market demands, ability to rapidly respond to customer feedback, often leads to strong customer loyalty and high retention

• Challenges: Building one-off solutions for specific customers, struggling with long-term product vision and coherence, risk of feature bloat and increased product complexity

• Examples: Salesforce, Oracle, Workday

• PM Role: Need strong communication skills and ability to manage customer expectations, focus on balancing individual customer needs with broader market demands, translate customer requests into scalable product features

• Signals in Job Descriptions: Emphasis on customer relationship management, mentions of working closely with sales teams, focus on enterprise or B2B products

Vision-Driven Culture

• Characteristics: Strong emphasis on long-term vision and transformative ideas, products often aim to create new categories or disrupt existing markets, high value placed on innovation and big-picture thinking

• Strengths: Ability to create revolutionary products, often leads to strong market positioning and thought leadership, can attract top talent excited by ambitious goals

• Challenges: Losing touch with current market realities, struggling with execution of day-to-day product development, resource strain if vision is too ambitious

• Examples: Tesla, SpaceX, early Amazon

• PM Role: Need strong strategic thinking and ability to translate vision into actionable plans, focus on balancing visionary goals with practical execution, communicate and rally teams around long-term objectives

• Signals in Job Descriptions: Emphasis on strategic thinking and vision setting, mentions of disruptive or category-creating products, focus on long-term impact and innovation

V. PM Culture Types

Building on the understanding of product cultures, PM culture types delve into the specific dynamics of how product managers influence and interact within their teams and organizations. Recognizing the PM culture type that best matches your working style can further enhance your effectiveness and satisfaction in your role.

came up with this framework, but I find it is useful for further assessing the fit for a company and product org. This distinction is primarily used to pattern match where you have thrived and where you have struggled in your career. Most will say that PM-Guided Culture is ideal, but I have found many PMs who thrive in a PM-Dominated Culture or PM-Serviced Culture, regardless of the trade-offs for those organizations cross-functionally.

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Summary of PM Culture Types

PM Culture Types (based on Shreyas Doshi's framework):

1. PM Dominated Culture

   • PMs have high influence regardless of competence level

   • Other functions may be treated more as "resources"

   • PM title carries significant weight in decision-making

2. PM Guided Culture

   • High-competence PMs have high influence, low-competence PMs have less

   • Merit-based rather than title-based decision-making

   • Balanced input from different functions

3. PM Serviced Culture

   • PMs have low to medium influence regardless of competence

   • Another function (often engineering or sales) is primary decision-maker

   • PMs primarily support the dominant function

Question for Your Profile: Which product culture and PM culture type do you think you'd thrive in most? Choose one of each.

VI. Synthesizing Your Product Leadership Profile

Instructions: Fill out the "Your Answer" column with the options that best describe your profile.

Based on this profile, craft a brief (3-5 sentences) product leadership statement that encapsulates your unique blend of archetypes, superpowers, and expertise.

Example: "I am a Growth Driver with strong UX Innovator tendencies, excelling in Product Crafting and Growth Expertise. My experience spans B2C and B2B2C markets, with deep knowledge of subscription and marketplace business models in the FinTech and HealthTech verticals. I thrive in data-driven product cultures where PMs are guided by merit-based influence, allowing me to leverage my analytical skills and user-centric approach to drive product success."

This comprehensive profile will serve as a powerful tool in your job search and career development. Use it to target roles that align with your strengths, articulate your value in interviews, and identify areas for future growth and development.

Homework Instructions

1. Take the Quiz:

   TAKE THE PRODUCT ARCHETYPE QUIZ

   • Complete the quiz to help identify your PM archetype, superpowers, and preferred cultures.

   • Use the insights from the quiz as a guide for the following steps.

2. Identify Your Personal PM Leader Archetype & Profile:

   • Review the descriptions of different PM archetypes.

   • Choose your primary and secondary archetype.

   • Answer the question: Which two archetypes do you most identify with?

3. Determine Your Core Product Management Superpowers:

   • Review the descriptions of different PM superpowers.

   • Choose your primary and secondary superpower.

   • Answer the question: Which two superpowers do you feel are your strongest?

4. Identify Your Expertise Areas:

   • Review the different markets, business models, industry verticals, and technologies.

   • Choose your areas of expertise:

     • 1-2 markets

     • 1-2 business models

     • 1-2 industry verticals

     • 0-2 technologies

   • Answer the corresponding questions for each category.

5. Understand Your Preferred Product Culture:

   • Review the descriptions of various product cultures.

   • Choose the product culture you thrive in most.

   • Answer the question: Which product culture do you think you'd thrive in most?

6. Identify Your Preferred PM Culture Type:

   • Review the descriptions of PM culture types.

   • Choose the PM culture type that best matches your working style.

   • Answer the question: Which PM culture type do you think you'd thrive in most?

7. Synthesize Your Product Leadership Profile:

   • Fill out the provided table with your chosen options for each section:

     • Primary Archetype

     • Secondary Archetype

     • Primary Superpower

     • Secondary Superpower

     • Market Expertise

     • Business Model Expertise

     • Industry Vertical Expertise

     • Technology Expertise

     • Preferred Product Culture

     • Preferred PM Culture Type

   • Craft a brief (3-5 sentences) product leadership statement based on your profile.

We know first hand that the answer is yes.

Meet Annie Murray, one of the best negotiation coaches in the tech world.

I've personally negotiated compensation at all levels, from junior roles to 7-figure executive positions. That's why I'm so excited to share this article from Annie Murray - she's one of the best negotiation experts I know, with a wealth of experience as both a recruiter and a negotiation coach.

I personally selected Annie to lead a success-based tech negotiation coaching service, Valued.

Learn More

Annie has helped over 200 tech professionals negotiate job offers for higher compensation and up-levels. Using her Microsoft and Amazon recruitment experience, she has developed a strong reputation among top tech talent.

Over the course of her career, Annie has worked with a diverse range of clients, from Commercial Counsel to Chief Operating Officers, across a vast array of tech companies, including FAANG, Microsoft, Airbnb, TikTok, and many high-profile startups.

She has also shared her expertise with Her Skill Academy, Grace Hopper, and Oxford University.

Annie and I have very similar approaches to negotiation. Many of the strategies she outlines here are ones I've used successfully throughout my career, from entry-level to the C-suite. I highly recommend paying close attention to her insights.

Now, let's dive into Annie's expert advice on navigating the post-2023 negotiation landscape. I'm confident it will give you a serious edge in your next compensation discussion.

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Can I negotiate my tech job offer in 2024?

It was the summer of 2022. Amazon had just amended their long held policy of keeping the entire staff (from L7 to L3) at a base salary cap of $160k, to now being able to offer folks bases more aligned with their level and experience. I’d just helped a client get an increase in their offer that was well above the top of the listed salary band, something that was extremely common to do with Amazon at the time.

It was a boom market in the tech industry, where if you weren’t negotiating, you were guaranteed to be leaving huge sums on the table. The percent likelihood of an offer being rescinded was 2%, and in my 2 years of negotiating competitive compensation for tech leaders across hundreds of companies, I had never had an offer pulled for any client.

Then, in a blink of an eye, the whole playing field changed. Amazon kicked themselves for changing their base salary policy, and doubled down on a new no-negotiation policy, regardless of level. I saw L7 individuals being denied increases in their comp, even with strong competing offers as leverage.

But the wheel of time continues to spin forward, and now we’re seeing positions opening up again at major tech companies across roles and locations. While the dust is still settling, the question on many folks minds is - are we re-entering the negotiation space we left behind in 2022, or are things still as dire as they were last year?

The answer is more complicated than you may think. It’s really coming down to whom the market is deeming as worthy of heavy comp increases. In 2022, that really meant anyone on the technical side of things. These days, it’s not as universal as it once was. It’s been evident that the tech industry is funneling more and more money and effort into the AI space, so now, the strongest job title to get a great negotiation outcome is Research Scientist. It’s always had the highest bar of pay, but now it’s at a point where just having that job title alone is extremely strong leverage.

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That’s not to say that negotiation is impossible without that job title, far from it. In the past year alone, I’ve helped Data Scientists, Product and Project Managers, and Software Engineers get increases in their offers. It just takes more strategic planning and a different way to present your leverage to get those substantial increases. In the following steps, I’ll outline how to set yourself up for success and help get the odds in your favor in your next negotiation in this uncertain market

Step 1 - Don’t talk yourself out of it before it happens

The number one thing I hear from clients of all leveling placements and job titles is “I’m bad at negotiating”. That, in and of itself, is a huge hurdle to overcome in the negotiation process. 

If you go into a conversation where your objective is to advocate for yourself, but there is an inherent doubt within yourself if you’re worthy of advocacy, that fully undermines your argument. Recruiters may not have the technical knowhow regarding the specific work and skill sets you need to be a strong hire, but they can read people very well, and get a good sense of their confidence and general character from brief dialogues. That’s why they are appointed as the gatekeepers for first round interviews - they can do a great job of weeding out folks at a glance.

That’s not to say that the fear isn’t coming from a legitimate source - considering how rare opportunities are these days, it can feel like a massive risk to push for more. The state of the economy has triggered a mindset shift in the general employment market - folks used to think “What value am I bringing to this organization?”, now they’re thinking “I can’t afford to lose this opportunity, so I should be open to whatever they offer me”. And companies are using this mindset shift heavily in their favor.

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The most important thing to remember is that successful negotiations are still occurring on a daily basis. Just last month, I saw someone make the transition back into tech after years in the academic space, and of course they were very nervous about their leverage and potential for upside in this negotiation. By having someone there to affirm their value and encourage them to push back, they were able to get a substantial increase in their compensation. 

There is no opportunity without risk, and as scary as it can be to put yourself out there and ask for more, oftentimes folks are willing to work with you if you approach your request from a position of kindness and authenticity. So many times I would be on calls with clients where they had just done their counter offer, and they remarked at how easy and straightforward that conversation had been, and how they had agonized for weeks about what ended up being a 5 minute dialogue that went very well. The biggest enemy in any negotiation is ourselves and our inner saboteur, don’t let that voice tell you that you can’t - because you can!

Step 2 - Make sure to ask the right questions

One of the more challenging aspects of negotiating in today's market is getting a solid understanding of the risk level for any given opportunity. A job posting could pop up that seems secure and optimal, but that same posting could get reprioritized and no longer available in a matter of hours. In my own job search experience, there were countless examples of times where I did well in interviews and expected an offer, when suddenly I’d be told that they were doing a last minute evaluation of all open roles, and the role would no longer be open at this time. 

It may seem impossible to get that internal context without having someone on the inside feeding you that intel, but there are definitely strategies to gain that insight. It partially comes down to the types of questions you ask, and to whom you pose the question. 

In the first round phone screen, make sure you ask how long the role has been open for. This piece of information can really help you get a better understanding of the potential risk for layoff/reprioritization. If a role has been open for a considerable length of time (longer than 2 months), the probability of that role being cut is pretty low. More often than not, the longer the role’s been open for, the more dire of a need it is for the company. It likely has already gone through a few rounds of reprioritization and since it’s survived those, it’s improbable that the role will be impacted in the future.

The other big question to ask in the first interview is the proximity of this role to the profit arm. Unless you’re a salesperson, it can be hard sometimes to know how impactful your team is on the overall gain for the company. Particularly if you’re working on a new product or piece of technology, it’s not often clear how much stake the company has put into that teams specific project. If your job title is recruiter, you know for a fact how far away your team is from the profit arm (in the massive tech layoffs last year, 70% of those impacted were recruiters). A good example is Microsoft - the two teams on the biggest profit arms of Microsoft are Azure and Security, so you know if you’re placed there it’s unlikely you’ll be laid off.

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As you continue moving forward in interviews, see if you can get time with team members. I know it can be tough with companies like Google and Meta, where team matching occurs later on in the process, but for most other companies it’s pretty standard to have chats with the hiring manager and team members before hearing a first offer. On those specific conversations, see what context you can glean regarding the overall team culture and morale - you don’t want to commit to a toxic work environment, and those questions can give you some insight before you’ve signed the offer letter. 

Also, while talking to the hiring manager or team members, try to get insight about what problems the team is facing, whether thats a bug in the code that they’re struggling to overcome, limited team finances for the scope of the project, or retaining customers long term - this is going to be key insight for what you’ll be working on day-to-day. This will lay the foundation for you to present your potential impact to the hiring manager after you’ve been given the first offer (see Step 3).

Step 3 - Getting creative with leverage

Another roadblock that is commonly put up by folks is that they don’t feel they have sufficient leverage for this negotiation. That begs the question - what is sufficient leverage? There are a few schools of thought on that, and it’s partially predicated upon the company you’re talking to, as companies like Google will demand for proof of competing opportunities in writing, while most of the other big techs don’t ask for such things.

Some folks feel that the only leverage they need is the data points they’ve found doing online research and heard anecdotally from colleagues. While those data points are valuable, the argument “Based on data points I saw online, I’d be looking for X” is less useful. Most recruiters want to hear what makes your situation unique, and Googling “Comp L6 SWE Bay Area” isn’t very unique to you. Same goes with arguing about cost of living and family expenses - while those are legitimate reasons for needing more pay, recruiters don’t typically agree, as many folks have families and are living in expensive areas. The best thing to do in terms of leverage is to make it specific to you.

This is why most folks will agree that having a competing offer in hand is a great source of leverage. But what if you’re still interviewing with other companies, and don’t have offers yet? Is that still useful? 

In my professional opinion, being in interviews with another company can be even stronger leverage than having an offer in hand. If you don’t have a firm offer from your leverage company, you’re not obligated to share numbers or level placement with the recruiter you intend to negotiate with. 

But without that offer in hand, how can I use that opportunity as leverage? It depends on how willing you are to risk that opportunity and use it to get more compensation elsewhere. For ease of understanding, let’s say you’ve gotten an offer from Meta, and you’re still in the early stages with DoorDash. Meta knows you’re interviewing with DoorDash, but not much else. You could go to your DoorDash recruiter (regardless of how far along you are in that process) and tell them “I got an offer from Meta, based on what they offered me, I’d be looking for a compensation of X base, Y equity, and Z annual bonus”. Those numbers you called out should be well above the offer you got from Meta, that way, you can go back to Meta and say “Well I chatted with DoorDash about a compensation of X base, Y equity, and Z annual bonus”. 

Technically everything you’re telling Meta is accurate - you did discuss those numbers with DoorDash, but it’s not as if DoorDash is committing to offering you that. All we have to tell Meta is “we discussed this compensation”. That should be sufficient enough for Meta to go back and try to increase your offer.

But what if you have no competing opportunities? What if this is the only company you’re interviewing with? Well, you could try to leverage eventual raises or promotions at your current company (if you’re still employed), and in most states in the US, recruiters cannot legally ask you what you’re currently making. That doesn’t mean they won’t still try to ask you, but you can hide behind “I’m not comfortable sharing that as it feels a bit too personal, but based on what I expect to make post promotion/post raise, I’d be looking for a compensation package of X, Y and Z”.

If you’re not currently employed, and you have no other competing opportunities - what are your options? In situations like that, it can seem impossible to be able to successfully negotiate. There is an opportunity for leverage here, one that I’d even encourage folks with other leverage to still pursue due to its high value and ability to increase your internal standing with whichever company you present it to. We call this your 30/60/90 day goal conversation. This is a dialogue you want to be having with the hiring manager, ideally after hearing the first offer. This is because the first offer can give a ton of context about where you stand within the company, including your finalized leveling placement, which you’d want to know before presenting your goals.

The 30/60/90 day goal conversation consists of you writing out your goals for your first 30, 60, and 90 days in this role. You should weave in your knowledge of the issues the team is facing and solutions they’ve attempted to implement in the past (see Step 2), that way your goals are very specific to the teams needs and will further demonstrate to the manager that you know what you’re getting into and you’ll make a huge impact. Make sure to include anecdotes of similar goals you’ve accomplished in the past and how you did it. 

For example, let's say you’re presenting your 30/60/90 day goals to Amazon, and you’ve been at Phillips for the past 3 years in a product manager role. You know the team at Amazon is trying to implement a new tracking tool to see how customers are feeling about the product after purchase, and you designed a similar tool at Phillips. Include verbiage like “based on the tool I built at Phillips that helped 50k customers report their feedback, I’d implement a similar tool here at Amazon to get that data”.

By presenting your 30/60/90 day goals to your manager, you’re indicating the level of impact you’ll have in this role, and further solidifying that you’re the best person for this role. Particularly if you’re lower to mid level, this isn’t something that’s usually done by other candidates, and signals a high level of seniority and motivation. When the manager is inevitably shown your counter offer for approvals (see step 4), it will be significantly easier for them to understand the value that you’re bringing to the company and why you’re deserving of higher compensation.

Step 4 - Who to negotiate with

Once the impact conversation is coming to a natural conclusion, this will be a great opportunity for you to pivot into compensation. Wait until the last 5 minutes or so, then you can transition by saying “thank you so much for helping me finalize these goals, really excited to dive in here! Based on the impact of this role, a compensation that would make sense for me is X, Y and Z”. 

You’ve just asked the manager for your compensation based on the 30/60/90 day goal document you put together, what if the manager responds with “this isn’t my job, go talk to the recruiter about it”? It happens more often than you may expect, usually managers feel it’s outside their purview to negotiate compensation with you. But if we are so confident that’s how the manager will respond, why bother doing the comp request during the impact dialogue?

Ultimately, the person who has the most influence over your future compensation that you have direct access to is the hiring manager. While the recruiter may be the person that is expected to discuss the offer with you, every counter offer you make will be taken by the recruiter straight to the HM to get their approvals before going to the compensation committee to finalize. 

So while it may seem like a fool's errand to ask the manager about compensation, it will not only prepare them for that impending counter offer, but also connect the dots that you’re leveraging your value add here. That signals a huge amount of excitement for the company, and that you want to get your hands dirty right away (won’t have onboarding syndrome and wait 3 months before diving in).

After making that compensation ask, and being told by the manager to go talk to the recruiter, best to follow that advice and set up time to chat with them. Now this is presupposing that the recruiter is an internal one for the company, but the more senior you become, the more probable it is that you’re working with an Executive Recruiter. These individuals are top-tier headhunters who are motivated with regards to the commission they’ll receive by placing you in a quality role. Contrast this with internal recruiters, who are motivated through their metrics to get you to sign an offer with their company, particularly if you have another opportunity with a competitor.

This is fundamentally why using external competing opportunities with internal recruiters is so effective. Telling Meta that you have an offer from TikTok is a great way to light a fire under them and get you that great compensation. Leveraging your potential impact with the internal recruiter won’t be as effective as it is with the manager, so following the leverage tips laid out in Step 3 would be the best practice with those individuals.

But if you’re talking to an Executive Recruiter, can you negotiate with them directly? Absolutely, but just because they’re outside of the company doesn’t mean you can fully avoid playing the negotiation game. Any compensation that you request through them must have an appropriate justification, and be aware that any information you share with them could inevitably be relayed to the company (particularly around compensation expectations). They may also be far more demanding to get a compensation range from you early, as they want to find opportunities that you’ll realistically accept.

The best way to utilize the Executive Recruiter while keeping yourself in a position of strength with regards to the negotiation is to share that: “based on what I’ve discussed with other companies about compensation, a yearly comp that I’d be excited to accept would be X, all in with equity and bonuses”. That way, you lay the foundation that you will be leveraging other opportunities after an initial offer is given.

If you’re at a senior level or above, and are struggling to find opportunities to apply to, definitely consider reaching out to an Executive Recruiter. Many jobs at a high level never get posted on career websites, as lots of these companies would prefer to utilize outside headhunters to get quality candidates. Like Contract Recruiters at the lower level, a good Executive Recruiter can get you into unique opportunities and take the lead on the job search for you.

Step 5 - What’s negotiable

If you’re nervous to negotiate, and are a high level individual, it’s not just money that you’ll be leaving on the table if you don’t speak up. Even if you’re a lower level individual, everyone who is getting a job offer from a company should inquire about that company's severance policy before signing the offer letter. 

You may be thinking - how can I ask about that before I’ve even started working there? Won’t that come across as me not having faith in this organization? Considering the recent events of the past 2 years, not inquiring about a severance package could really hurt you in the long run, as many folks directly experienced last year. Often times, once you’ve been laid off and are trying to negotiate severance, it’s much harder to do so without an internal contact at the company, and if you’re going up against a MANGA org, it’s even harder to get any change in the package since they like to standardize it as much as they can.

So if you’re able to bring it up early, after the offer’s been extended but before you’ve accepted, it can create a space where you get more context at the minimum, and at the maximum potentially protect yourself and your family from a tough experience in the future. The best way to make this inquiry with the company is to be more general. If you’ve had a layoff affect you in the past, that can strengthen this ask further. 

By asking about the policy instead of making a demand of X amount of compensation to be paid out, it opens the door to a dialogue where you can gain context on how negotiable or standardized these packages are.

