In one line
Calvin Dennis, a Business Performance Advisor at Insperity, spent 19.5 years as an "intentional individual contributor" in the same role before breaking into the top 1% of nearly 600 sellers, closing a 703 worksite-employee year against a 300 benchmark (about 2.3x Chairman's Club) on three drivers: belief, curiosity, and patience.
Who is Calvin Dennis?
Calvin Dennis is a Business Performance Advisor at Insperity, a long-time Chairman's Club performer who recently broke into the top 1% of nearly 600 sellers. He has 19+ years in the same sales role plus 10 years earlier as an Insperity customer, a rare long-term perspective. Insperity's service is HR, payroll, benefits, and regulatory support for small and medium businesses (roughly 5 to 150 employees), and Calvin sells it to owner-operators (plumbers, architects, physician practices, custom cabinetmakers). Before Insperity he sold airline tickets by phone in college, then ran his own travel agency and call center for years before the business failed in the dot-com era. Based in Fort Worth, Texas, he has attended the last several Sales Success Summits in Austin. He describes his top drivers as belief in what he sells, relentless curiosity paired with "control issues" over the sales process, and patience he now frames as compound interest.
Key questions answered
What are Calvin Dennis's top three drivers of sales success? Per Calvin Dennis (Insperity), on Sales Success Stories, three things carried him: (1) belief, a genuine conviction that Insperity's service improves the success equation of small and medium businesses, which sustained him while learning to sell a conceptual, non-tangible product; (2) curiosity and "control issues", refusing to stay in his own swim lane so any topic important to a prospect or client becomes important to him, while ignoring anything irrelevant to the sale; and (3) patience, which he has lately started calling compound interest, since some 2025 sales closed from conversations two and three years earlier. 0:01:21
How did Calvin Dennis get to the top 1% at Insperity? Per Dennis, the mark of distinction at Insperity is Chairman's Club, which requires selling at least 12 accounts totaling 300 employees in a year (roughly 312 unique sales). He has made Chairman's Club nine or ten times. Last year he sold about 703 worksite employees against that 300 benchmark, roughly 2.2 to 2.3x, in an organization with nearly 600 sellers, which pushed him from the top 2% into the top 1%. 0:06:56
What is Calvin Dennis's favorite sales story? Per Dennis, an attorney referral connected him to three brothers whose family business had acquired a brand that came with a roughly 75-person telephone sales force of stay-at-home moms; a required employment change risked a revolt that could have put the company at risk. Rather than sell tactics, Calvin brewed a pot of coffee and wrote "the FAQ document to end all FAQ documents", answering every objection those 75 employees might raise. The client, Ron, called the next day: "Calvin, you did it." He credits creativity and getting into the mindset of not just the owner but all 75 people. 0:15:06
What is Calvin Dennis's prospecting approach? Per Dennis, he rarely makes a truly cold call, calling his method a "spider web": he almost always knows something about a prospect first (a shared connection, a same-industry client, having seen the business), which in his mind makes nearly every outreach a warm call. His goal is not to sell Insperity but to get a dialogue, often opening with "I don't know if you need Insperity or not, I just think you need to hear what we're doing for people." He calls it "making new friends" and puts prospecting blocks on his calendar rather than scripting which channel he uses each day. 0:23:30
What sales philosophy does Calvin Dennis follow? Per Dennis, his answer is Jeffrey Gitomer, whose "Little Red Book of Selling" (modeled on Harvey Penick's Little Red Book of Golf) taught him to give value first without expectation of return, and that if you do, the return comes anyway. He says his best moments are the feel-good ones where he tells a prospect who is not a fit exactly what to go fix in their business, for free. 0:33:23
How does Calvin Dennis think about motivation? Per Dennis, "action precedes motivation." He does not believe a boss, a comp plan, or even you can reliably motivate you up front. Instead you just start: get the activity going, get the flywheel turning, and the motivation shows up once you see yourself near the top of the leaderboard. His closing challenge to listeners is to take the motivational poster off the cube and put your head down for two or three weeks until the flywheel starts. 0:35:16
Why does Calvin Dennis stay an individual contributor instead of moving into leadership? Per Dennis, he is an "intentional individual contributor", a term he credits Scott Ingram with, and he warns newer reps not to drift onto default autopilot into sales leadership. A unit or district manager's livelihood depends on what six or eight other people do daily, which is a tough road if it is not your skill set. Staying put also compounds relationships: he closed a deal five years after the first conversation, and the payroll specialist who once ran his account as a customer is now a vice president of field operations he can still call to solve a client's problem. 0:53:22
Frameworks & concepts
- Intentional individual contributor: a deliberate long-term choice to build a career as a top IC rather than defaulting into sales management, a term Calvin credits to Scott Ingram; he has held the same Insperity role 19.5 years.
- Patience as compound interest: staying in one seat long enough that sales close from relationships seeded years earlier; several of his 2025 deals traced to conversations two and three years prior, and one client returned four years after leaving.
- The spider web (warm-not-cold prospecting): rarely cold-calling because he almost always knows something about the prospect first, a shared connection, a same-industry client, or having seen the business, which reframes the outreach as a warm call.
- Make new friends / get a dialogue: instead of trying to sell Insperity, aim only to get the prospect to take a look and have a conversation, which "lets you off the hook for the results" and lowers resistance.
- Action precedes motivation: motivation is unreliable up front, so start the activity first; once the flywheel is turning it is easier to keep turning, and the motivation follows.
- Own your career / category of one: your company gives you a job, only you can give yourself a career; be a "category of one" by continually developing yourself, and read a business book rather than only sales books so you resonate with clients.
- "How was trip?": a filter for whose advice to take, taught to new reps in Insperity's "sales performance improvement" group; if the person advising you cannot enthusiastically answer that they earned the Chairman's Club trip, be careful about taking their advice.
Notable claims
- Per Calvin Dennis, last year he sold about 703 worksite employees against Insperity's 300 Chairman's Club benchmark, roughly 2.2 to 2.3x, moving from the top 2% into the top 1% of nearly 600 sellers. 0:06:56
- Chairman's Club requires selling at least 12 accounts totaling 300 employees in a year, which works out to roughly 312 unique sales; Calvin has qualified nine or ten times and earned the lower TRIP tier three or four times. 0:06:56
- He has held the same Business Performance Advisor role at Insperity for 19.5 years, and was an Insperity customer for about 10 years before that. 0:03:52
- In his favorite sale, a single FAQ document he wrote won over a roughly 75-person sales force whose revolt could have put the client's business at risk. 0:15:06
- His self-image / expectations "bracket" rose year over year rather than in one leap; he says it should not have taken him 19 years to reach the top 1%, and advises listeners to dream bigger sooner. 0:43:08
Companies, tools & books mentioned
Companies & organizations: Insperity, Sales Success Summit, Sales Success Society, Microsoft.
Tools: Salesforce, Outlook, Microsoft Teams, LinkedIn, ZoomInfo, 6sense, WebEx, Zoom.
Books & authors: The Little Red Book of Selling by Jeffrey Gitomer; Harvey Penick's Little Red Book (of golf), cited as its model; Mike Weinberg (prospecting philosophy, per the show notes).
Connect with Calvin Dennis: LinkedIn.
Quotes
"I've lately started calling it not just patience, but compound interest." — Calvin Dennis 0:01:21
"You looked up one day and you have 28 employees. Can I be honest? You're terrible at that. Why not let us help you with that so you can worry more about building cabinets?" — Calvin Dennis 0:05:34
"It's not really a cold call if I know something about you." — Calvin Dennis 0:23:30
"Action precedes motivation. Forget all the big charts and goals on the wall. If you'll just start, is my experience." — Calvin Dennis 0:35:16
"Your company can give you a job, but only you can give yourself a career." — Calvin Dennis 0:38:58
"If we would worry less about the things to say and the things to do and worry more about being the kind of person that our prospects and clients need us to be, then we would more naturally do all the right things anyway." — Calvin Dennis 0:41:50
"Take down the motivational poster off your cube and just get to work." — Calvin Dennis 1:01:47
0:00 Scott Ingram: This episode is brought to you thanks to the generous support of Nooks. Nooks is the agent workspace for intelligent outbound. For more, just go to nooks.ai.
