Career

Somewhere around year eight or nine, the question stops being hypothetical. Both paths are available. The organisation is large enough that both exist as genuine roles, not just titles. You have to actually decide. I’ve been close to this decision twice. The first time, at the startup, it was resolved by circumstance — there was no EM role to take, so staff-track it was. The second time, in a larger organisation, it was a real choice. Here’s the framework I used and what I’d change about it. ...

The startup had been good. We’d grown from twelve people to forty, shipped something real, and the technical foundations were solid. But the Series B had brought in a new leadership layer, the founding team’s velocity calculus had changed, and I found myself doing more coordination than building. I’d been at this inflection point before — at the institution, actually — and I recognised what came next. The new role was at a well-established European financial technology firm. Structured, profitable, engineering-first culture, around 400 people. Not a startup. Deliberately not a startup. ...

I left a well-paying, intellectually interesting job at a large financial institution to join a company with fewer than twenty people and less than a year of runway. My colleagues thought I’d lost perspective. My family was diplomatically concerned. Here’s the honest version of the reasoning. ...