If you’re talking to a big company, it’s less likely they’ll be able to customize the severance package very heavily, but if you’re looking at a smaller startup, it’s considerably more flexible. Oftentimes if you’re an early higher at a company, they may not have even thought through their severance policy yet, so it’s good to call it out early and flag to them that it’s something you’d like context on.

Depending on if the company is public or private, you could not only push for a different dollar amount to be given to you post-layoff, but also ask for expedited equity vesting or a vesting triggering of stock options. This can be advantageous if you anticipate the company to go IPO within a specific time frame, or if you need to build up cash before purchasing your options in bulk. Talk to your recruiter and see what can be possible, as you could potentially double or even triple your total cash gained from the severance with these negotiables.

The severance package isn’t the only thing that can be negotiable with regards to benefits, but we do see a direct correlation with level of seniority and flexibility with these bonus negotiables. If it’s a smaller company, again there’s a chance those benefits could be more malleable, but they’re level of incentive to adjust will be related to how big of an impact you’ll have on their company, and that is tied to seniority.

For example, I’ve seen clients before who were L7 or above with offers at companies where they were expected to travel 75% of the time. The client in that case was encouraged to ask for first class accommodations while making those trips, and the company was willing to accommodate. Again - it helps if you’re talking to other companies about similar benefits, as we know how internal recruiters are motivated (see step 4).

PTO is another thing that you can definitely bring up, but there is more potential for movement at smaller companies than larger. I’ve seen L7 and above individuals try to push for longer PTO at Amazon and get denied, so don’t die on that hill if you can avoid it. But if you’re looking at a midsize or early startup, there’s a decent chance you could get some traction there. Same goes with health insurance benefits, when I was hired at a startup they were unable to offer benefits, but I was able to get them to give me a stipend to cover my benefits added to my offer. Goes to show that you should ask and see what’s possible.

Step 6 - What happens if the offer is rescinded?

This is the question I’m confident most folks are asking at this point in the article. It can seem almost short sighted to make recommendations about negotiating without flagging the potential of an offer being pulled, especially with where the market is today. From 2021 to 2022, in the 150 negotiations I oversaw during that time, I had 0 clients get offers rescinded. But things took a turn once layoffs began hitting.

We saw the market do a 180 from companies eagerly hiring the best and brightest to having a massive influx of employees desperately vying to get any offer they could. All of the power shifted from the employee to the employer. While of course much internal tribulations were going on at the time, these companies noticed this trend within their hiring dialogues and doubled down on it. When so much fear is instilled in the general employee market, it really becomes a company's dream.

Amazon flipped from paying whatever it took to get top talent to denying requests for slight comp changes from L7 individuals and above. I did see more companies outright declining requests for compensation adjustments more than ever before, but I still wasn’t seeing a ton of offers getting pulled, at least not at MANGA orgs. 

We’d see opportunities get removed as roles would get reprioritized, but we knew that if an offer rescind was to occur because of a compensation request, that decision was likely made by the hiring manager. We also knew that it costs the average company anywhere from 10k - 30k to get a candidate moved through the process to the final round and get an offer extended, so it wasn’t in their best interest to rescind offers based on compensation requests. The only time a company seemed to be very motivated to pull offers was if the candidate revealed something about themselves that could be a liability, like saying something offensive, or asking for a massive amount of compensation that could never be accomplished (think asking for 2 million dollars yearly comp for an L5 SWE Meta role). 

But that was presupposing that these companies were playing by the rules that they had set before. I started seeing a trend of companies begin the “reprioritization” process coincidentally right after a counter offer was given. In my own job search in 2023, I had an opportunity with a small recruiting firm for a remote role. I had done a few rounds of interviews, and just met with the CEO. He assured me I was a perfect fit for the role, and gave me a verbal offer. I told him the compensation I was looking for, and asked about severance. He let me know he would see what could be possible and get back to me with the written offer soon.

The next day, I received an automatic decline from the recruiter. I was shocked - I’d never had an offer get pulled so suddenly over such a minor request. But this was a blessing in disguise - after looking into the company further, I saw alarming reports of rampant toxicity amongst higher ups, and even accusations of misogyny and racism. Now of course, not every company that pulls an offer is automatically the worst workplace in the world, but it can send a signal that this company doesn’t value its employees and isn’t interested in supporting someone who advocates for themselves.

While it seems like it’s impossible to know when to expect a rescinded offer, there are a few ways to protect yourself here, and warning signs to look out for. First - wait until the offer has been given to you before you attempt to negotiate it. The company will be less likely to send you an auto-decline when you have an offer in hand. Second, do your research about the company culture beforehand. See if you can learn of anecdotes of other folks negotiating there in the past 6 months - this is very important as any anecdotes from longer than that are likely stale and no longer accurate.

If you’re concerned an offer might get pulled or you want to do your best to avoid it, feel free to reach out.

With regards to warning signs, make sure you have a clear understanding of who you’d be directly reporting to, and work hard to build that relationship. If you’re getting signals that the hiring manager isn’t interested in you or seems cold, that’s something to look out for. Try the impact dialogue with them to help increase your internal standing at the company. If that doesn’t work, it may not be a good fit. And recruiters tend to be pretty upfront if they’re unhappy with a compensation request, they may warn you in advance.

Another helpful turn of phrase to throw out if the offer is threatening to be pulled is “I’m confident we can work together to find a number that works for both of us”. Don’t feel the need to die on a hill for compensation, make 2 - 3 counters but be aware that the more counters you do, the higher the risk is of irritating the hiring team and potentially causing the offer to be pulled.  

If you are told your offer has been rescinded by the recruiter, but haven’t talked to the hiring manager in a bit, try reaching out directly to them and emphasizing your excitement for the role and confidence that a solution that works for all parties can be achieved. Be sure to respectfully step back if the decision to rescind still stands - you don’t want to burn a bridge long term.

I would still say the probability of an offer getting pulled is relatively low, but not as low as it once was. Before the economic downturn, it was about a 2% chance for the inexperienced negotiator, but now I’d say it’s much higher. Be careful in how you negotiate, and always tie back to how interesting and exciting the opportunity is for you.

Step 7 - Negotiating internally

We’ve discussed primarily how to negotiate in a post-2023 market for folks looking at new opportunities, but what about internal promotions and raises? Are those still negotiable? While I’d definitely encourage folks to advocate for themselves at all performance reviews and raise cycles, it’s much more of an uphill battle than pushing for comp at an external company.

There’s a few reasons for this, the biggest one being that you have the most ability to move on compensation before you’ve accepted the offer. Usually on any given tech industry offer, there’s a range of yearly compensation that can vary by upwards of $50k - $100k depending upon how well you negotiate. But once you’re locked in at a company, whatever compensation you accept is what all future raises and promotions will be based upon. Even if you left behind $100k of annual compensation on the table in the offer acceptance, it’s extremely hard to then get that money. 

All raises, annual bonuses, and promotions are usually very standardized with the percentages they will offer. Obviously a bit portion of it is dependent upon performance, but depending upon the company, even if you go above and beyond that doesn’t always guarantee a massive bonus. Look at Microsoft - they advertise the potential to earn even higher annual bonuses above the cap listed on the offer letter if you perform well enough, but what they don’t tell you is that all annual bonuses come out of a budget allocated per team. If one person on your team does an exceptional job, it’s unlikely they’ll get a dramatically higher bonus because if they do, there’s a large chance someone else won’t get one at all, or will get a reduced amount.

The same goes with raises - usually the budget is very firmly set, and it’s challenging to get an amount above the standard percentage. Doing that 30/60/90 day goal conversation every raise cycle and performance evaluation is a great way to increase your odds of getting a higher end raise, but it’s even better for trying to get promoted, which of course is the best way to earn more internally.

Raises can be tough too, because if you’re close to the top of the salary band for your level, sometimes they won’t increase your compensation again until you get promoted. It’s a very common reason why folks will leave companies after a long tenure, simply because they’ve hit a ceiling that they can’t get past with regards to their pay. 

If you have the opportunity for potential promotion, you want to make sure you’re taking the appropriate prep steps before you go into your conversation with your manager. Lets say you have a promotion cycle coming up in around 6 months - first step that should be taken there is setting up an informational interview with someone at the level that you want to be promoted into. Get context from them on what issues their team is facing, what high level projects they’re working on, and if there’s anything that you can do to assist (maybe in a lower impact capacity) so you can get your feet wet in that role. 

As you work on that project for that higher level role, track the impact it’s having on that team. Make sure you note all the learnings you gained, and we’ll weave all of this information into our 30/60/90 day goal presentation for this promotion. Begin by mentioning the work you’ve done up till this point for the team, this will demonstrate to your manager that you’re already doing work of that level. This makes advocating for your promotion significantly easier on the manager's part, as you’ve already proved yourself to have taken initiative and are eager to learn.

But what if you’ve not got a promotion cycle on the horizon anytime soon? Is it still possible to push for a promotion, even out of the usual timeframe? The answer is absolutely yes, but it does require the same steps outlined above of beginning to take on work of the promotion role, that way you can easily demo to your manager that you’re ready for this advancement. As long as you do that, and present your 30/60/90 day goals to your manager in a one on one, there’s a decent likelihood that your manager would expedite the promotion process.

Remember - you know your manager well, and understand the ins and outs of that relationship more than anyone else that can give you advice. Make sure to hear your manager out and don’t risk alienating the relationship by pushing too hard. While there are select scenarios when you can leverage external opportunities to get a promotion, be aware that once you mention you’re getting offers outside your company, there is a strong likelihood your manager may just say “well best of luck with that new opportunity” and won’t bother pushing your request up the pipeline. 

And be aware too that if you have a massive deficit in your compensation compared to your colleagues (don’t be afraid to ask folks in your company what they make, sharing that info is highly beneficial to both parties, just don’t do it in front of your manager/HR) there is potential that your company could be persuaded to do a “Dive and Save”. That’s when the compensation committee will take another look at your current compensation compared to other folks in your same role and determine if an adjustment needs to be made. Make sure to have lots of evidence of a discrepancy in pay, and use your 30/60/90 day conversation to help justify the need for a bump.

Final Thoughts

Putting yourself out there and advocating for your needs is a risk. But our main goal here is to evaluate the probability of negative outcomes, and ways to avoid them. While you may hear horror stories on social media of what negotiation is like today, be aware that many of those posts go viral simply because of the drastic nature of their story. Usually the stories that go viral are either extremely negative or extremely positive, and don’t often reflect the actuality of the general masses experience, so don’t let yourself get too discouraged by the online rhetoric. There is still definitely ways to negotiate today that can keep you and the opportunity protected, and get increases in compensation and benefits. 

If you can walk away from this article with one nugget of insight, it’s that we are our own worst enemies in the negotiation space. If you tell yourself “I’m bad at negotiation, I can’t advocate for myself, I don’t do money conversations well”, then you’re setting yourself up to fail. If you can look at it from the perspective of “the work I do is valuable, and deserves a rate that is appropriate for that value”, it’ll be much easier to take this step of negotiation. But remember - you’re not in this alone, and if you ever need coaching or someone to talk with during this process, that’s what folks like myself are here for!

1. Check out Valued.

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1. Introduction: The High-Stakes World of Pre-IPO Companies

2. The Pre-IPO Landscape: Understanding the Playing Field

   • Current Market Dynamics: A Tale of Two Trends

   • The ZIRP Era Hangover: How Past Policies Shape Today's Opportunities

   • Sector-Specific Trends: Not All Tech is Created Equal

3. Top Pre-IPO Companies Analysis

   • Full List of Pre-IPO Companies

   • Company Profiles

   • Key Metrics to Watch

   • Industry Comparisons

4. Equity Compensation

   • Types of Equity: Options, RSUs, and More

   • Understanding Your Offer

   • Valuation and Dilution

5. Risk Management

   • Diversification Strategies

   • Dollar-Cost Averaging

   • Tax Planning

   • Long-Term Holding

6. Employee Stock Purchase Plans (ESPPs)

   • Post-IPO Participation

   • Benefits and Risks

7. Navigating Company Culture and Employee Treatment

   • Analyzing Culture Beyond Perks

   • Case Studies of Controversial Practices

   • Effective Research and Backchannel Strategies

   • Reverse Interviewing

8. Legal and Financial Considerations

   • Key Clauses in Equity Agreements

   • Tax Implications of Different Equity Structures

   • When to Seek Professional Advice

9. Future Outlook

   • Potential Regulatory Changes

   • Emerging Trends in Company Formation and Funding

   • Strategies for Long-Term Career Resilience

10. Conclusion

    • Making Informed Decisions in the Pre-IPO World

    • Key Takeaways

    • Balancing Opportunities and Risks

    • Final Thoughts on Navigating Your Tech Career

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1. Introduction: The High-Stakes World of Pre-IPO Companies

With fewer public company roles and layoffs continuing, as a tech professional in 2024, you’re probably considering joining pre-IPO companies. They promise innovation, wealth, and career advancement. These companies, often unicorns (>$1 billion valuation) or decacorns (>$10 billion), can seem like golden tickets. But, as you know, the reality is far more complex and risky.

Consider this: In 2023, the tech industry saw over 260,000 layoffs (layoffs.fyi), while only 142 companies went public, down from 980 in 2021 (NYSE data). This stark contrast highlights the volatility and uncertainty in the pre-IPO landscape.

Even the most sure-fire rocketships can change trajectory.

I personally have worked at several pre-IPO unicorns, all of which are still private. One of them, Noom, like many other of the high growth B2C companies at the time, was reportedly planning a 2022 IPO at a $10 billion valuation after raising funds from Silver Lake. That window quickly shut as public market demand turned off after market shifts heading into 2022.

The major catalyst was the end of zero-interest rate policies (ZIRP) as interest rates were hiked starting in March 2022 to combat inflation. This led valuation-to-sales multiples to decline and a ripple effect of high-cost capital causing funding to dry up. Consumer and enterprise demand trends, acquisition cost changes, and competitive dynamics post-pandemic all contributed to the number of private companies with declining valuations, declining business growth, and no clear exit paths in sight.

In this guide, we’ll:

• Dive deep into the current pre-IPO market

• Analyze top companies

• Decode equity compensation & ways to cash out

• Explore strategies for evaluating high-risk, high-reward opportunities

• Help you make informed decisions tied to personal and professional goals

Let's begin our trek through the pre-IPO jungle.

The Growing Trend: Three Archetypes of Pre-IPO Joiners

In this changing landscape, more professionals are considering pre-IPO opportunities. They generally fall into three categories:

1. "Have to": Entering the pre-IPO world out of necessity due to layoffs, hiring freezes, or lack of interview ability.

2. "Want to": Risk-takers who prefer fast-moving private companies to the more established public giants.

3. "Convinced to": Initially hesitant but persuaded by senior titles, more scope and impact, or a compelling vision. AI startup proliferation is adding even more fuel to this group.

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This trend is driven by recent big tech layoffs, creating a pool of talented professionals looking for new opportunities. As established companies become leaner, pre-IPO companies become a compelling alternative.

Why does this matter to you? Joining a pre-IPO company is a high-stakes decision that can significantly impact your financial future and career path. Whether you identify with one of these types or are curious about pre-IPO opportunities, this guide aims to equip you with the knowledge and tools to navigate this complex landscape.

2. The Pre-IPO Landscape: Understanding the Playing Field

The tech industry in 2024 presents a paradox that directly affects your career options. There was an explosion to over 1,200 unicorns worldwide as of 2023. But, there are way fewer tech companies going public. This presents both challenges and opportunities for tech workers like you.

Current Market Dynamics: A Tale of Two Trends

1. Unicorn & Decacorn Proliferation: The abundance of highly valued private companies might suggest a landscape rich with opportunities. However, it's important to look beyond the surface. Many of these unicorns are facing challenges in living up to their lofty valuations, leading to a phenomenon known as "paper unicorns" – companies valued at over $1 billion on paper but struggling to justify that valuation in real terms.

And we are seeing a very similar trend for decacorns (>$10 billion valuation).

Aside: I recommend and ’s article on unicorns as well as this one by Aileen Lee, who coined the phrase “unicorn”.

2. IPO Drought: Despite the plethora of unicorns and decacorns, few are making the leap to public markets. In 2023, only 142 companies went public globally, a stark contrast to the 980 IPOs in 2021. This trend has significant implications for your potential equity value and liquidity timeline.

What does this mean for you? This means there's a higher risk that the company will stay private longer than expected, delaying your chance to cash in on your equity. When evaluating opportunities, consider both the current valuation and the company's realistic path to an exit event.

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The ZIRP Era Hangover: How Past Policies Shape Today's Opportunities

The Zero Interest Rate Policy (ZIRP) era, which lasted from 2008 to 2022, has left a lasting mark on the tech industry. Its effects continue to shape the companies you might be considering joining:

1. Inflated Valuations: Easy access to capital led to skyrocketing valuations, often disconnected from fundamentals. Many companies raised funds at valuations that now seem overly optimistic in the current market climate.

   
   Example: Stripe's valuation soared to $95 billion in 2021 but dropped to $50 billion by 2023 as market conditions changed. This dramatic shift illustrates the potential volatility of your equity value.
   

2. Growth at All Costs Mentality: Many companies prioritized rapid expansion over profitability. This approach worked well in an environment of cheap money but has become problematic as investors increasingly focus on sustainable business models.

   
   Case Study: Klarna's valuation dropped from $45.6 billion to $6.7 billion in 2022. And although they target a Q3 2024 IPO at $20 billion, employees who received stock before saw their value drop by half or more. This dramatic decrease highlights the potential risks in the fintech sector, especially for companies with business models heavily reliant on consumer spending and lending.
   

3. Extended Private Periods: Abundant private capital allowed companies to delay going public. This trend has extended the timeline for potential liquidity events, affecting your ability to realize gains from equity compensation.

   
   Statistic: The median age of tech companies at IPO increased from 7.9 years in 2018 to 12.3 years in 2022 (PitchBook data). This trend directly impacts your liquidity timeline and should factor into your decision-making process.
   

Why This Matters to You:

These trends have created a landscape where the promise of pre-IPO equity comes with increased uncertainty. As you evaluate opportunities, consider how these factors might affect your long-term financial and career goals. The companies you're considering may be grappling with the consequences of ZIRP-era decisions, which could impact their stability and growth prospects.

Private Companies Are Not Worth What You Think

Valuations for late stage private companies were all down significantly in Q1 2024. “23% of all new rounds in Q1 were down rounds, the highest rate in more than five years.” (Carta)

On secondary private share marketplace Forge, where employees and investors sell their shares in private companies to other investors, the valuation discounts are down, but actually bouncing back.

For the month, private companies on Forge Markets traded at a median discount of -31%, which represents the smallest discount in two years. The top 10% of companies traded at a 47% premium and the top 25% of companies traded flat to their primary valuations.

But maybe Public markets will treat them differently than Secondary markets?

You can see that the private markets haven’t performed as well as public markets. There have been record startup shut downs and deflated valuations (as determined by how much people are willing to pay on secondary markets or investors in down rounds).

Public companies have been saved by having some liquidity on the public markets. Startups were overvalued, had high burn rates, and ran out of investors willing to inject capital after funds got burned since 2022.

Not all IPOs thrived, with 23andme taking in valuation. At least there was a liquidity event for earlier employees.

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Sector-Specific Trends: Not All Tech is Created Equal

The tech industry is not monolithic, and your experience and potential returns can vary dramatically depending on the sector. Let's explore how different sectors are faring in the current environment:

1. AI (Artificial Intelligence):

This sector continues to see strong interest and valuations, driven by breakthroughs in areas like large language models and generative AI. Companies in this space are attracting significant investment and talent.

Example: Anthropic raised $450 million in 2023 at a valuation over $4 billion. This level of funding in a challenging market underscores the sector's perceived potential.

Career Implication: There's high demand for AI talent, potentially leading to generous compensation packages. However, the rapid pace of innovation means you'll need to stay at the cutting edge to remain competitive. Even if the company fails, you still get exposure to the space for your next role.

Watch out: Even the successful AI businesses might not be able to grow into their valuations even at reasonably high growth rates when valuation multiples come back down to earth.

Just be wary of the high valuations. Even if AI will produce great companies, every wave leaves >99% of the early companies in the graveyard or in small acquisitions.

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2. Fintech:

The fintech sector has seen more volatility, with some high-profile companies experiencing significant valuation fluctuations. This volatility reflects both the sector's potential for disruption and its sensitivity to economic conditions. Just look at Robinhood or Coinbase stock fluctuations post-IPO.

Career Implication: Fintech offers the potential for high rewards but comes with increased risk. When considering a fintech opportunity, pay close attention to the company's path to profitability and its resilience to economic downturns.

3. Enterprise SaaS:

This sector has shown relative resilience, particularly in areas like cybersecurity and data analytics. The ongoing digital transformation across industries continues to drive demand for enterprise software solutions.

Example: Databricks has maintained its high valuation ($43 billion as of 2023), reflecting continued investor confidence in its data and AI platform.

Career Implication: Enterprise SaaS might offer more stability and steady growth compared to consumer-focused tech. However, it might lack the explosive upside potential seen in emerging tech sectors. Professionals specialized in this field weren’t immune to the downturn , but had an easier time finding roles than Consumer sector tech workers.

