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

Brian G. Burns  

And what were some of the kind of growth milestones as a rep that you went through that really changed how well you did?

Sean O’Shaughnessey  

Sure. So I can remember the first time I closed a million-dollar deal.

As deals got bigger and bigger and more complicated, back in those days, I was spending a lot of time with managers on bigger deals. The different things like learning how to do the negotiations. The give and take on the negotiations. All those things were things that you learn little by little as you go along. And so you learn that the first part of just being comfortable walking into a customer and spending time and really not having an agenda. Because not every sales call has to be the event. Some sales calls are just relationship building. I’m just gonna have coffee with you. I’m going to have a conversation. I’m going to learn about you as a person. Those are good things to do.

Events are good. Demos and whatever are good. But you need to do both. So that the comfort of being able to do all of those things. Some people gravitate one to the other because of your personal philosophy, but as you get accustomed to negotiations with multiple people. Or how do I play one person against another in the same organization? That’s always a fun job to do as well. Or in other cases, it’s how do I tell them, “This team over here is saying that and another team is saying that. You guys need to talk to each other.” It’s my job to put them together. Because my goal is to affect your decision. By the way, I need that decision by the end of the quarter.

Those are all the things I have to work through. But the whole growth of doing multiple things and getting comfortable with those. And then you find out that my manager is just coming along to give me credibility. But I don’t need him every day. That’s when you start saying, “Okay, now it’s time for me to be a manager and coach other people in the process as well.”

Brian G. Burns  

Yeah, I would go as far as building up like, you know, intangible skills, like reading people. Especially since you sold to both technical people and business people, people are optimistic, pessimistic, tell you what you want to hear, and play you against the other competitors and want a bunch of free stuff. 

Sean O’Shaughnessey  

Also, the whole goal of trying to read an audience is important. So you do a presentation to a group of people. You try to find out who’s getting it, who’s not getting it, who doesn’t care, who was like this, “I’m not gonna ever get close to you.” All of those body signals. When you’re a young salesperson, you may not recognize them, or you may intuitively recognize some of them. But it’s interesting to have a conversation after a meeting with a young salesperson and say, “Okay, what did you think happened? Who’s your enemy in that room? Who didn’t like what you had to say? Who’s going to be your best friend in that room?” Those kinds of things are what you just have to learn. Some of them come just because of who we are as people, and we can understand those things. But the innuendos are tough to do.

Brian G. Burns  

They are, and you know, because I always thought, you know, especially with large complex sales is how to spend your time. And with who to spend your time. Because you don’t have much time.

Sean O’Shaughnessey  

You don’t have much time. Exactly.

Brian G. Burns  

You know, especially you’ve worked with some popular companies where they probably get a lot of false positives. 

Sean O’Shaughnessey  

Absolutely. It’s really tough to say, “Do they like this conversation because of the company I work for?” Because sometimes, my company can get me in a room or into a meeting. Sometimes, just the logo on my card will get me a meeting. Other companies that I’ve worked for are not so well known. But that also leads to a degree of credibility. Sometimes that logo helps you with credibility. Sometimes the logo doesn’t give you any credibility; it’s all gonna come from you. 

The other challenge, of course, in complex sales is the number of levels of you that you have to deal with in a corporation. We alluded to this in dealing with the CIO and the VP. How are you going to do that? But also be able to relate to the guy on the ground that’s actually going to use the product. Because if he says, “No,” the CIO is never going to say, “Yes.” So those guys, the lower down people, they’re the naysayers. You need to be able to relate to them, as well. Understand their environment. What I call “Breathing the same air that they breathe.” What do they do when they’re not working? How do you relate? What’s going on the community that you’re calling on, especially if you have a large territory? Spending a little time understanding that area of the country, or an area of the town. Are they experiencing problems with their schools or whatever?

Be in touch. Never walk into a company where you don’t have an idea of what’s going on in the company. What’s going on in that community around the company, because that’s going to affect that person. The more you can talk about it, the better you are. I travel a lot, as we alluded to earlier in our conversation. I always know what’s going on in the city that I’m going to when I go there. If nothing more, I’m reading it on the plane as I get there. 

Brian G. Burns  

There’s no excuses anymore, either. You can get it on your phone.

Sean O’Shaughnessey  

Exactly. Suppose you haven’t looked at the press releases for the company. In that case, you’re going to see, especially if it’s a Fortune-500-size company, then you better. I mean, they may have made an announcement that morning, you should know that announcement. You might need to know that for the conversation. It may have affected your deal. If nothing else, it’s a credibility issue. “Hey, I see you announced this. How’s that going for you guys?” Or “Why to do that?” Sometimes it’s surprising when I’m telling them about what their company is doing, and they didn’t know. That’s okay, too.

Brian G. Burns  

It becomes a conversation point. It shows your interest and you’re caring— ingredients of trust. And then you can also find out can they afford what you sell? 

Sean O’Shaughnessey  

That’s a massive problem. That’s the gap that I talked about. You might want it, but you don’t have the money to do it because something bad has happened to you.

Brian G. Burns  

And people, how do you do that? It’s like, are they hiring? Are they laying people off? You know, you can see that their funding base, if they’re public, if they’re private, you can tell, you know, how many people do they have? And what kind of revenue did they have? It’s typically out there in some form that you can reverse engineer.

Sean O’Shaughnessey  

Exactly right. But like I said, if you’re walking into a Fortune 500 company, you probably should have read the annual report, maybe not the entire thing. You don’t have to be an investment expert just to make sales calls. But the CEO letter, that’s probably a good thing for you to read. Every salesperson should read the CEO letter; that’s important. I will tell you why? Things that the CEO says in his letter that they’re going to do the next year. Those things are getting funded. They will never not get funded. So if the, if the CEO says, “We’re really worried about security (and I don’t sell security products, let’s just pretend that I did). But, we’re really worried about security because we got hacked last year, and we’re not going to let this happen. I’ve got my reputation on the line.” Well, you better have that in your head. That’s the thing that’s going to get funded. 

And on the flip side. If you don’t sell security products, and that’s all he talks about in the CEO letter, good luck trying to get your deal funded and make it actually happen. And you gotta be really questioning, “Is this really going to happen? Because you get this big thing that you have to do? The CEO says you’re gonna buy another company; you’re gonna do a merger. Is that going to throw off my deal?” Those are things that you just have to pay attention to when you’re making complicated sales. 

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