We’ve talked a lot about hiring a great VP of Sales at SaaStr.  So many great posts and discissions.   But after 10+ years of SaaStr, I think we can almost boil it all down to 3 things to look for when you make your very first early stage VP hire — and 3 things not to look for as much.

  • 1/. Have they 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.


  • 2/ Have they 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.


  • 3/ Do You 100% Truly, Honestly Believe They Can Do It?  Way, way too many of hire for the logo, out of hope, because they talk the talk.  But if you aren’t 95%+ sure in your gut you have someone that can do it, don’t make the hire.  You’ve closed so many deals yourself, after all.  You don’t know the whole playbook.  But you can spot someone that can’t really do it, can’t really get there.

The truth is, very few candidates will actually, honestly pass all these 3 criteria.  They likely are enough to use to pick your first head of sales.

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.

and what you think matters and doesn’t:

  • Don’t expect everyone to love your top VP of Sales candidate.  Some will be threatened by the top candidate.  Others will worry more about their gaps than their strengths.  Still others won’t want you to hire a stretch VP of Sales and will want the perfect resume and LinkedIn.  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)

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