The Other Side. The Search.
part 2
When a corporate executive decides to move into private business, he usually begins the search the same way he has handled every career transition before it. He updates his LinkedIn profile, sends his CV to familiar recruiters, answers posted openings. Three or four months in, he realises nothing much is happening, and he comes to me with the question I hear over and over: where, exactly, are all these positions people keep talking about?
The honest answer takes some time. Private business hires executives in a fundamentally different way from a large corporation, and if you approach the search with your usual tools, most of what actually moves on this market will remain invisible to you. This is not a figure of speech, and it is not an attempt to inflate the importance of recruiters; it is a structural feature of how the market works, and one worth understanding before you start investing time and energy into the wrong channels.
What follows is about where opportunities actually surface in private business, why they tend to stay out of sight, what a recruiter does in this process and what you should not expect from him, and how to evaluate a company when there is almost nothing about it in the public domain.
How hiring works
In a corporation, hiring an executive is a process. There is an approved role, a grade, a budget, a job description, sign-off from HR, and a posting that goes up on the careers page and the usual aggregators. The whole thing takes weeks, sometimes months, but the opening eventually becomes visible, and anyone who is looking will find it.
In private business there is no single model; there are as many models as there are owners. Some treat hiring a key executive as serious work: they spend months on it, bring in a recruiter, meet a dozen candidates, personally check references through their own network. Others regard managerial talent as interchangeable raw material: today one, tomorrow another, plenty more where they came from. Both approaches turn up constantly, often among owners of comparable size in the very same industry. It is worth understanding this from the start, because an owner’s attitude toward hiring affects not only how you will search, but where it makes sense to look in the first place.
A word on the channels through which positions actually reach the market. There are several, and they work very differently from one another.
The most common channel is the owner’s own circle. He simply asks his partners, fellow entrepreneurs, people he trusts: “Do you know someone who could?” A significant share of CEO- and CFO-level hires in private business starts exactly this way, from a single recommendation inside a closed network. The position never becomes public because it closes before it has a chance to. And if you are not part of those circles, you can be the perfect candidate and still never hear about the role.
There is an old line that captures how this part of the market works. If you want someone to pay you a million, two conditions have to be met. First: you must personally know the person who will pay you. Second: he must personally know you. In the corporate world neither condition is strictly necessary, because there the decision is made by a system, and the system runs on formal markers: background, the brands on your CV, references, interview performance. In private business the decision is made by a specific person, and the higher the stakes, the less he trusts formal markers, and the more he relies on his own impression of you and on the judgement of people he already knows and trusts. A personal network is not a pleasant supplement to the search in this world; it is the actual mechanism through which anything happens.
The second channel is the recruiter. Not an agency with a database of fifty thousand CVs, but a specific individual who knows both the market and the particular owner, and who in the end shows up with just three or four candidates, each of whom speaks to the substance of the brief. The work of such a recruiter is closer in character to consulting than to recruiting in the conventional sense: he understands who the owner actually needs to be looking for, and often helps shape the role itself before it exists in the form of a job description. Owners who treat the hire of a key executive as an investment rather than as an administrative task use this channel.
The third channel is funds. When a business is owned by a PE fund or is going through a transaction, the fund’s management team usually keeps its own roster of candidates for key positions in portfolio companies. The logic here is closer to corporate, but access still runs through relationships rather than through an open market.
And finally, a fourth channel that tends to be forgotten whenever people talk about the “hidden market” of private business: the open market itself, meaning LinkedIn, Indeed, and the other familiar job boards. Some owners simply do not want to pay a recruiter, or cannot bring themselves to, and the vacancy ends up on these platforms, posted by whatever in-house HR the company happens to have. Such roles do exist, and occasionally you will find something interesting among them. But when the owner of a business at genuine scale is looking for a CEO through a public posting, that in itself tells you something about how he relates to the hiring process, and it is worth keeping in mind when you evaluate the company itself.
The picture that emerges is uneven. Part of the opportunity set is simply invisible from the open market. Another part does appear on LinkedIn and similar platforms, but what looks like a corporate-style listing hides a completely different logic from the one behind a posting at a large company. The pattern is simple: the more seriously an owner treats hiring, the greater the chance you will never see his position at all until you are already inside the right circle of people. It is an uncomfortable thought, but it explains why a search in private business never begins with a CV. It begins with conversations.
