Join the elite Institute for Excellence in Sales!

Subscribe to the Podcast now on Apple Podcasts!

EPISODE 152: DLT Sales Leader Chris Wilkinson Says Taking This Approach to Your Sales Career is Critical for Your Success

CHRIS’ FINAL TIP TO EMERGING SALES LEADERS: “Every day is a chance for a new beginning – embrace that opportunity. Focus on what you can control, influence what you can influence and smile otherwise.”

Chris Wilkinson is the Senior Vice President of Sales at DLT. DLT is an IES Premier Sales Employer.

Prior to coming to DLT, he held sales leadership positions at immixGroup and DHL.

Find Chris on LinkedIn!

Fred Diamond: Why don’t you tell us a something about you that we need to know?

Chris Wilkinson: Thanks, Fred. One of the things I’d like to communicate in the Game Changers podcast today is really around ownership and accountability. I very much view salespeople as a business owner, sales clearly being one of the most important pieces of building a business. Again, I feel like I’ve been privileged to have some tremendous opportunities in my career and some exposure to some tremendous training. I really appreciate being here today.

Fred Diamond: Tell us a little bit about DLT. Tell us what you sell today and tell us what excites you about that.

Chris Wilkinson: We sell a suite of services that accelerate public sector growth for technology companies, and as a solutions aggregator we represent best of breed technologies to three major customers. It’s typically our technology vendors, our value added resellers and solutions providers and then ultimately our joint government customers. A couple of things that really excite me about playing this role in the channel is one, the exposure you’re getting to emerging new technologies and staying ahead of the curve. We’re constantly being introduced to new capabilities that enable our customers to more effectively accomplish their missions.

Then I would say the second piece of it is more dealing with our customers, because we support three different constituents. We represent such a broad spectrum in technology, it’s very rare where we’re involved in a conversation where we can’t find a way to provide our customer some sort of value.

Fred Diamond: Tell us some of the technology vendors that you offer, just to give our listeners listening around the globe a little bit of context.

Chris Wilkinson: We’ve aligned our sales, our marketing and our chief technology office around six technology domains that really align well to the way our customers buy technology, and they typically align well to the way our vendors and our partners are coming to market. Some of our major providers are the Oracles of the world, the AWS’s of the world, the Red Hats of the world and then we’ve got some emerging new capabilities around big data and analytics in the HortonWorks (Cloudera), the cloud area relationships. From a cyber-security perspective, it’s everything from the McAfee’s, the Symantec’s, all the way through to some of the CrowdDtrikes and other emerging capabilities.

Fred Diamond: I want to go back to something you said in the introduction. You said “ownership and accountability.” Talk about that for a little more before we get into some details on the podcast.

Chris Wilkinson: I think as a sales rep you’re so responsible for driving and developing net new business that if you think about your role within that sale cycle as a business owner ensuring the success of both your organization and your customer, I think it makes the perseverance required to be a sales rep much more palatable.

Fred Diamond: What does that mean, what does that look like? We have Sales Game Changers listening around the globe. What should I be thinking about? I love the idea that you’re talking about here and we’ve had that concept numerous times on the Sales Game Changers podcast that at the end of the day, you’re working for yourself. You have to establish your business and you want to be the VP of Chris Wilkinson Industries, if you will and now you’re providing great service to DLT. What does that logistically look like to the people listening on the call today?

Chris Wilkinson: It’s a good question. I would say that it really involves you positioning yourself in such a way that you are interested in ensuring that you’re creating or maximizing the profitability of the business that you’re supporting for your vendor, for your entity that you’re working for. You’re also ensuring that your customer is successful with the implementation of whatever solution that you’re providing to them, striking that balance of profitability ensuring you’re doing the right thing for the business and being fair to your customer to ensure that you’re giving them the right solution to enable their success.

Fred Diamond: How did you first get into sales as a career?

Chris Wilkinson: It’s an interesting story. I studied psychology in college and I had a great psychology professor that pulled me aside after a couple of classes and asked me what I wanted to do after college. He then went into a bit of the economic realities of graduating after a 4 year degree in psychology and suggested that I might want to look at something like sales. I almost immediately transitioned my field of study and my major to business administration and a minor in economics, because I was really looking forward to getting out of college and launching myself into a career really beginning to build my own personal brand.

Fred Diamond: Was DHL the first place you went after college or did you do some other jobs before that?

Chris Wilkinson: Actually, I worked for an entrepreneurship at DMG Securities, I wanted to be a stock broker and that didn’t work out for a number of reasons. I interviewed at a couple of places, I ended up landing at DHL which turned out to be a blessing in disguise. It was a really tough job and it was a challenging sales environment but it was very rewarding and had a tremendous training program that I think I didn’t necessarily appreciate at the time compared to how powerful it really was. It really launched the foundation of my career.

