The top 3:
#1: Have they hired 2+ quota-meeting/exceeding reps before. This is #1 by far. If they’ve never hired 2+ great reps before, you are taking on a lot of risk. 95%+ of great individual contributor reps have zero experience hiring. Do you want to be the company where you learn if they can? Ideally, no. And this is not the same as simply being given a small team to manage. The question is, can they give the names of 2 reps they hired that hit plan? If they can, they’ll know how to hire 2 and then 20 more.
#2. Do they have proven success selling at your price point? Being great at $1k deals is not the same at $10k deal or $100k deals. Don’t gloss over the critical differences.
#3. Can they train you? See if they can train you to sell your own product. If they can, they can train others. If not, it’s risky. Training is a critical part of sales management.