[seregarev]

A few things: Startup founders need to be convinced that you'll be willing to do the work that at big companies you might have had a support team for. So you need to prove that nothing is beneath you. The best way to get their attention is to demonstrate the type of work you'd do for them right in your cover letter/email. (ex) In your case it could be sending a recording of how you might lead a technical demonstration for their product even if it's just a mock demo.

Also, I'm not sure how early stage you're willing to go (looks like you want at least 10-20 employees), but with your experience you can fairly easily start to engage startup founders that are just starting to think about building out a sales team and process, and help guide them. Whether it's tips on how to create pitch documents, how to set meetings, or the best way to think about how they will scale their sales team. I've seen a number of startups where someone has started off as an advisor (whether formal or informal) and later on was hired as a FT employee. This approach might take some time, but at the very least you'll build relationships with interesting companies and get to see how they're run before joining them.