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 the talk, and run the report, and discuss quota attainment all day long. But actually isn’t great at sales herself or himself.

I can tell you empirically the best VP of Sales I know were strong salespeople at least in their early career. Not always the #1 top salesperson, but very strong. In the top 20% or so, often much higher. They were almost always the best at something in sales before they became a sales manager.

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 actually common in larger tech companies is that “sales” in very large, very well established companies is often something quite different from startup sales. 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 and has been for years. 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.  Without even really knowing the competitive landscape. 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, 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.

Here's why:

• The top salespeople know. They know if the VP of Sales is great or not. And they won’t respect her if he/she isn’t. And really, they won’t even join the company to work for him or her.
• 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. 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 more for budget than truly with other, bigger vendors. 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. And then they just go 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 were promoted to manager only in very large companies, or at dated, fading companies, or non-competitive companies. They may be good at many things. But they don’t learn these critical start-up sales skills.

Not sure if she/he is great at sales? I’ll give you a top tip. 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.