0:17 Scott Ingram: You're listening to the Sales Success Stories podcast, where we deconstruct world-class sales performers to provide insights and strategies to help you improve. To learn more, visit us at top1.fm. Here's your host, Scott. Ingram.
0:33 Scott Ingram: Today on the Sales Success Stories podcast, my guest is Calvin Dennis. After many years as a top Chairman's Club level performer at Insperity, as a business performance advisor, he finally broke into the top 1% so we could do this interview, as has long been prophesied. Welcome to the show, Calvin.
0:51 Calvin Dennis: Hey, thanks. It's been a long time coming. I'm certainly glad to be here.
0:55 Scott Ingram: Yeah, I think this is the first time I've ever done one of these interviews where my guest is actively in their hotel at What is it called, Calvin?
1:05 Calvin Dennis: Pinnacle Summit, right? Chairman's Club trip.
1:07 Scott Ingram: Yeah. Thank you for making the time. So excited that we got to come together to do this. And as you know, I always like to start with that immediate value. So let's talk about the top 3 things that you believe have contributed the most to your success in sales.
1:21 Calvin Dennis: Thanks for the opportunity. It's a real blessing to be here. And I've listened to basically every one of your podcasts, and I hope these 3 are relevant and meaningful to everybody. But number one is belief. I, it may sound sappy or emotional, but I really believe that our service improves the success equation of small and medium-sized business. I think that what we do matters. I think we help people. There's great value there. And that has really seen me through some of the hard times when you gotta learn how to sell this product that's conceptual. It's not like selling a telephone where it's a piece of equipment, right? It's a, it's not an easy thing to sell, but belief has been important in that. We can talk about that later. Number 2, call this 2 or 3 different things, right? One way to call it is I don't stay in my own swim lane very well. We sell a relatively complex service because it's all about employment and the stuff that you have to do when you have employees and keep them happy. And they're humans too. And sometimes things don't work out. And we've got lots of experts in lots of ways, right, that I can engage and do when I need to. But if a topic is important to my prospects or clients, I feel like it should also be important to me. I'm curious about all the things that they experience. I was one of them for a while. We can talk about that as a business owner for a while. So I internalize that. Now, the other flip side of that coin is that I can also completely ignore stuff that's irrelevant to the sales process, whether it's a prospect thing that we need to steer away from or maybe an internal thing that we don't need to waste time on. So it's kind of two sides of the same coin. I joke that really Maybe in the end I should just admit that I have control issues, right? Maybe that's the easy way to call it. But managing the sales process is part of it. It's on me. Number 3, patience. I know that unless the Lord calls me home or to another job, I'm here for the long term. I'm patient. I've had clients that it's taken years before they said yes and came on. If the answer is not now, I'm good with that. If it's legitimate, right? If it's for the right reason, because I know that I'm going to need sales this year, next year, and 5 years from now. I'm okay with that. And I've lately started calling it not just patience, but compound interest, particularly in 2025. Some of the sales that I had were because 2 and 3 years earlier we talked to somebody, engaged with them, and I had a client that wanted to come back after they left and we told them they weren't going to like it when they left. And sure enough, 3 or 4 years later they came back. So some of that is kind of the compound interest just from being in this position a long time. So I think that's the top 3.
3:48 Scott Ingram: And speaking of patience, you've been at Insperity for a minute or 2 now.
3:52 Calvin Dennis: Yeah, 19 and a half years, in fact, in the same role. And that's been a lot of fun all the way.
3:59 Scott Ingram: Yeah. Yeah. As you talk about your control issue point, I think part of that is maybe knowing a little bit about you is probably, A, wanting to maybe remove some friction in the process with your clientele and not having to slow things down to go schedule somebody else to maybe be brought in there and just being more thoughtful about the process and their experience, even though you have that wealth of knowledge and resource on your side.
4:24 Calvin Dennis: I think that's fair. We all know that in sales, really, language is one of the most important things we can use effectively, right? I had a guy that was a great friend of mine that he told me, like, look, there's no… there's nothing more important you can do than, than learn how to say the same thing in a more effective way. He told the story of writing things down, like trying to figure out 10 different ways to say something. He said the first couple are easy, but when you get to number 7 or 8 or 9 or 10 way to say the same thing. That's hard to do. I think sometimes experts and other people, you're right that there's friction because they're explaining it. Maybe we know our prospect better and we really know what's the burning issue in their mind, and we just need to use the right vernacular to get that point across. I think that's it. Of course, the funny part is there was a guy that was a new rep in the office, and one time he said, hey, do you want me to write a… take a stab at writing that email to that prospect after that meeting, and then you can completely rewrite it before you send it. I said, yeah, why don't you start that? That'll be helpful. Because he knew I was probably gonna do that, right? But I don't know, what is it? Admitting you have a problem is the first step. Is that right?
5:27 Scott Ingram: There you go. There you go. Calvin, let's talk about what is your role and what did it take to the top 1% there at Insperity?
5:34 Calvin Dennis: My role is a business performance advisor. It's a sales role. Our market is small and medium-sized businesses based on employee count. I deal with people. We start engaging when you got 5 or 6 employees up to about 150 employees. When you're larger than that, we view you as a kind of a middle market client. We've got folks that engage with them. That's a different sale, of course. I deal mainly… and one of the reasons I love my job is I'm dealing with operators, right? Guys that own a plumber, commercial plumbing outfit, or maybe they're an architect firm or a physician practice or whatever it is you do for a living. When you have real employees and you got to do all the stuff that you have to do when you have real employees. You got to pay them and deal with government regulations and you got to provide for them or else they'll go to work somewhere else where they can take better care of their family. That's kind of what we do. We engage with those people who really know that that wasn't why they went into business in the first place. They maybe they want to build cabinets, right? They're a custom cabinetmaker and they look up one day and here's actually some of my sales dialog. I say, look, you looked up one day and you have 28 employees. Can I be honest? You're terrible at that. Why not let us help you with that so you can worry more about building cabinets? That's how we engage with folks.
6:47 Scott Ingram: Fantastic. And then put your results in perspective for us. Maybe not just this last year, which I know is a great one for you, but you've had pretty consistent performance over time as well.
6:56 Calvin Dennis: Yes, thankfully. The real mark of distinction around here is Chairman's Club, right? You get automatic qualification to the trip each year. Chairman's Club, you need to sell at least 12 different accounts in a year and add up to a total of 300 employees at all those accounts. Right. And by the way, that's harder than it sounds, right? So one guy may have 12 employees, somebody else may have 5, somebody has 20, 50, or 100. You got to get to about 312 unique sales. And then sometimes we split them, right? And maybe a new rep gets an appointment set and they need some help doing it. So we may only get half a deal at a time is where you got to get to by the end of the year. Chairman's Club, I've been blessed to make it, I think, 9 or 10 times since I've been here. There's a slightly lower level you can qualify for, TRIP. Done that 3 or 4 times as well. And the last few years I made Chairman's Club in a row, which is a real blessing. Last year, just to be specific, if Chairman's Club is 300, last year I sold, I think it was 703. So it was about maybe 2.2, 2.3x over what Chairman's Club was last year. It was fun, put it mildly.
8:02 Scott Ingram: Fantastic. Fantastic. And again, I knew that you had a lot of success over the years that we've known each other with Chairman's Club there, but my criteria criteria with the top 1% is very strict and very ridiculous. And I'm thrilled that you got to this point and we get to have this conversation.
8:17 Calvin Dennis: You and I both decided we weren't going to even think about having a podcast with an asterisk. Just so everybody knows, Scott Ingram has standards, right? There's the first thing.
8:26 Scott Ingram: I don't know. Absolutely. Absolutely. And again, it's just been great having you be a big part of this community over time. You've been to the last, what, 4 or 5 Sales Success Summits here in Austin, and we've had an opportunity to do a little bit of work together and Like I said, really great to have you in this position. Goes to show that even the top 2% didn't make the cut like you were at last year.
