EPISODE 656: Leadership Insights from IES 2024 Lifetime Achievement Award Winner Dell Technologies Federal Sales Leader Jim Kelly

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Today’s show featured an interview with Jim Kelly, Senior Vice President and General Manager, Federal at Dell Technologies. Jim is the 2024 IES Lifetime Achievement in Sales Award Recipient.

Find Jim on LinkedIn.

JIM’S ADVICE:  “Know your brief. Do the research, understand how each spoke in the tire actually impacts the other. That’s what we do a good job of, I think, at Dell, is understanding how security and zero trust impacts AI, which impacts user experience, which impacts the edge and multi-cloud environments, and then all the way into next generation US telco ecosystems. That is understanding not only what those products and solutions and outcomes are, but how they impact your customer. I’ve probably given the brief about 70 times in the last three or four months to almost every segment of customer, partner and community. It resonates when you know it.  It makes an impact.”


Fred Diamond: Jim, I’m excited to talk to you. You will be the 14th Institute for Excellence in Sales Lifetime Achievement Award recipient. We’re going to be having our award event in May 17th in Northern Virginia. We’re going to be recognizing you for your lifetime achievements, which we’re going to be talking about on today’s podcast. We also have our Women in Sales Leadership Award recipient, Gerilyn Horan from Hilton. We have our entrepreneurial sales leaders, Reggie Aggarwal and Chuck Ghoorah from Cvent. Rebecca Wetherly is the IES partner of the year. Margo Edris from Salesforce is the Jay Nussbaum Rising Sales Star Award. Jay Nussbaum was our second Lifetime Achievement recipient. It’s going to be a great day. We’re going to have a lot of Dell partners there. We’re going to have a lot of people there looking to talk to you and to pay their tribute to you for the tens of thousands of people that you’ve led over the years and the dozens of partners. First off, congratulations on being our 14th Lifetime Achievement recipient.

Jim Kelly: Thank you, Fred. This is an incredible honor. I’m excited not only for the ability to accept the award, but also for the entire panel of people that will be recognized in May. Unbelievable list of folks, unbelievable list of past award winners, and I’m just honored to be a part of it.

Fred Diamond: We’re excited. Of course, one of your good friends, Joe Ayers, was our Lifetime Achievement recipient last year, 2023, and he’ll be at the event to participate in the festivities. Give us a little bit of an introduction to your career. You’ve done some amazing things, and then we’re going to get deep into getting your understanding of what sales leaders should be doing right now and how sales professionals can take their careers to the next level.

Jim Kelly: I actually started in the early ‘90s, dating myself a little bit here, but early ‘90s started at a small reseller, which is one of the few birthplaces of a lot of the IT professionals that sit around. It’s called BTG. Had no IT experience and zero experience working with the federal government. I remember calling my grandfather, who was one of the first systems administrators at MetLife in New York City, and said, “Hey, I just got this job selling IT. I don’t know anything about it. Any advice?” He said, “Just learn. Everything they know will be obsolete in six months.” I think that is continuing throughout my career, the advice that I live by.

I was at BTG for a number of years, left and went to Dell in 1999. Spent 14 years at Dell. Then spent a couple years at Microsoft and then came back to Dell a little over eight years ago. Mostly started in the US Army business and defense side of the house, growing the last three years into the entire federal portfolio, including all the federal systems integrators in that community as well.

Fred Diamond: We’re close to 700 shows. I’ve interviewed tons of leaders of the sales organizations for public sector. You just said that you devoted pretty much two decades of your career to servicing public sector. You’re so highly regarded in that customer base, which is one of the reasons why the Institute for Excellence in Sales is recognizing you. Why public sector? Why have you devoted a good portion of your career to serving that? Give us a little bit of an insight for the people listening who may not understand what public sector does, why you devoted your career to serving that marketplace.

Jim Kelly: It’s really around the commitment to the mission. The more you understand how your actions impact the security and the operations of our country, it really does hit home. It just makes you feel like you’re a part of something greater. I always say it is our goal to serve those that serve. That’s the commitment that we have across the federal organization. Usually, people get into the federal marketplace and they don’t leave. It’s a rarity that they transfer out of fed or public sector because you have that commitment to the admission in its entirety, and you know what you’re doing is making an impact on human lives.

