A letter to anyone leaving a scale-up, or just out of one

You’re senior at a scale-up, and you’re thinking of leaving. Maybe you already have.

I spent six years at Google and two at Amazon, and I’ve been a C-level leader myself, as CPO of a 40-person startup. Since 2016 I’ve worked with founders and executives across Europe and the US, including 16 startup leadership teams.

I’ve coached many senior leaders through working out what they want next, and the same things come up: burnout and boredom, conflict with people, disagreements on strategy, and the money not working out as well as you’d hoped.

I know some of this myself. As CPO, I remember the feeling when I realised the founders were comfortable selling something we knew we couldn’t build. And we weren’t funded well enough to build it, even if we’d wanted to.

You’ve done the job. Maybe you joined when the company was half the size, or were hired to bring “big company experience”. You built the team, got through a reorg or two, sat through the board prep, and helped close the round. On LinkedIn, it reads well. But now you’re bored. Or it’s grown to the point where it’s wearing you out.

Or it’s the people. You still like the work. The problems are interesting, and you’re good at them. But the culture just doesn’t feel like a fit. The company says “one team” and treats people as disposable: they called it a family at the all-hands, two weeks before the layoffs. You notice you’re more cynical in meetings than you used to be, and you don’t like bringing that home.

Or it’s the strategy. You don’t believe in it anymore. The CEO changes direction after every board meeting, or every podcast. Or perhaps you’ve learnt enough that you don’t think there’s a path to success, or you realise there’s not enough cash in the bank to get there.

Maybe this isn’t the first time. If you left your last job because of the CEO too, you’re starting to wonder what that says about the next one.

And there’s the money. The salary is okay, but the equity was meant to be the real prize. Then the next round came in flat, and now you’re not sure what your options are worth, or whether you can afford to exercise them if you leave.

Maybe you’ve already gone. You’re between jobs. The recruiters called before your notice period was up. Every role they send looks like the one you just left: another VP Product seat, another founder who says they want a partner. You could take one tomorrow, and that’s what worries you.

What gets in the way. You make big calls every week at work, but this one keeps sliding. Everyone has an opinion about what you should do: your old team, your family, the headhunter, the founder friends who say “just start something”. None of them is lying to you, but none of them can be neutral either.

And underneath sits a quieter question: without the title and the company, what do you want, and who do you want to spend your working days with?

What would give you your energy back?

Maybe it’s another senior role, where this time you choose the people as carefully as the company: the CEO, the board, and the team you’d inherit.

Maybe it’s fractional or advisory work, with a few companies you believe in, on your terms.

Maybe it’s your own company, the one you’ve been sketching while fixing someone else’s.

Or maybe it’s something you haven’t let yourself say out loud yet.

What it looks like when you’ve worked it out. You know what you want from the next role, and what you won’t accept. You can tell in the first meeting with a CEO whether you’d want to work with them, and you trust that read. Your energy goes into the work again, and you come home with some left.

I won’t tell you what to do. Another senior role is a real answer, and so is building something, or something in between. You’ve made this kind of call for a company many times. This time, make it for yourself.

Richard

If you’d like to work it out with me, here’s how it works →