The thing about being a CTO (or any role for that matter) is that it changes over time, and needs to. They purpose, value, and goals of a CTO are completely dif

The thing about being a CTO (or any role for that matter) is that it changes over time, and needs to. They purpose, value, and goals of a CTO are completely different with 3 people, 30 people, and 300 people. This is much like software - what is ideal at a scale of "just do it" is completely different at a scale of "okay, breathe". It's the norm to rain fire and brimstone on someone's past decisions when they become your inherited present. At the same time, there's a reality that those past decisions were probably made for reasons, known to be not ideal, and have to change in the future. Personally, I'd much rather never have those technical trade-offs; but I'm also a realist. The same is true of process - certain things that are bread and butter to small companies are anathema to an organization of 300. We seem to lose sight of that.