This is a story about an underdog.

It's about a sales guy whose resume barely made it through to the interview round. He made it through to the second round based on one thing he did in his past. And then I hired him based on how he answered one question. The odds were against him. Maybe 100-1. Maybe 1000-1. Today, he works for our company.

It's worst to first.

I have hired hundreds of salespeople in my career. I used to run a sales group with a headcount of 164. I've probably interviewed thousands. I used to follow a fairly prescriptive hiring formula. I had my questions to get through and the "right" answers to listen for. I hired some rock stars and some duds.

Over time, I relaxed quite a bit. I went more on feel. I think I just became better at reading people. Hiring became more art than science.

So, after closing a recent round of funding for my current startup, I set out to hire some sales people. I posted to various boards and proceeded to roll tap my fingers on the desk anticipating the deluge. And they came.

I only had time for about 10 interviews so I set out to pull what looked like my top 10 resumes. The first 5 or so tend to be pretty straight. Yes, yes, for sure, YES, and definitely. The bottom third are pretty easy too. No, no, definitely not, no, nope. It's 7 through 14 that are difficult to parse. They're all pretty similar at that point. So, it's usually just a thing or two. How they phrase something, a good social profile, or a misspelled word. I finally settled on my top 10. But, Number 11 kept popping up. There was something about him that rattled me.

College athlete. Good experience. No job hopping. Modest achievements, but he just came across as solid. Worth a try, I finally concluded. As I interviewed my way through the list, I finally made it to Number 11.

Something he said to me just stuck. At a previous company, he elected to make a somewhat lateral move from customer service to sales. The company had little to no sales training. He knew he needed to learn the craft. So, he trained himself.

"You did what?" I asked.

"Well, I went out and found a Miller Heiman sales training program. I couldn't afford it. So, I met someone in the class, asked them to get an extra set of materials, and studied it and practiced on my own." he said. "Eventually, I drilled it enough that it became my sales system. I even taught it to some of the other guys."


OK, Number 11 gets a call back. That story alone is worth a second interview. I want to see how this plays out.

As part of the second round, I'll go to lunch or something social with my top 3. This time it was 4. At some point, I like to review compensation. I won't make an offer. I just want to make sure we're in the ballpark. I also want to see how these prospective sales folks handle a discussion about money.

Many sales people take this as an opportunity to show their negotiating chops. It's a jousting match. It's a poker-faced compensation tango dance. An early battle for the upper hand. I get it. They think if they display good negotiating skills in this opening volley, I'll entrust them to do the same once they're carrying my card.

One through three acted as expected. Almost on cue.

"Well, I have a few other things going on and I was hoping for a little more. Do you think there's any room there?"

Box checked.

Then Number 4. I explained the comp plan as a mix of salary plus bonus. I explained the upside. I explained how I needed a hunter.

Number 4 looked down at his notes. Silent. Contemplative. Breathless. I waited, determined not to save him. He lifted his head and looked to me. A more confident and deliberate move, I have rarely witnessed. He looked me straight in the eyes.

"Matt, if you offer me this job, and agree to pay me that package, you will never regret it. I will be successful. I will do whatever it takes. This company is my number one choice. I want to work for you and you alone. I will not let you down. And, that's my best shot. I want this opportunity."

Number 11 to Number 4.

Number 1.