The Product Leadership Job Search
Your In-Depth Guide to Landing and Negotiating a Product Leadership Job
The job market is finally opening up
I had the pleasure of writing this 20k+ word deep dive into the Product Leadership job search with . The full piece can be found in his Substack, one of the most-read newsletters among product managers with 105,000+ subscribers.
Update: Based on all of the interest, I am planning a live coaching program for Product Leaders on the job search. Get on the waitlist and take the survey here.
Here is a preview…
The job market is finally opening up
Right now, Product Leadership opportunities are being promoted on LinkedIn at Reddit, Google, MongoDB, Meta, Ramp, Netflix, and many more…
The best companies in tech are hiring leaders again. Folks who have been unemployed for several months, or were sitting tight for the last few years, are landing jobs they consider upgrades.
It’s not just a “so-so” market. It’s heating up. Of the 12 product leaders talked to for this piece, 7 have been regularly receiving recruiter outreach messages.
Given the new state of the market, I (Aakash) thought it would be the perfect time to discuss the critical meta that should govern a product leadership job search.
Introducing Colin Lernell
Who better to write with than someone who has done that job search many times?
I’m excited to introduce Colin Lernell. Colin has been a Senior Director of Product at Patreon, Noom, and Udacity. He has also landed offers for roles as a public company VP, a big tech Director, and an early stage CPO.
Colin writes the Top Tech newsletter, coaches product leaders seeking or negotiating job offers, and has experience from both sides of the product leadership job search.
Warning: This Might Make You Money
There’s a huge range of pay disparity amongst product leadership roles. Two rules govern these disparities.
First, the stage/revenue of the company determines your range:
If you’re not venture-backed, you can also roughly align these as: series A to $10M revenue, series C $10M, series E $500M, small/mid cap $1B, FAANG $100B.
Second, the success of your company has a huge impact. For instance:
Top-end VPs at highly successful Series C companies can make $400K base and $600K in equity
On the other hand, New VPs at struggling Series C companies can make $225K base and $300K in equity
That’s a TC difference of about 2x, or $475K per year.
Between those two rules, if you are able to move to a higher stage company or a more successful company, it will mean millions of dollars over the course of your career.
But there’s much more than compensation to prioritize when seeking your next opportunity…
Today’s Post
Words: 21,600 | Est. Reading Time: 98 mins
We’ve talked to 7 external Executive Recruiters, 2 internal big tech Executive Recruiters, 2 VC talent teams, and 12 CPOs/ VPs about the product leadership job search. Here’s what we’ve found:
1. How product leader (Director to CPO) searches are different
1.1 The (Actually) Hidden Job Market for Product Leaders
By my guess, anywhere from 10-30% of Director+ product roles never are posted. And as you reach the C-Suite, it goes to 70-100%.
—Product Leader for 10 years, current VP
At the Director level and above, the game changes entirely.
The stakes are higher
The competition fiercer
The opportunities more elusive
And here’s the thing: many of these top-tier roles never see the light of day on public job boards.
They're stealth missions. Companies often kick off these searches before they have a finalized job description. Companies post these roles much less often for a variety of reasons:
They don’t want the press to speculate
They don’t want the current leaders to know
They don’t want lots of low quality applicants
This is where your executive recruiter and VC connections become your secret weapon. They know about these under-the-radar opportunities long before the rest of us catch a whiff.
1.2 The Critical Role of Executive Recruiters and VCs for Leadership Roles
C-suite executives early on in my career told me the best thing to do is to find great exec 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.
—Colin, 3x Senior Product Leader
It’s not like your prior job searches
Contrast this leadership job market with the landscape for individual contributors (ICs). Sure, there are exceptions where ICs look more like leadership searches - roles requiring extremely niche skills or deep industry expertise.
But by and large, most IC positions will eventually find their way onto the usual job posting sites. Recruiters can still add value here, but they're more of a bonus than a necessity.
For leadership roles, though? Ignore them at your peril.
