Dear SaaStr: When Should a Startup Hire its First Sales Person, and What Should Their Profile Look Like?

We’ve talked a lot about this on SaaStr, let me summarize my top learnings from 15+ years

  • Try to close at least 10–20 customers yourself first, before you hire a sales rep. You can’t teach them how to do it if you haven’t done it yourself.  A bit more here.
  • Then, hire a sales rep to help you. Hire someone that has sold at your price point / deal size. If they have, they’ll roughly know what it takes to close your type of deals. The number of calls, Zooms, demos, discussions, etc.
  • Don’t hire someone that hasn’t worked at a startup. This almost never works. They can’t sell without a brand behind, without lots of sales ops help, without collateral, etc.  It’s not their fault.  They just rarely can survive without all that infrastructure and brand behind them.
  • Most importantly — don’t hire someone you wouldn’t buy your own product from yourself. Everyone makes this mistake. Leads are so precious in the early days. You can’t entrust them to someone you wouldn’t buy from yourself. No matter how impressive their LinkedIn, or how smooth their talk is.  I can’t tell you how many times I’ve talked to early-stage founders where their first few sales hires didn’t work out. I always ask, “Be honest.  Would you have bought your own product from them?”  The answer is almost always No, or a hedged Maybe.  More here.
  • Ideally, hire 2 reps at first, not just 1. If you just hire 1, even if they do well, you won’t be sure why. You want to run an A/B test and see how different things work, and when they don’t.  More here.
  • Remember a great sales rep is accretive. A poor one costs you money, though. The best reps close much more than they take home in comp, at least over the course of a year. So don’t be scared to hire a great rep.  They’ll more than pay for themselves.  And ultimately, move on from anyone that can’t close.
  • You’re usually not ready for a real VP of Sales, even a stretch VP of Sales, until you have hired 2 reps hitting quota.  There just isn’t enough process for them to build on and scale up.  The job of a VP of Sales generally isn’t to get the flywheel going.  It’s to accelerate it.  More here.

A related post here:

10 Common Blindspots When Hiring Your First Sales Team


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