8:47 Calvin Dennis: And I was close and we shared that, right? Hey, it was close. We were pushing till the very end, but it was a real blessing to get there.
8:54 Scott Ingram: Yeah. Yeah. It's a more impressive feat when you're in an organization with a lot of maturity, a lot of success, and nearly 600 other sellers.
9:03 Calvin Dennis: Right. There's people that are really strong and they're really great friends, right? It's funny. Yeah. We get competitive and know towards the end of the year who's about in what slot. But man, you never know because people push till the very end. I thought I was there, but if a couple of friends of mine had just had the last-minute sale come through, you never know.
9:20 Scott Ingram: That's how it goes. That's how it goes. Let's talk about the beginning. What is your origin story? How did you get into sales in the first place?
9:27 Calvin Dennis: We'll try not to make this too long, but I took a part-time job in college selling airline tickets over the telephone. Believe it or not, nobody really remembers this, but back in the day you had to call somebody on the telephone and they sat in a little office in a strip center down the street. And we used an airline mainframe and we punched in these cryptic codes and figured out what flight to put you on. And we printed out a cardboard airline ticket and that's what you used to get on the plane. And it was telephone almost exclusively, right? You could walk in, but it was almost exclusively telephone. And I learned so much doing that, listening to people and their emotions and what do they want. And sometimes they were happy and sometimes they were grief-stricken. Calling, but it was a great start. I had this burning desire to have my own shop, be an entrepreneur, and 2 or 3 years later got the opportunity to do that. Opened a small agency and it was fun for 7 or 8 years, worked pretty well, was not ever going to be a fantastic income, but it was enough to get by when I was young and dumb. As you may know, the internet started creeping in and that business radically changed along the way. I had a friend that took a job at one of the dot-coms and said, look, what I know you're really good at is having people talk on the telephone and really communication more than anything. You just happen to be selling the products. It's more about the telephone technique. So would you please start answering our phone calls? We need a customer service center. So we opened up a call center, kind of a sister operation that, I mean, if you were mad because you got double billed about something and you called that 800 number, we really answered the phone. That was fun. But the challenge was, even though we tried to diversify, the big customer we had was still travel related. I just couldn't get out of the travel space fast enough. And that big customer that had all of the volume, they ultimately got bought out by a big name you would know of, one of the dot-coms in the travel space. And they didn't need us anymore down in Texas. Somebody asked one time, did you sell it? And I was like, no, I just ended up turning the lights off. It was a real humbling experience. I will tell you, the internet was part of it that made it more challenging. But what was also the bigger picture was I was young and brash and driven by a lot of pride and a lot of ego and made some decisions that frankly were not God-honoring at the time. Failed to listen to some wise counsel, including my wife, who said, listen, gosh, this is risky. And when you're an entrepreneur, one thing I love about entrepreneurs is they go, risk? What risk? We're building a great company here. And I had a good dose of that, right, rolling around in my brain. And ultimately it didn't work. And that's why I was so blessed when I didn't know what I was going to do and couldn't sleep one night. I'll just tell you, God laid Insperity on my heart, and it was not an audible voice, but I knew who was speaking to me. And I still didn't know, like, I felt kind of stuck or trapped doing what I'd been doing as a small business owner. And my wife again encouraged me. She said, look, you can do something else. You don't have to do what you've been doing. So I called my friends at Insperity because ironically I had used Insperity. I was their customer for about 10 years. That was the one part of the business that worked fantastic, right? All of the HR and stuff. That was never… didn't do the part I didn't do. Yeah, there you go. I've got a story there. Remind me, I'll tell you that later about some of the HR stuff they did for us. So I called them up, said, look, I want to come to work for you guys. I think I could sell it. I've been buying the service for 10 years. I think that'd give me an advantage. And then it was off to the races, and it has been When you go from having to run everything in a small business to coming in and they say, look, here's your laptop. If you have a problem, here's the help desk number, here's your paperwork, here's this. It was fantastic. All I have to manage is me, which frankly is hard to do on a good day. Let's just be honest. I really took to it. And as Scott has reminded us, the term is I am an intentional individual contributor. And that's been my role for 19 years and it's been a wonderful ride. I'm going to stop here and take a breath.
13:21 Scott Ingram: That's amazing. That's amazing. You've been doing it longer than I had at the point, but where I came to was very similar. I had run my own IT consulting company and sold that and had moved to Austin and was thinking about what's next. And that was really the point for me that I realized running a business is great, but there's a lot of parts of that that I'm not very good at, including managing people I'm not particularly good at. And I thought my favorite part is just working with customers and What an incredible opportunity we have to just do the sales stuff, get paid very well for that, and let other people worry about the payroll, the HR, the legal, the delivery, everything else that needs to happen inside of a successful business. I think this is an incredible place that we can carve out a little piece of success for ourselves.
14:11 Calvin Dennis: Well, you apparently were wiser than me because did you hear what you just said? You sold your business. I ended up… I don't know if you got a little or a lot. I hope you got something. But I ended up having to… somebody asked me one time, did you sell it? I said, no, I just had to turn the lights off. It was pretty dramatically bad. So kudos for you for getting some value out of it.
14:28 Scott Ingram: Yeah, I guess a little or a lot is all relative. I was also in my early 20s, and this is years ago.
14:33 Calvin Dennis: Yeah, yeah, we're all wiser, right? It's funny, people are like… we had a kid the other day. I was telling part of that story in the office, and, you know, I'm talking about answering the telephone to sell stuff. And he goes, well, why didn't they just book it on the internet? He was legit. I said, it was 1987 or not, that wasn't a thing. And he'd never thought of that, that you couldn't do everything online on your phone.
14:55 Scott Ingram: Yep.
14:55 Calvin Dennis: It's really different these days.
14:57 Scott Ingram: There was a time. There was a time.
14:58 Calvin Dennis: Yeah.
14:59 Scott Ingram: Calvin, speaking of stories, the show is called Sales Success Stories. What is your favorite sales story?
15:06 Calvin Dennis: I'm gonna tell this one On a day that started with getting stood up, my boss and I drove out to a bank to have… only to have the CEO tell us he didn't need to see our proposal. He knew everything. He was from California. He knew all about HR. And what I felt like telling him was, apparently you don't know that in Texas we don't talk to each other that way, but okay, thank you. So we headed back to the office, but on the way back to the office, I got a call or an email from an attorney who said, listen, I know Insperity and I know you. I forget, he knew me somehow. And he said, I've got a referral for you that there's 3 brothers and they need what you guys do. And I've told them that, please call them. So we set about engaging with them and they had a business that was quite successful, family business for several decades, selling sporting goods to big box retailers and stuff. But they acquired a new brand of product. And what came with that product was this outside sales force that was telephone-based. Of course, it was kind of fun. I was interested, like, wait a minute, I have experience in that. And these basically stay-at-home moms would get their kids off to school, come back home, fire up Salesforce, start dialing, make outbound calls to essentially every hardware store in America. And they sold this product to them 2 and 3 and 4 cases at a time. And the funny thing is, some of these stay-at-home moms made 6 figures doing it. It was the craziest thing you ever saw. But they had to change their model. They inherited this when they bought this brand of product from somewhere else. And there's some employment stuff that they had to change and they knew it. And their attorneys told them, you got to change it. And gosh, they were in 12 or 14 different states and there's regulations all over the place. And so they were doing the right thing, but it was going to be a major change for those outside sales reps because we touch all sorts of areas. We touch taxation and regulatory and benefits and retirement plans. We touch all that as part of our service. And they negotiated hard. In fact, harder than anybody at that point I'd ever been experienced with. But we got a proposal that would work for them. And the guy said, look, we want to do it. We need to do it. We basically kind of have to do it. But Calvin, if this sales force revolts against this idea, because it was a major change for them, if they revolt, not only are we going to have a hard time paying Insperity, like this could put the company at risk. Because if our revenue goes south from this, they're the tail wagging the dog at this point, right? It had grown so tremendously. And I said, okay, I think I know your heart in the matter. Let me, let me take a crack at it. And I brewed a pot of coffee, which is what I used to do when I had problems like this. And I sat down writing the FAQ document to end all FAQ documents. I thought of every reason these employees… I think there's about 75 of them… why they would hate this idea, why they wouldn't love it. What would happen about this? What about my taxes? What about my independence? Are you changing? Do you have to change? Why now? I wrote paragraph after paragraph, gave it to the guy. His name was Ron, and he called me, I think, the next day, and he said, Calvin, you did it. That's it. And other than changing some of the language just to fit our vernacular, because they were kind of country about it, he said, you, you understood our heart in the matter. I think this will work. So they move forward, and the funny part was Ron still said, now listen, We're going to announce this thing and we're going to have all these people on a WebEx. You are coming over to sit with me in my office when we're on this WebEx, right? And I said, sure, Ron, be glad to. But they came on and joined and then they invited me to go to their sales conference after that because they, man, they give these great prizes and you sell so much, you get a prize and a Tiffany gift card. And I was just… there were still some people that weren't happy that came up at my little booth because we still had some selling to do even after the decision. But it's my favorite because I learned that creativity and thinking through and trying to get in the mindset of not just this business owner, but these 75 people that could have frankly killed his business or come close to it if they didn't sign on to this idea. He was smart enough to know it was an issue, and it was a way that I could frankly use language, help him get past that, and help him get past that business. It's my favorite of after all these years.