4. Consumer Tech:

The consumer tech sector has generally faced more challenges, with some notable exceptions. Many consumer-focused startups have struggled with user acquisition costs, changing privacy regulations, and shifting consumer behaviors.

Avoid Consumer?

Of course, Consumer startups are getting the biggest discounts to their valuations. We have Series B data here, but it applies to late stage pre-IPO companies:

Example: Instacart's IPO in 2023 at a $9.9 billion valuation, down from a peak private valuation of $39 billion, illustrates the challenges in this sector. And that is a company with some network effects. Many of the D2C consumer companies had few moats and only grew on inexpensive-yet-volatile paid advertising arbitrage.

Career Implication: Be cautious when considering consumer tech opportunities. Look for companies with strong unit economics, strong retention, network effect or brand moats, a large serviceable market, and a clear path to profitability, not just user growth and acquisition cost efficiency.

As you navigate the pre-IPO landscape, understanding these sector-specific trends can help you align your career choices with sectors that match your risk tolerance and growth expectations.

3. Top Pre-IPO Companies Analysis: A Deep Dive

Understanding the landscape of top pre-IPO companies provides crucial context for any opportunity you're considering. Let's examine some of the most noteworthy pre-IPO companies as of 2024, and then dive into specific cases that illustrate key lessons for tech professionals.

This map gives a sense of the full list of unicorns who are potential IPO candidates, but we know first hand that many of these are NOT going to IPO in the next couple of years, if ever.

Here is the full 250+ unicorn list in a sheet.

Now, let's explore some of these companies in detail to understand what they can teach us about the pre-IPO landscape:

Stripe: The Valuation Rollercoaster

Stripe's journey exemplifies both the potential and pitfalls of the pre-IPO world. Its valuation soared to a peak of $95 billion in 2021, making it one of the most valuable private companies globally. However, by 2023, this valuation had dropped to $50 billion, a stark reminder of the volatility in private market valuations.

What This Means for Employees:

1. Equity Grant Timing is Crucial: The timing of your equity grant can significantly impact its potential value. An employee granted options at the $95 billion valuation might now have underwater options, meaning the current stock price is below the grant price.

Example: If you were granted 10,000 options with a strike price based on the $95B valuation, they might be worth significantly less now. This scenario underscores the importance of understanding the long-term value potential of your equity, not just its value at grant.

1. Layoff Risk in Highly Valued Companies: Despite its high valuation, Stripe laid off 14% of its workforce in 2022. This move highlights that even highly valued companies are not immune to market pressures and the need for cost-cutting measures.

Lesson: High valuations don't guarantee job security. When evaluating a pre-IPO opportunity, look beyond the valuation to understand the company's financial health and market position.

1. Resilience Matters: Despite the down round, Stripe remains a leader in its space with strong fundamentals. This resilience demonstrates the importance of assessing a company's core business strength, not just its current valuation.

Career Implication: When considering a pre-IPO company, evaluate its ability to weather market downturns and maintain its competitive position.

Databricks: Riding the AI Wave

Databricks presents a different narrative in the pre-IPO world. The company has maintained a strong position even in a challenging market, with its valuation holding steady at $43 billion in 2023. Its focus on data and AI has positioned it well in a high-growth sector.

What This Means for Potential Employees:

1. Sector Matters: Databricks' success underscores the importance of sector positioning. Its focus on AI and data analytics places it in a high-growth area with strong market demand.

Career Implication: Developing skills in AI and data science could position you well for opportunities in companies like Databricks. Consider how your skillset aligns with high-growth sectors when evaluating pre-IPO opportunities.

2. Consistent Growth Can Lead to Steady Equity Appreciation: Databricks has seen consistent upward valuation trajectory, which can translate to significant equity value for employees.

Example: An early employee granted options at a $1 billion valuation could have seen a 43x increase in equity value. This scenario illustrates the potential upside of joining a company with strong growth prospects early in its journey.

3. High Valuations Set High Bars: At $43 billion, Databricks will need significant growth to provide further upside for new employees joining at this valuation.

Consideration: When joining a company at a high valuation, assess the realistic growth potential from that point. The most significant equity gains often come from earlier-stage investments.

Instacart: A Cautionary IPO Tale

Instacart's 2023 IPO serves as a wake-up call for pre-IPO equity valuation. The company went public at a valuation of $9.9 billion, a dramatic decrease from its peak private valuation of $39 billion in 2021. This stark difference highlights the potential gap between private and public market valuations.

Crucial Lessons for Tech Professionals:

1. Private Valuations Can Be Inflated: The public market often values companies differently than private investors. This disparity can lead to significant adjustments when a company goes public.

Calculation Example: An employee with options based on a $39B valuation might have seen their potential equity value drop by 75% at IPO. This dramatic decrease underscores the importance of tempering expectations and not relying too heavily on paper valuations.

2. The Importance of Vesting Schedules: Employees who joined Instacart at its peak valuation but hadn't fully vested might have seen much of their expected equity value evaporate. This scenario highlights the critical role of vesting schedules in realizing equity value.

Tip: Always consider the vesting schedule in relation to potential exit timelines. A longer vesting period might expose you to more valuation risk but could also allow for potential recovery or growth.

3. Market Conditions Impact IPO Success: Instacart's IPO came during a period of market skepticism towards high-growth, unprofitable tech companies. This timing likely contributed to its lower public valuation.

Implication: When evaluating a pre-IPO opportunity, consider not just the company's performance but also broader market conditions and sentiment towards similar companies.

Less Flashy but Notable Contenders

While the unicorns often grab headlines, it's worth paying attention to some less flashy but potentially promising pre-IPO companies:

1. StubHub and SeatGeek: Both ticketing platforms are eyeing 2024 IPOs. StubHub is aiming for a valuation of at least $16.5 billion, while SeatGeek's plans are less clear.

Lesson: The live events industry's recovery post-pandemic has boosted these companies' prospects. When evaluating pre-IPO opportunities, consider broader industry trends and post-pandemic recovery patterns.

2. Turo: The peer-to-peer car-sharing platform has been considering an IPO but faces challenges meeting the increasingly high bar for going public.

Implication: Companies now often need $1 billion in revenue and a $10 billion valuation to be considered IPO-ready. This raises the stakes for employees joining pre-IPO companies, as the path to liquidity may be longer and more uncertain.

3. OpenAI: While not traditionally structured as a for-profit company, OpenAI is reportedly considering restructuring to enable a potential IPO.

Takeaway: Even non-traditional company structures in hot sectors like AI are exploring paths to liquidity. This underscores the importance of understanding a company's structure and potential exit strategies when evaluating opportunities.

These case studies illustrate the complex and often unpredictable nature of pre-IPO valuations and exits. As you navigate your own career decisions, use these lessons to inform your due diligence process and set realistic expectations for potential equity value.

Recent IPOs

You can see that if you joined some recent tech IPOs before they went public, you could have a large outcome (Coupang +567% on IPO) or a big loss, maybe even below your strike price (Instacart -75%).

And this mixed bag is in a relatively healthy post-IPO market in comparison to the drops in IPO prices immediately following 2021 IPOs.

4. Evaluating Pre-IPO Opportunities: Your Due Diligence Toolkit

When considering a pre-IPO opportunity, thorough due diligence is crucial. Here's a comprehensive toolkit to help you evaluate these high-stakes opportunities:

Financial Health Assessment

1) Revenue Growth: Look for consistent year-over-year growth. For SaaS companies, focus on Annual Recurring Revenue (ARR) growth.

How to obtain this information:

• Ask directly during interviews about revenue milestones and growth rates.

• Research press releases or news articles mentioning revenue figures.

• Check platforms like PitchBook or CB Insights for estimates.

Red Flag: Slowing or stagnant revenue growth could indicate market saturation or product issues.

2) Burn Rate and Runway: Understand how quickly the company is spending money and how long current funds will last.

Key questions to ask:

• "What's the company's current runway?"

• "When do you anticipate the next funding round?"

• "How has the burn rate changed over the past year?"

Red Flag: A runway of less than 12 months without a clear path to additional funding or profitability is concerning.

3) Unit Economics: Assess the profitability of the core business model.

Key metrics to inquire about:

• Customer Acquisition Cost (CAC)

• Customer Lifetime Value (CLV aka LTV)

• Gross Margin

• Net Revenue Retention

Ideal Scenario: CLV should be at least 3x CAC for a healthy business model.

Flag: Even with healthy LTV/CAC, if the business is low retention or the CAC is volatile (e.g. paid ads), there is still significant risk. This is why so few consumer subscription businesses succeed - they have very high churn rates relative to business SaaS (exceptions: Netflix, Duolingo).

Market Position Analysis

1) Market Size and Growth: Evaluate the total addressable market (TAM) and its growth trajectory.

Strategy: Cross-reference the company's claims with industry reports from firms like Gartner or Forrester.

If you want to go deeper, investigate their Serviceable Addressable Market (SAM) as well, which can give you a better view. e.g. Health markets can be 100s of billions, but the serviceable market of that particular company may only be a small segment of that.

Also look out for trends in these markets. Are they growing or declining?

2) Competitive Landscape: Understand who the major players are and the company's unique value proposition.

Approach:

• Use tools like G2 Crowd or Forrester Wave reports to see how the company stacks up against competitors.

• Ask about the company's win rate in competitive deals and their key differentiators.

Red Flag: If the company can't clearly articulate its unique value proposition or how it differs from competitors, it may struggle to maintain market share.

3) Customer Traction: Look for evidence of strong customer adoption and retention.

Questions to ask:

• "Who are some of your flagship customers?"

• "What's your customer retention rate?"

• "How has your customer base grown over the past year?"

Positive Sign: A diverse customer base with high retention rates and growing accounts indicates product-market fit.

4) Technological Moat: Assess the uniqueness and defensibility of the company's technology.

Strategies:

• Research patent filings (accessible through Google Patents)

• Ask about the company's R&D investments and innovation pipeline

• Inquire about any proprietary technologies or algorithms

Example: Stripe's advanced fraud detection algorithms and extensive integrations create a significant barrier to entry for competitors.

5) Other Moats: In addition to traditional competitive advantages, consider other strategic "moats" that can protect the company's market position and drive long-term success.

• Network Effects: Companies that benefit from network effects see their product or service become more valuable as more people use it. This creates a virtuous cycle of growth and user retention. For example, social media platforms like Facebook and LinkedIn become more indispensable as their user bases expand, making it difficult for new entrants to compete.

• Brand Strength: A strong, trusted brand can be a significant moat, creating customer loyalty and allowing for premium pricing. For instance, Apple's brand strength not only drives consistent demand but also enables the company to command higher margins compared to competitors.

• Proprietary Data: Companies with access to unique, high-quality data can leverage this asset for competitive advantage. For example, Google's vast amount of search data enables it to continuously improve its algorithms and offer more targeted advertising, creating a barrier to entry for other search engines.

• Regulatory Advantages: Sometimes, regulatory environments can act as a moat. Companies that navigate complex regulations effectively or benefit from favorable regulatory conditions can deter new competitors. For example, financial institutions with robust compliance frameworks can better manage regulatory risks compared to newer fintech startups.

• Customer Switching Costs: High switching costs can lock customers into a company's ecosystem. For example, enterprise software providers like Salesforce benefit from significant switching costs, as businesses rely on their integrated solutions for critical operations, making it challenging to switch to a competitor.

Understanding these additional moats can provide a more comprehensive view of a company's potential for sustained competitive advantage and long-term growth.

Red Flags in Business Models

Be vigilant for these warning signs when evaluating a pre-IPO company:

1. Over-reliance on a Single Customer or Sector: If a large percentage of revenue comes from one customer or a narrow market segment, it presents a risk.

Rule of Thumb: No single customer should account for more than 10-15% of total revenue.

1. Unsustainable Customer Acquisition Strategies: Be wary of companies heavily dependent on discounting or unsustainable marketing spend.

Example: Many food delivery startups struggled with profitability due to heavy discounting and high customer acquisition costs.

1. Regulatory Uncertainties: For companies operating in highly regulated industries or pushing regulatory boundaries, understand the potential risks.

Case Study: Cryptocurrency exchanges face ongoing regulatory challenges that can significantly impact their business models.

1. Frequent Pivots: Multiple significant changes in business model or target market can indicate a lack of clear direction.

Exception: Early-stage startups may pivot as they find product-market fit, but later-stage companies should have a stable direction.

1. Opaque Financials: If the company is hesitant to share basic financial metrics, it could be a red flag.

What to Look For: Transparent communication about key metrics, even if the numbers aren't perfect.

Understanding Funding History and Valuation

The timing and terms of a company's last fundraise can provide crucial insights into its financial health and future prospects:

1. ZIRP Era Overvaluation: Companies that raised significant funds during the Zero Interest Rate Policy (ZIRP) era (roughly 2008-2022) may be overvalued and struggling to grow into their valuations.

Red Flag: A company that raised at a high valuation in 2021 but hasn't shown significant growth since then may be overvalued.

1. Recent Bridge Rounds: Bridge rounds, especially if not publicly disclosed, can indicate financial distress.

What to Ask: "Has the company raised any capital since its last publicly announced round?"

1. Liquidation Preferences: Recent rounds, especially bridge rounds, may come with high liquidation preferences that can negatively impact employee equity in exit scenarios.

Key Point: High liquidation preferences (e.g., 2x or 3x) mean investors get paid out before employees in an exit event.

1. Valuation vs. Reality: Even if a company maintains its high valuation on paper, the reality might be different. Look at revenue multiples, growth rates, and unit economics to get a more accurate picture.

Strategy: Compare the company's metrics to publicly traded peers in the same sector.

1. Secondary Market Activity: If available, secondary market data can provide insights into how investors value the company.

Resources: Platforms like Forge Global or EquityZen sometimes offer data on private company stock transactions.

By thoroughly evaluating these aspects, you'll gain a clearer picture of the company's current position and future potential. Remember, your goal is not just to join a pre-IPO company, but to join one with strong fundamentals and genuine potential for success.

Investor Sentiment: The Market's Mood Matters

While the financial health of a company is critical, investor sentiment around a company's sector, market, or business model can be just as influential in determining its success. The following examples illustrate how shifts in investor sentiment can impact a company's prospects:

e.g. Generative AI (GenAI): In recent years, Generative AI has captured significant investor interest. Companies operating in this space have seen increased valuations and funding opportunities, even if their business models are still evolving.

The surge in interest around AI technologies has led to higher valuations for companies like OpenAI and Anthropic. Investors are willing to bet on the future potential of AI, driving up the market value of these firms.

e.g. SaaS vs. D2C: Software as a Service (SaaS) companies have remained in favor due to their scalable business models and recurring revenue streams. In contrast, Direct-to-Consumer (D2C) companies, once the darlings of the investment world, have fallen out of favor due to high customer acquisition costs and thin margins.

SaaS companies like Salesforce and ServiceTitan continue to attract strong investor interest, while many D2C brands like Harry’s struggle to maintain their valuations and secure funding.

Timing Matters: Tight IPO Windows

e.g. Edtech’s short IPO window

Edtech companies Udemy and Coursera both went public in 2021, but now their stocks have contracted and all the education companies that did not go public during that window are struggling to live up to their valuation. They are getting acquired or raising at lower valuations, making an IPO unlikely.

Understanding the broader market sentiment can provide valuable context when evaluating a pre-IPO opportunity. It's crucial to consider not only a company's internal metrics but also how its sector and business model are perceived by the investment community at any given moment.

5. Decoding Equity Compensation: The Pre-IPO Wealth Puzzle

Equity compensation is often the most alluring—and complex—part of a pre-IPO job offer. Understanding the nuances can help you accurately value your potential compensation package and make informed decisions.

Note: I highly recommend ’s book, The Startup Lottery on this topic.

Types of Equity

1. Stock Options: Stock options give you the right to buy company stock at a set price (the "strike price") in the future.

Two main types:

• Incentive Stock Options (ISOs): Offer potential tax benefits but are only available to employees.

• Non-Qualified Stock Options (NSOs): Can be granted to non-employees and have different tax treatment.

Key Concept: "Strike Price" - the price at which you can exercise your options to buy shares.

Example Calculation: Let's say you're granted 10,000 options with a strike price of $2 per share. If the company goes public at $20 per share, your potential profit would be: (Market Price - Strike Price) x Number of Options = ($20 - $2) x 10,000 = $180,000 (before taxes)

1. Restricted Stock Units (RSUs): RSUs are a promise to grant stock after certain conditions are met, usually a vesting period.

Important Note: RSUs are more common in later-stage startups and typically don't require you to purchase shares.

Example: You're granted 5,000 RSUs that vest over 4 years. If the share price at vesting is $15, the value of your vested RSUs each year would be: (5,000 / 4) x $15 = $18,750 per year (before taxes)

Valuation Dynamics

Understanding how your equity is valued is crucial:

409A Valuations:

This is the company's official valuation for tax purposes, typically lower than the last funding round valuation.

Why It Matters: A low 409A relative to the last funding round could be beneficial for option grants, as it results in a lower strike price.

Example: Company's last funding round valuation: $1 billion 409A valuation: $500 million Your option strike price will be based on the $500 million valuation, potentially leading to greater upside.

Preferred vs. Common Stock (Preference Stack):

Most employees receive common stock, which is valued lower than the preferred stock given to investors.

Key Point: The valuation you hear about in the news is usually based on preferred stock prices and may not reflect the value of your common stock options.

Real-World Example: When Square (now Block) went public in 2015, its last private valuation was $6 billion, but it went public at a $2.9 billion valuation. This discrepancy was partly due to the difference between preferred and common stock values.

Dilution:

As companies raise more funding, your ownership percentage may decrease.

Rule of Thumb: Expect 20-30% dilution between major funding rounds.

Calculation Example: You own 0.1% of the company. After a new funding round with 25% dilution: Your new ownership = 0.1% x (1 - 0.25) = 0.075%

Vesting Schedules

Vesting schedules determine when you gain full ownership of your equity.

Standard Schedule: 4 years with a 1-year cliff

What This Means:

• You gain no vested shares in the first year (the "cliff")

• After 1 year, 25% of your shares vest

• The remaining 75% vest monthly over the next 3 years

Example: You're granted 48,000 options on a 4-year vesting schedule with a 1-year cliff.

• At 1 year: 12,000 options vest

• Each month after: 1,000 options vest

Liquidation Preferences

Liquidation preferences determine the order and amount in which different stakeholders get paid in a liquidation event (like an acquisition or IPO).

Why It Matters: Strong liquidation preferences for investors can significantly reduce the value of common stock in certain exit scenarios.

Example: A company sells for $100 million. Investors have a 2x liquidation preference on their $60 million investment.

• Investors get: $120 million (2 x $60 million)

• Common stockholders get: $0 (since the sale price was less than the liquidation preference)

Case Studies in Equity Structures: Rippling vs. Stripe

To illustrate the diversity of equity compensation approaches in the pre-IPO world, let's compare two prominent companies:

1. Rippling's Approach:

• Offers a mix of ISOs and RSUs, with RSUs becoming more prevalent as the company's valuation increased

• Maintains a relatively low 409A valuation compared to its preferred stock price, potentially offering employees more upside on their options

• Known for offering generous equity packages to attract top talent

Key Takeaway: Rippling's approach aims to provide significant upside potential to employees, aligning their interests closely with the company's growth.

1. Stripe's Approach:

• Provides annual RSU grants based on a dollar value rather than a specific number of shares

• This approach protects employees from downside risk – if the company's valuation decreases, the employee would receive more shares to meet the promised dollar value

• Offers regular liquidity opportunities through tender offers, allowing employees to sell a portion of their vested equity periodically

Key Takeaway: Stripe's approach provides more predictable value and regular liquidity opportunities, but potentially less upside compared to traditional equity structures.

Implications for Employees:

• Risk Tolerance: Rippling's structure might appeal more to risk-tolerant employees betting on significant company growth. Stripe's structure could be attractive to those preferring stability and predictable value.

• Career Stage: Early-career professionals might be more willing to take the risk associated with Rippling's approach, while those with more financial responsibilities might prefer Stripe's stability.

• Financial Planning: Stripe's regular liquidity events through tender offers allow for easier financial planning and diversification.

Negotiation Strategies

Note: If you are in the job search, I offer job offer negotiation coaching for tech and product leaders and senior ICs.

1. For Early Stage, Focus on the Number of Shares, Not Just the Percentage:

   • Percentage ownership can be misleading due to dilution from future funding rounds.

   • The absolute number of shares owned is crucial, as their value can increase significantly with company growth.

   • Early-stage companies’ valuations can increase over time faster than your percentage ownership decreases, making even small ownership stakes valuable.

2. Understand Vesting Schedules: Typical is 4 years with a 1-year cliff, but some companies offer more favorable terms.

   • One-Year Vesting: Some startups offer a one-year vesting schedule to attract talent quickly. For example, a company might vest 100% of the shares after one year to incentivize short-term commitment.

