EPISODE 006: Paul Keefe Talks About How to Treat Your Sales Career As a True Professional to Get Ahead

EPISODE 006, Paul Keefe Talks About How to Treat Your Sales Career As a True Professional to Get Ahead

Paul Keefe is currently the director of sales for Dataprise, a Maryland-based IT managed-services provider, where he is reshaping the sales organization. He has been in sales for 35 years, mostly in the telecommunications industry.  Paul spent 10 years in Boston as general manager for XO Communications, where he established and managed XO’s Massachusetts operation, building it into a $60 million business, leading the sales, marketing, customer service, finance, operations, and engineering efforts. He also spent time at XO’s headquarters running client services and sales operations.

Find Paul on LinkedIn!

Here’s a transcript of the podcast:

006, Dataprise’s Paul Keefe

Fred Diamond: Today I’m very excited to be talking to Paul Keefe. Paul is currently the director of sales for Dataprise, a Maryland-based IT managed-services provider, where he is reshaping the sales organization. He’s been in sales for 35 years, mostly in the telecom industry. Paul spent 10 years in Boston as general manager for XO communications, where he established and managed XO’s Massachusetts operation, building it into a $60 million business, leading the sales, marketing, customer service, finance, operations, and engineering efforts. Paul also spent time at XO’s headquarters running client services and sales operations. Paul Keefe, let’s change the game. Fill in the blanks and tell us a little more about you that we need to know.

Paul Keefe: Thanks, Fred. And by the way, this is a great opportunity. I’m really excited to be here and speaking with you about a subject that I frankly love, selling. So I am a Boston guy. I’m an avid Boston sports fan, and that’s been a pretty good thing in the past few years. I live in Ashburn, Virginia. I actually moved from Boston to Ashburn eight years ago for a job opportunity. I’ve got four kids. I’ve got one grandchild, and my wife and I, our big hobby right now is mountain climbing. Earlier this year we tackled Mount Rainier, and next Memorial Day weekend we are going back to Washington to climb Mount Adams. So we’re pretty psyched about that.

Fred Diamond: Hopefully we’ll talk today about some of the mountains you climbed in your sales career and some of the things you’ve overcome to achieve the success that you’ve had as a sales game changer. So let’s get started. Let’s spend the first part of the podcast talking about your career. How’d you get into sales as a career?

Paul Keefe: I got into sales because my dad was a salesman. My older brother was a salesman. I’m the middle of three boys. My younger brother’s a salesperson. It just felt like it was in our DNA. I’ll tell you a funny story. I was talking to my mom about what I do, and I mentioned to her that cloud computing is a big part of what we do. My mom’s 90 years old. She goes, “What’s the cloud?” and I said, “Well, the cloud is like, instead of buying a bunch of computers and installing them in your office, you use a sort of shared environment, where you’re using someone else’s computers and you’re just paying for time on them.” She goes, “Oh yeah, that’s like time-sharing back in the 1970s. Your dad, that’s what he sold, time-sharing.” So I think it’s in the DNA.

Fred Diamond: Tell us a little bit about Dataprise and what you guys do. What exactly do you sell today, and what excites you about that?

Paul Keefe: Dataprise is a managed IT services provider. Simply put, we sometimes end up being the outsourced IT operation for our customers. What really excites me about it is, number one, Dataprise is really good at this, and number two, it’s a growth market. That is really exciting. There’s tremendous opportunity here. About four years ago, I was talking to a former channel partner of mine. This guy used to be a CIO for a major retailer in New York City, and we were talking about outsourcing IT, help desk, that kind of thing. He said, “Paul, when I ran IT for this major retailer, it was a constant battle, finding good people, keeping good people because they’re in such demand.” He ended up overpaying people to do menial stuff that’s important, like resetting passwords or helping people with applications. “That stuff is important, but it wasn’t the stuff that was helping me build my business, make my business more competitive. I always wanted to be able to say, Use my people and the resources to make my business stronger, and that’s the value of outsourcing.” And that’s kind of what we do. Our CEO, David Eisner, wrote a book called Why You Should Build Your Business Not Your IT Department, and essentially when we’re out in front of a customer that’s what we’re talking about. We are taking on the things that are important, that our customers have to do, and we are freeing them up to use their talent and their tools and their budget to help build their businesses, to make their businesses more competitive.

