The Top 10 Mistakes I See In The VP of Sales Hiring Process
"Just be honest. Would you still hire him or her ... if they hadnât worked there?"
So weâve 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 â or longer.
So I thought Iâd 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 Iâm right here :). I can tell you as a pretty good investor across many leading SaaS companies, Iâve never seen a VP of Sales thrive that didnât 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 â but never really understands what you do. Or puts in the effort to do so. Donât 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 â at least at first when I make the point. But later, they agree đ
#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 itâs 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 youâre ready to extend an offer, talk to them before you do.
#3. Hiring a VP of Sales That Actually Doesnât 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 donât really want to sell themselves anymore. Theyâll manage a team. Check the dashboards. Build process. But sell themselves?  Theyâre sort of done. We call this Mr/Ms. Dashboards, and itâs not a new thing per se. But itâs much more common than a few years back. Because SaaS is getting to be 20+ years old.
Donât hire this person. No matter how well they can talk the talk.
#4. Hiring a VP of Sales That Doesnât 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 wouldnât travel all the way to SF to visit customers because it was âtoo farâ. 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 donât want to do that anymore after years of working from home. Unless you sell 100% to SMBs, probably donât make this hire.  Ask.
#5. Hiring a VP of Sales That Doesnât Want to Close At Least Some Customers Themselves
Your VP of Sales canât carry a bag forever, at least not a full quota. But Iâve come to see that a new VP of Sales that doesnât 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 doesnât matter, that itâs all process? Maybe run.
#6. Hiring a VP of Sales That Has Gotten Cyncial on Startups, Tech, and Sales
Something I didnât use to see much, but now is pretty common. I get that everyone has a tough startup experience or two. But if you canât get past it, if the âsystem is riggedâ against you ⊠well I hear you. But donât 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? Iâve found they really want to be influencers, advisors, etc. They donât 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 đ But thatâs 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.
Donât force someone here. If a VP of Sales is done with that role and really wants a âbiggerâ job where they donât just own the new bookings number, that can have a place. But itâs not as your VP of Sales. Now a little titlle inflation IMHO isnât 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. â that can be OK. As long as youâre 100% clear here. 100% clear.
#9. Hiring a VP of Sales That Hasnât Been a VP of Sales in a While But Wants to âGet Back to Salesâ
I get this might work in a few cases. But 95 times out of 100, donât 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 itâs a big risk you are taking.
#10. Hiring a VP of Sales That You Wouldnât Hire If They Hadnât Worked At ________.
Ok my top flag is where we started the post â 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 itâs 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 hadnât 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? Youâre being blinded.
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