(And if you’ve had poor encounters with recruiting firms in the past? It is probably because they were contingency-based firms trying to compete to fill a role, and not the retainer-based executive search firms.)
How the job search changes as you rise up the leadership ranks
Sources:
*Executive Recruiter, VC, and Executive Leader first-hand experiences and estimates
**Riviera Partners US (VP, CPO) Executive Compensation Report and VC Firm (Director to CPO) Executive Compensation Surveys
But you can’t sit back
But here's the thing - you can't just sit back and wait for them to come knocking. Not even if you're a bona fide rockstar in your field.
Some inbound interest may trickle in, sure. But the real magic happens when you take the reins and proactively cultivate these relationships.
That’s what we’ll cover in today’s piece.
When executive recruiters and VC firms are involved
So when do companies enlist the services of recruiters and tap into their VC networks to fill a role? There are 5 main situations where external help is needed:
No Internal Expertise or Capacity
Business Critical Roles
Specific Skill Set
Speed is of the Essence
Company’s Pedigree is Lacking
Often, only external executive recruiters can give high-priority searches the white-glove treatment they require.
Exec search is a lot more consultative/strategic than IC recruiting
—Vidur Dewan, 8yr Recruiter, Partner at Artisanal Talent
1.3 How Product Leaders are Evaluated Differently
Three main criteria are used:
Reputation
Outcomes & Impact
Domain Expertise
But First, A Warning: The Criteria Will Evolve
A lot changes during the 2-7 month search process for a product leader.
In the first few weeks, employers will speak with many candidates as they are still figuring out exactly what they want and need from a role. They have only conducted these searches every 2-4 years, if ever. So, they do not have a great first frame of reference for what they need until they see a variety of candidates.
This means you need to have patience in your search and are likely to speak with companies who do not yet have their criteria solidified.
It is very common for companies to start with very strict criteria:
i.e. “We only consider candidates from top companies at our stage or higher, in our market, at this exact seniority level, who have done exactly what we need before successfully.”
But that often slowly shifts to tangential markets, up and coming candidates doing a level jump, and candidates who had a large impact at lesser known companies.
Some criteria is also very company, role, and hiring manager specific:
Expert vs. Generalist
Strategic vs. Player-Coach
Been There vs. Up-and-Comer
In-the-weeds vs. High-level narrative
You will need to leverage your recruiter or company contact to understand what they are looking for, how to interpret that, and how you fit their criteria.
A pretty common thing that we help clients work through is whether they need someone that has super specific domain experience or if what they really need is a general athlete with best in class experience from a tangential high growth company.
The other piece that is common...Do we need the person that has seen this journey before and is a tried and true leader, or do we feel like the more up and coming step up candidate will actually be hungrier and will be willing to put in the work that we need them to at this stage?
—Theresa Skelly, Director at Riviera Partners
Criteria 1: Reputation
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.
— Ken Sandy, 27Y product leader, CPO Coach, Author of The Influential Product Manager
The consensus among the executive recruiters and hiring managers we spoke with is that your reputation is one of the most important criteria for landing a role.
There are a few important signals for reputation:
Did you work for reputable companies?
Did you work for reputable leaders and managers?
Did you advance quickly at those companies with promotions?
But even more importantly…
Will reputable people speak highly of your accomplishments?
Will they verify a role is within your “ceiling” as a leader?
This validation from a trusted third party is necessary because:
It helps isolate whether you achieved outcomes by your own merits or just benefited from the company’s trajectory
To be successful as a leader, you need to build buy in and respect to have long-term impact at a company as it scales. How people perceive your achievements is nearly as important as achieving them.
This has 3 important implications for your job search:
1. Intros matter
Because reputation is arguably more important than on-paper results at leadership levels, cold outreach is less effective than at IC levels**.**
If you want to get connected with a hiring manager, an executive recruiter, or any decision maker at a company, you will first want to get a warm introduction from someone who can speak highly of you.
Past managers or executives, past colleagues, mentors, or even executive recruiters you have worked with in the past can all be potential connectors.