How to work with a recruiter
Now to the recruiter. I am aware that in what follows I am speaking about my own profession, and you have every reason to read it with some skepticism. I will try to be straightforward about it, including about the places where a recruiter’s usefulness ends.
Most corporate executives have had some dealings with recruiters by this point, and the experience has usually been of one kind. Someone calls, mentions “an interesting opportunity,” asks for a CV, and then you either move through the funnel or you do not. After two or three rounds of this, a quite rational impression takes shape: the recruiter’s job is to push your CV through to a client, and that is roughly the extent of his usefulness.
In executive search, particularly when it is aimed at private business, the mechanics work differently. A recruiter working with owners is not looking for a CV that matches a job description; he is looking for a person capable of solving a task. Sometimes the role is actually formulated during the search itself, sometimes it shifts after the first few candidates are presented. I have more than once watched an owner begin with the words “I need a commercial director” and end up hiring an operational one, because the conversations made clear that the real problem was not sales, but the fact that the company’s processes had never been properly built.
A relationship with a recruiter is worth building for the long term. A good recruiter who has understood you once and remembered you will come back to you with opportunities over many years. And the conversation with him is closer in character to a consultation than to an interview. A decent recruiter will tell you plainly that your compensation expectations are out of line with the market, that your industry experience transfers less well than you imagine, or that the company you are drawn to is, from the inside, nothing like it appears from the outside. Hearing this can be uncomfortable, especially if you are used to the politer register of the corporate world. But this is precisely what makes a recruiter valuable: he sees the market as it actually is. If, by contrast, a recruiter agrees with everything you say and promises to “see what is out there,” it almost always means you are one of many names in his database, and there is little more to expect from the contact.
That said, a recruiter cannot place you in a job. He can bring you to an opportunity, but the decision ultimately belongs to the owner, and a recruiter’s influence over that decision is real but bounded. Nor will he substitute for your own network; if you know people well in your industry, that channel is often both faster and more precise. And, most importantly, a recruiter cannot make up for a lack of internal clarity on your part. If you do not yet know what you want or what you are willing to trade for it, no recruiter will teach you that. I have had enough of these conversations to tell quickly whether I am speaking with someone ready to search, or with someone still listening to himself.
Two practical questions almost always come up at the first meeting. The first: who pays the recruiter. In executive search the fee is always paid by the hiring company, not by the candidate. This is worth keeping in mind, because it changes the nature of the conversation. The recruiter works for the owner; his task is to find the right person, and your relevance to him lies precisely in how well you fit that task.
The second question is confidentiality. As long as you are still employed in a corporation, it is critical that information about your search does not reach your current employer. Within the executive search ecosystem, confidentiality is not an optional feature but a baseline. The circle is narrow, everyone knows everyone, and any leak damages the reputation of all parties at once: the recruiter, the candidate, the owner. For that reason, the risk on this side is generally lower than corporate people stepping onto the market for the first time tend to fear.
The side they underestimate is the other one. Large corporations, and increasingly private owners as well, systematically monitor the behaviour of their executives on LinkedIn and other social platforms. A status change, a sudden wave of new connections, a freshly updated CV, an unexpected follow of well-known recruiters, a like on a career-related post: these are all readable signals, they are logged, and they are interpreted. This is not paranoia or a conspiracy theory; it has been standard HR practice for years at many companies. The simple fact that you are “just looking around” can become an internal problem for you well before you ever send your CV to anyone.
It is precisely this logic that gave rise to TopHeads, the platform I am currently building. It is aimed at executives in the $150K+ range: you upload a profile, I personally vet it, and the profile then becomes visible, in anonymised form, to a curated pool of companies hiring at that level. You stay invisible to the market until you yourself decide to reveal your identity to a specific employer. This is not a replacement for classical executive search, but a parallel channel: presence on the market without broadcasting that you are looking.
How to evaluate a company without an annual report
When you are looking at a role in a public company, you have the annual report, Glassdoor ratings, analyst coverage, and the share-price history at your fingertips. You can form a reasonably complete picture without really talking to anyone inside. In private business none of that exists. A substantial company may have never once been mentioned in the business press, and evaluating it has to be done almost entirely through conversations with people. Executives who have moved into private business unsuccessfully tend, afterwards, to formulate their main mistake in the same way: I did not ask the right questions before I said yes. For that reason, this stage deserves to be treated as seriously as due diligence on a transaction. In essence, it is due diligence; it is just that you yourself are the object of the deal.