   • Front/Back-Weighted Vesting: In front-weighted vesting, a larger percentage of shares vest in the early years, such as 40% in the first year and the remaining 60% over the next three years. Conversely, back-weighted vesting might vest 10% in the first year and 90% over the remaining years. This approach can be seen in companies looking to retain employees long-term.

   • Vesting Grants Based on Cash: Instead of a set number of shares, some companies grant equity based on a cash value. For example, a company might offer $100,000 worth of shares vesting over four years. If the share price increases, the number of shares decreases, and vice versa. This can be advantageous in volatile markets.

3. Look for Refresh Grants: Ask about the company's policy on granting additional equity over time. Some companies do this annually, some have no refreshers, and others base it on performance.

4. Negotiate for Longer Exercise Windows: If leaving the company, standard windows to exercise vested options are often short (90 days). Longer windows (several years) are more employee-friendly and don’t force you to drop a lot of cash you may not have in fear of losing out on exercising risky stock options.

   1. Cashless exercise: My extended 3-year exercise window at Udacity allowed me to sell my shares on the secondary markets at the same time as exercising (cashless exercise) when the prices were at their peak, reducing risk and increasing my gain.

5. Consider the Current Valuation: If joining a company that recently raised at a high valuation, try to negotiate a lower strike price based on a more conservative valuation.

Remember, while equity can be a powerful wealth-creation tool, it's essentially a lottery ticket until a liquidity event occurs. Base your career decisions on more than just the promise of equity riches, and always consider the total compensation package and career growth opportunities.

6. Assessing Exit Potential

Understanding a company's potential for a successful exit is crucial when evaluating pre-IPO opportunities. Whether through an IPO or acquisition, the exit event is typically when employees can realize significant value from their equity. Here's what you need to consider:

IPO Readiness Factors

1) Financial Metrics:

• Revenue: Many investment bankers now suggest a minimum of $100 million in annual recurring revenue (ARR) for a successful IPO. Note: Lately, some have suggested that $1 billion in annual revenue is the new benchmark

• Growth Rate: Aim for companies growing at least 30-50% year-over-year. The growth has to be stable, too. Bankers will usually look for 4-8 consecutive quarters of revenue growth.

• Profitability: While not always necessary (think Uber or Lyft), a clear path to profitability is increasingly important.

Example: Databricks reported over $1 billion in revenue for 2023 and has been growing at over 50% annually, making it a strong IPO candidate.

2) Market Conditions:

• Overall economic climate

• Sector-specific trends

• Investor appetite for new issues

Case Study: The 2023 IPO drought was largely due to unfavorable market conditions, with high interest rates and economic uncertainty making investors wary of new public offerings.

3) Competitive Position:

• Market leadership or unique value proposition

• Defensible technology or business model

4) Management Team:

• Experienced leadership with public company experience

• Strong financial controls and reporting capabilities

5) Corporate Governance:

• Board composition

• Financial audits and compliance measures

Red Flag: If a company has been "IPO ready" for years without making the leap, investigate why. It could indicate internal issues or an unfavorable assessment of market receptivity.

M&A Possibilities

While IPOs grab headlines, acquisitions are often a more common exit route for startups. However, the M&A landscape has its own complexities:

1. Current M&A Trends:

• According to Carta data, about 150 companies were acquired in Q2 2024, relatively flat compared to previous quarters.

• Roughly half of M&A activity involves pre-seed or seed companies, suggesting many are acquihires or feature acquisitions rather than major tie-ups.

Implication: The much-anticipated surge in M&A activity following the tech downturn hasn't fully materialized.

2. Sector-Specific M&A Activity:

• Some sectors, like AI and cybersecurity, are seeing more M&A interest.

• Consumer tech M&A has been slower, with buyers being more selective.

3. Potential Acquirers:

• Look at who the natural acquirers would be in the company's space.

• Consider whether the company has strategic partnerships that could lead to acquisition.

4. Impact on Employees:

• Understand how different M&A scenarios might affect your equity.

• Consider potential job security implications in case of an acquisition.

Case Study: Microsoft's acquisition of Activision Blizzard for $68.7 billion in 2023 took over 18 months to close due to regulatory scrutiny. While it offered a 45% premium to shareholders, it also brought prolonged uncertainty for employees.

Failed Adobe x Figma Acquisition: Regulators recently led Adobe to cancel it’s acquisition of Figma for $20 billion, costing Adobe $1 billion in cash and countless more costs during the long process.

Large tech companies are thinking twice before acquiring now.

Liquidity Without an Exit: Tender Offers & Secondary Markets

As a tech employee holding equity, you don't always have to wait for an IPO or acquisition to gain liquidity. Two common alternatives are tender offers and secondary markets. Here's how they work, along with examples and constraints:

Tender Offers

Definition: A tender offer is a company-initiated process where employees and early investors can sell their shares back to the company or to approved third-party buyers.

How It Works:

• The company sets the terms, including the price per share and the total number of shares they are willing to buy.

• Employees can choose to sell some or all of their vested shares during the offer period.

Example:

• Airbnb: Before going public, Airbnb conducted several tender offers to provide liquidity to its employees. These offers allowed employees to sell a portion of their shares at a pre-determined price, often based on the company's latest valuation.

Constraints:

• Limited windows: Tender offers are not available all the time; they usually occur at specific intervals.

• Price control: The company sets the price, which may be lower than the market value.

• Participation limits: There may be restrictions on the number of shares you can sell.

Secondary Markets

Definition: Secondary markets are platforms where employees and investors can buy and sell shares of private companies before an IPO.

How It Works:

• Platforms like EquityZen, Forge Global, and Notice facilitate these transactions.

• Employees list their shares for sale, and interested buyers can purchase them at an agreed-upon price.

Example:

• Palantir: Before its direct listing, Palantir shares were actively traded on secondary markets. Employees were able to sell their shares to private investors, providing liquidity well before the company went public.

Constraints:

• Approval: Companies often require board approval for secondary transactions to ensure control over their cap table.

• Pricing: Prices can vary widely based on demand and the perceived value of the company.

• Market access: Not all private companies are listed on secondary markets, limiting your options.

Key Considerations for Employees

1. Tax Implications:

   • Selling shares can trigger tax liabilities, including capital gains tax.

   • Consult with a tax advisor to understand the implications of any sale.

2. Dilution:

   • Keep in mind that selling shares can dilute your ownership percentage, especially in the case of tender offers where new shares may be issued.

3. Future Upside:

   • Selling shares early can provide liquidity but may limit your potential upside if the company's value increases significantly post-IPO or acquisition.

By understanding these options, you can make informed decisions about when and how to sell your equity, balancing the need for liquidity with the potential for future gains.

The "Zombie Unicorn" Phenomenon

The term "Zombie Unicorn" refers to companies valued at over $1 billion that are struggling to grow into their valuations or secure additional funding. This is a crucial concept to understand when evaluating pre-IPO opportunities:

1. Characteristics of Zombie Unicorns:

   • Stagnant or declining revenue growth

   • Difficulty raising new funding at higher valuations

   • Multiple rounds of layoffs

   • Pivots in business model or strategy

   • Delayed or canceled plans for going public

2. Risks for Employees:

   • Devalued equity: As the company's prospects dim, so does the value of your equity.

   • Job insecurity: Zombie unicorns often go through multiple restructuring phases.

   • Career stagnation: Limited resources can hinder professional growth and development.

3. How to Identify Potential Zombie Unicorns:

   • Look for companies that haven't raised new funding in 2-3 years in a bull market.

   • Be wary of companies that have had multiple down rounds or bridge financings.

   • Investigate companies that have delayed IPO plans multiple times without clear reasons.

4. Mitigation Strategies:

   • Diversify your portfolio: Don't put all your eggs in one pre-IPO basket. If you can get exposure to other stocks, sell your shares in tender offers or secondary markets, or find other ways to diversify, take those shots.

   • Stay informed: Keep track of your company's financial health and market position.

   • Have an exit strategy: Know when you might need to consider other opportunities.

The VC Debate: Private vs. Public

There's an ongoing debate in the venture capital world about whether companies should stay private longer or go public earlier. This debate has significant implications for employees:

1. The "Stay Private Longer" Camp (e.g., Marc Andreessen of a16z):

   • Argument: Staying private allows companies to focus on long-term strategy without the pressures of quarterly earnings.

   • Impact on Employees: Potentially larger equity upside, but longer wait for liquidity.

2. The "Go Public Earlier" Camp (e.g., Bill Gurley of Benchmark):

   • Argument: Public markets provide discipline, transparency, and liquidity.

   • Impact on Employees: Earlier liquidity opportunities, but potentially less equity upside.

Current Trend: The pendulum is swinging back towards earlier public offerings, but with a higher bar. Many now say companies need $1 billion in revenue and a $10 billion valuation to be IPO-ready.

Implication for You: When evaluating a pre-IPO opportunity, consider the company's stance on this debate and how it aligns with your personal financial goals and risk tolerance.

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7. Liquidity Events and Employee Considerations

Understanding the various paths to liquidity is crucial for maximizing the value of your pre-IPO equity. Here's what you need to know:

Lockup Periods for Employee Equity

Understanding lockup periods is crucial for employees holding equity in pre-IPO companies. A lockup period is a predetermined time frame after an IPO during which employees and insiders are restricted from selling their shares. This period is typically 180 days but can vary depending on the company's policies and agreements with underwriters.

Key Points to Consider:

1. What is a Lock-up Period?

   • A set timeframe (typically 180 days) after an IPO during which employees and early investors cannot sell their shares.

   • Designed to prevent a flood of shares hitting the market immediately after IPO.

2. Impact on Employees:

   • You can't immediately cash out your equity when the company goes public.

   • The stock price can fluctuate significantly during and after the lock-up period.

3. Purpose of Lockup Periods:

   • Lockup periods are designed to prevent a sudden flood of shares into the market, which could destabilize the stock price shortly after the IPO.

   • They provide a buffer period for the market to absorb the new stock and for the company to establish its post-IPO trading pattern.

4. Typical Lockup Periods for Tech IPOs:

   • For most tech companies, the lockup period is usually around 180 days.

   • However, it can vary; some companies may have shorter or longer lockup periods based on their agreements with underwriters.

5. Impact on Employees:

   • Employees may see the value of their equity fluctuate during the lockup period but will be unable to sell their shares to capitalize on favorable price movements.

   • It's essential to plan financially, knowing that you won't have immediate liquidity for your shares post-IPO.

6. Examples of Companies Without Traditional Lockup Periods: Direct Listings

   • Spotify: When Spotify went public through a direct listing in 2018, there was no traditional lockup period. This allowed employees and early investors to sell their shares immediately, leading to a different dynamic in the stock's early trading days.

   • Slack: Similarly, Slack chose a direct listing for its public debut in 2019, bypassing the traditional lockup period. This provided immediate liquidity for employees and early investors.

   • Direct Listings vs IPOs: IPOs raise new capital and involve underwriters with a lockup period, while direct listings do not raise new capital, have no underwriters, and typically no lockup period.

7. Strategic Considerations:

   • Be aware of the lockup expiration date, as stock prices often experience increased volatility around this time due to the sudden availability of shares.

   • Consider consulting with a financial advisor to strategize the optimal time to sell your shares post-lockup, balancing market conditions and personal financial goals.

8. Strategies for Managing Lock-up Periods:

   • Diversification planning: Prepare a strategy for when you can sell shares.

   • Dollar-cost averaging: Plan to sell shares gradually over time rather than all at once.

   • Tax planning: Consult with a financial advisor to understand tax implications of selling post-lock-up.

Employees left holding the bag after lockup periods

When Facebook (Meta) went public in 2012, its 180-day lockup period led to significant stock price fluctuations as large volumes of shares were released into the market.

Uber’s stock price dropped to about $27 per share six months after its IPO when the 180-day lock-up period ended. Employees had to pay income taxes based on the $45 IPO price, even though they couldn't sell at that price.

Understanding lockup periods can help you manage expectations and make informed decisions about your equity compensation, ensuring you maximize the potential value of your shares.

Secondary Markets and Their Limitations

Secondary markets allow employees to sell shares before a company goes public, but they come with limitations:

1. Platforms:

   • EquityZen, Forge Global, and SharesPost are popular secondary market platforms.

2. Benefits:

   • Provide some liquidity before an IPO or acquisition.

   • Allow diversification of personal portfolio.

3. Limitations:

   • Often restricted by companies.

   • May require company approval for each transaction.

   • Typically sell at a discount to the last private valuation.

   • Can have complex tax implications.

4. Case Study: Airbnb Prior to its IPO, Airbnb allowed employees to sell up to 15% of their vested equity on secondary markets, providing some liquidity while the company remained private.

Tender Offers: A Deeper Dive

Tender offers are becoming an increasingly common way for pre-IPO companies to provide liquidity to employees:

1. What is a Tender Offer?

   • A structured event where the company or an outside investor offers to buy shares from current shareholders.

2. Benefits:

   • Provides partial liquidity without waiting for an IPO.

   • Often done at a known price, reducing uncertainty.

3. Considerations:

   • May be offered at a discount to potential IPO value.

   • Often limited in size and frequency.

   • May have tax implications.

4. Example: Stripe's Approach Stripe has been known to conduct regular tender offers, allowing employees to sell a portion of their vested equity. This approach provides predictable liquidity events and helps retain talent.

5. What to Ask About Tender Offers:

   • Frequency: How often does the company conduct tender offers?

   • Eligibility: Who can participate, and are there any restrictions?

   • Pricing: How is the price determined?

   • Limits: Are there caps on how much you can sell?

Strategies for Managing Equity Post-IPO

Once your company goes public, you'll need a strategy for managing your newly liquid equity:

1. Diversification:

   • Consider selling a portion of your shares to diversify your portfolio.

   • The "5-10-15" rule: Some advisors suggest not having more than 5% of your portfolio in any single stock, 10% in your company's stock, and 15% in your industry.

2. Dollar-Cost Averaging:

   • Sell shares gradually over time to mitigate the risk of market timing.

3. Tax Planning:

   • Understand the tax implications of selling shares (e.g., capital gains tax).

   • Consider strategies like tax-loss harvesting or charitable giving of appreciated shares.

4. Long-term Holding:

   • If you believe in the company's long-term prospects, consider holding a portion of your shares.

5. Employee Stock Purchase Plans (ESPPs):

   • If your company offers an ESPP post-IPO, consider participating as it often provides discounted stock purchases.

Remember, every situation is unique. It's often wise to consult with a financial advisor who can help you create a personalized strategy aligned with your overall financial goals.

In the next section, we'll explore how to navigate company culture and employee treatment in pre-IPO companies, which can significantly impact your overall experience and success in these high-pressure environments.

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8. Navigating Company Culture and Employee Treatment

The allure of pre-IPO companies often overshadows the realities of working in these high-pressure environments. Understanding and evaluating company culture is crucial for your long-term satisfaction and success.

Analyzing Culture Beyond the Perks

1. Work-Life Balance:

   • Many pre-IPO companies demand long hours and high stress levels.

   • Ask about typical work hours, weekend work expectations, and vacation policies.

2. Growth Opportunities:

   • Look for companies that invest in employee development.

   • Ask about career progression paths and internal promotion rates.

3. Decision-Making Processes:

   • Understand how decisions are made and how much autonomy employees have.

   • Look for transparency in communication from leadership.

4. Diversity and Inclusion:

   • Evaluate the company's commitment to building a diverse and inclusive workplace.

   • Look for diversity in leadership positions.

5. Values Alignment:

   • Ensure the company's mission and values align with your own.

   • Look for evidence that the company lives its stated values.

Red Flag: If the company can't articulate its culture beyond perks like free meals or game rooms, it may indicate a lack of intentional culture-building.

Case Studies of Controversial Practices

1. Stripe and Rippling: Intensity and Fast Firing

   • Known for intense work environments and high performance expectations.

   • Reports of quick terminations for underperformance.

   Implication: While these practices can drive innovation and efficiency, they can also lead to burnout and job insecurity.

2. Databricks and OpenAI: High Compensation, Low Work-Life Balance

   • Offer competitive compensation packages but often demand long hours.

   • Employees report high-pressure environments with significant workloads.

   Trade-off: The potential for significant financial rewards comes at the cost of work-life balance.

3. Turo: Smaller Scale, Better Work-Life Balance

   • Reports indicate a more balanced approach to work hours and employee well-being.

   • Compensation may be lower compared to high-growth unicorns.

   Consideration: For some professionals, the trade-off of lower potential upside for better quality of life may be worthwhile.

Effective Research and Backchannel Strategies

Why You Should Research and Backchannel Companies

Researching and backchanneling companies are crucial steps in vetting potential employers, particularly pre-IPO companies. Here's why:

1. Assessing Stability and Growth:

   • Researching financial health and growth prospects can help you gauge the company's stability and potential for success.

   • Backchanneling can reveal unpublicized challenges or concerns, helping you make a more informed decision about the company's future.

2. Evaluating Leadership:

   • Strong leadership is critical for a company's success. Researching and backchanneling can provide insights into the leadership team's experience, vision, and track record.

   • Poor leadership can lead to strategic missteps, affecting the company's growth and your job security.

3. Understanding Market Position:

   • Investigate the company's competitive landscape and market share. A company with a strong market position is more likely to succeed and attract investors.

   • Backchanneling can provide insights into how the company is perceived in the industry and its ability to innovate and stay ahead of competitors.

4. Identifying Red Flags:

   • Online reviews and backchannel conversations can highlight potential red flags, such as high turnover rates, poor management practices, or unrealistic expectations.

   • Identifying these issues early can save you from joining a company that may have underlying problems affecting its long-term success.

The Importance of Reverse Interviewing

Reverse interviewing is the process of asking potential employers questions to assess if the company is a good fit for you. Here's why it's important in evaluating the company's probability of success:

1. Clarifying Business Strategy:

   • Asking questions about the company's business strategy, product roadmap, and growth plans can help you understand its long-term vision and viability.

   • Understanding how the company plans to achieve its goals can give you confidence in its potential for success.

2. Evaluating Financial Health:

   • Inquiring about recent funding rounds, revenue growth, and profitability helps you assess the company's financial health and stability.

   • Financial stability is crucial for job security and the potential for the company to go public or be acquired.

3. Gaining Insight into Company Challenges:

   • Inquiring about the biggest challenges the company is facing can provide insights into potential risks and areas of uncertainty.

   • Understanding these challenges helps you prepare for the realities of the job and assess whether the company has a plan to overcome them.

By conducting thorough research, backchanneling, and reverse interviewing, you can make a more informed decision about joining a pre-IPO company. These steps help ensure that the company has a strong foundation and a realistic path to success, ultimately increasing your chances of benefiting from its growth and potential public offering or acquisition.

1. Leverage Your Network:

   • Use LinkedIn to find current or former employees (ones that left for better opportunities who are less likely to be salty)

   • Reach out for informal conversations about their experiences.

2. Analyze Online Reviews:

   • Check platforms like Glassdoor and Blind, but be aware of potential biases.

   • Look for patterns in reviews rather than focusing on individual comments.

3. Ask Thoughtful Questions During Interviews:

   • "Can you describe a typical day for someone in this role?"

   • "How does the company handle disagreements or conflicting viewpoints?"

   • "What's the biggest challenge the company is currently facing?"

4. Observe Interactions:

   • During onsite interviews, pay attention to how employees interact with each other.

   • Look for signs of collaboration, respect, and engagement.

5. Research Press Coverage:

   • Look for news articles about the company's workplace practices.

   • Pay attention to how the company responds to public criticism or challenges.

6. Analyze Employee Tenure:

   • High turnover rates, especially in key positions, can be a red flag.

   • Use LinkedIn to gauge how long employees typically stay with the company.

Remember, while no company is perfect, it's crucial to find a culture that aligns with your values and work style. Be honest with yourself about what you're willing to trade for the potential upside of a pre-IPO opportunity.

9. Legal and Financial Considerations

Navigating the legal and financial aspects of pre-IPO equity can be complex. Here are key considerations to keep in mind:

Key Clauses in Equity Agreements

1. Vesting Schedule:

   • Standard is four years with a one-year cliff, but terms can vary.

   • Tip for executives: Look for acceleration clauses in case of company sale or your termination without cause.

2. Exercise Window:

   • Standard is 90 days post-employment to exercise vested options.

   • Some companies offer extended exercise windows (e.g., 7-10 years), which can be highly beneficial.

3. Repurchase Rights:

   • Some companies retain the right to buy back vested shares if you leave.

   • Understand the terms and potential impact on your equity value.

4. Transfer Restrictions:

   • Most agreements restrict your ability to transfer or sell shares before an IPO.

   • Understand any exceptions, such as for estate planning purposes.

5. Information Rights:

   • Look for clauses that give you the right to receive financial information about the company.

   • This can be crucial for making informed decisions about your equity.

Red Flag: Be cautious of any unusual or overly restrictive clauses. If something seems off, consider having a lawyer review the agreement.

Tax Implications of Different Equity Structures

1. Incentive Stock Options (ISOs):

   • Potential for favorable tax treatment if certain holding periods are met.

