EPISODE 088: DLT Sales Head Chris Dewey Shares How He Went from Making 125 Prospecting Calls a Day to Managing a $650 Million Book of Business

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Key lessons from your first few sales jobs: 05:07
Name an impactful sales mentor:
Two biggest challenges you face today as a sales leader: 10:00
Most important tip: 19:53
How do you sharpen your saw and stay fresh: 24:51
Inspiring thought: 26:24

EPISODE 088: DLT Sales Head Chris Dewey Shares How He Went from Making 125 Prospecting Calls a Day to Managing a $650 Million Book of Business

CHRIS’ CLOSING TIP TO EMERGING SALES LEADERS: “Sales can be hard, it can be frustrating, it can be stressful but it can also be very rewarding. Remember to always have a good work-life balance because sales can consume you. Don’t let it happen, just try to have a balance and you’ll be happier and a more successful person.

Chris Dewey is the Senior VP of Sales at DLT.

He’s the longest tenured employee at DLT coming up on 19 years. He worked his way into management early at DLT and started as a team lead managing two people.

Over the years he’s worked his way from team lead to manager to director and now VP. He manages four direct reports, a dozen managers, over 75 sales reps

He is responsible for more than $650 million in revenue.

Find Chris on LinkedIn!

Fred Diamond: Chris, it’s great to be here talking to you today. Why don’t you fill in some of the blanks and tell us a little more about you that we need to know?

Chris Dewey: I appreciate you having me on, thanks. I’ve been in the software or public sector sales game for about 20 years now. Prior to that I was selling a collection service for about 5 years so I’ve only had 2 jobs out of college. I’m currently married to a woman named Lora and have a 5 year old son, Beckham. I really enjoy working out, golf and I actually have a boat that I spend a lot of time on in the weekends during the summer, it’s good stuff.

Fred Diamond:  Very good. I’m excited to hear about DLT, high profiled company, a lot of success. Why don’t you tell us a little bit about what you sell today and tell us a little bit about what excites you about that.

Chris Dewey: As some may know, we don’t make or manufacture the technology. We are an aggregator which means we work closely with both our clients and customers to drive technology adoption to the Public Sector.  DLT provides a service that helps accelerate growth for software companies which is our client, selling into the public sector market space.

Like I mentioned, at the end of the day we provide complete software solutions but more important and what’s really exciting for me is that we get to interact with the software vendor reps, we get to build relationships and we get to help them navigate through the challenges of public sector. We also get to work with our partner community to help win complex deals and we actually make a little money on the side which is also fun. I also really enjoy the interaction with my team and I consider myself a very hands-on leader and I like to win as much business as possible and then it’s also a fun challenge and it’s why I’ve been doing it as long as I have.

Fred Diamond:  Very good. Who are some of the software companies that you help bring to the federal government?

Chris Dewey: Well, my baby if you will is a company called Quest Software that I’ve actually been managing and been involved with since ’99, that was actually what I started doing, I actually started as just a regular sales rep and I was probably one of the only ones, if you will. Then about 7,8 months in we started building up teams and I became a manager or team lead at the time.

The next biggest one is a company called SolarWinds and then recently we just built out a big data platform or a big data team that has Hortonworks, Informatica, Tableau, Elastic. I also have the Autodesk business, I just picked up the Oracle business which is one of our longest tenured clients, if you will. We’ve had them for 25 years and then I also have emerging tech which is a bucket of other technologies in the information management sector, Akamai, AppDynamics, Flexera to name a few.

Fred Diamond:  Very good, some big brands out there that you’re bringing to the marketplace. Tell us a little bit, Chris, about how you first got into sales.

Chris Dewey: I went to school for communications and I learned very fast that I wasn’t going to become the next great news or sports producer even though that’s what I thought I wanted to do when I was at Jacksonville. I went into the communications path and interviewed at ESPN and CNN and a bunch of other places and I learned very fast that it just wasn’t going to be for me. So instead of going to work at a restaurant or something like that I just wanted to jump head first into a career so I picked sales. I actually started working for a collection service selling it to hospitals, doctors, colleges and commercial real estate and I did that for almost 5 years before I got pulled over to DLT.