Start with the owner. A private company is an extension of the person who owns it, and his values, his style of management, and his relationship with people ultimately determine everything, from the speed of decisions to how long you will last in the role. During the negotiation stage the owner almost always presents the better version of himself: attentive, engaged, open to dialogue. The real face appears later. So look for conversations with people who have already dealt with him, and specifically not with the ones he offers as references, but with the ones you find yourself. Former partners, executives who have left, suppliers he has done business with for years. The right question to ask is not “what is he like,” but “how does he behave when something goes wrong,” because it is in those difficult moments that what you will actually live with every day reveals itself. I have seen more than one case in which a candidate noticed troubling signals already at the negotiation stage but convinced himself that it would be different for him. It almost never is.
Next, the business and its numbers. Ask for revenue, margins, the trajectory over the past three years, the structure of the debt. A private company is not obliged to show you any of this, but if an owner wants to hire a C-level executive and at the same time refuses to share basic figures, that is already a signal. Perhaps he is waiting for you to sign an NDA first, which is fair enough. Perhaps the numbers are not as flattering as his descriptions have suggested, which is less so. Either way, his reaction to the question will tell you more about your future job than any financial model. And look not only at absolute figures but at the trajectory: a company that has been losing margin for three years running may be an interesting challenge, but you need to understand clearly what you are getting into, and negotiate your terms accordingly.
A separate and chronically underrated topic: people. Who is on the team now, how long they have been there, and, most importantly, how often predecessors in your role have been replaced. If three people have cycled through this position in the past five years, the odds are that the problem lies not with them, but either with the role itself or with the way the owner handles his relationships with hired leadership. I always recommend that candidates speak with their predecessors, and they are almost always surprised by what they learn. This is easier said than done: there are usually no direct contacts, and you have to reach these people through mutual acquaintances, through LinkedIn, through industry connections, all of which takes time and effort. But if the stakes are real, such enquiries can always be made, and they are worth making. People who have already left tend to speak openly, and the information you get from those conversations is not available anywhere else.
And one final question that is often forgotten in the excitement of a new opportunity: why is the owner hiring now, and why does he need someone exactly like you? The difference between “the business is growing and we need someone to take over operations” and “we have been unable to turn a profit for three years, and the previous director could not manage it” is enormous. These are two different stories, with different kinds of tasks and very different risk profiles. Getting clear on this matters before you begin to discuss money, because it is the context that determines the terms on which entering a role of this kind makes sense at all.
Where to start
If the first article persuaded you that the move deserves serious thought, the most sensible first step is not sending out your CV; it is talking. Speak to two or three people who have already made a comparable move, not for advice but for the picture as they experienced it: how it actually looked, what they did not anticipate, what they would do differently. Conversations like these calibrate expectations better than any written piece, including this one. If after them you still cannot articulate clearly what you are looking for and what you are willing to trade for it, you are not yet ready to start the search, and it is better to realise that now than after three fruitless months.
In parallel, it is worth reaching out to one or two recruiters who specialise in your market. Not to “start looking,” but to understand the landscape itself: what roles actually exist, what compensation levels are realistic, which companies are active. This is reconnaissance rather than search, and the distinction matters, because in reconnaissance mode you are gathering information and making decisions calmly, not reacting to the first offer that comes along.
A separate question that always arises at the beginning is whether to switch your LinkedIn status to “Open to Work.” Opinions here diverge in interesting ways. Some consider the badge a sign of a weak position: the person is, in effect, putting up a notice that says “I need work,” and for a certain segment of the market that reads as “cannot find anything on his own.” Others, on the contrary, see it as a perfectly reasonable expression of adult agency: why hide the fact that you are open, if you genuinely are? My own view is that this is more a matter of personal comfort than universal strategy. If it feels inappropriate to you, do not do it. If you see nothing wrong with it, do it. But if your search is built around people, around conversations, around recruiters, there is a good chance the question will simply not come up.
If everything written above had to be reduced to a single principle, it would be this. In the corporate world you were looking for a job, and you could look for one anonymously, through a system, through formal channels. In private business what you are actually looking for is not a job but an owner: a specific person with whom you will spend the next several years of your life. Once that registers, the entire search looks different. The questions you ask change, the pace you follow changes, and, in the end, so does your own internal posture in the process.
In the next article in the cycle, I will write about how the meeting itself is structured: how to prepare for a first conversation with an owner, how to conduct it, what to show and what to leave out, and why interviewing with the owner of a business bears little inherent resemblance to the corporate interviews you are used to.