   • Be aware of Alternative Minimum Tax (AMT) implications.

2. Non-Qualified Stock Options (NSOs):

   • Taxed as ordinary income at exercise, regardless of whether you sell the shares.

   • Can result in a significant tax bill if exercised when the company's valuation is high.

3. Restricted Stock Units (RSUs):

   • Taxed as ordinary income when they vest.

   • Often, some shares are automatically sold at vesting to cover tax obligations.

4. Early Exercise:

   • If allowed, can potentially result in more favorable tax treatment.

   • Requires upfront investment and carries risk if the company's value decreases.

Example: If you early exercise 10,000 options at $1 per share, you'd need to invest $10,000. If the company fails, you lose this investment.

1. 83(b) Election:

   • Allows you to be taxed on the fair market value of stock at the time of grant rather than vesting.

   • Must be filed within 30 days of receiving the grant.

   • Can be beneficial if you expect the company's value to increase significantly.

When to Seek Professional Advice

1. Evaluating Job Offers:

   • Consider consulting a financial advisor when comparing complex compensation packages.

   • They can help you understand the potential value and risks of different equity offerings.

2. Tax Planning:

   • Consult a tax professional before exercising options or selling shares.

   • They can help you understand and plan for potential tax liabilities.

3. Legal Review:

   • Consider having a lawyer review your equity agreement, especially for executive-level positions.

   • This is particularly important if there are unusual clauses or if you're negotiating custom terms.

4. Financial Planning:

   • Work with a financial advisor to integrate your equity into your overall financial plan.

   • They can help with diversification strategies and risk management.

5. Approaching Liquidity Events:

   • Seek professional advice when your company is approaching an IPO or potential acquisition.

   • Experts can help you navigate lock-up periods, selling strategies, and tax implications.

Remember, while professional advice can be expensive, it can potentially save you significant money and headaches in the long run, especially when dealing with large amounts of equity.

Key Takeaway: Don't be afraid to ask for help. The complexities of pre-IPO equity often warrant professional guidance, especially as the potential value of your equity increases.

In the next section, we'll explore future trends shaping the pre-IPO landscape and strategies for long-term career resilience in this dynamic environment.

10. Future Outlook: Trends Shaping the Pre-IPO Landscape

The pre-IPO landscape is constantly evolving. Understanding emerging trends can help you make more informed career decisions and better navigate this dynamic environment.

Potential Regulatory Changes

SEC Scrutiny on Private Markets:

• Increased focus on transparency and investor protection in private markets.

• Potential new rules on reporting requirements for large private companies.

Implication: This could lead to more transparency for employees but might also make it harder for companies to stay private for extended periods.

Changes to Equity Compensation Rules:

• Discussions around extending the timeline for exercising options post-employment.

• Potential changes to tax treatment of equity compensation.

What to Watch: Keep an eye on proposed legislation that could affect how your equity is taxed or your ability to exercise options.

Cryptocurrency and Blockchain Regulations:

• Evolving regulations around crypto assets and blockchain technology.

• Could affect companies in the fintech and blockchain spaces.

Example: The outcome of the SEC's lawsuit against Ripple could have far-reaching implications for companies using blockchain technology.

Emerging Trends in Company Formation and Funding

Rise of Alternative Funding Models:

• Increased use of revenue-based financing and other non-dilutive funding options.

• Growth of venture debt as an alternative to equity financing.

Implication: These trends could lead to different equity structures and potentially less dilution for early employees.

Democratization of Startup Investing:

• Growth of platforms allowing retail investors to invest in pre-IPO companies.

• Potential for more liquidity options for employees.

Example: Companies like Carta are working on creating more efficient secondary markets for private company shares.

Focus on Sustainable Growth:

• Shift away from the "growth at all costs" mentality.

• Increased emphasis on unit economics and path to profitability.

What It Means for You: Companies with sustainable business models may offer more stable long-term prospects, even if they lack the explosive growth of some unicorns.

Remote-First Companies:

• Continuation of the remote work trend, even post-pandemic.

• Rise of "headquarterless" companies and distributed teams.

Career Implication: This could open up opportunities to work for exciting pre-IPO companies regardless of your location.

11. Career Planning In Pre-IPO Companies

Chaos Is A Ladder

The fact that Pre-IPO companies go through more frequent and volatile ups and downs means that there is more turnover at the top and more opportunities to lead or gain scope as teams and businesses grow and get added.

The “chaos” of the hypergrowth company life is an opportunity to advance in your career and prove yourself well before a big tech company would give you the reins.

Yo-Yo Strategy

(ex-VP Product at Meta, ex-CPO at Credit Karma) suggests a strategy of moving back and forth between large public tech companies and earlier stage or growth companies in your career.

When you move to growth-stage Pre-IPO companies, even if you don’t liquidate your equity, you can gain a larger scope, move up the seniority ladder much faster, and often come back to the FAANG+ companies at a higher level than if you had waited for promo.

When you move to a big tech job, you get exposure to how things are done at large scale in large organizations. Plus, you are often surrounded by top talent. When you go back to growth stage companies, it will often be in a higher seniority role and you will bring a brand and a network along with you.

12. Conclusion: Making Informed Decisions in the Pre-IPO World

Navigating the pre-IPO landscape as a tech professional can be both exciting and daunting. The potential for significant financial upside and career growth is balanced by increased risk and uncertainty. As we've explored throughout this guide, making informed decisions requires a nuanced understanding of various factors:

Key Takeaways

1. Due Diligence is Crucial:

   • Thoroughly research the company's financials, market position, and growth prospects.

   • Understand the terms of your equity compensation and its potential value.

2. Culture Matters:

   • Look beyond perks to understand the company's values and work environment.

   • Ensure the culture aligns with your own values and work style.

3. Equity is Not Guaranteed Wealth:

   • Understand the risks and potential outcomes of your equity compensation.

   • Don't make life decisions based solely on the paper value of your equity.

4. Stay Informed and Adaptable:

   • Keep up with industry trends and regulatory changes.

   • Continuously develop your skills to maintain career resilience.

5. Seek Professional Advice:

   • Don't hesitate to consult financial advisors, tax professionals, or lawyers when dealing with complex equity situations.

Balancing Opportunities and Risks

Joining a pre-IPO company is often a high-risk, high-reward proposition. Here's how to approach the decision:

1. Assess Your Risk Tolerance:

   • Be honest with yourself about how much uncertainty you're comfortable with.

   • Consider your current life stage and financial obligations.

2. Evaluate the Total Package:

   • Look at base salary, benefits, work-life balance, and growth opportunities, not just equity.

   • Understand how the role fits into your long-term career goals.

3. Diversify Your Career Portfolio:

   • Consider mixing experiences at different stages of companies throughout your career.

   • Balance high-risk opportunities with periods of stability.

4. Trust Your Instincts:

   • If something feels off during the interview process or in your research, don't ignore it.

   • Remember that no amount of potential upside is worth compromising your well-being or values.

Final Thoughts on Navigating Your Tech Career

The pre-IPO world offers unique opportunities for tech professionals to join high-growth companies. Here are specific areas to focus on for making informed decisions:

Key Considerations:

• Equity Package Details:

  • Vesting Schedules: Typically, four years with a one-year cliff. Executive-level candidates should look for acceleration clauses in case of termination without cause or company sale.

  • Exercise Windows: Standard is 90 days post-employment. Extended windows (e.g., 7-10 years) are highly beneficial.

  • Tax Implications: Understand the tax consequences of ISOs, NSOs, and RSUs. For example, ISOs can trigger AMT, while NSOs are taxed as ordinary income upon exercise.

• Company Financial Health:

  • Revenue and Profitability: Examine the company's financial statements or any available data on revenue growth and profitability.

  • Funding Rounds: Investigate recent funding rounds and investor profiles. Strong backing from reputable VCs can be a good indicator.

  • Burn Rate: Understand how fast the company is burning through its cash reserves. A high burn rate without a clear path to profitability can be a red flag.

  • Investor Interest: Track how investors treat companies with that sector, business model, and market. How likely will they be able to raise capital at favorable terms?

• Leadership and Vision:

  • Executive Team: Research the backgrounds of key leaders. Look for a track record of successful ventures and clear, transparent communication.

  • Company Roadmap: Ask about the product roadmap and strategic vision. A well-thought-out plan for growth and market capture is crucial.

• Work Environment:

  • Work Hours: Clarify expectations around work hours and weekend work. High-intensity environments may not suit everyone.

  • Employee Turnover: High turnover can indicate deeper issues. Use LinkedIn to gauge the average tenure of employees in key positions.

• Professional Advice:

  • Legal Review: Have a lawyer review your equity agreement, especially if there are unusual clauses. This is crucial for executive-level positions.

  • Financial Planning: Work with a financial advisor to integrate your equity into your overall financial plan. Diversification is key to managing risk.

• Industry Trends:

  • Regulatory Changes: Stay updated on potential changes in SEC regulations affecting private companies. Increased transparency requirements can impact company operations.

  • Market Position: Analyze the company's competitive landscape. Companies with a strong market position are more likely to succeed and attract investors.

Wrap-Up:

Navigating the pre-IPO landscape requires a strategic approach. By focusing on these key considerations, you can make well-informed decisions that balance potential financial gains with personal and professional factors.

Remember, your career is a marathon, not a sprint. Each decision should support your long-term growth and well-being. Stay adaptable and informed, continuously update your skills, and seek professional advice when needed.

I listened to their career narratives and stories, and eventually realized the common elements they were missing.

I was fortunate enough to have interviewed C-suite and VP candidates and hired Directors myself, so I got to learn by exposure. To coach others, I drafted a new framework.

The Triple-STAR framework is an effective approach for leadership interviews. It builds on the classic STAR method (Situation, Task, Action, Result) by adding 5 key components that are essential for showcasing your strategic thinking, business impact, and growth potential.

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Table of Contents

1. Introduction

   1. The Evolution from STAR to Triple-STAR

   2. Why STAR Alone Isn't Enough for Leadership Roles

2. Mastering the Triple-STAR Framework

   1. Crafting Your Situation + Stakes + Status

   2. Defining Your Task

   3. Crafting Your Action Story

   4. Delivering Your Result + Reflection + Repetition + Relating

3. Crafting Your Triple-STAR Stories

   1. Understanding the Hiring Manager's Criteria

   2. Equipping Your Interviewers to Advocate for You

   3. Creating a Teaser and a Longer Version of Your Stories

4. Applying the Triple-STAR Framework

   1. Applying to Product Management Questions

   2. Applying to Engineering Management Questions

   3. Applying to Design Leadership Questions

5. Delivering Your Triple-STAR Stories

   1. How to Sound More Senior

   2. Making Your Stories Memorable

   3. Handling Tough Questions

6. Getting Feedback and Practicing Your Stories

   1. Seeking Feedback

   2. Iterating and Improving

   3. Putting in the Reps

7. Crafting Your Triple-STAR Career Narrative

   1. Creating a Compelling "Tell Me About Yourself" Story

   2. Tying Your 30-Second Pitch Into Your Full Narrative

   3. Adapting Your Narrative for Different Audiences and Roles

Note: I’m launching a group coaching program on Maven for Product Leaders on the Job Search. Join the waitlist to stay informed here.

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The Evolution from STAR to Triple-STAR

Leadership interviews differ from individual contributor (IC) interviews.

While execution skills remain important, they become the minimum bar at the leadership level.

What distinguishes top candidates is their ability to think and operate strategically, drive outsized business-level impact, and extend their influence beyond their immediate team.

Examples of IC interview questions:

• "Tell me about a time you faced a tough deadline."

• "Walk me through how you designed a new [architecture/feature]."

• "What is your superpower as a [PM/Engineer/Designer]?"

Examples of leadership interview questions:

• "Describe a time when you set a new vision and strategy for your team."

• "How have you built and grown high-performing teams in the past?"

• "Give an example of when you've built a data-driven culture."

• "When's the last time you disagreed with the C-suite?"

• "What's your leadership style?"

To nail leadership interviews, your stories need to operate at a higher level:

• Explain the why behind your actions

• Highlight the so what of your results

• Show how you grew as a leader

Key areas that leadership behavioral interviews often assess:

• Strategic Thinking: Can you see the big picture? Do you have a clear vision for your area and how it fits into the overall business strategy?

• Business Acumen: Do you deeply understand your business model, competitive landscape, market trends, and key growth drivers?

• Influence and Alignment: Can you get buy-in for your vision and roadmap from a range of stakeholders?

• Team Leadership: Can you hire, grow, and motivate high-performing teams?

• Execution at Scale: Can you drive successful outcomes across multiple teams, products, or geographies?

To stand out in leadership interviews, you need to speak to these higher-level criteria, showcasing your strategic vision, business impact, and ability to scale your influence.

Why STAR Alone Isn't Enough for Leadership Roles

STAR falls short for leadership roles in a few key ways:

• Lacks strategic context: STAR focuses on tactical execution but misses the strategic stakes that leaders deal with.

• Undersells business impact: STAR emphasizes the what of your results but doesn't fully capture the so what—the broader business outcomes and learnings.

• Misses leadership growth: STAR shows what you did but doesn't highlight how you grew as a leader and applied lessons learned.

Triple-STAR fills these gaps by adding five critical elements that take your storytelling to the next level.

Mastering the Triple-STAR Framework

Triple-STAR takes the core of STAR and adds five key components for strategic storytelling:

1. Stakes: Why did this situation matter to the business?

2. Status: What was your specific leadership role and scope?

3. Reflection: What did you learn about leadership? What would you do differently?

4. Repetition: How did you apply those learnings to drive further impact?

5. Relating: How does your experience map to the role you're pursuing?

Here's how the full Triple-STAR flow works:

1. Craft a Situation that conveys the strategic Stakes and your leadership Status

2. Define your Task: the specific challenge and success metrics you identified

3. Walk through the Actions you took: the key decisions and initiatives

4. Share the Results you achieved and their business impact

5. Reflect on your leadership growth and lessons learned

6. Repeat how you applied those lessons in other contexts

7. Relate your experience to the role at hand

But first, a note on flexibility

The power of Triple-STAR is that it's a framework, not a rigid formula. You can and should adapt it to fit the specific question, context, and time constraints you're dealing with.

• Context-heavy: Sometimes you might spend more time on the Situation and Stakes to really set the stage for a high-impact story.

• Action-focused: Other times, you might focus more on the Actions and Results to dive deep into your approach and quantifiable impact.

• Teaser-only: And in some cases, you might opt for a quick, headline-style summary that hits just the key highlights to be efficient with time.

The key is to understand the purpose and power of each component, so you can flex them in the moment to craft the most relevant and compelling answer.

Throughout this guide, we'll explore different levels of depth you might use to adapt Triple-STAR to various contexts.

Let's dive into each component of the Triple-STAR framework in more depth.

Crafting Your Situation + Stakes + Status

The Situation sets the context for the challenge or opportunity you faced.

To make it impactful:

1. Start with a concise problem statement

2. Then layer in the Stakes to convey the strategic importance

3. Finally add your Status to clarify your leadership role and scope

Example (Situation only):

"When I became Director of Product at Dropbox, I took over a flagship product."

Example (Situation + Stakes):

"When I became Director of Product at Dropbox, I took over a flagship product that was losing market share to a competitor. This put our $200M revenue stream at risk and threatened our market leader position in an area that secured us top enterprise logos."

The Stakes highlight the strategic importance and potential impact of the situation. They answer the "so what?" and convey the urgency and magnitude of the challenge. Effective Stakes tie the situation to key business drivers like:

💰 Financial impact (revenue, profitability, valuation)

🤝 Customer impact (satisfaction, retention, market share)

🥇 Competitive impact (differentiation, positioning, advantage)

🤜🤛 Organizational impact (morale, alignment, agility)

🌟 Reputational impact (brand, credibility, trust)

Example (Situation + Stakes + Status):

"When I became Director of Product at Dropbox, I took over a flagship product that was losing market share to a competitor. This put our $200M revenue stream at risk and threatened our market leader position in an area that secured us top enterprise logos. I led a 20 PM team and reported to the CPO, often updating the board directly."

Concise Example (Situation + Stakes + Status):

"As Director at Dropbox, I led a 20 PM team reporting to the CPO to turn around a flagship $200m product that was losing market share and risking top Fortune 100 accounts**.**"

The Status clarifies your specific leadership role and scope within the situation. It helps the interviewer understand your level of responsibility, authority, and influence in driving the outcome. Key elements to highlight in your Status:

• Your title and level within the organization

• The size and scope of your teams, products, or business areas

• Your key cross-functional partnerships and influence

• Your reporting line and accountability to senior leadership

Putting it all together, a compelling Situation + Stakes + Status sets the stage for a powerful leadership story by conveying the strategic context, the urgency and importance of the challenge, and your specific role in tackling it.

Defining Your Task

The Task spells out the specific challenge you were responsible for, given the situational context. A strong Task statement should:

✅ Clarify the reasoning for your specific goals or objectives

✅ Outline the key success criteria or metrics

✅ Highlight any unique challenges or complexities

Example (Concise):

"I helped the CPO realize our top lever to turn around our market share decline was to win on experience and boost end-user engagement and retention with two quarters to test it."

Example (Extended):

"We had to turn around our market share slide and get the product growing again. I knew we needed to differentiate our offering and boost user engagement and retention by 20% in two quarters. I also wanted to close three big enterprise deals to validate our new value prop.

This was a tall order given we were in the middle of a major platform overhaul and my team was understaffed after a recent reorg. Plus, we had a tight timeline with our IPO coming up."

Depending on the situation and the question, you may choose to frame your Task more succinctly, hitting just the key objectives and success criteria. Or you may opt for a more expansive framing that dives deeper into the sub-tasks, workstreams, and complexities involved.

The right level of detail will depend on the specifics of your story and the airtime you have to tell it. The key is to provide enough texture and context to make the task feel substantial and challenging, without getting lost in the weeds.

💡 When defining your Task, focus on the "critical path" elements that were most essential to achieving your objectives. Use active, ownership-oriented language to put yourself in the driver's seat from the outset. Don’t take credit for other’s work, but show your own agency and that you thoroughly understood the decision-making of leaders above you.

Crafting Your Action Story

The Action story walks through the key strategies, decisions, and moves you made to tackle the challenge defined in your Task. A strong Action story should:

✅ Demonstrate your strategic approach and key decisions

✅ Highlight specific leadership behaviors and skills

✅ Illustrate how you navigated challenges and complexities

✅ Convey the scale and difficulty of the task

Action Example:

"I started by rallying the team around a new vision for the product as the leader in AI-powered productivity. We then dug into user research and data to zero in on our biggest AI feature opportunities to differentiate for the buyers and get the end-users engaging more.

To fill our talent gaps, I restructured the team into cross-functional squads and recruited top ML talent from a previous employer. I also negotiated with engineering to modernize our data infrastructure so we could test and learn independently while they worked on a separate platform overhaul.

When an unexpected privacy issue threw a wrench in our initial ML models, I worked with the team to quickly pivot to a new approach that balanced personalization and privacy. We had some heated debates, but I kept the team focused on our north star of the user experience and keeping the accounts from switching to competition.

Throughout, I made sure to keep the team fired up with regular stand-ups and demos to leadership. I told other leaders to celebrate the learnings as much as the key wins."

Concise Action Example:

“I got the team excited about a new AI-powered productivity positioning. Data and research helped us find exactly what the end-users would engage with and buyers would care about, but we lost engineers to other projects, so I had to reorganize the team into cross-functional squads and bring in ML experts I knew to fill the talent gaps.

We hit a privacy snag that messed up our ML models, so I helped the team switch to a new approach that balanced personalization and privacy, even if it was tougher. Keeping clients from moving to competitors was priority. The team was grinding and three engineers requested a transfer, so I made sure they stayed fired up with frequent company presentations so leadership could celebrate both the early learnings and wins.”

Curate your examples around the 3-5 most critical moves or decisions that best illustrate your strategic thinking, execution ability, and leadership skills. Keep your language crisp and use "micro-stories" to bring your leadership to life.

💡 Aim for a coherent narrative arc that demonstrates your overarching strategy and impact, rather than a laundry list of tactics. Highlight the leadership behaviors and decision-making principles that guided your approach. Make sure you talk about the problems or missteps you had to navigate or it won’t seem authentic.

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Delivering Your Result + Reflection + Repetition + Relating

The Result showcases the outcomes and impact of your actions. A great Result section:

✅ Quantifies achievements with key metrics

✅ Ties results back to the original Stakes and Task

✅ Demonstrates tangible business value and broader impact

✅ Incorporates leadership lessons (Reflection), application (Repetition), and relevance to the role (Relating)

💡A very common follow-up question to STAR stories is “What would you do differently if you could go back?” You can get ahead of this question by using this prompt for your Reflection.

Example of Result + Reflection + Repetition + Relating

"The revamped product took a few quarters to show results, but we widened our market lead, landed 5 new logos, and achieved the biggest jump in core engagement in years, despite occasional AI bugginess. The renewed momentum and AI features became a key IPO narrative.