Colin has coached product leaders who were successful at cold outreach, but generally an introduction is going to be necessary.
2. Backchannels are always done
Whether you agree with the practice or not, some clients wouldn't even have a first conversation unless we had at least 1-2 backdoor references from people they trust or know.
—Matt Johnson, 13yr Recruiter, Founder/CEO of Paradigm Search, ex-Daversa
None of the Executive Recruiters or executives we spoke with have hired someone without running a backchannel reference.
This means that at some point in the process, they are contacting your past manager, executives, or colleagues through someone in their network.
3. Tenure matters
According to Andrew Abramson — a 10 year executive recruiting veteran and ex-Partner at Riviera who founded Fusion Talent — leaving jobs too soon and creating a track record of job-hopping is the "single biggest thing killing a career’s momentum."
It creates a "perception by hiring managers that they won't stick around." Andrew advises that "a good stint is 3 years if no exit outside your control" and cautions against "back to back 1 year stints."
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.
Andrew also suggests going to high quality companies and warns against taking risky roles at early stage startups just to gain more scope. Even if you are CPO and do a good job, "You could find yourself looking again in a year due to factors that are completely outside of your control.”
Fair or not, this will stop many future employers from considering you if it is a repeated pattern.
Criteria 2: Outcomes & Impact
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.
—Andrew Abramson, 10yr Recruiter, Founder of Fusion, ex-Riviera & Korn Ferry
At the Director level and above, it is no longer enough to launch features, discuss how you did it, and talk about the product metrics you impacted.
You will need to start demonstrating significant tangible business impact from your work. That means increasing revenue, north star metric improvements, and strategically important outcomes.
It can also mean helping a company get to a successful IPO or acquisition, or even scaling a team 10x (though beware to whom you are talking about that—for a certain political class in Silicon Valley, org building is the now enemy).
Outcome Facet 1 - Company success
One signal of your impact and outcomes is having a long stint at a high growth successful company. That doesn’t mean you had to be CPO, but if you were accomplished and promoted frequently at a top tier company that was doing well, this will signal that you can make an impact that matters.
One mistake leaders make is optimizing for scope over quality of company, especially if you don't already have a great company on your resume. Founders look first at the best companies a candidate has worked at that had high growth. Even joining at the highest level at an earlier stage startup can prevent you from gaining this reputation for being a winner.
“Winners win.” is a quote recruiters often hear from founders. They assume that someone at a successful company during its growth phase will continue to win.
Outcome Facet 2 - Your measurable impact
It should be obvious by this point in your career that you need to show demonstrated, measurable impact in your narrative and resume. What changes at the leadership level is the scope and level of that impact.
Meaningful impact is typically a significant improvement in revenue, profit, or users. It can also be a significant strategic win.
This is tied to tenure at a company. It typically takes several years to have a meaningful impact on a company’s business trajectory.
Criteria 3: Domain Expertise
Multiple Executive Recruiters we interviewed mentioned how important domain expertise was to hiring managers for product leaders.
When they develop the “ideal candidate profile” (ICP) with the client, they often have a specific domain, team size managed, specific stage, and similar challenges faced.
They want to know that you faced similar challenges and built the necessary processes and infrastructure in a similar context.
This is unsurprising psychology by employers. They want to de-risk the hire as much as possible, and the best way to do this is by hiring someone who has “been there and done that.” If you do not perfectly match the ICP, you will need to show how your experience is analogous or tangential at least.
For All Criteria: Career trajectory
A heavily used heuristic for both a reputable and outcome-oriented candidate is whether they have a fast trajectory of getting promoted and increasing their scope.
A benchmark pace for promotions is every 12-18 months for top candidates. At least they should be increasing their scope and impact if not their level.
The opposite is true, too. If a candidate is stuck at the same level for several years, they could be screened out before anyone talks to them.
There is a paradox for leveling for leaders.