Fred Diamond:  What are some of the things you learned from that job, being in the collection space that has helped you along the way at DLT?

Chris Dewey: I just jumped in head first and basically I learned you have to work hard and hustle. You hear the cliché out there that, “It’s not a numbers’ game”, it absolutely is a numbers’ game at least for the initial success because honestly, when I first started I had limited training. Literally the first couple days into it they handed me a script and said, “Here’s your script and here’s your list of people to call and by the way, you have to go find X amount of deals” or whatever the quota at the time was.

I just said, “OK, this is what I need to do, this is what I’m going to do well” and the average calls was about 50 calls a day and I was making 125. I also realized that back in ’95 ish to ’98 technology wasn’t like it was today so you had to be organized, you had to use good time management to follow up with your customers and then I’ve just always been a believer about execution, so don’t talk about it, I just went out and did it and I think I excelled at the time. I had a pretty good jump start to my career, I hit all my goals and hit my numbers and I thought I was pretty successful.

Fred Diamond:  You said you were making 125 phone calls a day.

Chris Dewey: Yeah.

Fred Diamond:  Where’d you get those names, out of the phone book?

Chris Dewey: Yeah. In that industry, literally if you’re selling to universities you can just call the universities and just ask for the accounting department or the receivables department. The yellow pages was a big thing back then so I would just go through the yellow pages and just call doctor’s offices and just ask about their debt and see if they needed someone to call into it and then the commercial real estate was our primary focus and we actually had lists that we would call into and we would go to shows and conference and stuff and we would get names of property managers and we would call them and say, “Hey, how much debt do you have that you wrote off?”

Then I would bring those deals in and the then our collectors would collect on that debt and my commission was a percentage of what they collected off the paper that I brought in.

Fred Diamond:  Very good. Tell us a little more about yourself, what specifically are you an expert in? Tell us a little more about your specific area of brilliance.

Chris Dewey: When you first told me about this question, I don’t think that I’m an expert in anything. I would say that in this business especially that I’m constantly learning continuously. I like to think that I’m a really good problem solver. Throughout my years here at DLT I found that you need to be quick on your feet at solving problems and internally for your staff, I’ve always had a good sized staff and then for our end users, for our client vendor reps I rarely ever say no to them so we always find a way to make it work for them.

That’s always been a good challenge for me, I think that I’m very strong in and I would say execution is another thing I feel strong doing. I see a lot of folks out there that talk, have all the strategy in the world but you don’t see any results so I push down results oriented goals to my team and we’ve been very strong with that for as long as I’ve been here.

Fred Diamond:  We mentioned in the beginning that you’ve been with DLT for close to 20 years now, you started off on the phones and eventually became a team lead, became a manager and of course now you’re the senior VP of sales over here. Along the way you’ve probably had some mentors that have helped you move along in your career. Why don’t you tell us about a mentor or two and how they impacted your career?

Chris Dewey: I would say Rick Marcotte who used to be the CEO for many years and who I reported to for most of those years if not all of them here at DLT. One of the biggest things I learned from him was to separate emotion from the business, especially when making decisions, that really helped me. I still work on that today because I can be pretty aggressive at times but I’ve definitely improved over the years and it’s one of the things that I teach the folks that I manage today.

The other piece of it is I mentioned the prior sales jobs so I’ve only had the two jobs out of school and I had a communications degree so I didn’t really have the business acumen so one of the things that he taught me over the years was the business side of it because I always had a natural feel for the sales and the relationship part but didn’t really understand the ins and outs and the P & L and how to run a budget and the financial side of it. That was a huge plus for me in learning from him that I use today to help run business.

Fred Diamond:  We mentioned that you have four direct reports right now plus 75 reps. Do they seek advice from you, people come to you looking for mentoring along the way?

Chris Dewey: Yeah, absolutely. I think that’s one of the things I pride myself on is coaching and training folks and I’ve been doing that for a long time.

