It was painful going through the enterprise focus transition along with a nonsensical reorg imposed by the aforementioned Big Tech VP. One day we had focused platform-specific teams working on satisfying customers, the next we were moved to cross-functional feature teams and focused on enterprise features that (from our perspective) no one ever asked for.
I also felt the sting from mediocre engineering managers. I remember sitting down with Tracy and Ralph at Uptown Bar and giving them both barrels on what I thought of several managers. To their credit those managers weren't working there very long after that conversation.
IIRC Ralph asked if I wanted to move to being a manager and I declined but in hindsight I think that was a mistake - we needed good management in engineering more than we needed my code.
Another thing that hurt us was hiring a bunch of PMs. Most of them were condescending, ignorant, or both... but suddenly they were telling the engineers who had built everything what to do? IIRC we could have cut that department down to two people with no loss.
The leader of this product team was a manager that just didn't seem to be doing his job, only pushing paperwork and giving scatterbrained presentations. I never did find out why he was kept on so long. I think I very cheekily asked Tracy one time which of his relatives worked at Y2K or Sequoia such that he couldn't be fired because it was clear everyone in engineering was fed up with his nonsense. I'm pretty sure at least several top engineers quit due to that guy specifically.
Either way I don't regret my time at PlanGrid. It was a great team and I'm proud of what the team did and what I did.