How do you go from unemployed for 3 years straight to upper management? Were you already in a similar position in the past? I would think 3 years unemployed may not look good to people who don’t share your personal views (no judgement, I think if you’ve been unemployed for 3 years it shows good financial planning, I just doubt my conservative family would see it the same)

My last role was staff engineer/team lead. The company I was with was acquired and I was asked to take director of engineering post-acquisition. I was pretty stressed out about how the acquisition was being mismanaged and declined the role, but stayed at the company for another year when 95% of my coworkers left. I generated a lot of goodwill with the PE firm and C-suite during this time.

After I left, the PE firm finished the ~failed merger, flipped the company to another buyer, and the PE firm placed the CTO at another company. I've remained friends with the CTO and we have a monthly/bi-monthly check-in. He was very supportive of my side-projects and would've helped fund anything that I said had legs, but is equally eager to work with me again if given the opportunity. The company he's working at is going through a reorg and a position he thinks I'd be a good fit for (admittedly a growth opportunity) should open up.

If that falls through and I'm not able to get a warm intro somewhere then you're absolutely right. I'd focus on applying for IC positions, but clearly communicate that I'm interested in taking on leadership ASAP.