19:19 Scott Ingram: Love it, love it, love it, love it. Calvin, lots of success in your tenure there at Insperity. What are you most proud of?
19:26 Calvin Dennis: We've had the opportunity, for both good reasons and bad, when a client calls and says… I had a guy call one time and he was so new I didn't even know who his service team was. He called and said he had an HR issue, and he said, hey, I need to talk to somebody. And I said, man, you're so new, hold on, I got to figure out who you're supposed to call. And I was new too. He sent me like a 2-line email that said, Calvin, that worked great. I just wanted you to know. And it was an employee who needed to exit, and it would have been a devastating thing for him because they were making all sorts of challenges for him. And that worked great. I've had another client that a couple years ago called me and said, listen, I'm selling and I've got this deal to sell at this point, and I don't know if they're going to remain with you or not. But Calvin, at this point in my life, I'm selling a big check and we help them because there's nothing that'll mess up a sale quicker than an unresolved HR matter. Right? Let's be honest. Nobody's gonna buy your business if they think you're gonna have to spend half a million dollars on a wrongful termination lawsuit. Right? Stuff like that is really meaningful. Right? It's more than just, oh, I made a sale. I got to go on trip, which is cool too. Right? It's the clients that we impact. And it's also some friends I know. People in my job that the company has changed the financial trajectory of their life, including mine, right? Providing this service to people, but getting blessed along the way because we try to do the right thing. But it's really the clients that they call you for good or bad. We helped them through something that was really tricky and we're friends for life just because we helped them through. Now that gets, that's kind of sappy and emotional, but I think that's part of the reason I've lasted so long is I'm that kind of guy. I mean, it, That stuff resonates with me. Yeah.
21:10 Scott Ingram: Yeah. And that's the stuff that matters and that you remember long after the commission check has been come and gone.
21:17 Calvin Dennis: You know what's funny? In HR, I will tell you. So we have HR people, right? HR specialists. Now I'm convinced they have the best stories, but they don't ever share.
21:26 Scott Ingram: But they can't tell them.
21:27 Calvin Dennis: Right. And all they'll say is, yeah, I talked to client such and such the other day. I'll go, oh yeah, let's go. Yeah, they won't share. I'm convinced if they would ever just write a book, you'd figure out who they're talking about maybe. But They don't share.
21:38 Scott Ingram: Yeah. Kevin, what about the flip side? What do you find to be the most challenging, or what do you continue to struggle with at this point?
21:45 Calvin Dennis: I'm not particularly organized, right? There's the first challenge. I always have this vision that I'm going to miraculously change and have a day where I strategically think through what are my top things I'm going to think about and be like some ruthless attorney who gets productivity out of every minute of every day. And then I finally decide, look, I'm letting go of that. It's working just fine. It is challenging when you get a book of business, and we're compensated for that, right? We get a residual income as long as somebody remains a client. So we try to get the right people to join us for the right reason. You care about all of your clients, right? And you want to solve their problems. I do think I have a challenge. I need to engage the other people that are frankly better at that, and I have to put my ego in a box and say, look, I'm really not the best person to solve that problem. Let me get you over to the person that'll do it. Right? That, that still is hard for me. And I'm not very organized in the first place. So if you ask me to do it, it may take a while before I get around to it. So that's also a challenge. Just being honest.
22:43 Scott Ingram: I have to imagine that part of the challenge is given that after this long in the business and building up really significant kind of residual piece of business, that continuing to go out there and find new business takes a lot of work. What's your overall kind of prospecting approach? What does that look like? Before we get into the specifics of how Calvin is generating new business, this is probably the perfect time to talk about Nooks. Nooks is an integrated platform that the best revenue teams run on to consistently and predictably create pipeline. Their intelligent outbound approach combines their AI dialer, their powerful signals and intelligence engine, and now their brand new AI sequencing capability. To get your own unfair pipeline advantage, go to nooks.ai. And now back to Calvin.
23:30 Calvin Dennis: It is true that the perception is not… well, let me say this… the perception is not true that we just deal with inbound leads all day, right, from referrals. We do get some of those, and that's terrific. But even a tenured rep has to go out and what I call it is make new friends, right? Tell the story, try to get engaged with people. And that's not easy. It is… yeah, it is challenging because you've got, again, some client stuff and you manage it. We are not account managers per se, but we're tight with our clients. By the time you become a client, we're friends, right? We know what's going on in your business and we want to help. But my prospecting, I called it once maybe a spider web. I rarely make a completely cold call unless I'm trying to do it to help a new rep and I'm calling on their list just to frankly help them with some language. I usually know something about that prospect. I either know that they know Fred who recommended me, or I had a client in their same industry that might know them, or I've at least seen their business. I've gone by and maybe seen them in some capacity beforehand. And maybe that's just mental gymnastics, but in my mind, that makes most everything I do a warm call. And my approach really is just to quit trying to sell Insperity. My whole goal is just to get them to have a dialogue, right? And new reps, they're too wrapped up in trying to sell Insperity. I say, look, you just want to get them to take a look. And so I often call people and say, look, I don't know if you need Insperity or not. I just think you need to hear what we're doing for people, because for the right fit, this could be really game-changing for your business. And it's almost like I let myself off the hook for the results. But we use all the methods, right? When I started, it was almost strictly telephone. LinkedIn wasn't even a thing back then, if we can remember that far. Email was not really as nearly effective as the phone. And I like the phone when I do it because again, I had some early career experience. That's how I sold for years and years. But I call it making new friends.
25:27 Scott Ingram: It…
25:28 Calvin Dennis: maybe somebody might say that's psychological judo, but it's not really a cold call if I know something about you.
25:34 Scott Ingram: And how are you allocating time to do that work?
25:37 Calvin Dennis: Again, I wish I was completely organized. I put prospecting on the calendar. I don't overdo the details, right? I've seen people who say, okay, Monday at 10 o'clock, prospecting, LinkedIn prospecting, phone calls, trusting that… I trust that if I've got a 2-hour block of prospecting on my calendar, it will be some of all of that. And so I try to keep it on my calendar because it is true, if you don't have it on the calendar, we all know that there will be things that you all of a sudden think is a brushfire that, that come up. So that's the first calendar discipline. Every year I get a little better. I tell my boss, whoever it is, I'm like, look, I'm going to be more ruthless about my calendar this year, man. I'm really going to be calendar specific. I think I'm better than that than I was because white space is not good on your calendar, right? You got to fill it up. But I don't overdo it. If I know that I'm going to be 2 hours in prospecting, I don't have a plan that like, okay, Tuesdays I do email, Thursdays I do LinkedIn. That's too specific in my view.
26:34 Scott Ingram: Got it. Let's take a step back and let's talk about the way that you're structuring your day, the way you're structuring your week. Your alarm clock goes off. Tell me what time that typically happens and give us the blow-by-blow through a typical day.
