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Ask HN: Startup Head of Engineering

2•heroicmailman•1h ago
I'm going through a bit of a career crossroads at the moment and figured I'd ask the HN zeitgeist for its opinion.

A bit about me: I've got about 10 years of experience in engineering. I've worked at publicly-traded companies as both an IC and a manager, and also had two shorter stints at startups. Both of those startup experiences ended poorly, and suddenly, with no warning prior to being laid off or let go.

I'm currently a frontline manager at a larger, public tech company. While more comfortable, I do disagree with a lot of the ways that my company has chosen to scale (particularly post-COVID) and the way it handles process in the day-to-day. I don't feel a lot of agency or ownership over anything. There's also a bit of paranoia about job security.

Add in a bit of burnout and mistrust in any leadership team, given my personal experiences, and the state of the tech industry writ large, and I'm starting to seek other avenues.

I'm beginning to look for my next role and have actually been offered a role as a head of engineering at an early-stage startup.

What I'm looking for more than anything is opinions on making the jump from a frontline EM role into a Head of Engineering role at a startup. The engineering team at the startup is about the size of my team today at my current company, so I'm wondering more about the ancillary stuff that comes into play when you're representing the entire engineering function at a company rather than managing a single team.

Am I setting myself up for another bad startup experience, or will being in a Head role be different enough? Has anyone here had a similar experience?

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