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

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

I know many will disagree, but I’m right here :). As a pretty good investor across many leading B2B companies, I’ve never seen a VP of Sales thrive who didn’t really understand the product during the interviewing process. Never.

Too many B2B startups hire someone likable, 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.

Watch the YouTube videos. Do a demo. Listen to some Gong calls. Get close. If they can’t, they’ll never be able to.

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

This is a classic SaaStr point and it’s more true today than ever. About 50 % of what a VP of Sales really does is recruiting. The best VPs of Sales always have at least 2‑3 great folks lined up to come with them to their next role. Ask who those 2‑3 are, and if you’re ready to extend an offer, talk to them first.

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

Sales is hard and never really gets easier. At some point, some leaders don’t want to sell themselves anymore; they’ll manage a team, check dashboards, build process, but they’re done selling themselves. We call this Mr/Ms. Dashboards. It’s more common now that SaaS is 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 Visit Customers In Person

I recently interviewed a seasoned VP of Sales who lived in the South Bay and refused to travel to SF to visit customers because it was “too far”. I get traffic, but you still need to visit the bigger accounts. If the role is 100 % Zoom, that’s fine, but for most SaaS sales you must be willing to meet key customers in person.

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

A VP of Sales can’t carry a bag forever, but a new VP who refuses to close any deals when they start often never learns how to do it at all. A candidate who insists on closing deals themselves early on is a great sign. One who says “it’s all process” should be run.

#6. Hiring a VP of Sales Who Has Gotten Cynical on Startups, Tech, and Sales

If a candidate is stuck in the mindset that “the system is rigged” against them, they’ll bring that negativity to the team. Startups need pirates and romantics—people whose energy drives and guides the team, not someone who sees everything as a rigged system.

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

A few quality posts a week can be good for recruiting, but VPs posting 2‑3 times a day on LinkedIn are often more interested in being influencers than doing the tough, full‑time job of VP of Sales. Run.

#8. Hiring a VP of Sales Who Really Wants to Be COO, CRO, etc., Rather Than a VP of Sales

If a VP of Sales is already looking for a “bigger” title and responsibilities (e.g., owning marketing, customer success), they’re not truly focused on the VP of Sales role. Title inflation isn’t the end of the world, but you must be 100 % clear about the actual responsibilities.

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

A short break is fine, but a long hiatus from the role is risky. Most of the time, they struggle to get back in the saddle. Only consider this if you’re comfortable with the risk.

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

Don’t be blinded by a fancy logo on a resume. Ask yourself: would you still hire this person if you blocked that logo off their LinkedIn? If the answer is yes, go for it. If not, you’re being swayed by brand rather than capability.

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Thanks for reading SaaStr AI: How To Sell, Scale, and Win!