26:46 Calvin Dennis: Not as early as it once did, because we were in a school district when our kids were home where we had to be up at 5:30 or they weren't making it to school by 7:15 or 7:20. It was awful. I'm a little more relaxed now. It's great. But you get older and you can't sleep past 5:30 or 6 o'clock anyway, so I'm usually awake. I do the first tranche of work from home with a cup of coffee or 2 and the dog sitting at my feet, really figuring out what's going on. I'm in the office. I like being in the office. I get energy. I think still psychologically, part of me remembers that's where I learned how to sell in this business, in this industry. I just glommed right up next to the people that were being successful, and I would just watch them. And so I learned that being in the office has great advantages. Now, it's a different day nowadays. I get it. We're hybrid. We had COVID. But it's funny to me that some people don't want to be in the office. It's where I learned. So I'm still an office guy more than some. I like being in the office unless I'm out meeting people or I'm realistic. I have a life too that sometimes I'm working from home, but I'm more than likely being in the office. We operate through our day. I like doing things in person. Again, we deal with small and medium-sized business owners generally. There are people that like relationships with you. It can be different. Sometimes it can be online. That's cool. But you know what? It's really easy for a guy or girl to tell you thanks, no thanks, click, and your Zoom meeting is over. Being in person, I think, is a real advantage. So I'm out and about a lot. If I've got at least a couple of hours, I'll come back by the office to finish my day. But I try to be home around 6, which I'm… let's be honest, 6:15 to 6:30. That's when I get home. And occasionally we'll fire back up once the evening is done, handle some late night stuff. Not particularly organized. I had to… hate to admit that out loud now for all these people listening.
28:34 Scott Ingram: Are there other habits or routines that are central to the way that you operate?
28:38 Calvin Dennis: Yeah, I'm a pretty voracious… we'll get into this… I try to stay up on the news. At one point, man, I thought I was going to be an editorial writer. I'd get all these opinions, and politics once interested me. The older I get, the less it does. But some of the habits I have are going out in certain places. There are a lot of networking events that I think are a real drag and are not productive. And newer reps think that their success is gonna be found in going to these networking. I counsel them, there's good ones and bad ones, but there's certain rooms that you need to be in, whether it's a chamber or a local economic development place. We deal with small businesses. I have to be where those small business leaders are. And if you're in the right rooms, then you get the opportunity that, oh, there's Fred. I've not ever met Fred. Hey, let me go up to him and say, look, again, I work for Insperity. Great. Thank you much. Looks like you're expanding. You need to see us. So I think a key to that is I got to be in those rooms.
29:36 Scott Ingram: How are you differentiating between the good and the bad in those meetings?
29:40 Calvin Dennis: Great question. A lot of networking events, the easy answer for us is you have to have employees, right? If you're a mortgage guy, you really don't have employees. It's you. You taking mortgage apps, right? And at every networking event, if you go to the wrong ones, it's mortgage guy A, mortgage guy B, mortgage guy C, realtor A, realtor B, realtor C. They're more B2C, right? They're not people who have 25 employees and a staff and all the HR that goes with that. That's my distinction, because you can waste a lot of time. I used to go to… I'm in Fort Worth, by the way. We call it Fort Worth-Dallas, just so you know. I used to go to this Fort Worth Chamber event. It was kind of one of those Membership 101 or whatever they call it. And it was one of those where there'd be 75 or 100 people there and everybody is supposed to introduce themselves for only 15 seconds. And of course, then you're always mad because people take a whole 2 minutes and drone on and on, right? But I'd sit there and listen to 75 or 100 of them and I would come away with maybe 3 people that I would think, ooh, I didn't know you existed before. And I would call them later and say, listen, I didn't get a chance to meet you at that event because obviously it took a long time, but I'd like to come by and see you. It was more of like surveying or reconnaissance for me. So if you're going to go to those as a new rep, I always tell them, look, don't… that's what you're going to come away with is you're going to maybe have 2 or 3 names that, that you'll call about.
30:59 Scott Ingram: Yeah. What about your information diet? You mentioned the news, but what are you reading? What are you listening to? What are you watching? And when does that happen?
31:07 Calvin Dennis: I hate to admit it, but I'm online a lot, just various dot-com news sites, just trying to figure out what's going on. LinkedIn is relevant for me, right? Sometimes you want to go, hey gosh, it looks like Bob knows Fred. But we've all learned you got to verify with Fred that, hey, do you really know Bob, or was he one of those guys that just wanted to connect with you? Because some people are like that. I'm relatively skimpy on my LinkedIn. If I don't know you and you send me an invite, I'm not going to accept it. I don't know why I'm like that way, but You got to verify who knows who on LinkedIn if you want a referral. So LinkedIn, some news sites. Ironically, we can talk about this later. I, I'm an auditory learner, as you know. That's why your podcast appealed to me when we first met each other all those years ago. So I'm a pretty good podcast listener about sales, sales technique, and ironically, listen to some podcasts about sales leadership, which is funny to me because I'm an individual contributor. One guy asked me why I do that, and I say maybe it's self-preservation, right? I have good bosses, better bosses. Sometimes when you've been around a long time, part of your job is to help them. A lot of it is auditory. I think it comes from being a musician earlier in my life. A lot of it's auditory.
32:08 Scott Ingram: Excellent. What about kind of the tools and apps that you live on?
32:13 Calvin Dennis: We have all of them right at Insperity. We're a big company. We have all the gizmos and whatnot. I would tell you it's pretty basic for me. It's Outlook, of course, with Teams. And I wish Microsoft would just merge those 2. I just can't stand having multiple… all this meant sometimes is you have more than one inbox, right? And people choose Team or Outlook, right? Could we not merge those together and simplify life? But Outlook and Teams, of course, LinkedIn and the web. Then we have some internal tools, right? What I don't do is, again, because I'm not doing this anonymous stuff, we have… oh gosh, what's it all called? We have 6sense and we have the ZoomInfo and we have all of that. If you were brand new when we started, of course we just had directories, right? We would have thought ZoomInfo was Fantastic, right? I don't use those as much as some of the newer folks do because it's just different these days, but they're all available. So it's pretty old school, really. I'm more likely to pick up the telephone and say, hey, Bob, Fred said to call you and said you should see me, which is a lot more effective than sending a dumb email that probably won't get to them. And if it does get to them, they won't read it. I don't know. It's pretty basic.
33:17 Scott Ingram: Yeah. Calvin, along those lines, I wonder if you subscribe to a particular sales philosophy.
33:23 Calvin Dennis: I would tell you for a long time, my answer I think still would be is Jeffrey Gitomer. He's written a ton of books and I haven't really seen much of him lately, but 25 years ago, maybe, gosh, maybe a lot longer than that, he started writing The Little Red Book of Selling, which kind of modeled off that Little Red Book of Golf, I guess, from Harvey Penick. And his sales philosophy, he puts in that first book that I try to give value first and give value without expectation of return. And ironically, if you do that, you'll get a whole lot of return anyway. I hope that that still comes across in my sales methodology. I know that sometimes the ones I feel the best about are feel-good moments, are when you just know somebody's not going to be a client and they don't need you, or for whatever reason they wouldn't be a fit, but we've given them some solid advice about, hey, listen, you don't need to pay me, but here's this one thing in your business that is going to blow up and cause you significant significant pain. You better go fix this, and you don't need me to do it, but holy cow, you better fix this. Those are really feel-good moments for me. So I hope that I still do that. But Gitomer wrote some pretty good stuff. He's pretty direct, by the way. Apparently back in the day… of course, I have all of his books. There's red, green, blue, yellow, gold. There's all sorts of little books of every color. Just buy the first one. Most of them are kind of rehashed. He sold a lot of books, which is terrific. Apparently he came to an Insperity meeting one time before I joined, And he spoke to us back when he's writing the books. And I've gone to one of his meetings in person and I can validate that in person he's got a potty mouth. He was not going to get invited back to our company because apparently it was pretty out there. But his books are great.
34:59 Scott Ingram: Yeah, it's been a minute since I've heard or seen from Gitomer, but it could just be that I'm not paying attention in the right places. I certainly remember reading The Little Red Book, that's for sure. Calvin, when it comes to motivation and drive, how do you think about that? What keeps you going?
