A mistake many founders make is hiring a VP of Sales who has many strengths — but is not great at selling themselves per se.  A VP of Sales who is smart, polished, and worked at the right place, in a management-level position.  That can talk about quota attainment and sales operations and scaling and number.  That often has many thoughts on process and scaling a sales team.  But actually isn’t great at … sales itself.

I can tell you empirically the best VPs of Sales I know were strong salespeople in their early careers. Not always the #1 top salesperson, but very strong. In the top 20% or so, ideally higher.

“How can there be seasoned VP of Sales candidates that aren’t actually great at sales?”  you might ask.  How could this be possible?

The reason this is not just possible but common in larger tech companies is that “sales” in very large, very well-established companies with strong brands and account penetration is often something quite different than at startups.  When everyone on the planet has already heard of your product and used your product.  When every company on the planet is already an Opportunity.  Then yes, sales truly is a machine.  One you tweak here and there.  And here, it’s entirely possible to be a Director of Sales, or even beyond, in a large tech company without ever building a team yourself, without winning a tough bake-off, and without even ever visiting many companies.  They all just come to your Executive Briefing Center, after all.

But you don’t want to accidentally hire that polished sales leader that can’t sell her/himself, no matter how strong his or her LinkedIn appears to be.

Startups, even fairly late-stage ones, are nothing like F500 companies and top tech companies in how they approach and manage sales.

Most of us are looking for sales leaders to lead a team of 5, then 10, then a team of Directors to scale to 30, to 100, and beyond.

Here’s why hiring a VP of Sales that isn’t actually a great salesperson never works out:

  • The top salespeople know. They know if the VP of Sales is great or not. And they won’t respect them if he/she isn’t great.  And really, they won’t even join the company to work for him or her.  So mediocre VPs of Sales end up recruiting reps even worse than them.
  • VPs of Sales that don’t sell themselves never really understand the product.  And in all fairness, at really big, established companies, sometimes you don’t really have to.
  • They can’t recruit what they don’t know how to do. The mediocre salespeople I’ve seen promoted to manager levels recruit mediocre sales reps under them. Like all the time. They can’t get anyone else.  You don’t want this.  And very importantly, VPs of Sales that aren’t great at sales, or don’t really do sales anymore, tend to hire reps that never really understand the product, either.
  • Competing is too tough on sales leaders that can’t sell. You have to know how to win in very competitive, agile deals in most startups. In very big companies, sales is also competitive, but often simplistically so. The competitive dynamics in a feature-poor start-up are different. Big Company sales leaders who aren’t great salespeople wilt in the face of better-funded, more feature-rich competition.
  • They can’t diagnose problems. Sales leaders who haven’t been great reps have trouble doing root cause diagnoses. The ones that are great at sales, by contrast, figure out the root cause of issues in a few days. Max.  And solve those problems.  Sales leaders who aren’t great at sales blame everyone else for these problems, from marketing to the CEO to, always, the product.

If you want to be a successful VP of Sales, you have to work your way up. And you have to be at least Top Quartile in the beginning to get there.

Be careful of folks who got promoted to manager only in very large companies, or dated, fading companies, or non-competitive companies. They are good at many things.  But they don’t learn these skills.

Not sure if a VP of Sales candidate you are talking to is great at sales? I’ll give you 5 tips:

  • First, ask her for 3 customer references. Call those 3 customers. Ask how the candidate helped their customer. You’ll hear and learn if they can sell.
  • Second, ask her for references from 3 sales reps she hired. Call those reps and ask what they did to exceed quota together. Listen.
  • Third, be worried if your VP of Sales wants to do more than sales.  Sometimes this works out, but someone that loves sales and is good at it … wants to do sales.  Not Sales+Customer Success+Marketing.
  • Fourth, don’t hire a VP of Sales that doesn’t truly understand the value proposition.  You can’t expect a candidate to be an expert in everything before they start.  But a great salesperson at least almost immediately becomes an expert in the value proposition.  If you really like a VP of Sales candidate as a person and a leader … but he just isn’t really getting the value prop … well, time won’t cure that.
  • Fifth, you have to talk to their old bosses if you have any doubts.  Don’t skip this step.  Their old bosses may protect them, or disparage them.  They may say they were great — but only up to a point (this is common).  But they’ll know if they were a good salesperson.  That they will know for sure.  And they’ll be direct when you ask directly.

And finally, ask them to sell you the value proposition.  Can they really do it?  Or do they just talk recycled nonsense or buzzwords?

If you don’t make those calls, and it doesn’t work out, if you hire someone that doesn’t really get your value prop, well, remember you’re to blame here, not the candidate.

And if you don’t hear answers that inspire confidence — you don’t have a real VP candidate.

And last, let me share the stories of two smart VPs of Sales I just caught up with:

  • One moved on after a great 4+ year run and saw his startup become a decacorn.  And what did he do his first week at the job, back in the day?  Go sell himself.  Go talk to customers.  Go learn the product.  And he grew from doing sales himself to running revenue at a decacorn.
  • Another, who I like a lot personally, just lost his job as VP of Sales.  I asked him what happened.  He said he should have been more hands-on, and talked to customers in his first 60 days.  He said he didn’t really talk to customers or get involved in sales himself for the first few months.  Why not?  He was too busy in process and systems.  Sales plummeted, and he lost his role.

(note: an updated version of a classic SaaStr post)

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