I learned to assess the team before aligning on targets. Aligning teams around a bold vision is easy, but extending the timeline or adding resources could have achieved 90% of the benefit without burnout. I applied this lesson in my current role, launching an AI feature only after borrowing resources from another project.

It sounds like you’re also looking for someone to turn around the product trajectory, and we will be working with a scrappy team until the next funding round.

Focus on the 3-5 most relevant metrics and tie them clearly back to your original Task and Stakes. Use the Reflection and Repetition components to articulate the leadership lessons you learned and how you've applied them to drive further impact. Finally, use the Relating component to draw explicit connections between your experience and the opportunity at hand, showcasing your excitement and unique value.

💡 Quantify your results wherever possible, but also include qualitative indicators of impact for color. Keep the focus on strategic outcomes and leadership growth, not just tactical execution.

🌟 If you are having trouble crafting your stories, consider leadership job search coaching.

Leadership Job Search Coaching

Crafting Your Triple-STAR Stories

Now that we've broken down the components of the Triple-STAR framework, let's explore how to craft compelling leadership stories using this structure.

Understanding the Hiring Manager's Criteria

Before you start crafting your Triple-STAR stories, it's crucial to understand what hiring managers are looking for in leadership candidates. While the specific criteria may vary by role and company, there are some common themes:

✅ Ability to set a bold, inspiring vision and align the organization to execute

✅ Track record of delivering growth and innovation at scale

✅ Talent magnet who can build, grow, and retain high-performing teams

✅ Customer obsession and strong product/business/technical acumen

✅ Collaborative cross-functional leader who makes the whole organization stronger ✅ Strong communicator who can influence and inspire at all levels

✅ Ability to make tough decisions and navigate complexity

✅ Growth mindset and learning agility

✅ High integrity and values alignment with the company culture

💡 Your most effective Triple-STAR stories will highlight multiple of these criteria while still feeling authentic and specific to your individual leadership journey.

Equipping Your Interviewers to Advocate for You

Getting hired isn't just about impressing interviewers. It's also about equipping them to advocate for you behind the scenes.

After each interview, your interviewer will summarize your strengths, weaknesses, and fit to the hiring committee.

🎯 Your goal is to arm them with a compelling narrative that makes them fight for you.

To make this happen:

✅ Tell realistic stories with a clear narrative arc

✅ Show how you navigated challenges and made tough calls under pressure

✅ Weave in authentic details about people, missteps, and lessons learned

✅ Keep your responses crisp and well-practiced

✅ Focus on 2-3 key takeaways that highlight your unique strengths

Bad Example:

"The story was hard to follow and I wasn't clear on his specific role or impact. The results also sounded exaggerated—I'd need to dig into the specifics more."

Good Example:

"She walked me through how she led a major reorg to boost execution speed. She sized up talent, redesigned the org, and tracked progress with clear metrics. I was impressed how open she was about the disagreement with the COO, but she handled it well. Her strategic thinking and change management skills really stood out. The 20% productivity gain and positive team feedback spoke volumes. She'd be a major asset for our transformation."

💡 Arm your interviewers with memorable, authentic stories about your leadership journey. Summarize and spoon-feed the takeaways for them and how it relates to the role. Make it easy for them to go to bat for you with the hiring committee.

Creating a Teaser and a Longer Version of Your Stories

Interviewers can vary significantly in their preferences for concise versus detailed responses. To navigate this, it's helpful to prepare both a "teaser" and a longer version of your key stories.

The teaser (30-60 seconds):

• Gives a concise, high-level summary

• Piques the interviewer's interest

• Includes the strategic stakes and your leadership status

Example:

"At Netflix, I led a product team for our Interactive Content initiative. It was a big bet to set us apart and reduce churn, but we were on a tight timeline and needed close coordination across content, engineering, and marketing. In 6 months, we launched our first batch of interactive titles, which drove major engagement and signups. Even though they were one-and-done, we actually made an important splash. Happy to dive into more specifics on how we made it happen. There are some fun curveballs in there. Or I can share another leadership example if you prefer."

The longer version (2-3 minutes):

• Dives deeper into the situation, stakes, your actions, and impact

• Walks through your strategic approach and key decisions

• Shares leadership lessons and how you've applied them

Example:

"I had just started as Lead Product Manager at Netflix when leadership decided to take some bold bets with all of the new streaming services launching and scaling fast. User retention was a major priority, and my VP told us we needed to make Interactive Content work and asked me to find an innovative solution fast for an idea a partner studio had. If we could even just pull off the production and release of the title and features, we would get some major credibility in the market…

[Dives into Action, Result, Reflection, Repetition, Relating]"

💡 Start with a teaser to gauge the interviewer's interest and give them flexibility to steer the conversation. Always have a more detailed version ready to go if they want to double-click.

More Good and Bad Examples of Triple-STAR Components

Let's look at a few more examples to further illustrate effective Triple-STAR storytelling:

Bad Situation + Stakes + Status:

"In my last job, I was the most senior software engineer on the payments team. We had a buggy codebase that caused the system to crash a lot, causing customers to complain. I had to lead the initiative to fix it.“

Good Situation + Stakes + Status:

"When I joined Stripe as the only Staff Engineer on the Payments team, I took over an area that was struggling with reliability and missed deadlines. Our payments platform was going down every week, which was really frustrating customers and putting $50M in revenue at risk. The Director expected me to turn things around and deliver a stable, scalable system to calm things down before we did a big push to close some global Fortune 100 accounts."

Bad Task + Action:

"I was asked to fix the bugs and improve code quality. I started reviewing the codebase to find issues. I refactored some of the messiest parts and added comments to explain the code better. I tried to get the team to improve our manual testing and improve deployment tools, but it was hard to change how the team did things."

Good Task + Action:

"My goal was to stabilize the payments platform and get our on-time delivery to 95%+ within two quarters. I audited our systems to find the biggest blockers. Then I worked with the team leads to map out a phased approach - first rebuilding our core service for scale, then automating key parts of our QA and development process. Even after that, we still had a vendor outage right before a major deadline, so I jumped in to handle the incident response and got the team to put in a failover solution to minimize customer impact."

Bad Result + Reflection + Repetition + Relating:

"After I made those changes, the code was more stable and readable. We had many fewer bugs and much less downtime. I learned a lot about the payments domain and how to fix problems even though I was new to an established team with their own way of doing things. I think my technical and collaboration skills could be useful for your company since you also deal with financial systems."

Good Result + Reflection + Repetition + Relating:

"By Q2, we had slashed our payment failures from weekly to less than once a quarter, while getting our on-time delivery to 98%. The improved reliability helped us close several big enterprise deals, which contributed to us doubling revenue that year.

The main takeaway for me was the criticality of proactively identifying and mitigating risks. I applied this in my current role, implementing chaos engineering practices that the team tells me is a night and day improvement over how they were doing things before.

I see a ton of similarities between my experience and the challenges your org is facing with reliability at scale. I love this type of challenge, so I look forward to learning more about it and where I can help."

💡 Notice how the strong examples are concise, specific, and focused on strategic impact, not just team-level impact? The weaker examples are vague, tactical, and don't show tangible outcomes or transferable lessons.

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Applying the Triple-STAR Framework

Let's explore how to apply the Triple-STAR framework to common leadership interview questions across product, engineering, and design.

Applying to Product Management Questions

Question: "Tell me about a time when you had to make a difficult product prioritization decision with limited data."

Situation + Stakes + Status:

"As the Product Lead for our e-signature product at DocuSign, I was accountable for hitting growth targets in a competitive market. In Q4, a customer escalated a bug that put a $5M contract renewal at risk. This happened as we were preparing to launch new AI features at our annual conference, which was important for defending our market position against a competitor rumored to be unveiling a similar offering."

Task + Action:

"With two weeks before the renewal deadline and the product launch, I had to think beyond quick fixes. After assessing the issue with the team, I proposed a solution: we would decouple the customer's instance from our main codebase and assign a team to build a custom patch on a tight timeline, while the core team focused on the AI launch. I also worked with sales to craft a proposal for the customer, offering a multi-year contract with pricing incentives and early access to our AI capabilities in exchange for flexibility on the renewal timeline. I then engaged with the customer's engineering lead to discuss the plan, acknowledging the impact of the bug while presenting a vision for a long-term partnership."

Result + Reflection + Repetition + Relating:

"The dedicated team delivered the custom patch on schedule, and the customer renewed and expanded their contract, agreeing to be a reference at our conference. The core team successfully launched the AI features, supporting our position in the market.

I realized that trade-offs aren’t always binary either/or decisions. By taking a customer-focused view and spending time with the team to think through the problem before reacting, we were able to meet short-term needs and our long-term goals.

It doesn’t always work out as nicely as this, but when I became a Director, I learned to coach my PMs on patience when a priority conflict comes up to try to find alternative paths.

Your teams have a quarterly public release cycle, so I imagine similar deadlines come up with unexpected blockers here."

Applying to Engineering Management Questions

Question: "Describe a time when you led your team through a major technological change or challenge."

Situation + Stakes + Status:

"In my last role as Engineering Manager at Yelp, our monolith was straining under our growth, causing site instability and outages during peak traffic. This was frustrating customers, stalling our product velocity, and putting our revenue targets at risk. As the manager of the infrastructure team, I was responsible for architecting a more scalable, resilient solution to support our next stage of growth."

Task + Action:

"After digging into the data, I proposed moving to a microservices architecture on Kubernetes. This was a major shift that would impact every eng team. To build alignment, I pitched the exec team on the business case, highlighting the benefits of faster deployments, better fault isolation, and elastic scale. There was a lot of push back from Product and the go-to-market teams since this would push out timelines on feature enablement projects. I had to do a bit of a listening tour, but I realized that as much as we would miss out on feature launches, there were other priority projects that would not be blocked on the backlog. Plus, everyone was on board with stopping the continuous missing of SLAs, firefighting with customers, and weekend on-call alerts.

I got the green light from the CPO once I got enough advocates. I worked with the architects to chart our migration path and sequence the work in phases. I restructured the teams into cross-functional pods aligned to each major service boundary and put in place clear communication channels and development workflows to keep everyone in sync. We didn’t have program managers, so I assigned one of my engineering managers to run it and let his lead engineer manage her team’s day-to-day."

Result + Reflection + Repetition + Relating:

"Over the next year, we incrementally migrated all our core services to the new architecture. This let us handle 10x our previous peak load, while speeding up development cycles by 3x. We couldn’t get it all done at once - the last 10% always seems to take as long as the first 90, but it was enough to make a big impact. Strategically, the project helped shape our eng culture to be more agile, decoupled, and resilient. Teams were free to take on more risks.

The biggest lessons for me were understanding that you need to not only paint a compelling vision, but really listen to and empathize with stakeholders early to help get them on your side or find creative solutions.

Overcommunicating during the transition was also important toto keep everyone engaged. It gave our org more confidence going into some other hefty projects when we were trying to improve international performance.

I know your org still uses a monolith at scale and it’s working well, but that ownership culture change after the re-architecture was more impactful than the technical change itself."

Applying to Design Leadership Questions

Question: "How have you used design to influence product or business strategy?"

Situation + Stakes + Status:

"In my previous role as Head of UX at Squarespace, we were seeing a concerning drop in activation and retention for new sellers. Our product roadmap was packed with incremental UX optimizations, but lacked a coherent vision and retention growth had stalled for several quarters. I saw a unique opportunity to rethink our approach across my 17 designers and their product pods."

Task + Action:

"I initiated a design sprint to deeply understand the unmet needs and pain points of our new sellers. My team and I shadowed onboarding sessions, analyzed support tickets, and interviewed churned users. The insights were eye-opening - we were overwhelming new users with feature bloat and failing to serve the needs of key verticals like restaurants and service businesses.

I used the learnings to write up a UX strategy focused on personalized onboarding flows, verticalized in-product education, and a revamped dashboard experience. I then partnered with the product leads to translate this into a re-prioritized roadmap. To bring the strategy to life, I pitched the VP of Product on a reorg to align around this new vision. He was hesitant to break up teams already assigned to OKRs, so we mapped out how we could restructure the design org into embedded vertical pods, while still maintaining most of our goals. We established new rituals to tighten our feedback loops with users."

Result + Reflection + Repetition + Relating:

"The redesigned experience drove a 30% lift in day-7 activation, a 20% improvement in 12-month retention, and a 15% boost in NPS, while also accelerating our penetration in strategic verticals. We elevated the role of design in shaping product strategy and catalyzed a cultural shift towards a more customer-obsessed mindset. This was something I wish I had tried harder to do in my past roles, but one of the product managers guided me on how to influence and collaborate with that org instead of trying to combat them or go over their heads.

I know your org is looking to level-up the strategic impact of design, particularly as you expand into new customer segments without becoming a feature factory. I would love to meet with the product leaders and see how they are thinking about this challenge."

Crafting Your Triple-STAR Career Narrative

Beyond acing individual questions, the most impressive candidates weave their Triple-STAR stories into a cohesive career narrative. This is your chance to connect the dots across your experiences and paint a compelling picture of your unique leadership trajectory.

Creating a Compelling "Tell Me About Yourself" Story

Your "Tell Me About Yourself" response is the perfect place to set the stage with a high-level overview of your career journey and core themes. Here's an example of how you might structure it:

Example: Product Leader

"I've spent the last decade building products that make a real difference for customers. I started out at Microsoft as a PM on Office 365 when we were way behind on the cloud and trying to catch up with Google. I launched features that helped millions of users collaborate more effectively, which is harder than it seems when working with systems driving countless installed software versions and devices. This supported Microsoft taking back a lot of that market share.

I wanted to take on more of a consumer role and joined Lyft, where I led an core part of the rider app through a period of hyper-growth. I started shipping features, but quickly had to focus on building a world-class product org that could innovate and experiment at scale while staying obsessed with the user experience. I grew the team to 15. This was really interesting when we had to test in many different geographies. I can go into more detail later if you’d like.

Most recently at VRBO, I drove the end-to-end guest experience across all our platforms and regions. I set the long-term vision and strategy, and led a 20+ person team to bring it to life. Through it all, I've been passionate about how tech meets the real world to impact people’s daily lives. I'm excited to bring that passion for creating great human experiences to the CPO role here."

This pitch weaves together a clear thread around customer-centricity, business impact, and leading at scale, while giving concrete examples of the leader's progression and expanding scope. The interviewer walks away with a strong sense of their core values and a hook to dive deeper.

Tying Your 30-Second Pitch Into Your Full Narrative

Your 30-second pitch should serve as a compelling preview of your full Triple-STAR narrative. Distill the key elements of your most impactful Triple-STAR stories into concise, memorable bullets.

Example Pitch: Design Leader

"At Digit, I led 15 designers in launching our automated savings product amidst intense regulatory scrutiny, attracting 500,000 customers and generating $50M in year-one revenue, proving our ability to expand beyond our core offering.

I grew the design team from 8 to 20 at Gusto and redesigned our mobile app, a key driver of user growth and engagement, resulting in a 25% productivity boost and 15% adoption increase.

As the Design Director at Faire, I led the checkout redesign, a critical lever for increasing GMV, lifting conversion by 10%, average order value by 15%, and annual revenue by $200M.

With 12 years leading design teams and shipping products that drive core business metrics across fintech, SaaS, and e-commerce, I'm excited to bring my that experience leading design teams that actually move metrics to work with your data-focused product teams."

• This pitch starts with a punchy headline tying together design, user impact, and business results.

• It provides concrete examples of major Triple-STAR achievements from well-known companies, with specific metrics.

• It ties together the themes of design as strategy, user-centricity, and business impact.

• Finally, it ends with forward-looking excitement for the role and the impact they could have.

Adapting Your Narrative for Different Audiences and Roles

While your core Triple-STAR stories will likely stay consistent, you'll want to adapt your emphasis and delivery based on your audience and target role:

• Tailor to the role: For a CTO position, double-click on your experience setting technical strategy and building great engineering cultures. For a Head of Product role, amp up your customer-obsession, design chops, and track record of product innovation.

• Read your audience: If you're chatting with the CEO, hit on your strategic vision and business acumen. If you're talking to a future peer in Sales, spotlight your collaborative approach and success enabling revenue growth.

• Match the culture: If you're targeting a fast-paced, scrappy startup, lean into your entrepreneurial drive and comfort with ambiguity. If you're aiming for a more established enterprise, focus on your experience navigating matrix orgs and driving alignment at scale.

💡 The key is to shape your narrative in a way that resonates with your specific audience while staying true to your authentic leadership journey and strengths. The more you can demonstrate your understanding and embodiment of the company's needs and values, the more compelling your story will be.

Common Pitfalls and Best Practices

As you craft and deliver your Triple-STAR stories, watch out for these common traps:

❌ Rambling or losing the plot: Keep your stories concise and coherent. Every detail should serve the narrative arc and leadership themes.

❌ Getting too in-the-weeds: Stay focused on your strategic impact and key decisions, not the technical minutiae.

❌ Hogging the spotlight: Frame your achievements as team wins and give credit where it's due.

❌ Glossing over challenges: Be upfront about obstacles and failures, but pivot quickly to how you overcame them and what you learned.

❌ Faking it: Never embellish or misrepresent your role or results. Authenticity and humility are key.

And keep these best practices in mind:

✅ Know your endgame: Be clear on the key leadership traits and experiences you want to convey, and structure your stories accordingly.

✅ Paint a picture with data: Ground your results in specific metrics to make your impact tangible and credible.

✅ Show, don't just tell: Use concrete examples and anecdotes to illustrate your leadership in action vs. falling back on generic descriptors.

✅ Tie it together with themes: Link your stories together with common leadership themes and lessons learned to create a cohesive narrative arc.

✅ Speak their language: Tailor your language, examples, and emphasis to resonate with your particular audience and target role.

✅ Engage, don't just recite: Draw your interviewer in with eye contact, vocal inflection, and body language, and adapt your delivery based on their reactions and follow-ups.

✅ Practice makes progress: Every interview is a chance to sharpen your skills. Seek out diverse perspectives on what's landing, and iterate accordingly.

✅ Interview intelligence: Leverage the search firm recruiter or internal recruiting team to give you context on the interviewers, what styles and focus areas they prefer, and what they don’t like

💡 The best Triple-STAR storytellers are always honing their craft. They know their stories inside and out, but they also remain agile in the moment, reading the room and adapting their style to forge genuine connections. The more you practice, the more natural and impactful your delivery will become.

Delivering Your Triple-STAR Stories

Crafting compelling stories is only half the battle. To truly stand out, you also need to deliver them in a way that engages and persuades your audience. Here are some tips for making your Triple-STAR stories stick:

How to Sound More Senior

• Elevate the strategic: Emphasize the big-picture impact and implications of your work, not just the tactical details.

• Show, don't just tell: Instead of claiming to be a "strategic thinker," share tangible examples of how you've shaped strategy and driven high-level outcomes.

• Speak with authority: Communicate confidently about your decisions and impact. Avoid qualifying language like "I think" or "I just."

• Spread the credit: Acknowledge your team's contributions while still owning your unique leadership role.

💡 The most senior leaders communicate with clarity and conviction about their distinct value and impact. They frame their work in terms of strategic priorities and business outcomes, not just isolated projects or tactics.

Making Your Stories Memorable

• Lead with a hook: Grab your audience right away with a surprising insight or intriguing challenge that sets up the stakes.

• Create a villain: Frame the core obstacle as a compelling antagonist that you set out to overcome.

• Build tension: Structure your story with rising action, twists and turns, and a pivotal climax.

• Paint a vivid picture: Weave in sensory details and evocative metaphors that stick in your listener's mind.

• Drive it home: Close with a clear leadership takeaway or "aha moment" that crystalizes your impact.

💡 The most memorable stories take the audience on a journey, with a clear beginning, middle, and end. They forge an emotional connection and leave the listener with a specific, indelible impression of you as a leader.

Handling Tough Questions

• Acknowledge, don't dodge: Tackle the question head-on, showing that you understand the intent behind the ask.

• Reframe the context: Provide additional color that shifts the question in a more favorable light.

• Bridge to an example: Share a relevant Triple-STAR story that demonstrates your approach to the issue at hand.

• Boomerang it back: Close with a thought-provoking question that invites your interviewer into a dialogue.

Example: "Tell me about a time you failed"

"Early in my career, I struggled with delegation. I was so passionate about the work that I felt I needed to have my hands in everything.

It came to a head when I was leading the launch of a new payments feature at Square...

[Tells Delegation Triple-STAR Story]

Since then, I've become much more intentional about empowering my teams and focusing my energy where I can add the most unique value. I've found that when I give people stretch opportunities and coach them through it, we not only deliver better results, but I also free up bandwidth to focus on more strategic priorities.

I'm curious, how does your team think about balancing autonomy and alignment? I'm always looking to learn from other leaders."

The key is to reframe the question in a way that showcases your strengths and growth mindset. By bridging to a relevant Triple-STAR story, you can transform a potential weakness into a powerful learning that makes you an even stronger leader today.

