I was at Etsy after Dan left, and I think it scaled pretty well from the few hundred engineers when I joined to closer to 1000 when I left. Etsy's engineering culture had a lot of problems, but they weren't caused by empowering people. If anything, being encouraged to work cross-functionally built a lot of empathy and understanding for different roles and hats in the org, and made a lot of engineers a lot more effective.

There were some annoying parts of the ultra-permissive culture. Sometimes you'd need to literally beg people to stop YOLO-committing code into your UI component because they're not checking how it looks with your flag enabled and they're breaking your A/B test over and over and you just lost a week because you need to restart it. But we gained more than we ever lost.

fwiw, Etsy seems to have ~2.5k employees [1].

[1] https://en.wikipedia.org/wiki/Etsy

This is the problem all medium to large businesses face - red tape, faceless bureaucracy overloads the system

Every. Damned. Time.