Ask HN: Startup Head of Engineering

2 points by heroicmailman 188 days ago | 1 comment

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?

rchaudhary 188 days ago |

The biggest shift from a frontline manager to Head of Engineering at an early-stage startup is that your success becomes tied to outcomes, not output. You move from managing sprints and people to managing uncertainty, tradeoffs, and company direction. A few things to expect:

* You will need to be both strategic and hands-on - There is rarely enough headcount to delegate everything, so you will spend part of your day writing code or unblocking engineers, and another part setting technical vision, hiring, and negotiating priorities with the founders.

* You will represent engineering in every company decision - You will be the voice of technical reality, balancing product ambition, delivery timelines, and team health. This often means saying “no” diplomatically and helping non-technical founders understand tradeoffs without losing trust.

* You will need to build systems, not inherit them - Processes, culture, and hiring practices will not exist yet. You will define what “good engineering” looks like. It is both liberating and exhausting.

* Your job security will tie closely to company health - Startups are volatile, and even great leaders get caught in external turbulence. What makes it different this time is that you will have agency. You will help shape the runway, the hiring plan, and the company’s technical credibility.

When evaluating the offer, ask the founders candidly about:

* Burn rate and fundraising timeline

* How they make decisions today

* What success looks like for engineering in the next 12 months

* How much equity is being offered, and what percentage of the company it represents on a fully diluted basis

* What the vesting schedule looks like and whether there is a cliff

* How the company handles refresh grants or top-ups as it grows

* Whether there is an employee option pool increase planned in the next round

* How liquidation preferences or investor terms might affect eventual outcomes

If they can answer these questions with clarity and alignment, that is a strong sign you will be able to lead rather than just survive.