Hiring a VP of Engineering or CTO For Non-Techie (First Time) Founders

So you start a web service with some friends. They do the programming. You do everything else. Suddenly the service takes off. You are thrilled and getting ready to pop open the bubbly. But then things start to sputter as your service can’t handle the load. You put the bubbly back in the fridge (unopened) and wonder what to do. The next day you hire a kick-ass VP of Engineering, the service starts humming again and everyone lives happily ever after. The End.

Except for the part in which you have no idea where to find a kick-ass VP of Engineering, or how to tell one apart from the hundreds of impostors at your door. So what to do in real life? Here are some do’s and don’ts (mostly learned the hard way) presented as (only slightly) exaggerated scenarios.

1. I just met this guy. He’s totally awesome. He can solve all our problems. I am going to make an offer right away.

Don’t. First, ask yourself, how many people have I met for this position? If your answer is less than five, stop right there. You need to see at least five candidates. And that’s an absolute minimum. If you are a first-time founder you most likely have no point of comparison and it’s too easy for tech candidates to look great when in fact they are not. Also, make sure to get as many experienced people involved in the process as you can. This is where you need to lean on investors, board members, advisors, fellow entrepreneurs, etc.

2. This woman is amazing. She spent the last 20 years at Monsterously Big Corporation in IT. She has soo much experience. I will hire her immediately.

Don’t. Most people who have been in IT at large corporations have either forgotten or never learned how to get things done on a budget of less than a gazillion dollars and a three year development cycle. Similarly, you should be wary of candidates coming from academia or a company’s research division. They tend to be too theoretical for building robust production systems. Look instead for candidates who have actually delivered at early stage, high growth companies, ideally already in a VP of Engineering / CTO role.

3. Met this candidate. Blew me away. Our approach is all wrong. We have to rewrite everything in [insert programming language / framework here]. That’s how they do it at [insert successful startup here].

Don’t. Your candidate is likely to be a technology fanatic. Advocating a complete rewrite without having seen the existing code is not a sign of pragmatism, which is a key trait for actually getting stuff done. In any case, almost anything can (and has been) built in any language and complete rewrites that never really complete have been the kiss of death for many companies.

4. This engineer was a major contributor to a [insert open source project here]. He wrote a really cool mash-up using our API. He has great experience in a high traffic environment. Should I hire him even though we don’t yet have the VP of Engineering?

Do. Great engineers will be sufficiently self-directed. Also, there is likely to be much to do if you are really growing, from making small changes to improve performance (those always exist, by the way) to adding new features or writing ancillary systems. Even if you do find a great engineer, you should, however, resist the temptation to make them the VP of Engineering or CTO. It takes a pretty different skill set to manage people and process than it does to build stuff. That is not to say that a great engineering hire can’t step up and fill that position, but it’s much better to let that happen than to force it (in the latter case if it doesn’t work, you have just lost a bunch of time finding the right person and most likely lost a great engineer in the process).

5. We have seen tons of candidates. It was an exhaustive and exhausting process. We all love [insert name of kick-ass VP of engineering candidate] but she has three different companies wooing her. I want to make an aggressive offer with more equity than we had originally planned for this position.

Do. This is a clear case where the right person will grow the pie by a lot for everyone (in fact, there may not be a pie without the right person), so giving a bit more away makes total sense. Also, you will still want to have a 1 year cliff for the equity vesting, in case things don’t turn out as hoped for after all. If you really have to, in order to land the candidate, you might go down to a 6-month cliff, since you will (or should) know after a couple of months whether you made the right hire.

P.S. If you are a VP of Engineering or CTO with the right stuff, please write to us at [email protected] – we love to develop relationships for when the right opportunity comes along.