I was an engineer #1 hired by a "CTO" and we grew to 50 engineers. His story/growth didn't really change much, however. He was a coding machine, a true "10x engineer", and programmed day and night. He even started up a second company while working on the first. He built both codebases from scratch, and even re-wrote the first company's core codebase at one point.
He did attend exec meetings and make all major technical decisions, but I never really felt he had to grow into anything.
When we got big enough to start worrying about compliance, security, and HR tools, we did it together and moved on to the next thing.
There are a whole host of compliance and security issues that you don’t have to (and shouldn’t) worry about when you’re small. Employee background checks, documented disaster recovery plan, 3rd party pen testing, etc. Those are things you worry about once you have built something. It’s different than just application security which itself can always be improved over time even if it wasn’t an afterthought.
He did attend exec meetings and make all major technical decisions, but I never really felt he had to grow into anything.
When we got big enough to start worrying about compliance, security, and HR tools, we did it together and moved on to the next thing.