The Tech Executive's Job Search Playbook: Director to CXO

Job search and negotiation strategies from top Executive Recruiters, VCs, and Executives

Introduction

Earlier this month, I co-authored an article with

Aakash Gupta

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.

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.

The Product Leadership Job Search

When Aakash and I wrote the first piece, we realized that there was a significant gap in the content available online. To gather the insights and strategies shared in the original article, we interviewed

• 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.

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.

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.

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!