Fred Diamond: Just curiously, in retrospect what were some of those things that you learned there that you’ve employed over the course of your career?

Chris Wilkinson: It was early introduction to authentic selling, being yourself, following a process. It was a very rigid sales process to qualify a prospective customer and then frankly, just getting you out of your comfort zone introducing you to cold conversations on a daily basis.

Fred Diamond: Are you comfortable with that? You’re in a business where you have a whole bunch of inside sales people and they have to make phone calls. How did you get past that?

Chris Wilkinson: I think if you don’t feel the butterflies before your first few calls of the day, I don’t know that you’re doing it right. I played sports and no matter how long I played both in high school and in college, every game you had butterflies. As a sales rep I feel like if you’re not approaching those calls with those same sort of nerves and butterflies in your first few calls, you’re probably not as invested in it as you need to be to be successful.

Fred Diamond: When you have those butterflies and you’re concerned that you may not be ready to go, what are some of the things that you’ve instructed some of the young sales professionals over the years to get past those butterflies?

Chris Wilkinson: Just be themselves and just have a conversation. I think more often than not, as a sales rep you’re inclined to talk more and tell people what you know. I think you really need to focus on listening to your customer, don’t be afraid of silence, let the customer fill the gap, you’d be surprised at what they tell you sometimes when you’re on those first few sales calls and you’re feeling those butterflies. I think you have a tendency as a sales rep to want to fill that silence and limit that discomfort, when if you just give your customer some time to put some thoughts together and speak, you might be surprised at what you learn.

Fred Diamond: That’s very powerful. Let’s talk a little more about you, what are you specifically an expert in? Tell us a little more about your specific area of brilliance.

Chris Wilkinson: I don’t know that I really view myself as an expert, I do know that I’m willing to work very hard. I have found that it seems that I’ve got a skill set to be able to translate complex technological concepts into simplified concepts or into stories that you can tell. To train resources to be able to bridge the gaps between the technical resources within our customer bases that are really performing the services or providing a solution, bridging the gap with the mission owners and the business owners, helping them to communicate more effectively to leverage technologies to ultimately enhance or solve or perform their mission.

Fred Diamond: You’re leading sales here at DLT, again DLT provides solutions working with technology vendors, value added resellers to serve the government customer. You must have had some great mentors along the way, why don’t you tell us about an impactful sales career mentor and how they impacted your career?

Chris Wilkinson: To be honest, Fred, there’s been a lot of folks that have impacted my career at different stages of my development even in different specific skill sets. If you don’t mind, a couple that come to mind, Art Richer here, our CEO at DLT certainly taught me the power in natural charisma, really helped me to hone authentic leadership skills and also really taught me the power of having a thorough business plan to ensure that you’re executing effectively.

Steve Limbert was one of my first managers out of the gate, I’ve got to give him some credit back at ImmixGroup for putting up with me, helping me understand the power of professionalism both internal and external to the office. He also taught me some soft skills, the fact that your soldiers need to eat first and you need to really be about your team enabling them to be successful.

Bill Rucker is another name that has really helped me in different stages of my career, particularly as it relates to exposure to different sales techniques or even different perspectives that you bring to an everyday conversation. I find myself thinking back to a lot of the lessons that he’s taught me as I’ve gone through sales environments.

David Stewart really helped me with consistent sales operations and the need for the consistency in the way that you actually operationally manage your business to be effective, and then lastly I would probably want to give a shout out to Amy Kelly. I think she did a tremendous job at teaching me that having a very powerful peer relationship that could function as a sounding board really enables you to bring new ideas to market much more effectively.

Fred Diamond: Those are some great mentors. The Institute for Excellence in Sales, one of the sponsors of the podcast each year gives out a Lifetime Achievement Award to a high achieving sales leader and Art Richer was the recipient in 2016. Those are some very talented people. Before I ask you about the two biggest challenges you face, I want to go back to the concept of authentic selling. It’s come up a couple of times, you mentioned that Art even helped you understand that, or authentic leadership. Can sales professionals make the shift? And they have to at some point, because you’re right, at the beginning you want to give features, benefits, you have scripts, you don’t want to hear dead silence so you’re trying to do all those things that we just talked about. Does it happen one day, all of a sudden you’re authentic or does it happen over time? Do you remember when you made that shift?