Fred Diamond:  Very good. Why don’t you tell us about the two biggest challenges that you face today as a sales leader?

Chris Dewey: One of the biggest challenges that we have is finding the right candidates who are willing to do the work needed to be successful in sales. It’s a huge issue for us, it impacts our sales process in a lot of ways and it also can temporarily impact our relationships with our vendor clients because like I mentioned what DLT does is we represent and we offer service to help accelerate growth with our partners and our clients. If we don’t have the right staff then we can’t provide that service properly so that always puts us behind. It takes time to hire the right people, it takes time to train them, it’s a 3 to 6 month ramp period before they even start producing and that’s just the average. The other piece is getting our sales reps and mastering the phone sales portion of the job which is primarily what we do.

At the end of the day, we’re an inside sales organization representing our clients, the vendors and in some cases I wouldn’t call them cold calls but they aren’t warm and a lot of the times the end user on the side doesn’t really know why we’re calling and they get probably 20 other calls or more throughout the day so we have to figure out how to differentiate ourselves, why we’re calling, what our mission is, what we’re ultimately trying to achieve and to be honest it can take sometimes 3 to 5 calls to get to the right person so it’s a little bit of balancing that on teaching them what to say, how to say it, what to look for, how to navigate the complexities of the government and it’s all about what value are we adding to our clients which is our vendor.

Fred Diamond:  I have a question for you, you service the federal government primarily, correct?

Chris Dewey: Yeah, primarily like 99% of our business if you will is public sector so it’s the federal and state and local universities.

Fred Diamond:  We have a lot of people listening to the Sales Game Changers podcast around the globe who may not be necessarily familiar with selling to the federal government. Could you for a minute or two explain why it might be different and what are some of the challenges that people might face?

Chris Dewey: One of the things that we tell our clients especially commercial based company as they’re trying to break into the federal and state and local marketplace is that it’s almost like selling to an international government. You got to understand certain contracts, there are certain acronyms, there are certain rules and regulations, there’s all kinds of little nuances that come with it and if you don’t understand it, you’re not going to break in and sell into the federal marketplace. State and local is very similar, it’s not as hard but it’s definitely not like selling to commercial and I think that’s why these clients come work with DLT because that’s the value that we offer.

We can help bridge that gap and help them break in and not only that, we can help them be successful.

Fred Diamond:  Is that an additional complexity if you’re a sales professional to have to know some of the uniqueness about this marketplace?

Chris Dewey: It is, but I think one of the things that DLT prides themselves on is the training that we put people through. We hire a lot of folks whether they’re right out of college or they’re coming from the insurance business or selling cars.  We teach them everything about not only sales but we teach them the technology and obviously our clients are helping with that training, but then we also teach them about the government.

We teach them about what contracts mean and what GSA means and what suite means and you name it, we’re walking them through and we don’t really let them on the phone or let them go after stuff until they’re ready. We’re always learning about the federal government, even I do today, there’s always stuff we’re learning. That’s what we pride ourselves on, is training.

Fred Diamond:  For the Sales Game Changers listening to today’s podcast, if you’re looking for a marketplace to serve even with reductions in the size of the government etcetera, it’s still Fortune 1.

Chris Dewey: They’re the #1 consumer of technology in the world, a lot of people don’t realize that and like you mentioned, they are the largest. If they were fortune 100, they would be #1, they would be the largest company in the world. If you’re not in the public sector marketplace, you need to get into it.

Fred Diamond:  Yeah, it’s a great marketplace especially in the DC region. Chris, what’s the #1 specific sale success or win from your career that you’re most proud of? Take us back to that moment.

Chris Dewey: I would have to say because you asked earlier about the vendor clients that we represent and I would have to say and also bring Rick back into this, one of the beauties about working at DLT is you get to run and manage your own business. You really do, so I would say my biggest success is building the current team that I have from the ground up because like I mentioned a few times in this podcast is that I started 19 years ago, I was a sales rep, worked my way quickly into a team lead in the late 2000 time frame, I had two reps right out of the gate.

