So You're Running Engineering at a Startup Now

When I was in undergrad, Google was the hottest company in tech, and I wanted in. I interned there in 2011, in a class of thousands. I declined the return offer, disillusioned by the sheer size of it. So I joined Twitter instead, back when it was a fraction of Google's size — and then I watched it bloat until there was a team for almost everything. Git trouble? A team. Want to hire, or ship to production without taking the site down? Teams for those too.

The thing about that much structure is you stop seeing it. You spend years inside it and never think about how it works, because making it work is someone else's job. You only notice once some of it is gone. At Mixpanel the team that handled git didn't exist and safe deploys had to be built, so I helped build that structure inside engineering. But the systems that support engineering from the outside were mostly already standing by the time I had any say. Hiring, onboarding, career frameworks, comp cycles: every one is something engineering depends on without being engineering itself. At a big company someone else owns them. At a small one, that someone is likely you.

When I joined Pocus, the story I told myself was that this would be a return to the work — fewer meetings, managing ICs directly, hands on in the code. Most people picture their first small-company head of engineering job this way, and companies hire for it this way too, going looking for someone who has managed inside structure on the theory that the experience transfers. The startup brings in a name from a big company and only later finds the fit isn't what either side assumed. Someone who has only operated inside structure has never had to build it, and has always had support systems for everything that isn't strictly the job. What transfers is the half you can see; what's missing is the half that also mattered. If more engineering is what you want, a place with some structure is the better job. The small company gives you less of it, not more.

I did do the deep technical work, and none of it was the surprise. The surprise was the second job stacked on top, defined entirely by what didn't exist. I could only carry it because the engineers were good enough not to need handholding — the part the heroic version leaves out. None of the flexing into unfamiliar territory is possible if your team needs you in the codebase every day. Hiring well is, to my mind, one of the most important parts of leadership, worth a post of its own. But it earns a place here too: it isn't something you do alongside the work, it's what buys you room to do the rest at all.

Then there were the gaps. Hiring was the biggest. No recruiting function, so the pipeline fell to me: agency relationships, cold DMs on LinkedIn, getting creative with sourcing when it stalled. Some weeks I did twenty screening calls, unsustainable and a real bite out of everything else, but the pipe doesn’t fill itself. SOC2 I ran for three years. At Mixpanel a security team owned it and I barely knew it existed, and at Pocus I had to learn what it even was and how it touched nearly every policy we had. Dealing with vendors meant no procurement and no one to split good cop and bad cop with, which teaches you to cut to the actual issue fast. Even the offsites were partly mine, down to finding an Airbnb big enough and good enough to work. None of it was engineering, but all of it had its fingerprints on engineering. And every time, the job wasn’t just to get through it but to make the next round easier, so that when we hired the real experts, they weren’t starting from scratch.

So if you're being hired into one of these roles, or doing the hiring, ask up front what structure exists and what doesn't, what touches engineering directly and what touches it sideways: security, procurement, recruiting, the career ladder. The list is longer than it looks, and none of it comes up in the interview unless you raise it. Whatever's missing is likely your job, not instead of the engineering but on top of it.

The engineering is the floor. The difference between Pocus and Mixpanel was never seniority; it was the absence of everything I'd stopped noticing. If those gaps energize you rather than drain you, take the job. If you only wanted to build, you already know where to find that.