Fred Diamond: A lot of people ask me for career advice, obviously in sales, and I’ll say, “You want to be the guy or lady who’s selling a big brand to a big customer.” The example I always use is, “You want to be the Dell guy who sells to the Navy.” I like the way you talked about the mission there. We’ve had people on the show who’ve been almost in the same job. They’ve career progressed, but they’ve been serving the same customer, in some cases for decades. What a lot of people don’t realize when they go into sales is they may go from place to place. You mentioned that you went to Microsoft for a little bit, came back to Dell. Customers don’t want to leave. If they’re in IT at a government agency, maybe they’ll jump if it’s a promotion kind of a thing, but people don’t move from government to financial services, to hospitality, to healthcare. They want to have, especially in IT and IT related services, a relatively stable, almost like a risk-free type of career.

Jim Kelly: I couldn’t agree more. Obviously, you and I lived through the dotcom buildup and burst. I think a lot of my friends and colleagues that I grew up with in the industry, a lot of them took a shot at some of those small startups in the dotcom era. I kept saying, “Hey, look, I know my customer. I know how important the work that we do is to that particular customer. I also know that that customer is going to be around for a long period of time. If we do our jobs, we do it right, we’re open and we’re transparent about what we’re doing, and we provide that level of responsiveness that they desire and that sense of urgency that they expect from the same sense of urgency they have within their own missions, that we’re going to be rewarded.” I think that’s something that I’ve really taken throughout my entire career. There is no other segment I would ever want to support. I think our federal customer, it’s the greatest customer in the world, and it’s an honor to serve them in any capacity.

Fred Diamond: I worked for Apple Computer in its public sector division in the beginning of my career. I went on a sales call with a legendary sales leader at Apple, and he said, “I want you to come with me.” We got in the car, we drove into Downtown Washington DC, the District of Columbia. He parked his car in this neighborhood where there were dozens of ubiquitous government buildings. He said, “Take a look around here.” For people listening, the highest a building can be in DC, with the exception of the Washington Monument, it is nine stories, correct? Then he said, “Look at all these buildings. They’re not going to tear these buildings down.” He said, “This marketplace will be here forever. If you can understand what their mission is, you’ll have a great career in sales and sales leadership.”

Let’s talk about sales organizations right now. Again, you lead the business, but you also have a lot of sales leaders reporting into you. What are the biggest issues right now? Again, we’re doing today’s interview in February of 2024. What are the biggest issues facing sales organizations today?

Jim Kelly: Honestly, it’s the advent of AI. I think AI is going to have an impact on all organizations globally, the likes of which we’ve never seen. We’re excited and fearful of the impacts on the business. There’s a lot of uncertainty around it. You’ve got to quell those fears, but the possibility of increasing productivity by 20% plus across every single job category in an organization. Michael Dell always says last time he was this excited was in 1995 when the internet came on. He thinks this is an even bigger inflection point from technology perspective, but it’s impact on sales is going to be far reaching.

You’re going to have instant access to content, the likes of which you had never had in the past. Unprecedented access to historical pricing, and contracts, and regulatory guidance. Those things that sometimes it took days, weeks, months to access is now going to be at your fingertips in milliseconds and it’s going to have reference points to how you can move forward. We’re really excited about it. I know Microsoft likes to say with the Copilot being released, that it’s kind of banishing the busy work. I couldn’t agree more. I think it’s going to add a lot of time back into your day to hopefully focus and learn more about the customer’s mission, but it’s also going to give you accurate points to go chase business inside of your customer segments in a more meaningful way.

I joke, one of the folks that works for me, we were on a call with government relations back in November and they were walking us through what the continuing resolution was going to look like. Obviously, this is pre where we are today. At the same time, as we’re on the call, he typed into his Copilot, “What’s going on with the CR?” That was it. It spit out, “This is what a continuing resolution is. This is what’s on front of Congress right now. It’s a ladder step. First agency is January 19th, second agency is February 2nd. Here are the agencies that will be impacted.” Literally, he said he beat the government relation folks to the punch by getting the information accessed extremely fast and right at his fingertips. I think it’s going to be a big change to the way we do business.