35:16 Calvin Dennis: There are times, right, when… because I love the place, and I get it, it sounds sappy and emotional, right? And some people that meet me think it's kind of fake until they figure out I really do love the place. I feel an obligation, right, to sell because the company has really redeemed me from a financial pit, right? I want to honor that and sell because it's our job to bring the clients in the first place so that somebody can service them, right? So I take that personally, but there's also part of me that at least for me, I think… I don't know that a boss can motivate you or a comp plan can motivate you. I'm not even quite sure you can motivate yourself really in some ways. I've just figured out that action precedes motivation. Forget all the big charts and goals on the wall. If you'll just start, is my experience, right? If I get myself going and I get cranked up and I get the activity going, Once the flywheel is turning, it's a lot easier for me to keep it turning. And then the motivation comes like, oh wow, I'm close to the top of the leaderboard, man. Don't stop in the 4th quarter because those other guys might catch up to you. The motivation comes there, but it's almost like you just… it's okay not to be super motivated. Just get started. You know what to do. This is another thing that Gitomer used to say. He's like, look, you know what to do. You're just not doing it. Quit griping at your company. Just get better at your job. Why don't you read something instead of watching a rerun? I don't know if that makes any sense or if that's a psychological drama that somebody needs to unpack in my life. Um, but if you just get started, it'll be a great help to you.
36:49 Scott Ingram: Yeah, I think it does make a lot of sense. It certainly works and resonates with me, right? This idea of, I think, getting into action and just doing the work tends to build its own snowball, right? Rather than, to your point, being something external. Is it really going to be something that my boss said?
37:05 Calvin Dennis: Yeah. Some fantastic spiff they send out, right? Oh, that's really going to change my behavior. Wow, a spiff. By the way, Insperity is terrific about all that, right? We have lots of opportunities, and it's almost over the top how generous they are with us. But we're going to sell anyway, the people that are going to sell, because we have other motivations. Now, the challenging part about that is, let's just be honest right now. So you announced on the beginning of this recording, I'm actually on trip right now. Guess what? When I get back the year, emotionally, 2025 is finally over. We have our sales conference and some training in January. They announce who were the winners. And then 3 or 4 weeks later, we have TRIP, all the people that are TRIP earners. Just to be honest, there's a little bit of, okay, now 2025 is finally over because there's a little emotional overhang, right? You make sales, there's an onboarding, a client transition with us. We got everybody to start. So the month of January, you got all these new clients that We have people for that, but we still have to help with all the onboarding, right? There's stuff that we do and we made promises to these people and we're involved. When I get back, just to be honest, I got practically nothing. So this whole notion of me talking about getting the flywheel going is going to be a Herculean effort because I have worked here before where I got a call. My reputation used to be I was a 4th quarter guy and there would be like… and I would say, don't worry about it. I get excited about the 4th quarter. I'm a fall campaign guy. Don't worry about it. Whatever. And I've gotten calls from some pretty senior guys once or twice in my career that have said something like, it'll be June or July, right? And they'll call me and they'll go, Calvin, do you think like you could sell something in the first half of the year? Really? Could you? And I was like, yes, Roger, don't worry about it. Hey, we're fine. It's going to… it's going to work out. But I got to get back and get with it. There's that. Just being honest with everybody. Yep.
38:50 Scott Ingram: Yep, absolutely. Is there something you believe that the average or typical sales professional would think is crazy?
38:58 Calvin Dennis: It's crazy. Maybe not crazy. We've talked a lot about being in the right spot. And by the way, the Sales Success Society is a great place to unpack some of those ideas in a safe space, right, about being in the right spot. Maybe not crazy, but I don't know that people embrace this as much as I do. You got to own your career. It's on you. I got the chance at our sales conference a month ago talking about… we talk about our company as a category of one, and that's true in a lot of ways. But I said, look, the deal is you… I'm talking to this room full of pretty new reps… I said, the deal is you have to be a category one. It's on you. And it's okay if you're not when you begin here. Just get better so a year from now you're better and you're closer to it. And when you become a category one Man, the sky's the limit wherever you work. I think sometimes some sales folks are a little too passive about developing themselves. I think we have great training. We call it… by the way, language is important to us.
40:00 Scott Ingram: We…
40:01 Calvin Dennis: the titles of things like, I don't work in the sales department, I work for the growth organization. That's what we call ourselves. We don't have training, we have sales performance improvement, right? Because language matters. But people I think sometimes expect that sales performance improvement is going to tell them everything they need to know about how to do this job. And that's not true, I don't think, anywhere. One of the big regional vice presidents at our training meeting, she just let out a quote and I wrote it down and I showed it to her later because I sat on the back row at a breakout session with her. And I said, hey, you want to know the best thing you said in this training conference? She said, what's that? I said, look here, I wrote it down. And she was saying, look, quit… she's talking about… she said, look, quit reading sales books Read a business book, because if you're a business professional, you'll be able to better resonate with our clients. So I don't know that people think that's crazy, but I don't know that they embrace it as much as I do. Our clients lead… live a tough life, and sometimes it's quiet desperation. And if you learn how to resonate with them, they will tell you things that you just know they've not told their banker or anybody else. I hope people embrace that. Your company can give you a job, but only you can give yourself a career, if that makes sense.
41:06 Scott Ingram: Yeah, love that. I've been thinking a lot about this idea of, and this has been a theme over some of the years in previous times with the summits, but this idea of really sales being a craft. And to your point, I think it's a really important callout. Some of it is, yes, I want to be better at just the process and the approach of sales, but probably a bigger part of it is better understanding your customers, better understanding their industry and their situation and what they're trying to work through and how we're able to help through that. I feel like it's little to do with the very specific tactical thing that you say in a sales conversation. It's not really about that.
41:50 Calvin Dennis: I had a guy, in fact, it was funny. He was my sales rep when I was their client for 10 years before I worked here. He says it like this. He's retired now, but he said, listen, if we would worry less about the things to say and the things to do and worry more about being the kind of person that our prospects and clients need us to be, then we would more naturally do all the right things anyway. And I thought, wow, that's really wise from him. And so now we don't always do it right. It's easy to talk a good game, but at least that's the goal, right? To help your clients. And it doesn't matter what you sell, right? You can sell and have a noble calling whether you're selling employer HR stuff or you're selling ball bearings or you're selling pesticides to farmers. Right. Sales is a noble calling, and you've helped remind us of that through your podcast, through that sales is a craft. You wouldn't want a doctor or a pilot not to have practiced their craft. They don't just come out of school and never learn again. I think we ought to do the same with sales right now. Again, it's easy to talk a good game. You got to deliver, but it's fun. And then guess what? If you get good at it, they throw money at you like crazy.
42:58 Scott Ingram: Absolutely. Absolutely. Calvin, speaking of improvement, what have been the most important decisions you've had to make or the lessons you had to learn to really get to the level that you're at today?
43:08 Calvin Dennis: We may have already touched on this, but I think part of that is it is true that you can't sell much past your self-image or your constrained barriers that you put up for yourself. And I don't mean this in some psychological woo-woo way, right? I don't subscribe to that. I don't think it's biblical, right? It is true that my experience over the last few years, my bracket or my range of minimum and maximum expectations has continued to go up. And for me, it wasn't a dramatic, oh my gosh, next year I'm going to double. It was more of a slow and steady thing, and it should not honestly have taken me 19 years to get here. So if you're listening, don't make my mistake. What I should have done is dream bigger sooner, right? Would have helped me. But it is true that year over year, my bracket of maybe acceptable results that you think of what you're going to do has gone up each year. And I think that's okay to have an incremental approach as long as you're going up. That's been helpful. It wasn't some major, oh my gosh, now I'm going to decide. It was just more of a natural, hey, I'm a professional and I got to keep doing this.
44:11 Scott Ingram: I think how I felt about it, it kind of ties back to what you talked about at the very beginning in terms of patience and compound interest, right? As long as you are consistently getting better over time and consistently performing better over time, that really starts to get meaningful after a couple of decades. Right.
