CLOSURE

Stop trying to make CTO happen

March 31, 2024

Inspired by some discussion on Hacker News about whether it was a bad career move to switch from “CTO” to “developer”, I want to talk about CTOs. Specifically, CTO is not a real job and you should likely not aspire to be one1 especially if you view yourself as primarily someone who sticks to engineering career ladders, either as a manager or as an individual contributor.

TLDR: Don’t trust anyone who’s a “CTO” that’s not a technical cofounder.

There are two and a half valid forms of CTO. The two valid CTO roles are:

  • A technical cofounder who needs board oversight, and now acts as somewhere between a technical IC leader, and a chief product officer.
  • A public company that needs a person on the executive team to explain technology to the C-suite, and do technical marketing, and generally help with technology ✨ synergy ✨. Notably, this person is not in any form “leading engineering” or acting as a “chief engineer”.

The remaining half-valid form of CTO is actually just:

  • A VP Engineering (VPE) with the CTO title because it sounds cooler.

A VP of Engineering has all of engineering report through them, and is responsible for execution of an entire engineering organization. If you do this, but your title is CTO, you’re actually a VPE. I’m not going to harp on titles a bunch (call yourself whatever you want), but “in the literature”, that’s the role. This is obviously an important role, but it’s fundamentally an executive-level management role, not some sort of senior technical person that people often think of when they think of a CTO. Empirically, you’ve probably seen startups with an engineering department that does not actually report through the CTO2, especially if the CTO is a founder and the startup is >30 people. The person engineering reports through is the VPE.

If you aspire to be a CTO, you should actually be aspiring to be a technical cofounder or aspiring to be a VPE. The public company CTO archetype is often someone who was previously a VP Eng at a big company, like Kevin Scott at Microsoft.

VPE and the technical cofounder CTO archetype are two completely different roles and you should probably not be aspiring to be both of them. This is not to say that a VPE can’t start a company, but that they likely have another technical cofounder.

Technical cofounders with board oversight that are CTOs are likely not actively involved in day-to-day engineering decisions once the company is over 30-50 people. Nor are they some sort of “chief engineer” (and if they are, they are likely making their company worse). It can make sense for a technical cofounder to maintain veto power over technical decisions, largely used sparingly as an organizational fallback against repeated poor decision making by some other technical leader. A technical cofounder CTO should be bridging product, engineering, marketing, the C-suite and board. This is something that is only possible because the CTO has been present as a technical contributor since Day 1, and they are intimately familiar with the product, the engineering behind the product, the market, and the organization. You will not be able to get this out of a CTO who’s an external hire once a company has scaled beyond 10-30 people. In fact, I’d go so far as to say anyone who has the title “CTO” who is not a VPE nor a founder should likely be met with skepticism. For supporting evidence, go look at a number of mid-sized startups who have had “CTOs” who last less than two years and then move on3.

So to go back to the original discussion about is it a bad move to switch from “CTO” to “Developer”, there is no answer because the question is malformed. Better questions might be:

  1. Jumping the shark slightly, but “be a technical cofounder” is a perfectly fine goal. ↩︎

  2. It’s possible the VPE reports to a CTO, especially if the CTO is a founder. I’m not trying to harp org charts here, the distinction I’m drawing is that the CTO is not directly responsible for the execution of the engineering organization. ↩︎

  3. To be fair, this reflects at least as much on the executive team as it does the CTO hire. I’m not going to provide specific links because that’d be mean to some people I know and the companies they work at. ↩︎