4 Signs You Might Have a “Bad” CTO — Or At Least, One That Isn’t Going to Make It

Q: What makes a bad CTO?

While there is no legal definition for CTO 🙂 or bright line between CTO and VPE, I’d suggest a start-up CTO really only has to do a few things — which are very hard:

  • Assemble a small team (3–9) of very good engineers
  • That are super agile
  • And can ship a lot of very functional, very clever code that supports early, very rapid growth (from a very small base).

So … a “bad” CTO is one that can’t recruit a strong “pizza box” team. A bad CTO is an OK engineer him or herself but can’t get 3 other great engineers to join him/her. Ask her who she will bring with her.

A “bad” CTO isn’t agile enough, and can’t push out quick releases and features to save big deals, fix terrible bugs, etc. A “bad” CTO sometimes wants to do this, but just isn’t good enough. Or a “bad” CTO is a bit too unmotivated / whatever to do what it takes to keep up.

A “bad” CTO doesn’t care about growing very, very quickly.  About increasing velocity. So much changes once you have your first few customers. It’s exciting — but also tiring and very stressful. A great CTO embraces this change, participates actively in it, and drives it. Finds a way to increase product velocity when inertia starts to drag you down.  A “bad” CTO, though, resists the changes that come with scaling the early customer base.

A “bad” CTO never gets the release out.  A simplification of the prior 3 points.

The skills it takes to build a clever hack with a small team, and iterate that hack very rapidly to respond to customer and market needs … are not the same skills it takes to scale from 10–100 engineers. To refactor the code base. To ship truly enterprise-grade software. To walk into a room full of CIOs and instill confidence.

Sometimes, CTOs can grow into true VPs of Engineering. But usually, they don’t want to. They want the company to bring in a true manager to scale the team beyond 1–2 pizza boxes. While the CTO can focus on doing super agile, next generation things.

In SaaS, plan to recruit a true VP of Engineering around $5m-$8m in ARR. You’ll need her by then.

Just as important, though, make sure you have a CTO that can get you there.  From that slip MVP to $2m, $3m, $5m ARR at least.  If they can’t build the team, can’t get more agile over time, and don’t want to scale to meet demand … it’s not going to work.  You’re going to stumble just as it gets good.

Published on July 2, 2020

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