Getting Feedback and Practicing Your Stories

The best Triple-STAR storytellers never stop sharpening their skills. They proactively seek input, experiment with fresh approaches, and put in the reps to make their stories shine. Here are some ways to continually up your game:

Seeking Feedback

• Practice with pros: Role-play with experienced leaders or interview coaches. Ask for targeted feedback on clarity, delivery, and impact.

• Lean on peers: Share drafts of your stories with trusted colleagues who can validate the details and suggest areas to amp up your leadership.

• Tap your tribe: Pressure-test your stories with friends and mentors from different functions. Incorporate their diverse insights to keep refining your message.

• Learn from the users: Where fitting, share a story with someone who directly benefited from your work. Note what resonates most about the user impact.

Iterating and Improving

• Look for patterns: Mine your feedback for common themes. What parts consistently hit the mark or fall flat?

• Mix up your structure: Experiment with alternative story arcs or levels of detail in each section. Observe how different frameworks land with your audience.

• Crystallize your takeaways: Keep distilling the core leadership lessons you want each story to reinforce about your brand.

• Stay fresh: As you rack up new leadership experiences and insights, explore different ways to reinvent and extend your stories for maximum relevance.

Putting in the Reps

• Crawl, walk, run: Start testing your stories in low-stakes settings like team meetings, then build up to higher-profile opportunities like exec presentations or all-hands.

• Embrace the butterflies: Tackle your storytelling anxiety head-on by proactively seeking out chances to share - the more you do it, the easier it gets.

• Chunk it down: Master one Triple-STAR story at a time, nailing your delivery before moving on to the next. Momentum builds on momentum.

• Find thought partners: Buddy up with a trusted colleague to trade stories and hold each other accountable for consistent practice.

💡 Like any skill, Triple-STAR storytelling gets better with dedicated practice and refinement. The more you invest in it, the more confident and compelling you'll become not only in interviews, but in all aspects of your leadership communication.

Conclusion

Congrats! You now have a powerful framework for crafting and delivering leadership stories that set you apart. But remember, Triple-STAR mastery is a journey, not a destination. To keep growing as a storyteller:

✅ Go beyond the tactics: Contextualize your stories with the big-picture strategy, impact, and lessons learned.

✅ Weave a cohesive arc: Use your stories to connect the dots of your career journey and paint a vivid picture of your unique leadership trajectory.

✅ Meet your audience where they're at: Shape your stories to resonate with the specific needs and values of the role and company you're targeting.

✅ Aim for authentic connection: Treat your interviews as two-way conversations, adapting your stories on the fly to forge genuine understanding and rapport.

✅ Always be iterating: Put your stories through the paces, proactively seeking feedback and experimenting with new angles to keep raising the bar on your performance.

Your Triple-STAR stories are more than just a ticket to your dream job - they're the scaffolding for your leadership brand and legacy. By continually investing in them, you'll gain the conviction and credibility to inspire and mobilize others throughout your career.

So what are you waiting for? Go out there and practice like your professional growth depends on it - because it does! Sharpen your stories at every opportunity, big or small, and watch as Triple-STAR storytelling becomes second nature for amplifying your leadership impact.

The Triple-STAR framework is your foundation. Your own leadership journey is the raw material. Your willingness to build the storytelling muscle will be the bridge to the opportunities you most want to create. With focus and persistence, there's no limit to how far your unique voice and talents can take you.

So lead on, and may your Triple-STAR shine bright.

Key Takeaways

1. Leadership interviews require a different storytelling approach than IC interviews - one that emphasizes strategic thinking, business impact, and leadership growth.

2. The Triple-STAR framework provides a flexible but powerful structure for crafting these leadership stories, by adding dimensions of Stakes, Status, Reflection, Repetition, and Relating to the traditional STAR model.

3. Effective Triple-STAR stories balance strategic context with specific examples, quantify impact with metrics, highlight leadership skills and behaviors, own challenges and learnings, and relate back to the role at hand.

4. The framework can be adapted for different roles, levels, and contexts, from senior executives driving large-scale transformations to earlier stage managers leading more contained initiatives. The key is to frame your story in a way that showcases your highest level of leadership and impact.

5. Mastering leadership storytelling takes practice, iteration, and customization. By internalizing the Triple-STAR framework and tailoring it to your own experiences and audience, you can walk into any interview with the confidence to tell powerful stories that leave a lasting impression.

My hope is that this guide has equipped readers with a clear, actionable framework for crafting compelling leadership stories, as well as the inspiration and motivation to start putting it into practice. Whether you're gunning for your first management role or vying for a C-suite position, the ability to articulate your vision, impact, and growth through storytelling is an invaluable skill that will serve you throughout your career.

So take the time to reflect on your own leadership journey, identify those pivotal moments and transformative experiences, and start weaving them into Triple-STAR stories that showcase the leader you are and the leader you aspire to be. The interview room - and the business world - await your unique story. Go forth and make your mark!

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Earlier this month, I co-authored an article with titled "The Product Leadership Job Search." The piece, which clocked in at over 21,000 words, took a deep dive into the unique challenges and opportunities facing product leaders as they navigate the job market.

The response was overwhelming. The article resonated with product leaders at all levels, from aspiring Directors to seasoned CPOs, who found the insights and strategies both eye-opening and practical.

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However, what surprised me most was the feedback I received from tech leaders outside of the product function.

Executive engineers, designers, data scientists, marketers, and operations leaders reached out to ask whether the same principles and tactics applied to their own job searches.

The answer, in short, is yes.

While some specific challenges, nuances, and technical topics may vary by function, the fundamental truths of the executive job search remain constant.

1. The move to the hidden job market

2. The crucial role of Executive Recruiters and VCs

3. The compensation leaps, nuances, and high variance

4. The emphasis on reputation, network, and backchannels

5. The focus on narrative, executive presence, and company-level impact

These factors impact every tech leader looking to take the next step in their career.

That's why I've created this condensed guide, "The Tech Executive's Job Search Playbook." Drawing on essential insights from the original article, as well as new learnings from my conversations with top recruiters, VCs, and leaders, this playbook is designed to help tech executives at all levels – from Directors to the C-suite – navigate the job search process with confidence and success.

I recommend all leaders read the original article and bookmark it as a reference guide for their searches as it goes much deeper at 4x the length.

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• 7 external Executive Recruiters

• 2 internal big tech Executive Recruiters

• 2 VC talent teams

• 12 CPOs/ VPs

In the following sections, I’ll explore how the executive job search differs from the individual contributor experience and why a targeted, strategic approach is essential.

I’ll dive into the key components of a successful search:

• building your network

• crafting your narrative

• mastering the interview process

• and negotiating your ideal offer

Throughout, I’ll focus on providing concrete, actionable advice that you can put into practice immediately. If you find yourself needing more personalized guidance, consider exploring leadership job search and negotiation coaching services to help you land your dream role.

Whether you're actively seeking a new role or simply looking to keep your career options open, this playbook will arm you with the tools and knowledge you need to take control of your professional journey.

So let's dive in and unlock the secrets of the tech executive job search.

How the Executive Job Search Differs

If you've progressed through the ranks of individual contributor roles, you might think you have the job search process down pat. Update your resume, reach out to your network, reply to recruiter messages, apply to some listings, and ace the interviews – simple, right?

Not quite. When it comes to executive-level roles, the game changes entirely.

Here are a few key ways in which the executive job search differs:

The Hidden Job Market

Many of the most coveted executive roles never see the light of day on public job boards. As one product leader with 10 years of experience noted:

By my guess, anywhere from 10-30% of Director+ product roles are never posted. And as you reach the C-Suite, it goes to 70-100%.

Companies often kick off these searches before they have a finalized job description, and they may be hesitant to post the role publicly for a variety of reasons:

• They don't want to alert competitors to their strategic moves

• They don't want to create internal uncertainty or tension

• They want to avoid being inundated with unqualified applicants

This means that as an executive job seeker, you can't rely on passive tactics like applying to public job listings. You need to be proactive in tapping into the hidden job market.

The Crucial Role of Recruiters and VCs

This is where executive recruiters and venture capital firms come in.

A veteran CEO early in my career told me:

The best thing to do is to find great executive recruiters and build long-term relationships with them. This has served me well - they know and trust me after I get offers or pass interviews. I know and trust them to market me properly and prep me/take care of me during the process.

Executive recruiters, in particular, are retained by companies to conduct confidential searches for key leadership roles. They have deep networks and expertise in identifying and vetting top talent.

Even FAANG companies use the top global executive search firms and their own internal Executive Recruiting teams.

That means these recruiters and VCs know about high-level opportunities long before they become public knowledge, if they’re ever posted.

For example, Salesforce recently posted a CPO role for Slack, but that was likely after they had their top candidates deep in the pipeline and they were just checking a box for making sure there is a chance for more diverse candidates to apply.

The probability that they choose anyone who did not come through reputable network connection or recruiting firm outreach is near-zero.

For Director-level roles, whether they are run internally varies based on how hot the market is, how strong the internal executive recruiting capabilities are, and how selective the hiring manager wants to be.

But once you reach VP, SVP, and C-suite roles, executive hiring managers want to choose who they meet and want to tap into the network and experience closing top candidates that a search firm and VC can bring.

Some of the top executive search firms in the tech industry include:

• The “SHREK” Big 5 Global Search Firms: Spencer Stuart, Heidrick & Struggles, Russell Reynolds Associates, Egon Zehnder, Korn Ferry

• Riviera Partners: A mid-market firm specializing in technology leadership searches

• True Search: A mid-market firm with a focus on high-growth tech companies

• Daversa Partners: A mid-market firm known for its work with venture-backed startups

• Fusion Talent: One of the boutique firms specializing in product and technology leadership searches, founded by senior Partners from the mid-markets with deep networks

And these recruiters are your secret weapon.

• They help refine your pitch and sell you to companies

• They provide hard-to-find compensation and market information

• They prepare you for interviews

• They can help with your negotiations

And they even do this when you’re not actively working with them once they become a trusted partner.

“Lean on your recruiter for support and guidance end-to-end, even if they don’t offer it proactively. Ask for insight into what interviewers are looking for, the process, feedback on gaps to overcome, and help crafting stories.” —Theresa Skelly, Director at Riviera who helped Colin land a public company VP offer

Meanwhile, VCs have a vested interest in helping their portfolio companies build strong leadership teams. They can often provide valuable introductions and insights into emerging opportunities.

Some of the most active VCs in the tech executive talent space include:

• Andreessen Horowitz: Known for its in-house talent team and extensive network

• Sequoia Capital: Has a dedicated talent team and a track record of backing category-defining companies

• Accel: Active in helping its portfolio companies recruit top executive talent

A Head of Product candidate I was coaching got introduced to an a16z talent partner, who then introduced him to Executive Recruiters, who then connected him with multiple roles…

…including ones where he was the first and only candidate.

VC firms, especially those with Talent teams, will know a broader range of roles, since they often help connect founders with Executive Search firms. Executive Recruiters, however, are more directly incentivized by their retainer fees and want to build long-term networks, so they will help you throughout the entire process.

Alper Tekin, 2x CPO, suggests working with smaller, specialized firms:

They are more likely to pull top candidates from their roles and give them a better experience.

They also have a closer relationship with their network, especially if it is specialized (e.g. B2B SaaS Product leaders).

Vertical depth of specialization and horizontal breadth of network are the primary value search firms bring.

And that’s the key.

Executive Recruiters draw their value from their candidate-closing skills and from their network of tech leaders.

That’s you!

If you’re a great candidate, prepare for all interviews, and prove yourself to earn respect, then you provide them their core value.

I landed VP, CPO, and Head of Product offers with various recruiters and to this day I only have to email them to start getting opportunities or useful information.

That’s why VCs and search firms are important, but they aren’t the only differences when you hit the leadership level job search.

Evaluating Candidates Differently

When it comes to assessing executive candidates, companies are looking for more than just a strong resume and technical skills.

They’re evaluating and putting more weight on these factors:

1. Reputation

As Ken Sandy, 27-year product leader and author of The Influential Product Manager, put it:

Director is the point at which it goes from 'what I've done and how I did it' to 'my reputation'…and 'real business outcomes'…and that's why network becomes a lot more important.

Reputation is signaled in a few ways as a leader:

• How reputable is the person who vouched for you in you referral and in your backchannel references?

• How notable was the company and it’s trajectory while you were there and how did you contribute?

• Which leaders did you report to and how reputable were they?

• How quickly did you rise in scope and impact?

These are much more important than when you are an individual contributor, and a great interview performance may not be enough to get you an offer if you don’t check these boxes.

2. Impact

Andrew Abramson, 10-year recruiter, Founder of Fusion, ex-Riviera & Korn Ferry, emphasized:

Don't just list accomplishments as shipping a certain number of features. This signals a feature factory mentality. Instead, focus on the outcomes and impact, like incremental revenue or new channels.

3. Domain Expertise

Multiple executive recruiters mentioned how important domain expertise was to hiring managers for product leaders. They often have a specific domain, team size managed, specific stage, and similar challenges faced in mind for the ideal candidate profile.

4. Executive Presence

As I’ll discuss later, executive presence - your ability to communicate, present, and lead with gravitas - can make or break your candidacy, especially in the final rounds of the interview process.

Some of the most impressive candidates I’ve worked with have hit a ceiling at the C-suite level because of their communication style and content when presenting to C-suites and boards.

Putting it together

Navigating these nuances requires a different approach than a typical job search. You need to be strategic in how you build your network, craft your narrative, and position yourself as a top candidate.

If you're unsure how to effectively showcase your reputation, impact, domain expertise, and executive presence, consider working with a leadership job search coach who can help you refine your personal brand and value proposition.

In the following sections, I’ll dive into exactly how to do that – from leveraging recruiters and VCs to nailing the interview process and negotiating your ideal offer.

But first, let's take a moment to acknowledge the challenges of the executive job search. It can be a long, opaque, and sometimes frustrating process.

There will be moments of uncertainty and rejection. You may pour hours and even months into an opportunity that ultimately doesn't pan out.

According to Bobby Gormsen, a 20-year Executive Recruiter and Director at Paradigm who headed all Talent at Etsy through their IPO and Frame.io through the Adobe acquisition:

Many candidates are getting to final round interviews, [but] they’re being beat out by equally amazing people. And sometimes it comes down to preference. You may be a great fit for the role. Your feedback was probably positive across the board, but that there was just preference for somebody else.

There was nothing you could have done better in the process. It was just a decision that was made at the top to go with one individual over you…Sometimes the board will overrule the founder.

But with the right mindset and strategies, you can navigate these challenges with resilience and come out the other side with a role that truly aligns with your goals and values.

So take a deep breath, stay focused, and let's dive into the key components of a successful executive job search.

Building Your Executive Network

In the world of executive job searching, your network is your most valuable asset. It's your key to unlocking hidden opportunities, gaining insider insights, and ultimately landing your dream role.

But building a strong executive network requires more than just adding connections on LinkedIn. It's about cultivating genuine, mutually beneficial relationships with the people who can help you take your career to the next level.

Leveraging Recruiters and VCs

As I discussed earlier, executive recruiters and venture capital firms are two of the most important players in the tech executive job market. They have their finger on the pulse of the industry and often know about high-level opportunities long before they become public knowledge.

So how do you get on their radar and start building those relationships? Here are a few key strategies:

• Get Introduced: The best way to connect with a recruiter or VC is through a warm introduction from someone in your network. Leverage your existing contacts - former colleagues, mentors, investors - to see if they can make an introduction on your behalf.

• Be Specific: When reaching out to a recruiter or VC, be clear and specific about your background, your goals, and the types of opportunities you're interested in. The more targeted and relevant your outreach, the more likely they are to engage.

• Offer Value: Remember, building a network is about giving as much as you get. Look for ways to offer value to the recruiters and VCs in your network - whether it's sharing industry insights, making introductions to other high-potential candidates, or offering your expertise and advice.

• Stay in Touch: Building relationships takes time. Even if a recruiter or VC doesn't have an immediately relevant opportunity for you, stay in touch. Share updates on your career, congratulate them on their successes, and keep the lines of communication open. You never know when the right opportunity might arise.

I’m a 3x Senior Product Leader, and recruiters help me on each search.

But I have learned a few things about Executive Recruiters over the years:

• They won’t think of you: They’re often heads down in a single search and won’t even think to ping you or share your profile if another recruiters has a role that’s a fit

• They don’t talk to each other: Their internal CRMs are terrible and each recruiter at the firm will reach out to you separately and ask the same questions, even if just to do their own diligence

• They easily forget about you without specifics: If you ping them that you’re looking for a job, you may get a trickle of opportunities for a bit, but that will quickly trail off

• They can hide the good stuff: If you’re not clearly a top candidate, they’ll pitch you the less appealing clients.

I have seen the following work wonders for leaders to get the most out of recruiters:

1. Remind them: Ping them regularly every few weeks of your search so they remember you. Especially if you are in process with great companies so they know where your profile is resonating.

2. Ask them to shop you internally: They won’t necessarily think to share your profile with others internally. If you ask them, they’ll ask around their firm for any hits. I’ve personally had success with this and got 5 recruiters from a single firm send me opportunities.

3. Be specific: Tell them exactly what you want. Looking for Series C-E B2B Fintech Growth roles? They’re more likely to recall you when one pops up.

4. Signal your value: Take the time to get on a call or meet in person, even for a not-so-great company, so that you can show them how impressive you really are. Then let them know you are considering higher tier companies. They will tell you if you are not a contender.

Crafting Your Narrative

Getting on the radar of recruiters and VCs is just the first step. To truly stand out as a top candidate, you need to craft a compelling narrative that showcases your unique value and expertise.

Your narrative should be more than just a recitation of your resume. It should tell the story of your career journey, highlight your most impactful achievements, and demonstrate your leadership philosophy and style.

Here are a few key elements to include:

Your North Star: What drives you as a leader? What is the overarching mission or purpose that has guided your career choices and decisions? What opportunities will continue that journey?

Your Superpower: What is your unique strength or skill that sets you apart from other executives? Are you a master strategist, an inspiring communicator, a data-driven decision-maker?

Your Impact: What are the tangible results and outcomes you've achieved throughout your career? Not just on your product, but on the top-line company metrics like revenue, profit, and user scale. Be specific and quantitative whenever possible.

Your Vision: What is your perspective on the future of your industry or function? How do you plan to lead your team and organization to success in the face of emerging challenges and opportunities?

Vidur Dewan, Partner at Artisanal Talent, emphasized the importance of clarity in your narrative:

One of the biggest mistakes candidates make is not having clarity of thought and communication. First, sit down. Read through resume highlights. Then create a thesis, find the connective tissue, and hone in your message and narrative in a clear and concise manner.

This is by far the #1 most cited mistake candidates make: Not being prepared enough. That results in rambling, not having a clear narrative, and not having a thesis or even doing research on the company.

Even top resumes get rejections for skipping this.

Top mistake…Not researching the company and product and having an informed opinion by the time of the first interview. The best candidates are already excited about the company and full of product ideas by the time they talk to me.

—Katrina Benjamin, CPO at Axiom, ex-CPO at Apartment List, ex VP Product & GM at Upwork

Showing up unprepared is the most common mistake across all functions, whether it’s not reviewing the interviewer’s LinkedIn profile or being unaware of recent public announcements made by the company.

—Alex Klein, Nucleus Talent, ex-Partner at Artico and ex-True Search

The most common mistake is inadequate preparation. You have limited time to make an impression, so you’ve got to utilize your time wisely. Lack of prepartion is a big killer.

—Bobby Gormsen, 20yr Executive Recruiter, Head of Talent at Etsy and Frame.io

Always prepare. Even the most seasoned CPOs can use guidance on approaching upcoming conversations.

—Theresa Skelly, Director at Riviera Partners

You still have to prepare deeply for executive intro chats and interviews.

If you're struggling to articulate your unique value proposition, craft a compelling narrative, or come with a strong thesis, consider investing in leadership job search coaching to help you refine your story and positioning.

Tapping Your Existing Network

While building relationships with recruiters and VCs is important, don't overlook the value of your existing network. The people you've worked with throughout your career - former bosses, colleagues, mentees - can be powerful allies in your job search.

Here are a few ways to leverage your existing network:

1. Ask for Introductions

If there's a specific company or role you're interested in, see if anyone in your network has a connection there. A warm introduction from a trusted contact can be the key to getting your foot in the door. Starting with someone who is less connected, but high reputation can start a valuable “Reputation Chain”, which I will be writing about in future posts.

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2. Seek Advice and Insights

Your network is a wealth of knowledge and experience. Reach out to people who have recently gone through a job search or who have expertise in your target industry or function. Ask for their advice, insights, and lessons learned.

3. Offer Help and Support

Again, remember that networking is a two-way street. Look for ways to offer help and support to the people in your network, whether it's making introductions, sharing resources, or offering your expertise.

As Katrina Benjamin, CPO at Axiom, ex-CPO at Apartment List, ex-VP/GM at Upwork, put it:

Play the long game. Take every conversation that comes your way. Let a trusted network of people know you’re looking. Use trusted peers to help with interview preparation.

Treat your recruiters well. Take the calls. Take the interviews and prepare for them.