The same recruiters and hiring managers will say both:
“We don’t want title and scope-chasers with an ego”
and
“We want to see title and scope growth”
Ken Sandy, who has been a Director+ since the 90s and helps CPOs build teams, says that “titles do matter”. If you go to VP or CPO at a reasonably mature company, “once you’re in, you’re in.”
Balancing the advice of quality of company vs. scope-chasing vs. title progression is something I have personally struggled with. 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.
—Colin Lernell, 3x Sr. Director of Product
1.4 How Product Leaders are Compensated Differently
Big jumps
There are increasingly big jumps in compensation as you move into leadership and up the leadership seniority ladder.
A Director can make 1.5-2x what a Group PM or Principal makes.
A VP can make much more equity than a Director, sometimes 2x TC
A CPO has such a varied TC that top candidates make multiple millions per year
Highly variable
The variability in compensation is also much wider as you increase in seniority.
Colin once received a growth-stage Director offer for $450K and another for $850K in the same week.
Data sources change
Finding accurate and reliable compensation data at the leadership levels is also a mystery to new leaders. Other than a few Director roles at FAANG+, you are unlikely to get many data points from the typical sources like Levels.fyi or Blind that you used as an IC.
Instead, you will want to use your Executive Recruiters, VCs, and fellow executives to find both the survey and anecdotal research you need.
So how much do they make?
Many of you will be familiar with Nikhyl Singhal — he is a VP at Meta, ex-CPO at Credit Karma, and coach to 100+ product leaders over his career.
He provided this chart in 2021 as a rule of tumb for “elite” (meaning top of market) leadership candidates in tier 1 US tech cities and companies. He claims that this was consistent for several years, with some years (like 2021/early 2022) going above and other years tracking slightly below. 2023 was a tougher year, but this has started to return.
If we compare that to the top 25% of offers in 2024’s Riviera Partners Compensation Report, we actually see higher numbers this year:
VP Product, Series A+, $1B+ valuation
Cash: $390K
Equity: 0.25% ($625K+/year)
CPO, Series B, $100M-$300M valuation
Cash: $450K
Equity: 1.75% (median was >1%)
The VC survey data aligns closely with this.
Note that anecdotally we have heard from recent Directors who landed roles coming in at lower TC for growth-stage companies. This was mostly due to lower equity grants. Recent data from equity management platform Carta has shown the same, but this is starting to increase again.
VPs at Meta or Google can make $4m+, while tier 1 big tech company CPOs can make into the $X0M range. Chris Cox, CPO at Meta, made $23M last year, with $18.5M in stock awards.
How power dynamics change
Another major difference in the job search for product leaders is the amount of power an employer has vs. you. If you are a serious candidate, you are not only allowed to reverse interview and vet the company just like they are assessing your fit for them, you are often expected to do this. Not doing so can be treated as a red flag.
If you are a serious candidate, you are not only allowed to reverse interview and vet the company just like they are assessing your fit for them, you are often expected to do this.
Not doing so can be treated as a red flag.
1.5 Product Leadership Hiring Trends
Continue reading on Aakash’s Substack…
Here’s what’s included:
How product leadership (Director to CPO) searches are different
The (actually) hidden job market for product leaders
The critical role of Executive Recruiters and VCs in leadership roles
How product leaders are evaluated differently
How leaders are compensated differently
Product leadership hiring trends
How recruiting firms and VC talent teams actually work
Inside a Recruiting Firm
Inside a VC Talent Arm
What it means for you
The job search process
How to find opportunities as a product leader
How to leverage VCs and Executive Recruiters in your search
How to prepare your narrative
Inbound, outbound, and firms
Targeting roles and tapping your network
How to land and negotiate offers as a product leader
How VCs and Executive Recruiters help during interviews
How to handle the interview process
How to handle backchannel references
How to reverse interview and evaluate opportunities
How to negotiate compensation, scope, and title
Bonus: Tips for hiring product leaders
It was a pleasure to collab 🙌
You have amazing insights, an amazing network, and writing speed.
Look forward to Top Tech’s story over time.
Glad to have worked together.