The hidden job market for C-suite roles, and what actually gets you shortlisted: Evan Grossman of True Search

The most frequent question Michael gets on this show is how to land a C-suite job when those roles are almost never posted. That is the hidden job market, and this episode is the answer, from the person who runs the searches.

Evan Grossman is a partner and head of the CEO and board practice at True Search, one of the largest executive recruiting firms, working with public, private-equity-backed and pre-IPO venture-backed companies on CEO, COO, president and non-executive director assignments.

His firm's position is unusual and relevant: twelve years old and among the six largest search firms in the world, which he attributes largely to building technology rather than headcount.

Most of the work happens before the search starts

Grossman's opening point reframes the whole problem. A great deal is done before a search is formally kicked off, and smart companies actively try to spare themselves the pain of running one.

Which means the route in is the network, and he breaks it into three specific channels.

People you have worked closely with, who have a clear view of your strengths, your weaknesses, and where you are on your career trajectory.

Talent partners at venture and private equity firms. These people are one click removed from almost everybody, and their job is to put strong candidates in front of a CEO or board long before a search begins, often for calibration. Being in those conversations early is a direct route to bypassing a search entirely.

Search professionals themselves, ahead of any specific role.

His observation about how small the world is deserves attention. Talent diasporas exist across consumer and enterprise software: cohorts of people who came up together and grew into senior roles, most of whom know each other. Even one click outside that circle, the odds you know someone who knows a decision maker are higher than people assume.

What the search firm is actually doing early

Michael's obvious question: if a CEO already knows who they want, where does a recruiter come in?

Grossman's answer is validation, and his worked example is clarifying.

Suppose you and a CEO worked together for fifteen years. When a need arises, they will naturally think of you. They may also have ten other people who could plausibly do it.

So the value of staying top of mind is being in the consideration set at all. And his advice on how to do that is worth noting precisely: make it a friendly conversation about how you are thinking about your career, not a transactional one about landing a job.

Then the search partner enters to help define what this person actually needs to do. Their contribution is saying they have someone in their network who solves for 80% of it, and can this candidate be assessed on where they are genuinely strong against those specific needs.

Because, as he puts it, it all comes down to core need. There are many excellent people for whom there is no immediate need, and much of the job is narrowing the funnel to whoever will drive maximum impact.

Why these roles stay hidden

Michael asks the direct question: why is this market hidden at all?

Grossman's answer is efficiency, backed by a number. At any given moment, roughly 20 to 25% of people who want a C-level role could genuinely make sense for one. It is a small pool relative to demand.

Run that process the way you would run a search for a sales manager and you get the corresponding result: inundated with candidates of wildly varying quality, unable to be targeted, and without the resources to go deep with the few strong ones.

His word for what that produces is the one that should worry any board: settling.

Why now favors unconventional backgrounds

Grossman argues this is an unusually good moment for people with less traditional backgrounds, and his reasoning is structural rather than optimistic.

Search can be paint by numbers. If you are a $100 million software company selling into financial services, the ideal candidate is someone who just took a $100 million software company selling into financial services to $250 million. As black and white as it gets.

The problem is supply. Many proven CEOs and proven number twos have done well enough over recent years that they may not want to do it again. Add the changes everyone has absorbed since 2020 and some seasoned operators would rather sit on boards or play golf.

That creates a talent gap at the top, which cascades. People slightly earlier in their careers step into larger roles, and there is no natural pyramid of successors behind them.

His concrete example of the crossover now happening: people from services businesses joining software companies in numbers, because profitability matters far more than it did, and services operators have spent their careers on it while many software operators have not.

His caveat is honest. If you are so far afield that it is a pipe dream, be honest with yourself and with whoever is advising you. But boards and hiring managers are being more creative than he has seen before.

How they de-risk an unconventional hire

Michael raises the obvious objection: bringing in a fish out of water is a risk.

Grossman's example is a recent CEO search for a $100 million software company where two candidates fit the conventional profile exactly.

What he listened for in the brief was the actual need: reaching profitability, expanding into new markets, product marketing. And what he did not hear: fundraising experience, deep technical work, or go-to-market leadership, because the business already had a strong revenue chief.

That opened the door to a genuinely unconventional candidate. A career investor, mid-career, who had spent five years running value creation and had therefore been deep inside the reacceleration of growth at many companies. Which is exactly what this business needed.

His logic: who better to think about reaccelerating growth than someone who had just helped fifteen other companies do it? They may not have led the teams, but they carried a playbook.

And the process he ran to test it is the part to copy. Give them the same data as everyone else. The board decks. The financial profile. Time with the founders and board members to understand the nuances. And a working session with the board to demonstrate what they can actually do.