Chris Wilkinson: It happens over time. I don’t know that I can point to a specific instance where a lightbulb went off, I almost wish I could. The reality is as you’re getting exposure in any sales environment, you’re going to be taught Sandler, you’re going to be introduced to a number of different sales concepts that in and of themselves are really tremendously effective at helping you to bring products to market to enhance your own skill sets. I think you need to look at bringing those together with your own personality in order to be effective. It’s very easy when I work with junior sales reps to see them using the same philosophy, the same technique repetitiously.

It’s easy to poke holes at that philosophy and I haven’t seen that to be as successful as leveraging different pieces of each of those different methodologies that are more natural to you, authentic to you. I think over time you start to find a way to be yourself yet employ these different techniques to help you be effective at one, qualifying your prospect, overcoming objectives and morphing to their different personality and their skill set as well. Your customer brings a very critical component to the sales equation in their personality and the way that they need to come to a solution or a conclusion throughout that process. I feel like if you’re forcing methodology onto them and it’s not connecting, you’re not going to be successful. It’s really about bringing those different techniques together with your own personality and your natural charisma.

Fred Diamond: What are the two biggest challenges you face today as a sales leader?

Chris Wilkinson: If I had to limit it to two, I would say time management as it relates to prioritization. Fortunately or unfortunately, there’s no shortage of opportunity in our organization right now but I think in sales in general. It’s very difficult to make sure that you are spending your time in the areas that are going to offer the greatest return on investment for you and for the company in a lot of cases.

I would say the second challenge that I’m having right now that’s very top of mind is staffing resources, particularly leadership resources with the right skill sets, with the right capabilities in the right seats to perform the mission that we’re bringing to market right now. We’re going through some tremendous growth here and we’ve got a number of new opportunities that we need to fill. The reality is there are some folks out there that have been trained at interview very well, it’s almost like you’re getting a different person the first day that they show up on the job sometimes. That’s a challenge that I think that everyone faces pretty regularly, but right now those would be the two that probably jump top to mind.

Fred Diamond: Tell us about your #1 specific sales success or win from your career you’re most proud of, take us back to that moment.

Chris Wilkinson: The guidance is probably debatable, but I’ve enjoyed the career. I’d say it’s a little bit difficult. In our role as a solutions aggregator in the market space there’s a couple of different types of sales. Clearly, it’s exciting for us whenever we’re able to bring our suite of services to bear to a qualified prospect to bring them into our programs. Signing some big name accounts over my past 13 or 14 years or so in the space like Adobe, BMC, Tenable, some of those big companies have been very exciting. Progressing AWS to distribution here at DLT, very exciting.

Then there’s the other side of our business where we work very closely with the demand generators, the demand creators of our technology vendors and our partner ecosystem. There’s been a couple notable wins that come to mind over my career, one would be winning a 5 year IDIQ with a strategic vendor and partner of ours a few years back, winning a 5 years SEWP EWA after our partner at that time had been challenged to do so for at least 6 years in advance, that was a pretty exciting moment for us. I’d say probably the one that stands out the most from that side of our sales success would be winning my first 8-figure deal, those are pretty special deals and that one will always hold a special place.

Fred Diamond: Before we get to a quick message from one of our sponsors, again we’re talking to Chris Wilkinson, Senior VP of Sales at DLT. Chris, did you ever question being in sales? I really like the stuff we’re talking about here as it relates to authentic selling, authentic leadership, ownership and accountability, but sales is hard. Especially to have gotten to the level where you are and the marketplace that you’re competing in is extremely competitive, it’s very difficult. One thing we didn’t talk about is the challenges facing your customer, your government customer. Did you ever question being in sales? Did you ever say to yourself, “It’s too hard, it’s really just not for me”?

Chris Wilkinson: Very early on selling DHL, absolutely, I’d say probably within the first 6 months of that job. If it weren’t for qualifying for advanced basic training that they had and really learning different ways to approach my customer, there were times where I questioned whether it was the right career move for me. It was a challenging environment, so I’d say yes, absolutely, I did experience some time where I wondered if sales was the right thing for me. I think I’m pretty fortunate to have overcome that challenge early on in the career, not to say that you won’t face that challenge again at any point in time, but without a doubt the first 6 months selling DHL was a very difficult time.

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

Chris Wilkinson: Hard work ethic is very big with me. I would want to make sure that I talk about the value and just working hard, and outperforming your peers to naturally accelerate within an organization. Be naturally curious, human nature is to be curious and at some point it seems as we go through sales training we begin to lose that and we want to talk and tell as opposed to listen more than we talk. I mean that both with your customers and also with your peers. Be a sponge on both sides of it, from a customer perspective certainly understand what it is they’re really trying to accomplish and help them be successful, and then from a peer perspective you’re always exposed to opportunities to continue to learn as you’re engaging with peers and with mentors.

