Writing
How to hire your first engineering leader when you are not technical
The first engineering leader is the most expensive hire a founder makes, not because of the salary but because of what a wrong one costs: a year of the roadmap, the trust of the engineers you already have, and often the engineers themselves. It is also the hire founders are least equipped to judge, because the work is invisible until it is late. Here is how I run it.
Which title, at your stage
At one to ten engineers you almost never need a CTO in the sense a board means it; you need someone who will run the team, ship, and grow into more. That is a Head of Engineering. A VP of Engineering is a title for when there are managers under the role, typically twenty engineers or more. A CTO at your stage is either a technical cofounder or a title you are using to attract someone who wants it, which is fine as long as you both know what the job actually is. Hire for the job you have for the next eighteen months, and let the title follow.
Define the role before you write the description
Job descriptions are lists of wishes. A role definition is a short document that says what this person must have made true by month six and month twelve, what they will own and what they will not, who they report to and who reports to them, and what the three hardest problems in the company look like right now. It takes an afternoon and it is the single most useful thing you can hand a candidate, because the good ones will tell you immediately whether they have done it before.
The scorecard
Every candidate should be measured against the same five or six things, written down before the first interview, with a definition of what strong and weak look like for each. For a first engineering leader mine usually include: has shipped a product with a team of this size; has hired and, at least once, let someone go; can explain a technical decision to a non-technical person without condescending; has run a planning and delivery cadence and can describe it in detail; and has opinions about quality that come with evidence. Each interviewer scores independently and writes their notes before hearing anyone else’s. Debriefs without written scores turn into a conversation about who was likeable.
Questions that separate builders from talkers
Ask for the story of the last thing they shipped, and keep asking what they personally did until the answer becomes specific. Ask what they would do in their first thirty days here, having read your role definition. Ask about a hire that did not work out and what they learned. Ask them to explain a system they built to you as if you were the customer. Ask what they would need from you. Vague answers to any of these are the answer.
Reference calls that tell you something
Ask every reference the same two questions: would you hire this person again, and what did they need help with. The pause before the first answer tells you more than the answer. Ask to speak to someone who reported to them, not only someone they reported to.
The first ninety days
Write the plan before the offer, share it during the close, and review it at thirty, sixty and ninety days. The plan is mostly listening in month one, one visible improvement to how work gets shipped in month two, and a roadmap the whole company can plan against by month three. If you do not know how to write that plan, that is a reasonable place to ask for help; it is a few hours of work and it sets the terms of the relationship.