1- Am I willing to give up some control over my vision?

People who agree to be CTO also want to be very involved in the business. You're bringing on a partner not just a programmer.

You shouldn't expect that the tech you're developing can or should be siloed away from the rest of your business. If your business was a village, your tech isn't the ice cream shop, it's the potable water supply. Since the tech affects many aspects of your business, you should expect the CTO will also.

The CTO shouldn't only take ownership of the code, but also be a valued contributor to the direction of the company. Your CTO will expect their opinions and experience to be valued and impact key decisions, and not just decisions about what hosting service to use, but also decisions about things like product roadmap and features, launch strategy, and organizational structure.

2- Am I confident that I can get along well with this person for years?

Startups can be very stressful and test even longstanding friendships.

How well do you know this person and are you confident that you won't want to kill them after your 100th late night stressing over a deadline together?

YC's essential startup advice stresses the importance of relationships to startup success, citing that "most companies fail fast because founders fall out." Even if you're not looking for your CTO to also be a co-founder, a bad relationship with someone in such a vital role can be toxic for your company. Make sure you trust and like working with them enough to be in it for the long-haul with them.

3- Do I know that this person is actually a competent developer?

Answering this can be especially challenging for non-technical founders. Even for developers, it's notoriously difficult to predict with total confidence that someone will be good on the job based on the limited info you can glean from interviewing.

Some developers are also great at talking the talk, but aren't great at actually coding and architecting complex systems. Are you sure you'd be able to tell the difference before it was too late?

4- Can I be confident that this person up to the unique challenges of leading the tech development at a startup?

Being a developer on a 500 person team is very different from being 100% responsible for all the tech aspects of the business.

Is your potential CTO capable of being scrappy when they need to be? Are they comfortable with all aspects of the stack + devops and can they just 'get stuff done'? Can they manage people if they need to? Can they talk to potential investors?

There are a lot of traits that an ideal early-stage startup CTO would have that are unique to the role and that they might not have previous experience with. It's important to know if they'll be able to rise to the challenge.

5- Am I hiring this person because I genuinely believe they will do an awesome job, or because I think they're a good deal?

There is rarely such a thing as getting a good deal on a programmer. Please see this flowchart to predict potential outcomes when trying to hire an underpaid CTO:

If you answered no to any of the above questions, then you probably shouldn't hire a CTO.

alternatives to hiring a CTO

Sometimes hiring a CTO isn't actually the right thing for your startup, but what else can you do?

  • hire freelancers to do work for you
  • work with a development agency
  • investigate any pre-rolled solutions you can use (squarespace, shopify, etc.) and potentially combine with freelancers or agency if necessary

shamless plug

I'm a full stack developer & PM at AE Studio and like many of my teammates am also a former CTO/startup co-founder.

If you can't find a good CTO or realize that its not a good fit for you, development agencies like AE Studio can do a great job filling in as your entire tech team. Working with us is as collaborative as having an in-house team, but we have the benefit of having done this a bunch of times before, we're here to give you advice but not steamroll over your vision, and we have a bunch of experts in various things that we can bring in whenever needed. And since full-time developer salaries are expensive and we help clients to really focus their scope and can scale up or scale down our services depending on what needs to be done, working with us can actually be cheaper than hiring an in-house team. You can schedule a free consultation on our website if you want to chat and see if we could be a good fit for your company!