I'm largely in the same boat. I was part of the founding team, architected our systems, wrote a good part of it, and eventually look over leadership of the engineering and product teams as the CEO had to focus on more external matters. I played the SE role on any meaningful call, worked closely with marketing, and even did sales directly a couple of times landing us an LOI at a critical time.

We had an "ok" exit, not enough to never work again by any means but it put some decent amount of money in the bank.

After riding out the acquisition for a year I've been looking for my next role and it feels like I don't fit in anyones box well enough to get the nod. Besides landing an exec position at a startup with funding, the big tech companies of the world seem like the only place to get good compensation for that expertise. From what I can tell, the big tech places don't seem to be interested in hiring people from startup-heavy backgrounds nearly as much as they used to be.

My approach is to try to reestablish some networks, and tossing resumes are interesting job listings. But the reality is that almost no one is getting hired for great roles without a warm intro to a hiring manager. Dusting off the old personal website never hurt either, it might at least let you get into the right kind of conversation after the warm intro.

It feels like I'd be in a great position to start a startup but with spouse and young kids its not the right time (especially now) to do that sort of thing.