The real power of these relationships comes in your next search.

When I went on my second leadership search, I simply pinged the recruiters and VC contacts who saw me do well in my first search.

They immediately went to bat for me with clients and others in their firm or network.

They knew how to sell me.

The leader, VC, and Executive Recruiter relationships you build today will turn into step change opportunities in the future.

As you build and nurture your executive network, keep in mind that it's a long-term investment. The relationships you cultivate today may not pay off immediately, but they will serve you well throughout your career.

By being strategic, proactive, and generous in your networking efforts, you'll position yourself for success in the executive job market - and beyond.

Strategically Choosing Your Next Role

As an executive job seeker, it's easy to get caught up in the excitement of new opportunities and the desire to make a move. But before you jump at the first offer that comes your way, it's important to take a step back and think strategically about your next career move.

Your next role isn't just a job - it's a critical step in your long-term career journey. It's an opportunity to build new skills, gain exposure to new industries or business models, and position yourself for even greater success down the line.

So how do you choose the right next role? Here are a few key factors to consider:

Evaluating Opportunities Based on Long-Term Objectives

Start by getting clear on your long-term career goals. Where do you want to be in 5, 10, 20 years? What kind of impact do you want to have on your industry or function?

Then, evaluate each potential opportunity through the lens of those long-term objectives. Will this role help you build the skills, experiences, and relationships you need to achieve your goals? Does it align with your values and leadership philosophy?

The decision is not always clear cut. I turned down a public company VP role in 2021 and then a Series B CPO role and a public company VP role in 2022 for a Series F Sr. Director role because of the perceived quality of a company. The net impact of those decisions is still to be seen, but each company thinks about it very differently.

Mitigating the Impact of Short Stints and Controversial Brands

Especially recently, it's not uncommon for executives to have a few short stints or now-controversial brands on their resume. Perhaps a startup you joined didn't pan out, or a company you worked for became embroiled in a public scandal.

While these experiences can feel like black marks on your career history - and most executive recruiters and executives explicitly stated that multiple short stints were a red flag - they don't have to permanently define your future prospects. The key is to be proactive in how you address them and position them in your narrative.

Here are a few tips:

• Be Transparent: Don't try to hide or downplay short stints or controversial experiences. Instead, be upfront and honest about what happened and what you learned from the experience.

• Focus on Your Impact: Even in a short stint or challenging situation, you likely made some positive contributions. Focus on highlighting your specific achievements and the value you added during your time there.

• Pivot to the Future: Use the experience as a springboard to talk about what you're looking for in your next role and how you plan to apply the lessons learned to be an even more effective leader.

As Andrew Abramson, Founder of Fusion Talent, suggested:

Leaving jobs too soon and creating a track record of job-hopping is the single biggest thing killing a career's momentum. If you are coming off a short stint, don't just take the next job - do deep referencing on that company/culture to ensure you'll be set up for success…or you might end up looking again in 12 months for factors outside your control.

Designing Your Career Narrative

As you evaluate potential opportunities and make decisions about your next move, keep in mind the overall narrative arc of your career. Each role you take should build upon the last, creating a cohesive story of growth, impact, and leadership.

Think about how you want to be perceived by future hiring managers, recruiters, and colleagues. What do you want to be known for?

Mastering the Executive Interview Process

You've done the hard work of building your network, crafting your narrative, and targeting the right opportunities. Now it's time for the main event: the executive interview process.

At this level, interviews are no longer just about assessing your technical skills or experience. They're about evaluating your leadership potential, your strategic thinking, and your ability to drive business results.

To succeed in these high-stakes conversations, you need to be prepared, polished, and purposeful in your approach.

Preparing for Common Interview Challenges and Questions

Executive interviews can be intense, rigorous, and wide-ranging. You may be asked to present a strategic plan, analyze a complex business problem, or role-play a difficult leadership scenario.

To feel confident and prepared, start by anticipating the types of questions and challenges you're likely to face. Here are a few common themes:

Vision and Strategy: Be prepared to articulate your vision for the role and the company. How would you approach the key challenges and opportunities facing the business? What would your 30/60/90 day plan look like?

Leadership Style: Expect questions about your management philosophy, your approach to building and motivating teams, and your strategy for driving results. Be ready with specific examples of how you've led through change, navigated conflict, and inspired high performance.

Industry and Market Insights: Demonstrate your deep knowledge of the company's industry, competitive landscape, and target customers. Share your perspective on emerging trends, disruptive technologies, and potential growth opportunities.

Behavioral and Situational Questions: Be ready to share detailed examples of how you've handled challenging situations in the past. Use the STAR format (Situation, Task, Action, Result) to structure your responses and highlight your impact.

Or as I like to use with my leadership candidate coaching clients, the Triple-STAR format.

Colin’s Triple-STAR:

• Stakes / Status / Situation: Make sure you are setting the stage for why this was strategically important and critical for the company at that time, as well as your leadership role.

• Task: Waste less time on details but offer to go deeper in any areas they want.

• Action: Think higher-level as well as in-depth where relevant. What functional leadership collaboration or internal/external hurdles did you have to move mountains to overcome?

• Result / Reflection / Repetition: Demonstrate a company-defining impact, reflect on what you learned or could do better, then show how you used that to repeat your success.

Demonstrating Strategic Thinking and Leadership Capabilities

To stand out as a top candidate, you need to go beyond just answering questions and actually demonstrate your strategic thinking and leadership capabilities in action.

Do your homework

The first thing to do - and I will repeat it again from before - is to prepare. Come in having tried the product, done some research, developed a thesis, raised some intelligent questions, and even have some suggestions and questions to validate your hypotheses.

Even just preparing your personal narrative and stories so they are concise will do wonders.

Have a short version and then offer to go deeper in different areas where the interviewer wants.

Storytelling

Another way to do this is through the use of storytelling. When asked about your experience or approach, don't just recite the facts. Paint a picture of the situation, the challenges you faced, the actions you took, and the results you achieved.

Relevant Level of Impact

Use data and metrics to quantify your impact whenever possible. Share specific examples of how you've grown revenue, reduced costs, improved efficiency, or drove innovation. And make sure these are strategically meaningful. New channels, unlocking market saturation curves, scaling revenue, or preventing company disaster can all be ways to be at the leadership level. Just make sure you note the second order effects of your impact.

Reverse Interview Thoughtfully

Another way to demonstrate your leadership potential is by asking thoughtful, probing questions throughout the interview process. Show that you're thinking strategically about the role and the business by inquiring about the company's goals, challenges, and opportunities.

As Janice Power, a 30-year executive recruiter with 14 years at LinkedIn, advised:

The interview process is very much a two-way street. You are interviewing the company as much as they are interviewing you. Do your research, ask the right questions, and make sure the company aligns with your goals and values.

We rejected a top candidate for not reverse interviewing well

I was hiring a Senior Director level position where a candidate had great feedback from everyone and was just going to a sell call by our CFO. But they asked such surface level questions with sense of strategic thought or intelligent conversation about the business fundamentals, strategy, or market that we ended up rejecting the candidate.

Cultivating Executive Presence

Beyond your technical skills and experience, one of the most important factors in landing an executive role is your executive presence. This encompasses everything from your communication style and body language to your ability to inspire confidence and influence others.

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In fact, several recruiters and executives I spoke with shared stories of candidates who had all the right qualifications but ultimately didn't land the role because they lacked executive presence in the final rounds of interviews.

This is one of the most common things I have heard from leadership candidates. Particularly those with shy dispositions, highly technical backgrounds, or from certain gender and cultural intersections. They will often get beaten out by candidates who “seem more senior”.

There is some research data around the drivers that I will cover in future posts.

For now, how can you cultivate and demonstrate executive presence throughout the interview process? Here are a few key tips:

Communicate with Clarity and Confidence: Speak slowly, clearly, and concisely. Avoid filler words and phrases like "um," "uh," and "you know." Use strong, active language and make eye contact with your interviewers. An app like “Poised” can give you real-time feedback in video conferencing tools like Zoom. Pause and reduce your pace instead. This is an area I work on.

Listen Actively and Attentively: Show that you're fully engaged in the conversation by listening carefully, asking follow-up questions, and building upon the ideas being discussed. Don't just wait for your turn to talk.

Project Confidence and Credibility: Sit up straight, use open body language, and maintain a calm, confident demeanor even in the face of tough questions or challenges. Remember, you are an expert in your field and have valuable insights to share.

Be Authentic and Relatable: While it's important to project confidence and authority, don't be afraid to show your human side as well. Share personal anecdotes, admit to past mistakes or challenges, and build rapport with your interviewers.

Come with a Point of View: Being wishy-washy in a final round C-suite or board interview can mean an immediate rejection. Although you want to work for a company that considers options, leaders need to have a strong perspective and willing to take measurable bets to prove it right. Cultures vary between big bets vs. fast iteration, but I have found that in both types of company, leaders with a confident perspective are preferred and respected.

Don’t Over-Prove Your Point: Many leaders feel they need to prove every point they make with lots of data and slides. The number of slides eventually becomes inversely proportional to your influence and persuasion on the crowd, though.

But, as Katrina Benjamin, CPO at Axiom, shared:

Authenticity is key. Don't try to be someone you're not or pretend to have all the answers. Be genuine, honest, and transparent about your strengths and growth areas. That kind of self-awareness and humility is a sign of true leadership potential.

If you're unsure how to effectively demonstrate executive presence in your interviews, consider working with a leadership interview coach or an executive communications coach who can help you refine your communication style and presence.

I will be working on executive presence content in the near future. Comment below if you are interested.

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Evaluating Opportunities and Asking the Right Questions

Finally, remember that the interview process is a two-way street. Just as the company is evaluating you, you should be evaluating the company to ensure it's the right fit for your goals, values, and leadership style.

Throughout the interview process, ask probing questions about the company's culture, the team dynamics, the key challenges and opportunities facing the business, and the expectations for the role.

Pay attention to red flags or warning signs, such as high turnover, unclear expectations, or a lack of alignment between the company's stated values and actual practices.

As Jack Breslauer, VP Product, shared,

I always ask about the company's vision for the role and how it fits into the overall business strategy. If they can't articulate a clear plan or seem to be making it up as they go, that's a big red flag for me.

Jack also noted how important it was to know whether the CEO saw your role “as a service organization or a strategic center for the company”, and to sniff out if other executives resented the hiring for this position.

Remember, an interview is not just a test to be passed, but an opportunity to gather information and make an informed decision about your next career move.

By approaching the executive interview process with preparation, strategy, and discernment, you can not only increase your chances of landing the role, but also ensure that it's the right role for you and your long-term career success.

Negotiating Your Ideal Offer

Congratulations! You've made it through the gauntlet of the executive interview process and have an offer on the table. Now it's time to negotiate the terms of your new role.

At the executive level, compensation packages can be complex and multifaceted, encompassing everything from base salary and bonus structure to equity grants, signing bonuses, and executive benefits.

To negotiate effectively, you need to have a clear understanding of your market value, your personal priorities, and your bottom line.

Understanding the Key Components of an Executive Compensation Package

A typical executive compensation package will include several key components:

Base Salary: This is your fixed annual pay, usually expressed as a monthly or bi-weekly amount.

Bonus: Many executive roles come with a performance-based bonus, often expressed as a percentage of your base salary. Bonuses may be tied to individual, team, or company-wide metrics.

Equity: In many tech companies, equity is a significant portion of an executive's total compensation. This can come in the form of stock options, restricted stock units (RSUs), or performance-based stock grants.

According to Riviera Partners' 2024 Executive Compensation Report, the median compensation package for a VP Product at a Series A+ company with a $1B+ valuation includes:

• Base Salary: $390,000

• Equity: 0.25% (worth $625,000+ per year)

For a CPO at a Series B company with a $100-300M valuation, the median package includes:

• Base Salary: $450,000

• Equity: 1.75%

Benefits: Executive benefits can include things like health insurance, retirement plans, life and disability insurance, and perks like car allowances or executive coaching.

As you evaluate an offer, consider the total value of the package, not just the base salary. A lower base with higher bonus potential and generous equity grants may be more valuable in the long run than a higher base with minimal upside.

Less Obvious Compensation Components To Negotiate

Acceleration and Change of Control Clauses

Many companies get acquired or sold to Private Equity. You can protect yourself with a Change of Control Clause that accelerates the vesting of your options in case of an early exit. I will go deeper on this in another article on executive compensation.

Early Exercise

There can be significant tax savings by exercising (i.e. paying for) your stock options earlier than you actually vest them, so that their value is low. This costs you cash, but can save you a lot if there is a big exit. I typically do not encourage this, but have seen many executives do so. You can also have the company issue a promisory note to essentially lend you the cash for a cashless early exercise. You lose the equity if you don’t pay it back, though.

Extended Exercise

Don’t get me started on the ridiculously short 90-day window after leaving a startup to exercise your stock options. You can negotiate an extended exercise window when you get hired so that if you leave - not fired for cause - then you can have several years to exercise.

Separation Agreement

If you are laid off or leave on mutual terms, you have very little leverage at that time to ask for more runway in terms of months of salary, unvested equity, or pro-rated bonus payouts. You can actually negotiate these things when you join the company. It is more common than you think, so it is just about how you frame the discussion. You have likely been in companies that did layoffs recently and the leaders have probable laid people off recently, so this is a reasonable safeguard to have in place.

Think of it as a pre-nuptual agreement for your long-term working relationship.

Leveraging Market Data and Recruiter Insights

To negotiate effectively, you need to have a solid understanding of market compensation data for your role, level, and location. This is where your relationships with recruiters can be invaluable.

As Theresa Skelly, Director at Riviera Partners, shared:

Recruiters can share market benchmarks they're seeing and advise on how an offer stacks up. However, they have to avoid directly negotiating against their client. Develop relationships with multiple recruiters to have impartial advisors for negotiations.

In addition to working with recruiters, do your own research using tools like Levels.fyi, Glassdoor, and Blind. Look for data specific to your role, industry, and company stage.

Some of the most respected compensation data sources for tech executive roles include:

• Riviera Partners Executive Compensation Report: Includes data on base salary, bonus, and equity for product, engineering, and design leaders at various stages and valuations. Publicly available here.

  

• Andreessen Horowitz's Annual Compensation Survey: Not public but widely shared with executive recruiters and VCs. Includes data on executive compensation at early and growth stage startups.

• Carta's Compensation Data: Carta's new "Friend" service allows you to look up compensation benchmarks based on its database of hundreds of thousands of data points from startups and private companies.

Armed with this information, you can benchmark the offer against market standards and identify areas where you may have room to negotiate.

Aligning the Offer with Your Career Goals and Value

As you negotiate your offer, keep in mind your long-term career goals and the unique value you bring to the role.

If the initial offer is below your expectations, consider how you can frame your counteroffer in terms of the impact you'll have on the business. Highlight your past successes, your relevant experience, and your vision for the role.

As Andrew Abramson, Co-founder of Fusion Talent, advised:

Your leverage is highest after strong interviews. If they say, 'I can't imagine running without this person,' they'll go above and beyond.

At the same time, be realistic about the company's constraints and the market conditions. Don't demand so much that you price yourself out of the role or damage the relationship before you even start.

Matt Johnson, CEO at Paradigm Search, shared:

If excited about an opportunity, lean into it. Don't play games or posture. Whoever cares less wins the negotiation. I think that's kind of silly. If you're interested, lean into it.

I did a long video training about salary negotiations, but am planning some much more detailed content on the topic.

If you need support negotiating what can be $100,000s in offer increases at the leadership level without risking your offer, consider a salary negotiation coaching service.

Getting Creative with Compensation

If the company can't meet your salary or equity expectations, consider other ways to bridge the gap. This could include things like:

• A signing bonus

• Accelerated vesting of equity grants

• A six-month or annual performance review with the opportunity for a raise

• Additional vacation time or flexible work arrangements

• Professional development opportunities or executive coaching

• Relocation assistance or housing allowance

…or any of the special offer components I mentioned earlier.

Work with the recruiter or hiring manager to explore creative solutions that meet both your needs and the company's.

As Janice Power, a 30-year executive recruiter, suggested:

Negotiate on scope and scale if the role feels like a step back. Is there anything more we can give? You really want this person, but they need more. We are willing to give them a greater title, scope, or team.

Closing the Deal

Once you've aligned on the key terms of your offer, get everything in writing. Review the offer letter and any related documents (like an equity grant agreement) carefully to ensure they reflect your understanding.

If there are any discrepancies or areas of confusion, don't hesitate to ask for clarification or revision.

And then, once you're satisfied with the terms, you have built advocacy with the hiring team, and you have leveraged your internal and external negotiation power to increase your offer, it's time to sign on the dotted line and celebrate your new role!

Remember, negotiating your offer isn't just about getting the best possible compensation package. It's about setting yourself up for success in your new role and ensuring that you're valued and supported by your new employer.

By approaching the negotiation with professionalism, preparation, and a collaborative spirit, you can lay the foundation for a successful and fulfilling next chapter in your career.

Conclusion

Navigating the tech executive job search can feel like a daunting task, especially in today's competitive and fast-paced market. But with the right strategies, mindset, and support, you can confidently take the reins of your career and land the leadership role of your dreams.

Throughout this guide, we've explored the key components of a successful executive job search, from understanding the hidden job market and leveraging recruiters and VCs to crafting a compelling narrative, nailing the interview process, and negotiating your ideal offer.

We've heard insights and advice from seasoned recruiters, venture capitalists, and executives who have been in your shoes and succeeded in their own career journeys.

But more than just a collection of tips and tactics, I hope this guide has empowered you to think strategically about your career and to be proactive in designing your professional path.

Remember, your career is a marathon, not a sprint. Each role, each experience, each relationship is a stepping stone to your long-term success and fulfillment.

So as you embark on your executive job search, keep these key principles in mind:

1. Build Relationships, Not Just Transactions: Your network is your most valuable asset. Invest time in cultivating genuine, mutually beneficial relationships with recruiters, VCs, industry peers, and colleagues. Give as much as you get.

2. Craft a Compelling Narrative: Your story is your unique value proposition. Develop a clear, concise, and compelling narrative that showcases your strengths, your impact, and your vision. Use it to guide your job search and to stand out in the interview process.

3. Be Strategic and Intentional: Don't just chase any opportunity that comes your way. Be thoughtful and deliberate about your career moves, evaluating each role for its alignment with your long-term goals and values. Say no to the good to make room for the great.

4. Prepare, Practice, and Ask for Help: The executive job search is not the time to wing it. Invest time in preparing for interviews, practicing your pitch, and seeking feedback and guidance from trusted advisors. Leverage the expertise of recruiters and the insights of your network. If you need extra support, consider investing in coaching or find mentors in your network willing to help you navigate the process with confidence.

5. Stay Resilient and Adaptable: The path to your dream role may not be a straight line. Embrace the twists and turns, the rejections and the pivots, as opportunities for growth and learning. Stay focused on your ultimate goals, but be willing to adapt your strategy as needed.

As you navigate the challenges and opportunities of the executive job search, remember that you are not alone. You have a wealth of resources, relationships, and experiences to draw upon.

And most importantly, you have the power to shape your own career destiny.

Start searching with confidence, clarity, and conviction. Your next great leadership role awaits.

Come back and tell me when you land that great leadership role!

Here are 5 that some of my coaching clients are considering that really surprised us.

These may not be the flashiest, fastest-growth, highest-paying companies, but they have a few really positive things going for them.

Best of all, they are not the most competitive.

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5 under-the-radar tech companies to consider

1. Ramp - The corporate credit card company just raised a Series D at a $7.6 billion valuation from Khosla/Sequoia and are growing. The recent fundraise means they’re probably going to be hiring and jobs aren’t even listed yet. Time to do some outreach!
   (Private, New York/Miami/SF/Remote, 65 open jobs)

2. StubHub - This legacy ticket marketplace is planning an IPO this year and actually pays very competitively despite limited data on Levels.fyi
   (Private planning IPO, New York/Los Angeles, 73 open jobs)

3. Upwork - This freelancer marketplace is public, fully remote, and although it doesn’t have top-tier pay, equity refreshers and promotions can happen quickly.
   (Public at reasonable valuation, Remote, 53 open jobs)

4. Acorns - This consumer fintech pays decently well, is highly recommended as a place to work by its employees (better than 80% of tech companies), and is remote-friendly.
   Flags: The last fundraiser was two years ago, there are only a few roles open, and there has not been much big news lately.
   Pros: I saw how they treated the interview, negotiation, and hiring of a coaching client. They did it with very high integrity and respect.
   (Private, Remote or Irvine, CA, 6 open jobs)

5. Brex - Maybe not the most under-the-radar fintech, but they pay very well, are loved by employees, and are remote-first. Make sure you check how they value equity (current 3rd party estimate at $3.1B, not $12.3B).
   (Private, Remote, 38 open jobs)

BONUS!

6. Rippling - This HR software platform just raised $200m at $13.5 billion, an increase from their last round. They are growing revenues very fast and growing their teams faster!
   (Private, SF/Bangalore/Remote, 313 open jobs)

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