Brian G. Burns Interviews Sean O’Shaughnessey On How To Win Large Enterprise Deals

Brian G. Burns  

What do you like about sales?

Sean O’Shaughnessey  

I like to solve customer problems. I’m a big believer that as salespeople, our goal is to influence the decision-making process of our prospects. And help them make that decision on our timeframe and make the right decision, in our opinion. I do that primarily by just hanging out with a customer. Trying to understand what their goals are. How they’re missing their goals? How they’re not achieving what they want to achieve? And then trying to figure out how my products are going to help them get there. If we can’t do that, then I move on.

If the customer is trying to accomplish something, how can I help them accomplish it? It is much more of a solution sales process. It’s a very common thing to say “solution,” but I want to know how I solve their problem. I talk a lot about the business benefits.

I’m also very quick to say I can’t help you, but maybe Joe down the street can. Then I’ll reference a friend or a buddy that sells something else if I can help them. I don’t try to force-fit anything. Customers are too precious to force-fit something bad.

Brian G. Burns  

And do you feel growing up with a parent and a family that was kind of sales-oriented helped you?

Sean O’Shaughnessey  

Absolutely! Absolutely! When I was a young boy, I used to sell fruits and vegetables off the table in the fruit market at the farmers market. My dad said, “You should never be in anything but sales. Unfortunately, you’re really good at math, so go be an engineer, but you’re really a salesperson.”

I got a lot of encouragement growing up. I saw the ups and downs of sales. I’d remember, my dad wouldn’t sell something. He sold heavy construction equipment. I remember him not selling something for a couple of months, especially during the winter. And him having to deal with that budget problem that happens when you’re doing that. He was primarily commission pay only. So that was a really tough life that he dealt with, but he did really well as a career. He had a long career. He was very, very successful. It gave me that comfort that I can do this, and I can be a successful salesperson.

Very few people in the enterprise IT sales industry are commission-only, but there’s still the ups-and-downs. There are those times where orders aren’t coming in. And then at the end of the Q4, in our business, you gotta get it done.

Brian G. Burns  

Yeah, I mean, you know, I’m commission only now. But, you know, I certainly remember the roller coaster, because it’s not only the pressure you put on yourself but also the pressure the company puts on. 

Sean O’Shaughnessey  

Exactly.

Brian G. Burns  

And trying to manage that, not get too excited when things are going well. Exactly. Have a go to your head and not get too desperate when things aren’t going well.

Sean O’Shaughnessey  

And the other thing is to do things that you know are still going to be farther out so that you really can deaden the ups-and-downs of that. As an enterprise IT salesperson, you have to really think ahead and be proactive in worrying about that deal I am going to be closing in six months because my sales cycle can be six to 12 months for many of my products. Especially now in the products that I sell, it’s definitely six months plus.

If I’m not thinking about what’s going to happen six months from today, then I’m going to be in trouble. Now I’ll be honest; nobody ever anticipated COVID screwing things up. Screwing up all the buying decision cycles that I was going to have right now, but you have to be as proactive as possible when you’re in sales. Especially with long lead time products where I’m going to have to sell to a dozen or 25 people. In order for all of them to say, “Yes,” to get a customer to buy.

What I sell, one person is not making a decision, 25 people are making the decision. I’ve got to touch them all. I’m always going to be thinking ahead about that deal that I’m going to close in six months. That’s very, very important. It’s one of the things that I really pushed on my salespeople today is trying to be as proactive as possible. Take the long road. Get to know them. Those deals will happen. That way, you don’t have the ups-and-downs too much.

Brian G. Burns  

I was also raised by two salespeople. And I think what I learned through that process is to think like other people think because they’d always kind of flip things to explain to me what the other person is viewing this.

Sean O’Shaughnessey  

Exactly, exactly. That’s the benefit of trying to think about, “What are their goals? What are the goals they are trying to achieve?” So, I’m an old guy. I’ve been around for a long time. Miller-Heiman strategic selling was the first thing that I learned from back when I was a young man. Before, I had all this gray hair.

One of the things that they taught back then, so something I learned early on was, you sell by trying to figure out what the gap is between where you want to be and where you are. Mr. Customer, “Where do you want to be, and where are you now?” If that’s a small gap, then we are probably not going to spend a lot of time on it. But if it’s a big gap, that’s one that we will spend time on. That’s also ‘Getting to know their customer’s business.’ Understanding how do they make money? How did they lose money? I think that’s actually critical in a larger enterprise sale. How companies actually lose money or how they don’t succeed is a really good thing to know. Your understanding of your customer’s business is critical. Try to figure out how to help them achieve those goals and minimize those gaps is really important.

There is more to read. Go to the following pages to read:
Introduction
Why does Sean like the sales profession?
The transition from salesperson to sales manager
Growth milestones
Rep radar and Always Be Learning