His conclusion: that puts everyone on a level playing field, and a different perspective can be additive.

What culture fit actually means at this level

Grossman's take is more interesting than the usual version.

If you are hiring a CEO or a number two to a founder, the culture is probably acceptable but can be optimized. Which means someone who is a 100% culture fit may be the wrong person, because the culture may need shaking up, or may need performance injected, or more rigor around certain processes.

Someone who shows up to go along and get along is not ideal.

The other end of the spectrum is worse. Someone culturally misaligned risks what he calls organ rejection.

How he assesses it: extensive time up front with the directors, listening to what they say and how they say it, their body language, their values, and ultimately the mission of the company. His illustration is a vertical software search for a company in the brewery space, where a CEO who does not enjoy a beer is unlikely to fit the team.

Then meeting candidates in person, which he considers a lost art since 2020 and insists on.

And then blind references. Calling people they worked with at different points, to get past this person seems great and into how they lead when things are going badly. Occasionally they call people the candidate fired, with simple questions.

His framing of why nobody should take offense: everyone has blind spots, and you would hear good, bad and ugly about any of us who spend time in this ecosystem.

What separates a good first conversation from a bad one

Grossman receives fifteen to twenty inbound messages a week from people who want to be a CEO, a COO, or a board member. His filter is whether he can genuinely help: if someone comes from a sector he does not serve, he would rather route them to a colleague than give false hope.

On what impresses him, his first point is about polish, and it cuts against expectation. You can be too formal. People trained in large, older institutions are taught to speak a certain way, and the old-school salesperson who uses your name fifteen times in a conversation is deploying a technique that no longer lands with every audience.

His preference is simply being yourself in an honest one-to-one conversation. And a warning: if you have an agenda, he can feel it, because detecting that is what he does for a living, and it will make him wonder what you are trying to extract from someone trying to help you.

But the thing that genuinely separates candidates is self-awareness. Honesty about where you have been, what you did, what you want to do, and where you are strong and weak.

His illustration is specific and probably uncomfortable for some listeners. Many COOs are classically trained with strong pedigrees, time at top-tier banks or consultancies, polish, presence, often former student athletes from strong universities. People who have succeeded at nearly everything they have attempted.

So when one tells him they took a company from $2 million to $10 million and would now like to be CEO of a $50 million company, they often lack the self-awareness to see how large that gap is. And nobody is going to tell them they cannot do something when they have succeeded at everything else.

The version that works: I took a company from $2 million to $10 million, I would like to do the $10 to $25 million journey, and that might set me up for the next one.

His supporting evidence is a question he asks CEOs constantly: where do you need a strong lieutenant? No successful CEO has ever told him they are perfect and will do it all themselves. They name the finance person, or the revenue chief, or say they want to spend their time on product or with customers and need a chief of staff to hold their life together.

That level of self-awareness lets him make a stronger case for you, and once you are in the seat it makes you more successful, because you know where the gaps are and how to fill them.

How to be credible about what you have not done

Given that companies are now hiring people to go from Y to Z who have only done X to Y, Grossman's advice on handling the conversation is directly usable.

Call it out. I have done $2 to $10 million, I would like to do $10 to $25 million, I have not done it before, and here is how I would approach learning what I do not know.

His reason is counterintuitive and correct: if you present as though you will walk in and succeed from day one, that raises suspicion.

Then play to strengths, and specifically to strengths that match the company's weaknesses. A CEO candidate who is exceptional on product adds less to a company that already has a strong product chief than someone world class on go-to-market.

And his closing point on this is about nerve. The last few years have been hard enough that many people do not want to bet on themselves, and take larger public company roles instead. Which is fine work. But if you want to be in build mode, you have to take some risk, and that is where careers accelerate.

The interview advice

Michael describes his own oscillation between rigorous scorecards, weighted against core competencies, and more subjective methods, and asks how to evaluate someone in thirty minutes.

Grossman thinks the answer sits in the middle, and that interviewing is often over-complicated because people try to solve for everything in a short window.

His advice, which he gives to founders hiring an executive team for the first time and to board members asking about CEO candidates: you are hiring somebody for a reason, and underneath that there are probably two or three simple core needs.

So spend most of the time on those. Culture fit you will feel along the way. Aptitude comes out in the questions they ask you. Enthusiasm shows up in follow-up notes and additional calls.

His summary: going deep on three things beats going shallow on nine or ten, because you are solving for something specific.

What it actually takes to join a board

Grossman is blunt that everybody wants a board seat and that the market is small.

