Ask HN: Startup Head of Engineering
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* 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.