Some good advice here. One thing you may want to consider is that CTO of $x MM company and CTO of $100x MM company are two completely different roles. As different as engineer vs manager.
If you haven't actively adapted over the last 8 years, this may just be the result of being in a job you don't like. Whereas regular-exec work might be a lot of management, architecture decisions, etc., high-level-exec work is more pure politics, storytelling, and resource allocation.
There's a reason a lot of startups replace their sr execs every 10x-100x growth period or so.
This rings true.. I was a CTO of a startup growing to $10x M company, and now am the CTO of an $100x M company, and the envelope of work is very very different.
I spend far more time thinking about, researching about, and developing about what we will do in 2-3 years, instead of 2-3 months.
If you haven't actively adapted over the last 8 years, this may just be the result of being in a job you don't like. Whereas regular-exec work might be a lot of management, architecture decisions, etc., high-level-exec work is more pure politics, storytelling, and resource allocation.
There's a reason a lot of startups replace their sr execs every 10x-100x growth period or so.