Yes, Your VP of Sales Also Has to Be a Great Salesperson Herself

A mistake many founders make is hiring a VP of Sales who has many strengths — but not at sales 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. 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 is often something quite different. 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 their 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.
• 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.
• Competing is too tough on sales leaders than 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 she or he is great at sales? I’ll give you 5 tips:

• First, ask any VP of Sales candidate 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 them for references from 3 sales reps they 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.

If you don’t make those calls, and it doesn’t work out, 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.