Don’t Hire a VP of Sales Everybody Loves

So this is a seemingly simple post, and one with a title that is purposefully a bit binary.  Yes, sometimes it’s OK to hire a VP of Sales that everyone loves.  But not usually.  At least 9 times out of 10, if everyone on the team loves a VP of Sales, it’s the wrong hire.

And this especially matters because I often see CEOs picking between 2 final VP of Sales candidates.  The one that’s more edgy, that’s more opinionated, and/or the one that folks are less unanimous about … loses out.  And almost always, that was a mistake.  Let’s explore why:

• Your entire existing sales team should NOT love a great VP of Sales candidate.  Why?  First, the lower performers will be threatened by someone great. They know they’ll likely be moved out.  And also, top performers may be threatened as well.  Why?  Because things will likely at least change.  And top performers are usually comfortable with the way things are, at least for them.  The best VPs of Sales immediately identify the top performers and make them want to stay when they join.  But this doesn’t eliminate all anxiety or change.  I almost always see the top performing IC sales execs at a startup preferring a “nice” VP of Sales that often doesn’t know the product, pace or industry — but will support them and leave them be.  Logical, but usually the wrong choice for the company.  Still, if they are 100% opposed to a candidate, that is a sign to generally not make the hire.
• Your management team often should be split on a top VP of Sales candidate.  Why?  First, of them don’t really know what a VP of Sales does, so they’ll be blinded by the one that talks ARR and NRR the best.  Second, just like your AEs, they’ll be looking for fit.  Someone that fits in well with the existing VPs, with the vibe.  You do want this.  But again, you also need someone usually to mix it up, however.  At a minimum, I often see the newest VPs loving the more mediocre final candidate. They often just don’t know yet.  Be a bit wary of their input.
• Your board often doesn’t know.  Really, they rarely know.  How many of your investors were CEOs?  Even if they were, how many hired a VP of Sales at your ACV before?  That’s worked with your type of customers?  VCs love VP of Sales that sell up well.  You don’t need that.  Most VCs give you the wrong advice here between 2 final candidates.  Not all, but most.  So just don’t be looking for unanimity here, that’s all.  Usually at least half your board votes for a suboptimal VP of Sales candidate.
• The popular ones, they’re often too big company, or not hands-on enough.  The VP of Sales candidate everyone loves — they often love because she came from Twilio, or Datadog, or Salesforce.  If the candidate everyone loves also has no startup experience at your scale — be extra wary.  And folks that aren’t hands-on spend a lot of time on people stuff.  Which is good.  But if they aren’t a little rough around the edges, it usually means they don’t actually do sales anymore.  You’re not ready for that.

If nothing else, don’t pick a VP of Sales candidate just because everyone likes Bill or Elaine.  That’s a sign of not the best possible hire — but a suboptimal one.  And definitely don’t hire a VP of Sales that you aren’t sure about, just because they are the best fit.  Push on and find someone you are sure about and believe in.

Net-net, if you’re down to 2 final VP of Sales candidates, generally don’t pick the one everyone likes the most.

They’ll make the least change.  And that’s not what you need.  What you need is to grow a little bit faster, and to scale with the right team, on time.

And when you do grow faster, in the end, everyone will love the VP of Sales that got them there.  Not the one that got all High Fives in the interview process.

And also note, yes, most if not all of this applies to every VP-level position.  Not just sales.

A related post here: