It’s happened multiple times for me, all with extremely well known VC backed companies. Once at later stage, but applying for a very senior role, and another at an early stage, where there was a good fit.

It can be a tough sell, and recruiters are trained to just say no, but persistence pays off. Same thing applies to getting jobs in general. If you aren’t persistent in your application process and aggressive in your negotiation process, you simply won’t have the best outcomes. It just becomes easy to turn you down.