I'm in a similar position to Steve Blank: early employee navigating various role transitions as the company grows. Would appreciate additional resources like the above, recommended coaches, books, etc. if anyone can offer.
I'm not sure it's exactly the coaching or books you're looking for but YC itself did a series of interviews called Employee #1 about how different people in different roles navigated being an early employee of a successful company to varying outcomes. I found it helpful if not directly instructive.
You have a certain specific set of skills. That set of skills comprises of what you had when you started at the company, grew with you being in the company and probably now has a sprinkle of play during "the company in transition" phase.
The problem is that the company that you are with is unlikely to care about those skills of yours if you are noticing what is currently happening in a company and are looking for additional resources.
Look to go to another company that would value your set of skills.
https://blog.ycombinator.com/category/employee-1/