Fred Diamond: That’s a great example of using AI to get ahead of the curve. It’s interesting, even when you started, you mentioned in the late ‘90s, salespeople were walking brochures. I remember when I was at Apple and Compaq, we would do daylong strategy sessions with our five-year plans. Like you just said, a customer can now type in, “What is Dell,” or, “What is Apple’s five-year plan?” Within seconds it’ll shoot from somewhere. That being said then, we’ve heard a lot about how the government customer, not just government, but any IT customer, any customer in anything for that matter, whatever it is we’re buying, has a lot more information at their fingertips. What does the government customer then demand from sales professionals? What does the customer expect from your team to deliver to them knowing that all this access to information is available to them?

Jim Kelly: First, they demand that we understand their mission and their priorities before we step into the room. I always say it’s important to know your brief, but it’s even more important to know your brief in the context of your customer. Why do they care about what it is you’re selling? If you don’t have the ability to tie that to their mission objectives or priorities, then you’re doing yourself and your customer a disservice. That’s number one, is you got to know your customer’s priorities and their mission objectives.

The second one is this is no longer the days of when you and I grew up in sales where you sold on speeds and feeds and feature sets. It’s all about outcome-based selling. How are you working with your customer to deliver an outcome that’s going to make their organization function more effectively or efficiently, or deliver some type of mission objective that is critical to the success of their organization? I think outcome-based selling is the new solution selling, and then knowing your customer and knowing your customer’s mission is the only way you can truly do outcome-based selling.

Fred Diamond: Let’s talk about what the best sales reps are doing right now. Again, you represent Dell into the public sector. Dell, it’s a top five technology player. What are the best reps doing? Let’s talk about two. Let’s talk about the sales rep who’s been in it for 20 years, who’s risen up. Maybe they’re still an individual contributor because that’s what they want to do. Maybe they’re managing a team or a territory, whatever it might be. Then I also want to get your insights into what the junior people, people who are maybe their first job out of college or second job out of school. Let’s talk right now, what are the best, for lack of a better word, senior sales professionals doing right now to be successful? Then what are the people who are brand new who want to achieve in their career doing?

Jim Kelly: The senior folks, the ones that truly succeed, have the ability to leverage the entire organization, what we call the matrix, inside of Dell. You’ve got to be able to get every single person that’s assigned or touching your account in any capacity to understand what your plan is, have a robust account plan with actions, everybody contributing and getting them moving forward. I always like to use the analogy of the boat. We need everybody in the boat knowing exactly where we’re going. Everybody’s got to have an ordinary hand, and they need to be rowed. We can’t have any passengers. We just don’t have enough capacity to cover every single customer inside of this environment. We need to make sure everybody’s functioning and working together.

That’s what the best salespeople do. They leverage the entire team. They make sure that they’re on message, everybody’s agreeing with the plan going forward, and then they all have their action items and they report back. It’s that constant iteration of updating the plan, focused on the plan, and getting everybody working together to achieve the desired results. That’s the big one.

On the young in career, by the way, I’ve never seen such a great young, diverse talent pool that’s hitting the market like we’re seeing right now. For the most part, they’re digitally native. They’re coming in with a different expectation around utilizing tools. They’re highly motivated and driven. They usually have extremely high intellectual horsepower. It’s really exciting about them coming in. But you got to keep them engaged. I always say there’s three major pitfalls from people, kind of going from inside sales to outside sales or young in career.

The first one is maturity. Being able to prioritize and manage their time effectively. This is the first time they’ve been on the road a lot. First time they’ve actually been out of the office four or five days a week. Managing your time is extremely important. Managing your expenses is a pitfall that all these young career people get into. That is a challenge. The second one is demand on their resources. Once again, they’re coming in extremely competitive, motivated, driven. They’re usually the best of the best inside of their inside sales, if they got promoted into outside sales. Unfortunately, they expect the same level from the people supporting them, and it can be a little disheartening. They need to take a leadership path in that. Even if you’re just leading a team, you need to understand that you’re as responsible for the development of all the team members as their leaders are. I think that the folks that have embraced that and move forward are the most successful.

Then the last one, and this is the biggest pitfall in my eyes, because it goes back to point one on what do the really good salespeople do? It’s they think that they have to prove themselves that they deserve the job they got. Therefore, they feel their fingerprints have to be on every single action. They have to make sure that their name is associated with every win. Unfortunately, that is counter to what the great successful salespeople do in the business. They’re good at delegating, they’re good at empowering individuals on the team to go out and sell. It’s a counter piece. I always say, hey, you really do need to take a step back, understand your team, the strengths and weaknesses on the team, and make sure that you got the right people focused on the right problem sets, so that you can, once again, achieve those desired results.

