We’ve written a lot about this over the years, but for most start-ups, you can boil it down to two criteria any first VP of Sales, most likely a stretch VP of Sales, just has to meet:

  • Has she built at least a small team before — herself? Have they hired at least 2–3 reps that have performed well? This isn’t the same as having been a great rep herself, or having inherited a team. If you can hire 2–3 great ones, you can likely scale and hire 20–30. Do the diligence here to make sure she’s really been able to recruit at least a few successful reps. This is a tough skill to develop. More here: https://www.saastr.com/what-a-vp…


  • Has she sold as your price point, approximately? Sales of $3,000 a year products are very different from $300,000 or even $30,000 a year products.

What is much less important:

  • Don’t overindex on domain expertise. This can be learned in a month or two. The skills to build a team at your price point? That takes years to learn.
  • Don’t expect a VPS candidate to be good at everything — no one is. No VP of Sales is equally great at both inbound and outbound sales. At both big deals and small deals. Etc. Etc. Mostly, experience selling at your target price point solves for the trade-offs here. Don’t expect your VPS to be great at all the aspects of sales. More here: https://www.saastr.com/your-vp-o…

And … my #1 to flag if they seem to pass the basic test above, AND you like them and believe in them, and a few others related:

  • If they mainly talk about “process”, that’s a flag.  Now process is obviously crucial to scaling in SaaS — I’m not saying it isn’t.  Half the job of a VP of Sales is recruiting, hiring and scaling the team, and then putting in the processes so they can scale from 3 to 30 to 300 reps and beyond.  But a VP of Sales candidate at an early-stage startup (<$8m-$10m ARR) that mainly talks about process, about systems, and documentation during the interviews .. and not the tactical steps it will take to win this year … well, they are just too Big Company.  It’s a sign they aren’t likely going to make it.  Not unless you are growing so fast, you’ll be past $10m-$20m ARR within just a few months.  You just aren’t ready in the single-digit millions ARR for a VP of Sales that is all about process.  That works best when you’re brand is firmly entrenched and established in the marketplace.
  • If they don’t have anyone strong to bring with them, that’s a flag.  A VP of Sales that says “I’ll hire some recruiters” to get the first 1 or 2 reps to join them … that’s such a big flag I’ve never seen a hire like this work out in practice.
  • And so finally, make sure you talk to the 1-2 reps they claim are coming with them.  Make sure you think they are at least pretty good.  You don’t have to think they are amazing — they may be different than what you are used to.  But you have to believe they can do the job, and that they will … come!

OK now that sounds simple.  But if you cut the corners above, your first VP of Sales probably won’t work out.


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