44:30 Calvin Dennis: And I don't take that for granted. There are people that don't have, for whatever reason, they don't get to stay in a position long. But your comments are spot on, right? Moving every 2 years would be terrible. And it's not just salespeople, by the way. I had a client, new client that came on last year. Great people. They looked at us. During COVID I remember they looked at us and said no at the time, came back around. And there's a good plug for Salesforce because I was on the initial opportunity, even though I split it with somebody. It came back to me 5 years later. Of course, we remembered it. Great people. We brought them on this time, worked great. There's a plug for making sure you're documenting what you do in Salesforce. But they came on and it was only because I'd been there before. You get that opportunity because 5 years later it was the right time for it. And it wasn't the right beginning, and I just had to be patient. Oh, I know what it was. Here's the point. Uh, thanks to Alex in advance for editing. This client that came on had, I don't know, 40 or 50 people. Nice sale. They're about to get a contract, and they may add 100 people like overnight, which would be a real win for us and a reason they used us, because that's hard to do. Um, but the guy that was their controller, uh, great guy, helped with the transition, he has recently decided to leave. They've been with us a few months, and we learned that he was leaving, and he completely was getting out of his role as a controller to go do something completely different like wealth management or something. And his reasoning was, listen, I'm a controller, I'm about to become a CFO, and the life of a CFO, you have to go to a new spot every 2 to 3 years for a career. And he was smart enough in advance to know that I don't want to do that and be at 20 different places by the time I'm finished with my career. And he was pretty wise to not get on that path anyway because I'll bet most of them think that they can do it otherwise, and they end up bouncing around. And then 10 places later, then they get out of that industry. But it's not just sales that feels like they have to move around to improve their life. It happens to CFOs too.
46:26 Scott Ingram: It's so interesting. You and I were talking about this separately, just this idea of what I think of as the sales carousel. In this most recent change that I just made, not only am I an intentional individual contributor, I'm also pretty intentional about my own career and the moves that I'm making. And one of the things I was very explicit about, that I would call this out, is I'm actively trying to avoid getting on the sales carousel that I see a lot of people get on, where they essentially have to change roles every 18 to 24 months. And I feel like it takes at least a year. If we're really honest with ourselves, it's probably close to 2, maybe even 3 years to get really good inside one particular organization. And what I mean by that is Really understanding your customers, understanding the absolute ins and outs of the product offerings of your team, and just how to get things done. A lot of the way that I always see my role is I kind of wield my organization on behalf of my clients. In order to do that, you've got to have a lot of depth of relationship and really just understand how things get done. You never get to that point If you change jobs every couple of years, you're always starting over rather than being in a position to allow that compounding of knowledge and experience to take effect.
47:53 Calvin Dennis: Oh, it would be awful. And we all know that we're salespeople, we have egos, we think our prospects are perfect, right? But oftentimes a deal has complexity. The only reason it works around here is I know that obscure person in a certain department Because I've been here that long. You know what's really fun to support your theory? Again, I've worked here coming up on 20 years, but I was their client for 10. The lady that was the payroll specialist that ran my payroll when I was a client is now the big dog vice president of field operations. And of course, we always joke. I'm like, let's compare our career paths. I'm still an individual contributor. You're a big muckety-muck. Wait a minute. Who did better. But we've been friends for almost 30 years, and we laughed. She's like, oh yeah, I used to run Calvin's payroll when he was a client. But I've had… in the… this last year, I had a sale-ending challenge with a prospect who was kind of funny. I told you I like going out, out to see people. I get this email that they were in the middle of onboarding, right? And it was a… I got an email from the president of this prospect that said, Calvin, We may have to call a halt to this, full stop. We got this issue. We need you to come see us. I was one block away.
49:08 Scott Ingram: I remember when this happened. This is funny.
49:10 Calvin Dennis: One block away, randomly. I pull in and I walk in their conference room. These people look at me like, what in the world? And I said, now listen, it will not… I can't promise it'll always be like this way, but I was at the red light, so here I am. What's the problem? And it was fun to do. They told me the problem and I said, look, Look, let me just sit here in your conference room. You got Wi-Fi, you got coffee. I'm not leaving. We're gonna figure this out. And I got to call that lady that I just mentioned who said, wow, that's an interesting conundrum. Hmm, give me a minute. And we worked it out, and I was able to go back with them before the day was over and say, here's the answer, this will be fine, here's what we need to do, don't worry about it, and validate. And of course the guy was like, would you send that to me in an email so I have it in writing? It's like, sure, no problem. And we solved But had I not known what to do, that particular conundrum would have been sale-ending. To your point. Yeah, I get it. You and I are both talking about this because we believe in it. Not everybody gets this opportunity. And I know our audience, some of them have had to move because they get in bad situations, and I feel for them. Right. It's not always because they want to move. Sometimes it just happens. I pray that people mainly get in the right spot. And can make a career like that.
50:20 Scott Ingram: Yeah.
50:20 Calvin Dennis: Because it sure makes a difference.
50:22 Scott Ingram: I think my point is just be mindful of it, be thoughtful of it. There's often things that are out of your control, or you end up in a situation that I was in. I hit a 10-year anniversary. I was with an organization for 10 years, but it just wasn't going to allow me to continue to grow in the ways that I wanted to. Like, okay, I'm kind of at the end of my road here. I had a great run. It was absolutely incredible. Great company. But it was time for me to make a change and to get on another path.
50:49 Calvin Dennis: We're excited for you because listen, at a 10-year hop, you're certainly not a job hopper. You're at the other end of that, right? Whatever you would call somebody that stays a long time. So you made that… we know, the people that know you, mate, you absolutely made a mindful, deliberate, I want to honor. And we… I know some of the backstory that you honored what you had at your previous spot. You treated them correctly. And not everybody does that either, right? Some people jump and they're kind of butts about it, right? You did it the correct way and we're excited for you. Some people are different. I get it. But man, you can't even figure out where the coffee pot is if you don't stay long enough.
51:25 Scott Ingram: Yeah, I'd say.
51:26 Calvin Dennis: Speaking of coffee, I have one sales story to tell you about coffee. I've cut back a little bit on my coffee, but I was a coffee fiend for a long time. Back when I had the call center, I had the big client that we had that was, you know, 90% of our business or more. I was over at their office all the time. They had these leased office space and they had this couple of coffee makers, right? Back then you had to brew coffee, right? It was before all this one-cup business. And there was a Post-it note on there and they used Starbucks French roast, fine ground coffee that was very strong. And there was a Post-it note that said, use 5 scoops when you're making coffee, use 5 scoops. Everybody I would talk to, we'd all drink coffee and we'd all talk about how terrible the coffee was. It was too strong. And everybody over there would put a little hot water in their coffee to dilute it because it was just undrinkable. So I'm over there one day, they were out of coffee. So I thought, well, I'll just make a pot. And the CEO, a lady who was an attorney, as I recall, came in. She said, oh, you're making coffee for us? I said, well, listen, I'm over here all the time, you know, drink your coffee all the time. I thought at least I could make a pot. But gosh, I'm only using 3.5 scoops because, you know, we all talk about it. This coffee is way too strong and nobody can drink it. We're always putting hot water in it. So I'm using 3.5 scoops. And this lady looks at me with an icy stare and she says, No, use 5 scoops. And it was at that moment I learned that the Post-it note came straight from the top. So I said, well, absolutely, 5 scoops is the perfect way to make this coffee, and everybody knows you should make 5 scoops. And I'm like overdoing it, right, being funny. And she finally cracked a smile and said, okay, fine. I was like, listen, you want it strong, I'm with you, ma'am. Just sign my checks, pay my invoices, right? But that's when you never know How high up the chain the Post-it note comes from. There's your advice, your sales advice.
53:09 Scott Ingram: That is too funny. All right. We're going to keep going with advice and for the folks who are earlier in their careers, who are at the start of a 20-year stint, what advice do you have for them? What do you tell folks that are just kind of starting out?