Fred Diamond: When you’re selling complex and enterprise technology, you’re not just selling it to a person. It’s not just one call, as you know. Especially the customers that you’re selling to who have 2, 5, 10-year plans, and the investment they’re making in your solutions, it’s so large and it’s so intent. Your team, the sales team, it’s not a hero sport. It’s a team sport. You’re on the grid iron. Someone that you and I have in common, Gary Newgard, when he was on the Sales Game Changers Podcast, he said, “Selling to the public sector market is the NFL of professional sales.” Every company is in it. It’s the biggest marketplace in the world.

If someone was let’s say a senior in college and thinking about moving into professional sales at a company like Dell, what might be some of the things that you would advise them? You just gave some great advice for junior people, but what might you tell them to do right away to be successful in their sales career?

Jim Kelly: In all honesty, I think the training programs throughout the industry are unparalleled to any time that I grew up in sales. They kind of threw us on the phone and said, “Hey, go do it.” Now, some of these are 16, 18, 24-month sales training programs that get them acclimated to the business sector, acclimated to the products that they’re selling, but also getting them to understand how your customers acquire IT. There’s 20 plus different routes to market to get to a lot of these customer segments, so really digging in. I would tell them, go research companies that have good solid training programs, because getting your feet wet in that environment is extremely important.

You and I have a good friend, Craig Abbott. His sales training program is fantastic. Dell has a great one. We’ve got Next Generation Sales Academy where we pull people directly out of college and put them in a training program for six months, and then we put them on the phones for another 12, and then they get attached to an account. Then after two years, they hit the ground as an AE. But they have a roadmap, they have timelines, they have goals that they have to achieve every step of the way, but more importantly, it is immersive. You are involved in the customer. You’re involved with account teams. Usually, you’re assigned mentors early on in the career set so that you can gain some level of understanding of where you can be most effective. In my opinion, that is the single biggest opportunity for a young person in career to grab hold of sales and get embedded quickly. Otherwise, you’re going to have to cut your teeth doing inside sales or other activities before you get to the outside. But I think the training programs are key.

Fred Diamond: Again, the IES, the Institute for Excellence in Sales, we have our Premier Sales Employer designation and our Premier Women in Sales Employer designation, where we recognize companies that have programs like that. Jim, we have time for one more question before I ask you for your final action step. A lot of people want to know this, Jim, after I do a podcast with somebody, they want me to ask, what is their guiding principles? Again, it’s interesting, we’re recognizing you with the Lifetime Achievement Award. I have a feeling you’re probably going to have another 10, 15 years in your career.

Jim Kelly: I hope.

Fred Diamond: Just as a joke. A lot of our first-time recipients retired after they won. I’m sure some people have communicated that to you, but I’m sure you’ll be sticking around. You got a lot of a lifetime to go. Talk about some of your guiding principles. What are some of the things that you’ve done that you’ve held onto? We talked about as a sales leader, understanding the mission, et cetera. But you, Jim Kelly, as a person, as a leader, what are some of the things that you hold onto? I’ll be honest with you, when we announced that you’re going to be a Lifetime Achievement recipient, I didn’t really know you all that well. We had some mutual friends. Of course, I knew of you because of your role in the industry, but the feedback that I’ve gotten from the people in the industry who have either worked for you, worked with you as a partner. I even talked to some customers who have been connected to me. Just the response has been, “You picked the right guy. We’re excited to recognize JK,” they call you, I guess. Tell me about some of your guiding principles. What is it about Jim Kelly that has gotten him to this point?

Jim Kelly: I’m always challenging myself to get better. I don’t think anybody’s ever at the top of their game. Going back to my grandfather’s comment, constantly and consistently learning and understanding the impacts we can make on our customer. But for me, what excites me is the people part. Developing people inside of the organizations, helping them see what the next steps are in their career, getting them there. There’s a lot of people, a laundry list, Joe Harris, for example, that spent a lot of time, and Steve Harris, spent a lot of time getting me to where I am today. I tell my teams all the time, there’s nobody that is more responsible for your career than you, so you better be prepared to do this. You better make sure that when the opportunity arises, you have the ability to articulate why you are important, and why you deserve the role that you’re going to get. I think it’s really important.