Five years later I had managers that were reporting to me and I had over 10 reps. You fast forward to about 2015 and we already surpassed 300 million so I would think that would probably be one of my biggest moments that I’m proud of, and then honestly it all started like I mentioned with the Quest Software, they’re still relevant and one of our largest clients today even though they’ve gone through lots of change. I think it’s amazing to look back after all these years and look at the growth that was there for all those years in a row.

We continued to grow the Quest account and brought on other partners, clients like Solarwinds and Akamai we’ve done some really good things and honestly I learned a lot. Met and coached hundreds of sales reps that if you look now I pride myself because I can point to a lot that are those folks that work for me 2, 3, 5 years that are at vendor clients today and they’re very successful working directly for those vendors which is one of those challenges that we have because I mentioned training, I mentioned all the good things that we do and then sometimes a vendor client gets some and takes some because I guess the grass is greener.

No, I think that in itself has been something that I’m very proud of and continue to be proud of.

Fred Diamond:  Did you ever question being in sales? Was there ever a moment where you thought to yourself, “It’s too hard, it’s just not for me”?

Chris Dewey: I honestly question almost every day. It is not for everyone. It’s a career that I chose and it’s what I do and I don’t think there’s ever any time going back especially with the money that can be made but I don’t think it was ever too hard for me but it’s definitely times where this job or just sales in general can be very difficult and sometimes honestly no matter how hard you work, sometimes it just isn’t enough in this business and it could be just a scenario where you kill it one month or one quarter and then the next month you don’t do so well and everyone’s asking a bunch of questions and it’s like, “Wait a minute, what about that quarter or that year that was great?”

I think that’s one of the challenging things, it’s always more, more, more but with that being said, it’s a very challenging career and honestly, if it’s done properly there’s some really good money to be made. It’s also very satisfying when you do have a good month and quarter and just remember if you get into sales that feeling will last for a short time because then you have to go hit the new number and a new set of goals so just always be thinking about the future, don’t just get wrapped up in the moment of that one big deal is what I always tell my folks. It’s always about what’s the new pipeline or what’s the new funnel look like. I think overall I’m obviously very happy with the career I chose.

Fred Diamond:  Chris, what’s the most important thing you want to get across to the junior selling professionals listening to today’s podcast to help them improve their career?

Chris Dewey: A lot of what I’ll say may sound obvious or cliché but I’ll tell you, I’ve managed hundreds of people over 19 years and here’s some advice. One of the things is I would always be the hardest working rep on the floor or on the sale staff. I would always stand out because you never know what can happen and if you’re not top of mind in management and whoever you’re working for, it’s not a good thing. I would get as much training as possible and always learn from someone that has a proven track record.

I would even take the time to maybe get a mentor and then apply and more importantly execute what you learn. Don’t just go to trainings, don’t just do things to check a box is one of the things I always tell my folks because at that point you’re wasting your time and just be prepared. Don’t just get by or wing it and that goes for whether you’re making just a simple one-time phone call or you’re preparing for a meeting. You have to be prepared. It that’s not the attitude that you’re going to have going into it then I wouldn’t even bother getting into sales.

You always need to understand what you’re doing and be prepared meaning that you need to understand your customer, understand what their problems are, you got to go into each call or each appointment or whatever you’re doing but you have to be knowledgeable about what you’re doing. Then out execute, apply everything you’ve learned and know your sales process. I’d be proactive and make it happen, I wouldn’t sit on the side lines and wait because your competition if they’re doing it right would out-sell you.

Fred Diamond:  What are some of the things that you do to sharpen your saw and stay fresh?

Chris Dewey: I always have mentors on the side that I’m always reaching out to whether it be a client, manager or some of that’s been in the industry or consultant. I use a lot of social media, I follow trends, that’s big for me nowadays and should be for a lot of people. More importantly, there’s a lot of “sales experts” out there that have different podcasts just like this or they do other seminars or they write books so I follow a couple of those folks and read some of their books and use some of their methodologies.