53:22 Calvin Dennis: Well, here's a main objective. I hope you're in a place where you don't automatically or accidentally take a job in sales leadership. If that's your heart about the matter, if that's where you see yourself, I'm all for it. But just don't automatically go on default autopilot that you're going to sell for 2 years and then be a unit manager and then be a regional manager, because that might or might not be your skill set. Scott and a lot of us that hang around this podcast have made careers being at what we think Scott invented the term intentional individual contributor. You can have a great career, you can have work-life balance, you can have a family life, Because it's not easy. Let's talk about being a unit level or a district manager or whatever you call it. All of a sudden your life and your livelihood is based on what 6 or 8 goofballs do on a daily basis that either you knew about it or you should have known about it. That's a tough road. It's fine if you want to go into it, but just don't do it automatically is my strong advice. I hope that makes sense.
54:22 Scott Ingram: Yeah, absolutely. I love that. I love that. Now I want to give the advice to… maybe this is to Calvin 5 years ago, maybe 10 years ago. What would you tell somebody that is, hey, look, I'm doing fine, like I'm making President's Club every year, but I want to do this top 1% thing. What do you tell them?
54:41 Calvin Dennis: That's a great question I didn't prepare for. I hadn't thought about this much, so this is spontaneous. I think personally, for me, my income had continued to ratchet up, and you know, you get a little more comfortable. You're not desperate maybe anymore. You're making life, but you're not where you need to be ultimately to provide what you want to do for your family, I guess first of all, don't stop. Keep going. If you're in the spot you need to be, keep going. But I will tell you, I have some great friends that I watched do it ahead of me that they pulled me along, right? They're like, what do you mean you're not going to sell X hundred this year? Yes, you are. We would be friends and we would talk very plainly to each other. So wherever you're at I forget the name, but you're going to make… what's the stat? Your income is going to be the average of the 5 people you hang around with. I have no idea if that stat is actually true. It sounds right. But we have a guy in our… remember I told you we don't call it training, we call it sales performance improvement. There's a guy that works for us in SPI, and he says it this way. He, he has these new reps come in for training, and one of the things he tells them is, you're going to go back to your office and you're going to have a lot of people who have been here for a little while. Start giving you advice on how to do it. Here's the way I would do it. Here's the way you should do it. Here's what you should do. He said the first word out of your mouth needs to be, how was trip? And if the first thing out of their mouth is not, well, it was great, let me tell you all about it, he says be careful about taking advice from them. There's lots of people that you can take advice from at your company, and if you're going to take advice from some of them, just be mindful of who you would talk to. So in my case, yeah, I was doing fine. I'd obviously made trip a bunch of times, but there was a time that, that bracketing we talked about earlier about my expectations, my internal expectations just got bigger because I'd hit something, go, well, hmm, okay, that's now the minimum. There was a time when I had to listen to some pretty direct language from some of my friends that have the same job that I do and said, listen, you got more in you. There's another gear, so why don't you get with it? That's true. I needed them to speak into me.
56:47 Scott Ingram: Hmm. Can I translate that and say, I heard 2 things there. I heard one, basically confirmation of what this show is all about. I started this show because I was reading a lot of books and consuming a lot of information from folks who really hadn't carried a quota in, I don't know, decades on average. And I really wanted to hear from people who were really at the top of their game. That's very intentionally where I wanted my advice coming from. So one, Being mindful of the sources of advice and guidance that you're getting, but also maybe being more intentional about who you're surrounding yourself with, who, again, maybe it's the same answer, just putting yourself in a position that you are around people who get to know you well, but who also have the kind of experience and have experienced the kinds of success that you're looking to achieve.
57:44 Calvin Dennis: Yes. And by the way, that's what makes the podcast so fantastic. Nobody is on here trying to hawk a training program or whatever that hasn't carried a bag in 20 years. It's real stuff. You have to be willing. We have even this trip, probably. I mean, or in the last couple of weeks, I've had people because I got to be on stage at our conference and, you know, they make a big deal when you get there and write. I've had people randomly ask me and call me like, hey, How'd you do it? What's that? And they're well-intentioned, I think, but you can kind of tell that not everybody that you know will welcome that advice. So for a seller that really needs to kick it into a next gear, I think you have to be mindful and be willing to receive it, right? And again, I've had people speak really directly to me going, look, Cal, you can keep going what you're doing, but I mean, do you want to be in the great ones? Like, you got another gear there. So, and we're friends enough, by the way, we have a little Teams group with some of the people that have been around for a long time, you know, where it's both nuts and bolts. But within that, there's some deeper friendships that, that's really what this trip is about. It's not the fantastic place we go. That's almost irrelevant. It's sitting around and going, hey, how'd it go? What's going on? How's old Barbara? How's John? How's Fred? The friendships that you make. And it doesn't have to be your own company. It can be the Sales Success Society or your local Chamber of Commerce. You've got an accountability group somewhere. And if you're at a small company, you may have to work to find them, but you gotta be willing to let people speak into your life.
59:09 Scott Ingram: Yeah. I think for me, that's a huge goal of what we do at the summit every year is bringing this caliber of people together. And I think you're yet another testament to… this is my very favorite conversation to have, is somebody who listens to the podcast, has gotten involved with us. And has kind of seen the art of the possible and said, you know what, it's going to be me. I knew that you and I would be having this conversation one of these days. And here we are around the group.
59:39 Calvin Dennis: Just so you know, we call this what? Podcast worthy. You got to get yourself and you become podcast worthy at one spot. I don't know if you want to publicize that term, but yeah, I love it.
59:50 Scott Ingram: I love it. No, it's strong.
59:51 Calvin Dennis: It's true. And that's why you and I didn't want to do this. And you wouldn't have anyway if it was an asterisk like, oh, you're close. Let's round up. Let's take it out to the 6 decimal places. No, that wasn't it, right? It was, we're going to wait until you make it. But one other thing I would say is kind of answer this question about advice is you do have to own it. And now we talked about this earlier, but my boss, I don't know if she made it up or she got it from somewhere, but she says, look, I can give you a job, but I can't give you a career. That's on you. And that's made all the difference, right? It's a great world whether you sell services or ball bearings, as long as it's noble and legal, I mean, everybody makes life better.
1:00:31 Scott Ingram: Yep. Calvin, this has been awesome. We have covered a ton of ground. Is there anything else that you had hoped that we would talk about that maybe we didn't quite get to?
1:00:42 Calvin Dennis: Well, I doubt it. I would like for everybody to know, and I'm certainly open to conversation about it, I want everybody to know work consumes a lot of our brain, right? It just does. But real life is a lot more important. And I just want to tell you that my personal feeling is the Bible is a reliable source of guidance for your life. And I would encourage everybody, God can handle your questions or even skepticism. And for me, eternity is a lot more important than what we do for a few decades on this earth, which is but a vapor. So I would encourage everybody, and I know sometimes on these podcasts we've had people talk about their faith a little bit, which is really exciting. I would encourage everybody to think about that for their life and their family. That's in the end of things a lot more important than some of what we do at work anyway.
1:01:34 Scott Ingram: Yeah, thanks for sharing that, Calvin. And then like we always try and do, let's figure out a way to make this actionable. What would you challenge our listener to do over the course of the next 1 to 2 weeks to improve themselves and improve their results?
1:01:47 Calvin Dennis: I would say take down the motivational poster off your cube and just get to work. Put your head down for 2 weeks, 3 weeks, however long it takes you in your particular role to notice, and see if that doesn't make an incredible difference in what you get started. Because once the flywheel starts… and it might be hard in the beginning… once it starts, I believe you'll be more motivated then to keep it going than when you started.
1:02:11 Scott Ingram: I love that, Calvin. This has been awesome. I knew it would be. Thanks for taking the time, my friend.
1:02:15 Calvin Dennis: Listen, you're great, Scott. And here's a plug: come to Austin in October. The summit is 2 days of this kind of stuff. Lots of great people give us lots of great things to think about at the summit, and it's worth every ounce of your time.
1:02:29 Scott Ingram: Awesome.
1:02:30 Calvin Dennis: Thanks for listening to the Sales Success Stories podcast. To be sure you never miss an episode and for an invitation to our Sales Success Community powered by Influitive, subscribe to our newsletter at top1.fm.

