Many non-technical founders make this mistake when hiring their first technical leader: they treat it like a senior hire instead of what it actually is.
A founding CTO is not an employee in the usual sense. They are choosing a partner, in the building of both a product and a business.
At the earliest stage, there is no engineering org in place. There is no roadmap that has survived reality. There is no team to lead. There is just a problem, a hypothesis, and a lot of uncertainty. Whoever steps into this role is signing up to turn ambiguity into something real.
If you get this framing wrong, everything else breaks.
Working in a startup is not a typical job. The attributes that will determine whether a person will thrive in your startup are not only different from high performers in a larger organization, they are different from other startups.
You are not looking for someone who can operate inside structure. You are looking for someone who can create it, while building at the same time. This is why job posts rarely surface the right startup leaders.
Stage fit belongs at the very top of the requirement list. Ahead of domain expertise. Ahead of specific tech stack. Ahead of titles.
The right person:
This is also why many excellent engineers are the wrong fit here. Risk tolerance is not evenly distributed, and early-stage work is all risk.
Technical strength and stage fit are necessary, but they are not sufficient.
At this level, misalignment on vision, values, or working style will surface quickly and painfully. You will be making decisions together under pressure, with limited data, and often without time to debate every angle.
You need alignment on:
This is not about liking each other - though clearly this is ideal! It is about being able to work through hard moments with respect and without erosion of trust. Bring this level of fit assessment not only into hiring your leaders, but also the rest of the team.
At zero-to-one, someone has to build. On day one, there is no team. Architecture diagrams are not a product that can be shipped.
Your founding CTO does not need to write production code forever, but they need to be capable of building the first version themselves. Especially if the problem is technically complex.
A surprising number of “CTO” profiles fall apart here. The title exists, but the muscle memory does not.
Look for people who have shipped real systems, not just overseen them.
A founding CTO has to move fluently between worlds.
They need to go deep technically, but also explain tradeoffs to non-technical founders, investors, and customers. They need to make product decisions, not just technical ones. They need to be credible in a room, not just brilliant alone.
This rules out a large portion of research-first profiles. Not because they are weak, but because they are optimized for a different outcome.
Understanding the customer and then shipping a product is the point. Research brilliance might be nice, but it could also be the thing that holds you back.
At this stage, there is no place to hide. The best candidates talk about outcomes, not tasks. They think in terms of “we” instinctively. They take responsibility before being asked.
If someone needs clear boundaries, clear instructions, or a stable environment to do their best work, this role will be miserable for both of you.
That is not a character flaw. It is a mismatch. And please write that name down and be ready to call them back when you’re hiring employee #50.
If you align on stage fit and vision early, the rest of the process becomes far more predictable.
Read more insights from our team.
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Founded by Kristina McDougall in 2013, Artemis has grown to become Canada’s most trusted boutique executive search firm for startups.
We recognize that our work takes place on the traditional lands of the Attawandaron, Anishinaabeg, Haudenosaunee, and Mississaugas of the Credit. We honour Indigenous stewardship and commit to embedding reconciliation into our work, holding ourselves and our clients accountable.
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