Ask HN: How do I hire commissioned salespeople?

Accordingly, this is the kind of thing where a salesperson is involved and I was planning on being this salesperson -- I can say that in my spare time I am checking out books from the library about sales and reading them. It's outside my comfort zone but it's the most plausible way I can spend the next few years working on what I believe in.

So I hear from some guy who's a specialist in this kind of system, he's excited about what I'm doing and he's looking for an engineering role.

Well, I wish I could say I had a lot of revenue and could hire him and a whole "dream team" to do all of the things I'd like to see happen but of course that depends on the revenue, which depends on the sales.

So I float the idea he can work as a commissioned salesperson. This fits in just fine with my cost structure. It frees up my time, means I have someone who can drop in on customers in a different geographic zone, and means I have a second salesperson who can team sell big clients and have a different p.o.v. about my marketing problems.

Anyway, at the very least I need to write a contract but the more I think about it there are complications like I'll probably need to write this guy a 1099 if he sells anything.

It seems to me that this could be profitable for all concerned and could help us get a useful product in people's hands, but I can also see screwing this up and having a lot of hard feelings.

Any idea of how I should get started on this?