I’m past this point in my career but I’m hanging onto this to forward to people who might need help or guidance beyond having a chat with me! Don’t let the github link hold you back – it’s also available from all book sellers as a printed book instead of a pdf or .md file.
As of today I have not read this book, so don’t consider this a recommendation (yet).
https://github.com/ZachGoldberg/Startup-CTO-Handbook