In fact, we brought some of those folks in here to train and so that’s probably the key place where I’m doing that. Plus again, you’re leaning from folks that work for you too, then you take best practices from some of the other teams or some of the other management and you apply it across your team.

Fred Diamond:  You have a lot of younger people on your staff in sales, obviously.

Chris Dewey: I would say so. We’ve changed the profile a little bit as it relates to just taking the sales reps right out of college because it doesn’t scale properly like some of our competition out there does, but yeah, I would say for the most part.

Fred Diamond:  I was going to ask what are some of the things that you’re learning. You mentioned you learn from the people in your team, what are some of the things that you’ve learned from some of the people who are new in sales on your team?

Chris Dewey: I think what happens there is if we’re managing properly, we’re listening to their phone calls and we’re assessing what they’re saying and we’re helping them with their business plans and their goals and what happens is they get on the phone and then if you have the right training in place they come to you with saying, “OK, I learned this situation on this call” or “I had this conversation with this customer” or “I had this situation come up” and then what you do is you use that as an exercise to train them and help them.

Then what you find is that you’re now learning new techniques and new ways to go about the sale or like I mentioned earlier, I’m using some of the best practices that I learned around other companies or from our clients or from some of these sales experts that I follow on social media. I’m applying it all together.

Fred Diamond:  Very good. What’s a major initiative you’re working on today to ensure your continued success?

Chris Dewey: At the end of the day, we service our client vendor partners and so it’s very important that we’re always trying to do more with our clients. I always want to go all in with our clients being that we want to add as much value as possible because what we’re trying to do is we want to try to be all things to them in public sector. We want to be the one stop shop so they don’t have to worry about or have their sales reps worry about things and that’s what we’ve prided ourselves on for years.

If you’re a vendor sales rep and you come to DLT, you don’t have to worry about anything. We’ll help you with your contracts, we’ll help you with the quoting, we’ll help you with you follow up, we’ll find leads for you, we’ll do marketing for you, there’s really not much we can’t do so again, it’s really a full service platform of value that we can provide and I think that’s honestly the most important thing, initiative that we always have on your minds is to continue to drive that success with our clients.

Fred Diamond:  Very good. Chris, Sales is hard. People don’t return your calls or your emails. Again, you’re selling to fortune 1 like we talked about but there’s still a lot of challenges. You need to know how to work with them and contracts are a big part and of course there’s external things that sometimes happen. Why have you continued? What is it about sales as a career that has kept you going?

Chris Dewey: Besides the obvious that I can’t now decide I want to be a doctor – that’s why I stay in sales – but I think if you go into sales knowing that it’s hard and it’s a challenge then you can quickly move past that thought process that it is hard and you just eliminate that from your though process because at the end of the day, it’s hard but it’s also funny that you bring it up because when I interview people especially folks that are just breaking into sales I actually oversell how hard the job is. I actually had interviewed [a candidate] just recently and I don’t want people to think they can just come in and sales is easy or all you do is just take people out to dinner and play golf and business is just going to pour in.

It’s not how it happens so I actually convince people that it’s so hard that they really need to think about do they really want to get into sales. Especially if they’ve never had a sales background before so I want future candidates to understand that it’s difficult and you have to apply yourself and work hard to succeed.

Fred Diamond:  Why don’t you give us one final thought to share with the Sales Game Changers listening to today’s podcast around the world?

Chris Dewey: Do you have college listeners?

Fred Diamond:  College? Yeah, possibly. Most of them are first job out of school.

Chris Dewey: If any of those folks are listening, you might want to study real hard and become a doctor, lawyer, some sort of specialty field. No, I’m just kidding. Sales can be hard, it can be frustrating, it can be stressful but it can also be very rewarding. It’s fun at sometimes, it’s very challenging and competitive so if you’re coming from sports or something with that mind frame, it’s very competitive, it’s really fun, you can actually make a really good living and remember to always have a good work-life balance because sales can consume you and I wouldn’t let it, don’t let it happen, just try to have a balance and you’ll be happier and a more successful person.

Transcribed by Mariana Badillo
Produced by Rosario Suarez


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