[ghiculescu]

This sounds familiar! Is the CTO also the (co)founder?

If yes, then he probably agrees with you about being in semi-retirement.

But he has been “needed” in this company since day 0, so this new feeling of not being needed (because of the great job you’re doing) is strange and uncomfortable. He probably hasn’t worked out how to explain to his co-founders and CEO (let alone to you) that it’s time for the next thing.

If it’s in the company’s interests for him to launch a new product or revenue stream, that could be an exciting and engaging project for a while.

But ultimately it’s gonna work best if you make it easy for him to let go and move on to his next project. Encourage him to explicitly take a vacation and have someone else (or you) act in his role. This will make it easier to realize that his work is done, when he returns.

If no, ignore all this.

Source: I was once this CTO. Had an awesome VP Eng and CTO-in-waiting who helped me hand things over. Happy to discuss more candidly over email.

[headscientist]

That would be great. I'll send you an email later this evening. Thank you!