But at least they get the job, so they can try to learn. Hence it doesn't go both ways.
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.
It can be but doesn't have to be. A lot of people prefer to hire folks with some small startup experience because such people almost always better at thinking about businesses holistically. Many people who spend their entire careers at big companies can only reason about their little slice (lots of bad takes on businesses here).
A common way to make VP of engineering at big tech is the following 5 job hops:
1. Manager at big tech
2. Manager at startup -> promotion to director
3. Director at big tech
4. Director at startup -> promotion to VP
5. VP at big tech
The problem comes when someone gets too senior with relevant experience at scale. I (generally) can't hire someone with 15 years of experience who's never worked at scale. They're going to be bored out of their mind with mid-level work but simultaneously I can't actually trust them to not screw up something in senior+ roles, either technically or socially.
But you can absolutely come into an engineering role at a company with 40 engineers (40 person org charts to director at BigTech), grow into leadership of a 200+ person engineering (charts to vp) and then go back to BigTech for bigger bucks.
I have trouble landing interviews at FAANGs with 15+ years as an eng. and successful acquisitions as a founder - but those don't mean anything if you don't have direct knowledge of certain tools to handle scale or experience guiding projects across departments, etc. Which makes sense for any role past junior, since part of the value you bring is experience and only some of your experience is directly applicable. Vaguely being competent doesn't really move the needle.
On the other hand, I've heard stories of people getting hired from a FAANG going to a startup and not able to shift their mindset to a "make it work" approach, so the challenge goes both ways.