Fred Diamond: You mentioned at the beginning part of your career you were in telecommunications.

Paul Keefe: Yes.

Fred Diamond: And now you’ve shifted over to managed IT. How have you seen the difference in what you did for the first two decades or so in sales of your career and what you’re now selling a service such as this?

Paul Keefe: The basics are still the same. The how you do it is maybe a little bit different now. There are a few more different techniques and tools. But at the end of the day it’s about keeping your funnel full of opportunities so that you never have that situation where you’ve closed the big deal, you’ve had three months of success, and now all of a sudden you’ve got an empty funnel. The tools are different now that the approach is different, but in principle it’s still the same. You’ve got to maintain that rich, deep funnel.

Fred Diamond: So, let’s go to the beginning of your career. Tell us one of the first jobs that you had and maybe something you learned from those first sales jobs.

Paul Keefe: I think about this every day when I’m talking to salespeople. I think about the first lesson I learned from my first sales manager, when I worked at the New England Envelope Company, very low-tech. He told me, “Paul, you’re like a doctor. Don’t go in and offer the cure before you see what ails the patient.” That’s a phrase I repeat very frequently with my reps when I find that they’re just not doing enough discovery, not trying to get to dominant buying motive, they’re just showing up and spitting out the value prop when they don’t even know whether or not it’s going to resonate with the customer.

Fred Diamond: With a lot of the young people we deal with who are new in sales, their expectation of a sale closing is dramatically different from what a lot of the sales leaders that we’d spoken to had had to deal with in the course of their career. Some of them think, “Okay, well, a customer opened my email. I’m halfway there” or “I got an appointment. I’m halfway there.”

Paul Keefe: Right. We really try to focus here at Dataprise at getting to what is called the dominant mind motive because that’s a real powerful motivator. It’s not about my features and their benefits. It’s really about what does it mean to your customer that we are able to handle IT help-desk issues that crop up on the weekend that used to consume our customer’s time when he was trying to go to ballgames or at a tournament somewhere or trying to just have dinner with his wife. These are very powerful things, and we really try to uncover them and appeal to them when we’re making that final pitch.

Fred Diamond: You mentioned your first sales manager. Take us back and talk to us about a mentor—maybe it’s him, maybe it’s someone else—and the impact they had on your career.  

Paul Keefe: So, it wasn’t the first sales manager. It ended up being the second sales manager who was my mentor and still best friend to this day, best man at my wedding. I was probably five years into my selling career, and I thought about giving it up because I wasn’t successful, or I was sometimes successful and sometimes not, and when I look back on it I was what you would call unconsciously incompetent. In other words, I didn’t know why I wasn’t succeeding. If I had a successful sale, I didn’t know why I won it. My manager, and now best friend, convinced me that “what you need to really focus on this: You need to train yourself. Selling is a profession. It’s not just something you show up and do. It’s a profession, and you need to work on it.” He recommended that I enroll in a Dale Carnegie sales training class, and I said, “Great. Will the company pay for it?” I was working for Wang Laboratories at that time. You see, I graduated from the envelopes to Wang Laboratories.

But I said “Great. Will Wang pay for this?” and he looked at me and he said, “This is the important thing.” He looked at me and said, ”No.” He said, “This is an investment you need to make.” This is also something that I share with every sales rep who ever worked for me. It’s an investment. This is a profession, and you need to invest in it and don’t look for me to come and train you. I’ll do whatever I can to help you, but at the end of the day this is something that you need to commit to and invest in.

