A lot of this was fixed by working remote, and being a founder of the company.
I'm CTO of a very small startup, and we're experimenting with an organizational structure based on the causes of this list and a bunch of other stuff-- found a CEO whose really all about the love- there is no other word for it.
If you get there, I'll be interested to see your org get to 20+ people and if you can keep all your rules. No more than 2 mandatory meetings a year seems tough to me. The limits on flex time seem tough as well, especially for leaders. Sometimes your team is going to want to actually talk to you.
If the meetings are worthwhile, they don't need to be mandatory. Quarterly company review? Ok, make it good, and I'll be there. Mandatory is used to excuse bad meeting making. Mandatory safety meeting? Ok, that's one of your two.
Yeah, the rules are different for founders, etc. More meetings, more availability, etc.
Why didn't you go the co-CEO route instead? From my experience CEO has a tendency at some point to dominate other CxOs for whatever reasons (usually business guys view tech as inferior).
That's sort of what our relationship is-- from my view-- but I believe that at some point someone has to make a decision. Some of them are coin flips, or can be changed before too long if they turn out to be mistakes. I don't want to spend time on a lot of stuff that's not about building the product.
The CEO is also the domain expert in this situation, and we have a great personality fit.
Ideally I think engineers should be CEOs. Engineers can learn business a lot easier than biz guys can learn engineering. But it's not always going to be the right choice.
I really hope it would work for you and you found a reliable CEO. Just recently a friend of mine, CTO of a startup, was cheated out of equity by CEO & CFO of the company he founded (while being assured all the time they are BFFs and bros). That's one of the reasons I would never go for less than co-CEO and a legal requirement to have my approval required for any decision... I would also love to see more engineers as CEOs.
