Your leadership team is full of promotions nobody made

Every successful founder reaches a point where the leadership team finally takes shape. The senior roles are filled: someone leading engineering, someone leading commercial, someone across operations and finance. After years of carrying most of it yourself, it feels like the transition from startup to scaleup is underway.

But is this truly the leadership team to take the company to the next level? Was each person selected for that particular role, or did they assume it by default?

In many cases, few of those roles were ever ‘decided’. Someone joined early, took on a little more each quarter, and became head of their function without anyone saying the words. The title caught up with a job they had already drifted into. The role kept growing, and no one stopped to ask whether the person who found themselves in the seat was still the right one to hold it.

Even posing the question feels like a betrayal of the people who got you here. It is not. The role has changed, and asking whether the person has changed with it is not just fair, it is a critical test for the aspiring scaleup founder/CEO.

There are two tests: Can the person stop doing the job that made them a high-value contributor in the first place, now that the senior role is a different job, not a bigger one? And are they able to step up to lead a large, complex function that may be way beyond their prior experience? Willingness and capability are different, and a founder has to weigh both.

This is the third of three notes on building a leadership team that no longer runs through the founder. The first described the founder as the point every decision routes through, an asset that becomes a bottleneck. The second turned to the leadership meeting, too often a forum for status reporting rather than decision-making. This briefing note faces an even harder reality: how someone reached a senior seat, by drift rather than choice, says nothing about whether they can hold it as the company grows.


The default setting is loyalty

Left alone, the drift typically resolves one way. The person who has been there longest, and given the most, keeps the growing role. Taking it from them feels like punishing their service and commitment, so no one does.

Investors who have watched this many times name the trap without sentiment. The people who get you from zero to one are not always the ones who can scale the company from there, and at some point, you have to value performance over loyalty.

Your first commercial hire closed the early customers, built a small team around themselves, and now carries the title head of sales. That does not make them the VP of Sales a scaling company needs. Finance, product, operations: each has its own version of the same drift. And nowhere is this drift more apparent than in the engineering function.


Where the role explodes

Take your day-1 lead developer. They built the core of the system when the company was five people. Across the early Seed rounds they picked up a couple of reports, then a handful, and became head of engineering without anyone ever using the phrase officially.

Then the technology matured, and the role exploded. One deep problem became many: product development, project management, design for manufacture, test and reliability, a technology roadmap, and a headcount that doubled and doubled again.

They now answer for disciplines they have never practised, running a function several times larger than any they have ever led. And they got there without a day's notice that the job was changing. This is not a story about someone out of their depth through any fault of their own. It is a story about scope outrunning a person faster than anyone had even considered.


A different job, not a bigger one

Here is what the drift hides. The head-of-engineering job at forty engineers is not the same job at four, scaled up. It is an entirely different job.

The first is done by the best engineer in the room. The second is done by someone who may not be the best engineer, but someone who can build the machine that lets forty engineers do their best work without running every problem through them.

Where the founder is the lead engineer, this year's global DeepTech study makes a stark observation. Technical experience on its own has no significant effect on the capital a company raises or the valuation it reaches. What predicts success is technical depth combined with real management experience.

So, the promotion by default makes the classic mistake. It reads mastery of the old job as proof of fitness for the new one, when the two share a title and little else. Some people are willing to let the old job go and still cannot do the new one. Others could do the new one but will not let the old one go. Being brilliant at the founding job answers neither question.


When the seat belongs to a co-founder

Now the extreme case of DeepTech. The engineer in this story is not a regular employee but your technical co-founder. They have carried the title CTO since the company was two people and an idea.

Everything above applies, but the stakes are higher. Their title was fixed on day one, written into the founding equity, so the drift beneath it is invisible. The word CTO has not changed; the job it names has, completely, from the person who invents the technology to the person who must run a large, multidisciplinary engineering organisation. No one decided that either.

Two questions sit under the title, and founders often ask neither. Can they lead an organisation that big and complex? And do they even want to, or was their ambition always to pioneer the next breakthrough, not manage the people building the product that incorporates it? Those are two different people, and only one belongs at the head of the function.

Get this wrong and the cost is not just a struggling function. Wasserman's study of why startups fail put roughly two-thirds of failures down to people problems inside the founding team, not the product. The co-founder split rarely starts as a row over strategy. It starts here, in a role that quietly outgrew one founder, and neither of them said so in time.


The tell

So how do you tell, before the drift decides for you, who can make the change? Not by effort, and not by loyalty. The people who drifted into these roles are the committed ones by definition. Commitment is not what decides it.

The real signal is whether they can give away the work that made them who they are. Molly Graham, who scaled teams at Facebook and Quip, calls it giving away your Legos. As a company grows, the pile you built with is broken up and handed out, and the people who rise are the ones who pass on the piece they love the most so they can build something new.

Do they hire people who might one day be better than them at the thing they do best? Do they take pride in what the team shipped, or only in what their own hands touched? And, for the co-founder above all, do they truly want to run an organisation, or are they saying yes because stepping aside feels like loss?

The one who can let the craft go is telling you they can grow. The one who cannot is telling you something too. That is something to plan around, not a verdict on their worth.


The honest options

From here there are three honest ways forward.

The first is that they grow into the seat. It happens, but the odds are sobering. Startups move fast, with little runway to learn a big role on the job. Some have the appetite and aptitude; many do not, and you cannot coach in what is not there.

The second is to keep them where their depth is the point: a principal engineer, or for a co-founder a chief scientist driving the innovation while a VP of Engineering runs the org. In DeepTech these are real senior roles, not a siding, but only if the move is genuine. Offer it to a true pioneer and you free them; offer it to someone who wanted to lead a product team, and you have wrapped a demotion in a grand title.

The third is that they move on, early and with faith kept. What founders call kindness, the waiting and hoping, is usually the opposite. Carrying someone into a role they have outgrown fails the company, and fails them, tested in public in a job that was never set for success.


The room is watching

Everyone who stays is watching how you handle the person the role outgrew, and so, from a distance, is your board. A founder who cannot turn drift into a decision has not made their own transition either.

We wrote recently about the skill investors quietly test: whether the founder can grow as fast as the company does. The changing roles and senior appointments are where they silently watch it. See the shift coming and shape it yourself, or wait, and let the board shape it for you. The reorg you will not run gets run on you.

The leadership team has been the thread of the last three briefing notes, so we end with three founder questions, one from each. Is yours a real team with delegated authority, or a working group that still routes every decision through you? Is the leadership meeting a forum where decisions get made and the culture is set, or a status update that waits on you? And are the people who got you here the ones who can take you where you are going, or have some been left behind by seats that grew faster than they did?

These seats get filled either by your conscious decision or by drift. Making that call early, while it is still a choice and still a kindness, is your job now.

Let's talk.