Interviewing for the role of CTO of an early-stage company?

Here is what CEOs look for in their potential CTOs..
I recently came across someone who was consulting for a seed-funded startup that had a great team and a great product. He was one of the first few engineers on the team. They recently climbed out of pre-revenue status and were rapidly growing adoption. The company was closing its next round of funding and were looking to expand their team and hire a full-time CTO. Having worked with and built a relationship with the team for a few months, he was definitely interested in pursuing that CTO spot but needed some help with convincing the CEO and the board to hire him. So I wondered - what could he do bag an interview and what would be his pitch to the CEO and the investors?

Firstly, it’s not about the interview. It’s about showing your value as a leader to the founders. If there’s room for you to run the team effectively, for example, hiring, organizing the team and set a culture, setting a technical vision for the organization, contributing meaningfully to the product roadmap, and helping craft messaging about the technology for future investors or customers, your CEO will recognize that they have someone they trust playing that role already. The challenge you’ll have beyond the above is often that founders are looking for wisdom in their executive team. They often look for people who’ve done the job and know which risks to look out for and avoid making beginner mistakes which can be outwardly costly to an early-stage startup. You may have to position yourself as a Senior VP of Engineering that can carry the team to the next phase and then the company can hire a CTO or promote you if you’ve been doing the job successfully for n months/years. In essence, you need to:

1) Become a strategic partner for the founder/CEO, and

2) Effectively remove any need for them to think or worry about the technology team. They need to feel like you’ve got it under control and that you can do the job far better than they could.

Achieving both is quite challenging for anyone without a lot of experience. There are simply too many landmines to step on. But everyone has to start somewhere.

To achieve #1, you must grok the business and product strategy to the level of the founder/CEO and use your creativity to help craft a path for the company as a whole to achieve your goals. Help craft milestones and help the other executives understand what the company needs to do from a technical standpoint to achieve it — this includes everything: roadmap, hiring, process, and more. If your executives are not technical, you’ll need to communicate in a language that they can understand. Do not be overly prescriptive, be collaborative. Learn their pains and blockers even those they don’t verbalize and alleviate them even if you’re not directly responsible.

For #2, this is a bit simpler: it’s team building and team execution. The engineers under you should be raving about you. A few of them at least should say you’re the best manager they’ve ever worked with. They need to feel fulfilled, that they’re working on the right tasks, learning regularly, and that blocking issues are addressed quickly. This includes establishing a culture that’s enjoyable for your engineers and a process that’s at least respected, if not fully embraced. They must also feel that their careers are on the right path, that the system you’ve put in place for evaluating engineering performance is fair and produces accurate assessments. They must also feel that you’re decisive with removing teammates that are not a net positive for the company — culturally or technically. You will also need to establish a technical roadmap for how the engineering team will evolve. Hopefully, there are folks in your team who are eager to design a technology direction, and you’ll need to get high approval on this direction from your team.

Now, if either of the scenarios above is scary because you wouldn’t know how to start — you’re probably not ready to be CTO. If either scenario above seems uninteresting, that’s also a red flag. If both of them sound exciting and you at least have some plan for how you’d achieve both, that’s a pretty healthy signal that you should at least give it a fair shot. Also, you’re joining an early-stage startup, and accepting that the high risk of working for a startup is worth it because of the high upside in learning and financial growth. If you don’t think you’re a great person for the job, I would try to embrace that and help hire a technology executive that can help you grow while growing the company. In the end, it would be what’s best for your career and your finances.

To sum up:

1. Understand the criteria that they would be looking for from this role.
2. Get yourself on the shortlist.
3. Understand your gaps and mitigate them.
4. Build consensus and a case for yourself
5. Try to be involved in the hiring of the CTO. Talk to the CEO about the role. What are they looking for and how you and others within the company can help you hire for the role. I would try to take a genuine interest in how to help bring onboard a CTO that the company needs.
6. Sometimes what they are looking for is not something you can talk yourself into. You just need the Skills/Knowledge/Experience which is developed over time and if that’s the case bow out gracefully and continue to double down on hiring for the role.
7. If not though, have a conversation with the CEO about what you want to do long-term (without mentioning this role). This will, if done correctly, signal your interest without needing to be explicit. If the CEO is paying attention they will begin to consider you for the role and at minimum give you an interview to keep you engaged. If this doesn’t work then maybe you would need to be more direct, something like “Hey X I’ve been thinking about the role and I’d like to discuss whether I might be able to interview for it.” This has worked wonders when the other person didn’t see me in the same light. Expect a “no” and plan for the objections you might encounter; you should be able to turn it into a “yes”.
8. Talk to prior bosses and your current boss about your gaps. I would also go interview for a “CTO” role at comparable startups. This will help both with identifying the gaps and helping to build a case.
9. If you land a role and still want to try out for your role, I would ask your CEO for advice and share the news. Because you’ve already shared what you want to do long-term this shouldn’t be much of a surprise to them (but is always mildly risky). If you do it well then the CEO will know you have comparable options and you’ll have de-risked yourself from being considered for the role
10. If you’re good enough for the other company, it’s not crazy to give you a shot.

Finally, you need to be confident and let it show that you want it and you’ll have the drive to stick through the lows. This should likely be a large part of what they are looking for and if you’re genuinely enthusiastic it will be difficult to compete with you for the role.