The Two Most Important Things To Look For When You Hire Your First VP of Sales

We’ve talked a lot about hiring a great VP of Sales at SaaStr, and I’ve relinked to some of the most popular posts below.

But after 5+ years of, I think we can almost boil it all down to 2 things to look for when you make the hire — and 2 things not to look for as much.

  • Has she built at least a small team before? 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.


  • Has she sold at 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.

also less important …

  • 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. So just focus there.  Most VPS that are good at $10k deals aren’t great at getting on jets and closing $1m deals.  That’s OK.  Just optimize your VP of Sales’ experience around your core customer.  Don’t expect your VPS to be great at all the aspects of sales. More here.

KISS.  You can give on a lot when you make your first hire here.  You’re likely going to hire a stretch candidate and take some risk.  Just don’t take the risk in the first two points above.  You can take all the other risks.  You most likely have to.

(note: an updated SaaStr Classic post)

Published on March 12, 2021

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