Going on 22 years or so, but the best move was going to a small, bootstrapped startup. I was Engineer #2, and after a couple years, also was the lead for the "org" which included a few other Engineers and a couple offshore people.
My responsibilities ran the gamut from zero to one architecture and software development, answering the phones, product management, running our infra, managing the budget, and everything else. I gained such a broad view of how things work, what customers want, sense of product, etc. that it's helped every other job I've had since.