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Working in a coporporate environment for pretty much most of my career, I am being interviewed for a CTO position for a startup. Currently, I am managing a team bigger that the team I will be responsible for, if I get and accept the CTO position (CTO is responsible for a team of 15). I have learned about start-up life mainly through books and blogs due to my continuous thought of wanting to establish my own business one day. However, I have no first hand experience in this environment. This is totally new to me, and I do not know what I do not know. Therefore, tapping into the experience of those whom has been in similiar situation, I want to clarify as much as possible before I accept this position (final interview is around the corner). It is a 7-year old FinTech company, about to qualify for Series-C funding.

  • What points I should clarify?
  • What red flags I should watch out for?
  • If you had worked as a CTO in similar environment, what things you wish you had known before you took the role?

I found this question to be useful. I am looking for more tips relevant to CTO role

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    Do you hold equity or not? Are you going to be compensated in equity or not? If it is a real startup, almost no technical questions make sense because you make those decisions. If the CEO steps in and starts dictating your T decisions, then he's the acting CTO and you're just a puppet.
    – Nelson
    Oct 5, 2021 at 4:22
  • I checked the link you shared and also found it useful, like you said. What's even more, I consider that all of them also apply for the case the job is the CTO position... is there something you feel those answers are missing? Many of the relevant tips suggested there are questions that, perhaps, affect the CTO even more strongly than other (subordinate) roles.
    – DarkCygnus ♦
    Oct 5, 2021 at 4:47
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    A 7 year old start up? Some companies have started, profited and closed in that time. 7 week startup or 7 months maybe…
    – Solar Mike
    Oct 5, 2021 at 4:50
  • @DarkCygnus what i feel missing is: 1) anything specific to CT position 2) anything specific for something coming from enterprise to startup?
    – TAM
    Oct 5, 2021 at 5:02
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    My initial thought is: If you have to ask this question, you're not ready for the position.
    – Joel Etherton
    Oct 5, 2021 at 21:59

2 Answers 2

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I think the two biggest questions you need to answer are "what does the CTO do at this place" and "why are they looking to bring in an outsider as a CTO?"

At a big corporation, the CTO is usually a technical strategist; at a small firm, the CTO is a technical tactician (i.e. architect, tech lead, technical PM all rolled into one). I'd guess that for a 7 year old firm, with a technology team of 15, the role will skew much more towards the tactician side, but it is really important for you know exactly what the job will look like.

The second question derives a bit from the first. Maybe they've never had a technical strategist before, and need one, so they are creating a new position. In this case, it might make sense to bring in an outsider, with different skills and experiences than what they have.

If the role is a tactical role, it is very fair to ask why there is a vacancy, and why they aren't promoting someone who is already there. Maybe there is a huge amount of technical immaturity and they need to bring in someone with more experience to start redesigning things. Or maybe there is discord and strife between teams and among people and they need an "adult" to come in and take control.

As you can see, the answers to these questions will really help you understand what the job will be like, and what it will take to succeed.

With regards to how this job will differ from your corporate one, take a look at this answer from another question - Is it normal for people to take things personally when rebuked/disagreed upon in a startup environment?.

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Seven years is quite a long time to still be a startup, especially in a fast-moving world like FinTech - but then it's a word that means different things to different people. I'd certainly want to dig into that a bit more into that and find out what stage they're really at. Are they still trying to create an MVP after 7 years? Did they have an MVP 6 years ago, but are struggling to attract customers? Do they have a small but profitable company, and are looking for more funding to grow?

As the CTO, you'll ultimately be the one responsible for making technical decisions, but if they're already got 15 people who would be reporting to you and have been going for seven years, a lot of those decisions have already been made. You should try and find out more about how they work, including things like:

  • What is the current technology stack?
  • What changes are coming in the next couple of years that might affect that?
  • Do they have good development processes (source control, CI/CD, etc)?
  • Do they have good change control and ops processes?
  • Who has been making technical decisions up until now? How is that going to change when you come onboard at CTO?
  • What are the main areas of technical debt in the organisation? How bad are they, and what's the plan to deal with them?

FinTech usually means having to comply with various regulations, and as the CTO that might fall onto your plate, so think about:

  • Is someone responsible for security, compliance and governance (CIO/CISO/etc) or will that be you?
  • Do you have to comply with specific regulations (such as PCI DSS), and do you understand them?
  • How mature is the company from a security perspective? Is everyone logging in as root/domain admin? Do they have third-party security testing/audits? Are they working towards standards like ISO 27001?
  • Will you have support from the existing techies implementing security, or will they fight against it? Will you have support from management?
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