Deciding between working at a FAANG vs trying to chase an exec position at a startup.
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PM Manager, early 40s, married and ENM (Ethical Non Monogamous) AMA
Become CEO and get the startup bought by them. Or get a director level position and get promoted. You don't just magically become a Fortune company exec from the outside, where a single org's headcount can be bigger than several established SMBs combined. Edit: Sorry, misread that. For startup exec positions, go to meetups to talk to VCs and founders. Take them out for a follow up, sell your vision and experience for what they're trying to build.