Only so many private companies are at a scale where they need a genuine independent director. And for public companies, if you are not a multi-time public company executive and officer, you are unlikely to get a shot, which removes roughly 90% of the ecosystem immediately.

Encouragingly, about half the board members his team places are joining a board for the first time.

What makes someone ready is specialization rather than range. Companies bring on independents to supplement the founder, and the gap between a strong independent and a strong functional executive can be fifteen years of experience, more scale and more scars.

Which produces his sharpest observation on the subject: the generalists who can do a bit of everything tend to do less well here than people who are specialized. Deep rigor on the audit committee if you are a finance leader. Deep expertise in regulation or cyber if that is your background. This is where the black and white has not gone away in executive search.

His live example: a board search for a $100 million infrastructure company whose purpose was reaccelerating go-to-market, building channel strategy, and adding marketing depth to support a pivot.

The second requirement is experience working closely with a board and helping manage one. Some founders call wanting an independent to rubber stamp them and push back on investors. Grossman is clear that is not how it works. A board member has to be able to tell the founder they are wrong and explain how to think about it instead, and if you have never led those conversations you will not be effective.

COO to CEO

Grossman notes the data shows COOs becoming CEOs faster than ever, then draws a distinction that every COO should read carefully.

In growth businesses there are two spectrums: value capture, meaning go-to-market, and value creation, meaning product and technology. To sit on top of an entire organization, you really need experience across both.

Which is different from what he calls the trains-on-time COO: the person running OKRs and KPIs and making sure the business cadence is smooth. Doing that well is a real skill. But if you are not touching and owning the functions that create and drive revenue, you will be lost in a CEO seat. He says he has seen very few trains-on-time COOs at growth companies step into one.

So his advice to bright COOs who see the business from every angle is to get hands-on experience in product or go-to-market, even if it means stepping down a level to become a VP of sales or a VP of product. The foundational breadth translates well into territories, compensation plans and quotas.

The 5 things I took away from this conversation

1. Be in the conversation before the search exists. Most of the work happens before a role is formally opened, and companies actively try to avoid running a search at all. Which means the useful move is a non-transactional conversation about where your career is going, with people who will remember you when a need appears.

2. Self-awareness about the size of the jump is the differentiator. Evan's example of the COO who took a company from $2 to $10 million and wants to run a $50 million company is a specific, recognizable failure. The credible version names the next increment and says what you have not done yet.

3. Naming what you have not done raises your odds. This is the counterintuitive one. Presenting as though you will succeed from day one triggers suspicion. Saying you have not done this before, and here is how you would learn what you do not know, is what makes the bet defensible to a board.

4. Interview against two or three core needs, not nine. You are hiring for a reason. Spend the time there and let culture fit, aptitude and enthusiasm reveal themselves through the questions asked and the follow-up.

5. Boards want specialists, not athletes. The generalist skill that makes someone a strong operator works against them here. Companies bring on independents for a specific gap, and the ability to tell a founder they are wrong is a requirement rather than a bonus.

FAQ

What is the hidden job market for executives? The large majority of C-suite roles are never posted publicly. Companies work through networks, venture and private equity talent partners, and retained search firms instead, because the pool of people genuinely suited to a given C-level role is small and an open process produces volume rather than fit.

How do you get a C-suite job that is not advertised? Grossman names three routes: former colleagues who know your strengths and trajectory, talent partners at investment firms who are one step from almost every board, and search professionals themselves. He stresses making those conversations about where your career is going rather than about landing a specific role.

Why do companies use executive search firms? Efficiency and depth. Roughly a quarter of people who want a C-level role could actually do one, so an open process floods the company with candidates it cannot properly assess. Search firms narrow the funnel against the specific core needs and run validation, including blind references.

Can you become a CEO without having done the same scale before? Increasingly yes, because of a genuine shortage of proven operators at the top. Grossman's advice is to name explicitly what you have not done, explain how you would learn it, and demonstrate strength in the areas where the company is weak rather than where it is already covered.

What do companies look for in an independent board member? Specialized depth in the specific area the board needs, rather than general capability, plus real experience working with and helping manage a board. Grossman notes that generalists tend to do less well in board searches than people with deep expertise in one domain.

Also mentioned

• True Search and Thrive, its recruiting platform, used by large corporations and competing firms
• Blind references, including calls to people a candidate has let go
• Talent diasporas, the peer cohorts that quietly control most senior hiring
• Value capture and value creation, the two spectrums a CEO needs to have touched
• Who, the hiring methodology and scorecard approach Michael has experimented with

Listen to the full episode

Evan Grossman on Between Two COO's

Between Two COO's is hosted by Michael Koenig. Subscribe on Apple Podcasts, Spotify, or wherever you listen.