I’m a big subscriber to the “as one more question philosophy.” When you’re uncomfortable and you think you’ve asked all the question you can ask, push yourself to ask one more question. We’ve talked about it throughout the podcast today, but be authentic, that’s another piece that I think is critical. If you don’t believe in what you’re selling, if you’re not passionate about what you’re selling and if you’re not being yourself, it’s probably going to be difficult to be successful.

Fred Diamond: What do you do when you see sales reps who don’t have the passion that you have?

Chris Wilkinson: There are certain things that you can do to try and train because I think sometimes to get the passion out of them, they need to believe that they can be successful. If you can help them through techniques to find their first few successes, I’ve seen that passion will naturally present itself. In other cases, to be honest with you, we’ve helped some sales folks by demonstrating that this might not be the right field for them. I like to joke that I’m a simple guy so I think in simple terms. If you put me in scrubs, I’m just not going to be a doctor and the same can be true for some sales folks.

Fred Diamond: What are some of the habits that you historically have put into play to ensure your success?

Chris Wilkinson: I learned very early on one of the habits that’s been very powerful for me is not being afraid of silence. Again, I mentioned a couple of minutes ago in the podcast here that it is human nature to fill the silence in a natural conversation. When you’re selling, you’re even more eager to fill that silence because it becomes even more uncomfortable, I’m very mindful to not fear that silence. One of the other things that I’ve embraced early on is sales is a number’s game and we have the ability in sales to measure key performance metrics certainly around effort and certainly around results as well. I learned very early on that I was going to work harder than the person next to me and I was not going to allow them to beat me in the metrics that measured effort. I may not always win in result, but I wasn’t going to be beaten in effort and if I was, you were going to have to work really hard to do that. I think that was very powerful early on in my career, especially when I think I was closing deals in brute force more than finesse.

Fred Diamond: Tell us about a major initiative you’re working on today to ensure your continued success.

Chris Wilkinson: Personally, it’s a commitment to ongoing education and self-improvement, a big initiative for me. Then I’d say professionally it’s a mental commitment to innovation and constantly evaluating what could we be doing new in our business to provide more value to our customers.

Fred Diamond: Again, we’ve talked about the fact that you’re in a very challenging marketplace, we talked about some of the challenges of finding great sales leaders, and sales is hard. To be at the highest level of sales especially in the marketplace that you’re competing in, people don’t return your phone calls, there’s a mackerel of things. The marketplace that you worked for shut down at one point in the not too distant past, if you will, but why have you continued in sales? What is it about sales as a career that has kept you going?

Chris Wilkinson: I’ve eluded to it earlier, I see myself as a business owner and I’m driven to build the best business that we can possibly build for myself, for the people around me and ultimately for my customers as well. I think that feeling of ownership and accountability makes it easier to be persistent and makes it easier to not get to high with the highs and not get too low with the lows. I’d say that’s probably a big piece of it.

Fred Diamond: That’s a pretty big message there, the whole concept of business ownership and a lot of the stuff we’ve talked about today. I think you really do need to believe in what you’re selling, you need to believe in the mission of your customer. We haven’t really talked about that too much, but to hit the highest level of sales, you really need to have that. I love the concept, the through line that we’ve had on today’s podcast is authentic leadership and how you as a sales professional listening to the podcast can be as authentic as possible. Chris Wilkinson, you’ve given us some great insights today, you’ve given us a lot of great ideas, I want to thank you for being on the podcast. We have Sales Game Changers listening around the globe to this podcast, why don’t you give us one final thought to inspire them today?

Chris Wilkinson: A cliché comes to mind immediately: every day is a chance for a new beginning. I would say embrace that opportunity, focus on what you can control, influence what you can influence and smile otherwise. I’d say find something that you can believe in and that you can be passionate about, believe in yourself. Embrace development opportunities, they really are all around you. The other thing is be proactive, it’s so easy in any career to be reactive to just the day to day things that are thrown at you in business. Making time to be proactive is critical to be successful in sales.

Fred Diamond: Mental commitment to innovation. Good for you, very good stuff.

Transcribed by Mariana Badillo
Produced by Rosario Suarez

The post EPISODE 152: DLT Sales Leader Chris Wilkinson Says Taking This Approach to Your Sales Career is Critical for Your Success first appeared on Sales Game Changers Podcast.

Subscribe to the Podcast now on Apple Podcasts!

KEY MOMENTS
Key lessons from your first few sales jobs: 05:07
Name an impactful sales mentor: 08:33
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

The post 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 first appeared on Sales Game Changers Podcast.