The Top 10 Mistakes I See In The VP of Sales Hiring Process

So we’ve spent a ton of time over the years on SaaS talking about hiring a great VP of Sales. Not only because it really matters, but because hiring the wrong VP of Sales can set you back a year — or longer.

So I thought I’d come back to the classic topic and make a list of the Top 10 Mistakes I See Founders Make When Hiring a VP of Sales:

#1.  Hiring a VP of Sales Who Never Really Understands Your Product During The Interview Process

Ok I know some even many will disagree, but I’m right here :). I can tell you as a pretty good investor across many leading SaaS companies, I’ve never seen a VP of Sales thrive that didn’t really understand the product during the interviewing process.   Never.  I see so many SaaS startups hire someone likeable, who can talk the talk on sales hiring and processes — but never really understands what you do.  Or puts in the effort to do so.  Don’t make this hire.  They never invest the time after they start, either.  Or they are never able to.

This has almost become my #1 flag now.  Way too many folks give managers a pass here that never understand the product.  You gotta watch the YouTube videos.  Do a demo.  Listen to some Gong calls.  At least get close.  Or you just plain never do once you start.  So many VPs of Sales disagree with me here — at least at first when I make the point.  But later, they agree 😉

#2.  Hiring a VP of Sales With No One Lined Up to Follow Them

This is a classic SaaStr point and post from over the years, and it turns out it’s more true today than ever.   50% of what a VP of Sales really does is recruiting.  So the best VPs of Sales always have at least 2-3 great folks lined up to come with their to their next role. Just ask.  Ask who those 2-3 are.  And if you’re ready to extend an offer, talk to them before you do.

#3.  Hiring a VP of Sales That Actually Doesn’t Want to Sell Themselves Anymore

This one has really become an issue in recent years, and the one hand I get it.  Sales is hard.  And it never really gets easier.  So at some point in their careers, some some leaders don’t really want to sell themselves anymore.  They’ll manage a team.  Check the dashboards.  Build process.  But sell themselves?   They’re sort of done.  We call this Mr/Ms. Dashboards, and it’s not a new thing per se.  But it’s much more common than a few years back.  Because SaaS is getting to be 20+ years old.

Don’t hire this person.  No matter how well they can talk the talk.

#4.  Hiring a VP of Sales That Doesn’t Want to Go Visit Customers In Person

This is newer, but common these days.  I recently interviewed a seasoned VP of Sales that lived in the South Bay in the Bay Area (San Jose).  He said he wouldn’t travel all the way to SF to visit customers because it was “too far”.  I get it, with traffic, it can take 90 minute.  But give me a break.

There are sales jobs that are 100% on Zoom.  But you gotta at least visit the bigger ones.  Many don’t want to do that anymore after years of working from home.  Unless you sell 100% to SMBs, probably don’t make this hire.   Ask.

#5.  Hiring a VP of Sales That Doesn’t Want to Close At Least Some Customers Themselves

Your VP of Sales can’t carry a bag forever, at least not a full quota.  But I’ve come to see that a new VP of Sales that doesn’t want to close deals themselves when they start often never really learns how to do it at all.  A VP of Sales candidate that insists on closing deals themselves when they start?  A great sign.  One that says it doesn’t matter, that it’s all process?  Maybe run.

#6.  Hiring a VP of Sales That Has Gotten Cyncial on Startups, Tech, and Sales

Something I didn’t use to see much, but now is pretty common.  I get that everyone has a tough startup experience or two.  But if you can’t get past it, if the “system is rigged” against you … well I hear you.  But don’t make this hire.  You need Pirates and romantics in a startup, folks whose energy drives and guides and leads the team.  Not someone who sees the whole system rigged against them.

#7.  Hiring a VP of Sales Constantly On Social Media, Especially LinkedIn

I do believe some of this promotion is good.  It helps with recruiting, and more.   But the VPs of Sales that are posting 2-3 times a day on LinkedIn?  I’ve found they really want to be influencers, advisors, etc.  They don’t really want to do the tough, full-time job of VP of Sales.  I know some will challenge me here.  A few great posts a week on social can be good.  But a few a day?  Run.

And yes, I know I and SaaStr post a lot on the socials 🙂  But that’s our job, folks.

#8.  Hiring a VP of Sales That Really Wants to Be COO, CRO, etc.  And Not Really Be a VP of Sales.

Don’t force someone here.  If a VP of Sales is done with that role and really wants a “bigger” job where they don’t just own the new bookings number, that can have a place.  But it’s not as your VP of Sales.  Now a little titlle inflation IMHO isn’t the end of the world.  If your VP of Sales wants to be called CRO but their real job is VP of Sales, not also owning marketing, customer success, etc. — that can be OK.  As long as you’re 100% clear here.  100% clear.

#9.  Hiring a VP of Sales That Hasn’t Been a VP of Sales in a While But Wants to “Get Back to Sales”

I get this might work in a few cases.  But 95 times out of 100, don’t make this hire.  VP of Sales is a tough job.  Taking a short break?  No problem.  But going off and doing something else for a long time?  I rarely see them really able to get back in the saddle again.  Once in a while, yes.  But understand it’s a big risk you are taking.

#10.  Hiring a VP of Sales That You Wouldn’t Hire If They Hadn’t Worked At ________.

Ok my top flag is where we started the post — a VP of Sales that never understands what you do.  But this one is close.  Everyone gets blinded by that great LinkedIn, by that fancy logo on the resume.  If you love Doug, but in part it’s because he worked at Datadog, or Snowflake, or Asana, or wherever, so be it.  Just be honest.  Would you still hire him or her if they hadn’t worked there?

I ask founders to do this one exercise: block that fancy logo off from their LinkedIn.  Literally, with your hand. Now, would you still hire them?  If so, go for it.  If not?  You’re being blinded.

(what do you do image from here)