Fred Diamond:  The message that you just said is one that comes up all the time, as well as the notion that sales is a profession. And a lot of people, they do their practicing on sales calls. Well, if you’re going to be a professional athlete or a professional musician you’ll have spent thousands, if not tens of thousands, of hours working on your skill and getting better. One message I’ve heard from guys like you as we’ve been launching the Sales Game Changers Podcast is that is you need to invest in yourself. You need to treat it as “What can you do to get better at this profession that you’ve chosen.”

Paul Keefe: We do a lot of training. I’m a big proponent of training, and the funny thing is I’m a big proponent of basics. A couple of months ago we went through a training session on‘how to conduct a scoping call. Now, for Dataprise, “scoping call” is a term we use for lan early qualification call or meeting where you bring a technical resource out. You go through the customer’s IT environment. You’re really discovering what the opportunity might be. You’re trying to find that dominant buying motive. It’s all very basic stuff, and the stuff that we cover is really very simple stuff. And I always tee up this training by saying, “What happens every year in the February, March timeframe?  What happens in Major League Baseball? The greatest players in the world go south and what do they do? What do they practice? They practice hitting and fielding.” So I’m a big proponent of the basics. I’m a big proponent of going back to the basics on a regular basis, and I think that’s the only way you ensure that your bad habits aren’t creeping in.

Fred Diamond:  Paul, take us back to a specific sales success or win from your career that you’re most proud of.  

Paul Keefe: The one that I’m most proud of, or the one that I will be most proud of, is my next sale.

Fred Diamond: Okay.

Paul Keefe: The one we’re going to make tomorrow. There have been a lot of sales over the years. If I could look at a body of work and say, This is what I’m most proud of, it’s really building that market for XO Communications, employee number one, building it and running it for 10 years and getting it up to $60 million at its high mark. I kind of jokingly said, “My next sale is the one that I’m going to be most proud of,” and I really mean that. I’m really excited about the sales call that I’m going on tomorrow, and I’m really looking forward to closing that one because that’s the sweetest one.

Fred Diamond: You’ve alluded to this before. Did you ever question being in sales? Was there ever a moment where you seriously thought to yourself, “It’s just too hard. It’s not for me”?

Paul Keefe: I was at a point in time where I was questioning “Is this for me? Is sales for me?” I thought, “Yeah, I should have been a lawyer.” And I’m so glad that I didn’t become a lawyer. I am so glad that I had the mentorship of the guy who’s now my best friend and he kind of steered me in the right direction.

Fred Diamond: Before taking a break, you’ve mentioned the mentor, your best friend. Do you want to give out a shout-out to him, tell us who he is that you’re referring to?

Paul Keefe: Yes, Scot Wilks up in West Newbury, Massachusetts, working for the past 22 years for BI Performance Systems.

Fred Diamond: Paul, let’s talk a little bit now about some advice you would give to sales professionals on their way up or sales professionals who want to take their career to the next level. What’s the most important thing you want to get across to junior sales professionals to help them take their career to the next level?

Paul Keefe: So, Fred, I said it earlier; it’s fill your funnel. Let me expand on that. Manage the entire funnel, not just the bottom of the funnel when the deals are ready to close. There was a point in my time early on when I was a sales manager and I was having meetings with salespeople, and I still to this day have one-on-ones with every one of my salespeople on a very regular basis, weekly here at Dataprise. Sometimes with larger teams it’s harder to do. But the thing that I always hated was the meeting where a sales rep will come in, and you say, “Johnny, your results over the last 90 days aren’t where I need them to be. I have to put you on a performance plan.” And what the sales rep was hearing was, “Wow, I’ve got 60 days to find a job because HR is making them put me on a 60-day performance plan.” I always felt like a failure at that point. I always felt like the performance plan was the horse out of the barn. It’s late for the performance plan… It’s like, “John, based on your history, your rolling 12 months of sales data, everything that I know about you is that you need to be finding 12 opportunities each month to fill your funnel because your average sale that you’re booking is $20,000. Your quota is $60,000. You have to make three sales to make your quota, and I know you’ve got a 25% closing ratio right now. So every month you need to be finding 12 good opportunities, qualified opportunities, and putting them in your funnel because we know historically that you’re going to close 25% of them to make your quota.” So the discussion that you need to have with the salesperson is, “John, we’re halfway through the month, and I’m seeing you’ve only created two opportunities. Let’s put a plan in place right now where I can help you find more opportunities, devote more time. Let’s dig into it. Is it the sale you made that’s bogging you down, preventing you from doing all of your prospecting that you need to do? Let’s get to the bottom.” That’s the kind of conversation that we need to have as sales leaders with the people who work for us.

