Salesperson Direction: Facing In or Facing Out?

In my book, I talk about the process of hiring salespeople. Technical founders are notoriously bad at doing this well. Research and professional sales are two very different fields.

In a startup, the most effective salespeople are the founders—the folks who really understand the technology involved and have been thinking for a long time about how it might be used. Eventually, though, it’s likely that you will need to hire some people who aren’t techies, who are there primarily to sell.

At the point where you’ve had enough success that your founding team is busy with things like general management, HR, delivering what you’ve contracted for, improving your products, and the like, you will need salespeople.

What a Good Hiring Process Looks Like

If you do it right, you’ll interview multiple candidates, pretty much simultaneously. You’ll check references, see what your senior staff think of the candidates, and so on. You’ll hire one or more salespeople, on a tryout basis, with a package of base salary and commission.

Then you’ll let them sell.

After some time—once they’ve learned about the company, your technology, and your offering—you will need to make sure they are focused on prospects and leads, rather than on things inside the company. They’ve been good at selling you on their qualifications; now the question is, can they sell to prospects? Are they pointing in or pointing out?

A Startup Sales Story

Along with some other mentors, I was working with a venture that had some excellent technology. The CEO, in his somewhat shy, techie way, had managed to make some sales to important customers.

The mentor team encouraged him to hire some sales help, and one of the other mentors put him in touch with a salesperson he’d worked with in the past. The CEO brought the salesman on board as his sales manager.

A few months went by, and the new sales guy didn’t seem to have done much, at least not yet. We had a mentoring meeting with the CEO and the sales manager. I listened to the vague generalities being uttered by the sales guy, then asked him some pointed questions, but in a matter-of-fact, non-hostile way:

Q: “Do you have a prospect list in a spreadsheet (or some other form), with prospects, their status, next actions, ticklers to tell you what to do when?”
A: No.

Q: “Do you have a Top Five prospect list?”
A: No.

I asked a few other questions, and it was clear that the salesman was not well organized. I left the interpretation to the CEO, who had heard all of the conversation.

By the time we had our next meeting, a month later, the salesman was gone.

This was an example where the salesman was comfortable talking with people inside the company, but not very energetic or organized as an outward-facing sales executive.

(If you’re thinking of hiring salespeople, I recommend you read this post about the differences between big and startup companies.)

Another Example: Wrong Role, Wrong Fit

Another example, more obvious, involved a salesman who worked with a boutique investment bank where I worked part-time when I was finding out if I wanted to be an investment banker. (The answer was no. I prefer to work long-term with companies, rather than focusing on making a transaction happen and moving on to the next one.)

The individual was a nice guy, very friendly with all of us inside the small firm. He had met the CEO through their church.

He and I attended a meeting which might have been described as a “target-rich environment”—lots of companies were there that might have been prospects for us.

I networked and chatted with people. He sat and read documents and looked at his phone. I went over to him and encouraged him to meet people. He told me he knew he should, but just couldn’t do it.

He was a nice man, but he knew he should move on and did. In fact, he wound up working for the church, for much less money, but much more comfort.

The Takeaway

Make sure that your salespeople do well facing outward, even if they’re charming and pleasant inside the company. That’s nice, but it doesn’t help you get sales and revenue.

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