I’ll tell you a quick story just on that preparation piece. When I got the job that I got, my boss’s boss at the time called and said, “Hey, Jim, your boss is leaving. Do you have interest?” I said, “Absolutely.” I was at a baseball game, my son was still playing high school baseball. I stepped out and said, “Yes, I’m interested.” He said, “Great. You’re interviewing tomorrow morning with Michael Dell and Jeff Clarke,” and all these executives inside of the company. I said, “Fantastic. I’ll be ready.”

I had just left and gotten my second COVID vaccine. I woke up the next morning with 103 fever. I was delirious. I don’t even remember two of the interviews at all, including the one with Michael. I have no recollection of it, because I was probably hallucinating at the time. Afterwards, one of the executives called me and congratulated me on getting the job. I told him that story, and he said, “You were a little red-faced and I thought it was nerves.” I said, “No, it was definitely a fever.” He said, “But you articulated your plan so effectively that that just further proves that you were prepared for the role, that you had gone through this in your head a thousand times prior to getting the opportunity. When the time arose, you were ready to take advantage of it.” I think that’s an important piece, is take control of your career and make sure that you’re an effective leader. I believe culture is king in a lot of space and breeding a winning culture is very difficult to do without turning it to a negative. I think that’s the balance that I’ve been able to really set inside of the company and just about any team that I’ve ever led.

Fred Diamond: I got to ask you one last question before I ask you for your final action step, final bit of advice. Whenever I’ve interviewed people from Microsoft, they say the first question they always get is, “Have you met Bill Gates?” You just alluded to the fact, obviously, you spent time with Michael Dell. If you don’t mind, what’s it like to be in a room with a guy like Michael Dell? Michael Dell, for people who don’t know, created the direct to consumer, direct to business marketplace with PCs from his college dorm in University of Texas, I believe it was. Just FYI, he’s also built some amazing community centers in Austin that have served hundreds of thousands of people. I actually had the chance to meet him once. I mentioned before I worked at Compaq. He’s my age and he has such a presence about him. If you don’t mind, what’s it like being in the room, spending time with one of the luminaries in the history of technology, Michael Dell?

Jim Kelly: Bottom line, it never gets old. It never loses the luster. He has that rockstar type of persona. It’s really built around his intelligence and his understanding of the market. But I would tell you, as much as he’s a technologist, financially, he may be even more brilliant in that regard. He’s a personable guy. I always joke, I’ve had multiple three, four-star generals literally shaking and nervous to meet him, which shocks me all the time when we go into that because he is really down to earth. Just a dynamic speaker on trends and new technologies that are arriving in the marketplace.

I’ll tell you, it never gets old. I do get a lot of time with Michael. Michael’s father was in the Army. That’s how he ended up really at University of Texas, because his father was stationed down at Fort Hood. He has a special place in his heart for the federal government. He supports our customer on a very regular basis. We have him in DC and in front of customers as often as we can. He is open and honest and transparent about trends in technology that he’s seeing currently and in the future that he thinks will impact human lives. I think that’s what Dell’s been built on, and the culture that he built is something that I absolutely not just recognize, but try to emulate.

Fred Diamond: It’s quite a great story, Dell’s success in the government and how impactful Dell Technologies have been to the citizens from a safety perspective, from a pure service perspective, and how a lot of the infrastructure of the company is built on Dell technology. Once again, Jim Kelly, you’re going to be the 2024 14th annual IES Lifetime Achievement Award recipient on May 17th. Give us one final thought. You’ve given us so many great ideas, Jim, on what sales professionals can and should be doing to be successful right now with any customer, not just in public sector, at the senior level and mid-level, and how they can manage their careers. Give us a final action step, something they can do or should do right now to take their sales career to the next level.

Jim Kelly: I would just reiterate the early point, you’ve got to know your brief. Do the research, understand how each spoke in the tire actually impacts the other. That’s what we do a good job of, I think, at Dell, is understanding how security and zero trust impacts AI, which impacts user experience, which impacts the edge and multi-cloud environments, and then all the way into next generation US telco ecosystems. That is understanding not only what those products and solutions and outcomes are, but how they impact your customer. That’s the key. I think if you do that, you do it right. I can tell you, I’ve probably given the brief about 70 times in the last three or four months to almost every segment of customer, partner and community. It resonates when you know it. I can tell you, it makes an impact.

Transcribed by Mariana Badillo

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