Fred Diamond: I like what you just said about when you put a rep on plan, the first thing that they probably think is “I got to find another job.”

Paul Keefe: Yeah, yeah.

Fred Diamond: What are some of the things that you’re doing today to sharpen your saw and to keep Paul Keefe staying fresh?

Paul Keefe: Earlier I said that the basics remain the same but there are certain tools, techniques, and strategies that are different, and as a sales leader, that’s what I try to keep up on. So I get emails and phone calls every single day from people and companies trying to sell to sales managers to make them more efficient, more successful, and I take every single one of them. I take it upon myself to do that kind of discovery to find out what’s out there, what are the best practices that are out there, and you can really find out a lot of that by taking these calls and talking to these companies that have these tools. I take them all. The other thing I do is I routinely reach out to people who are in positions of sales leadership, people I don’t know, and I say, “I’m looking to network in terms of sales and what’s working for you. I’ll share with you what’s working for me.” Just kind of create this little network of people where we share ideas and practices and strategies.

Fred Diamond: What’s a major initiative you’re working on today to ensure your continued success as a sales game changer?

Paul Keefe: I have data on every single one of my salespeople that I can pinpoint for each one of my reps, and I can tell you what levels of activities they need to do, what they need to do today in order to be successful six months from now. I can tell you their closing ratios, their average sales. They’re all different, and I try to manage and work with each one to those levels. That can get kind of tedious if it’s all numbers, so I like to keep it fun. I like to run contests, and right now I’m running a contest. I’m going to apologize for the name—this is the reason I’m not in marketing—but I’m running the Fall Funnel Filler and it’s all around rewarding the behaviors that lead up to filling a funnel. I’m looking to build my funnel for Q1 next year, so I don’t want to let off the accelerator in September through December, as often happens. I want to build a strong funnel. We’ve designed a program that will reward the different things that we do to prospect calls, emails, qualifying prospects, making presentations, making sales, and like a special kicker for high bigger revenue earn more points. What I do is I’m creating a point system, and you earn points for all this stuff. I like to introduce a raffle aspect into every contest that I run, and the reason I’ve always done that is a lot of sales contests I’ve been involved in, somebody wins, like, in the first week. So I’m running a three-and-a-half-month contest.

Fred Diamond: What is one final thought you can share to inspire our listeners today?

Paul Keefe: You’ve got to have a vision. Sometimes it could be very personal. Every year I will sit down with each one of my reps, and I don’t ask them to share their vision because sometimes they are personal, but it’s sort of the baseline of “Look, why are you showing up for work? What are you here for?” And I’ll share mine from 30 years ago. Mine was I want to earn enough money so that my wife could stay home with our newborn baby and be a stay-at-home mom for the first five or six years. I had a card with that goal written out. I had my baby’s picture on the card, and I kept it in my briefcase. It was with me every morning when I got up. It was like, This is what I’m doing this for. Every time I got that hang-up, rejection, door slammed in my face, it was like, “Yeah, but this is what I’m doing this for.”


1 thought on “EPISODE 006: Paul Keefe Talks About How to Treat Your Sales Career As a True Professional to Get Ahead”

  1. Excellent interview with a great sales leader, Paul Keefe. Working on Paul’s Boston XO team was a privilege. Keep on rockin’ Paul!

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