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.
Congrats on launch. Two questions from a user perspective. 1) How do you handle spec changes across document revisions? 2) Can users export the analysis with links to the exact tables and figures in the PDFs?
Solid questions, you've clearly been burned before lol.
1) Document revisions can be a bit hard to handle, but we currently look for any dates or document numbers present, and when possible we just show the latest. However, plenty of times there are no dates OR revision numbers, and we'll get different documents from multiple sources. In this case we show all the documents, and have prompted the AI to flag this risk to the user if the question is answered differently between documents. Not the ideal approach, but working with what we're getting...
2) Hmm, not really. You can share the chat, and the specific response, but the only way to export the source would be to screenshot it... Adding it to our list of potential next features!
Appreciate the detailed response. Showing all conflicting docs and flagging inconsistent answers is a practical interim step. Long term, version tracking across sources could be a real differentiator since engineers live and die by revision history. On exports, even a lightweight “copy link to figure/table” feature would go a long way for collaboration.
Investors would want to see your cap table during the due diligence process as they want to make sure that they are not investing in a company with messed up cap table.
* 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.