Q: Dear SaaStr: What Are The Top 3 Criteria for Hiring Your First Head of Sales?

We’ve talked a lot on SaaStr about hiring that first VP of Sales.

But what if you can’t find the right person, and you’ve spent months looking?  What risks should you take when you’ve realized Ms or Mr Perfect just isn’t going to happen right now?  At some point, you have to take some risk.  I’d boil it down to 3 factors.

If your risky candidate passes all 3 criteria, and you haven’t found your “true VP” after 4-5 months (possibly less), I’d go ahead and make the hire:

#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 making them your director of sales or first “head of sales”. 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.

#2. Do they have proven success selling at your price point? Being great at $1k deals is not the same as $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.

Finally, before you settle — have you made sure you can’t promote from within?  You probably have.  But if not, challenge yourself if you have 2-3 performing reps to see if one can step up.  Maybe give her a shot at hiring a great sales rep.  If she can bring in a great rep that would work for her, then you may have your stretch first “head of sales” candidate right inside your office already.

I know these 3 criteria seem basic.  But you’d be surprised how many CEOs hire a first VP of Sales that doesn’t meet all 3.  Then, they find they need their second VP of Sales rather quickly.

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