[dasil003]

I've also had the experience of failing FAANG interviews after being very successful at smaller scale. Since then I've made the leap, and I can tell you that experience in the 10-100 developer range is extremely valuable and can make you very upwardly mobile once you get a foot in the door. People that have spent their entire career in big corporations often have a lot of assumed constraints based on groupthink and the vagaries of whatever specific org leaf nodes they've been exposed to. Often they will have worked for years under bosses with no real clue about the actual decision making process and strategy behind their work. It's extremely hard to develop an end-to-end understanding and strategic viewpoint in these environments. Startups offer much more opportunity to learn the big picture and the strategic considerations behind different functions. Obviously anyone can claim to be doing a startup—there's a lot of the blind leading the blind, and people playing house—but if you find one with an interesting vision, a bit of traction, and good colleagues you can learn lessons that will translate well to leadership at big tech.

Coming in the front door will be hard though, because recruiters and the first layer of technical interviewers will likely not have context to judge your 15+ years of experience. Look for referrals and directly talking to hiring managers. Also, read some writing from notable SV management writers like Will Larson and Camille Fournier, this will help you learn some of the shibboleths and how hiring managers think. Finally, if you don't have legit scale-up experience, look for that first. There's a range of companies with engineering teams of all sizes which can provide good stepping stones for learning as well as hireability optics.