Much has been said about sales as a profession. Whether you’re a seasoned veteran, a rookie entering the field, or even just considering becoming a salesperson, there’s no shortage of opinions and articles on the world of sales. Though some of these opinions may not paint sales in a favorable light, if you have the right mindset, a career in sales has the potential to change your life!

In this special episode of INSIDE Inside Sales, Darryl is joined by globally recognized sales leader and author, Scott Leese. Darryl and Scott discuss how the importance of commitment, mindset, and self-awareness can drastically change and improve your career in Sales. Scott also shares how his career in sales changed his life for the better, as he delves deeply into his early struggles dealing with illness and addiction. Learn how he tackled his role head-on without a “Plan B” and through will and determination found ways to excel in sales, on this episode of INSIDE Inside Sales!





Host: Darryl PraillVanillaSoft

Guest: Scott Leese, Scott Leese Consulting and Surf and Sales


A Career in Sales Can Change Your Life

Darryl Praill: How is everybody doing today friends? Or should I say family? Cause you know what you really are family to me. Hey, here’s the thing, I got to thinking. I got asked a question the other day. It was a good question. It was one of those questions where it was somebody young and they actually said to me, “Darryl, do you regret your career choice?” And I was like, “Oh, that’s a good question.” That’s a good question.

Darryl Praill: And so, I went on to say, what career choices are a fluid, you know, and you gotta figure out who you are, and then you got to… You either have to embrace your choice or not. And you’re gonna make… You’re gonna grow as a person. And that means you need to be able to adapt to your growth. So I use the example of me. You know, I’m a by education, by my degree that hangs on the wall at home, I’m a computer programmer.

Darryl Praill: I’m not a marketer, yes, I’m a CMO at VanillaSoft, but I’m a computer programmer. But I’ve been a marketer for many years. I did sales for many years. I’ve been a VP of Sales and of course VP of Marketing. And, but I began life as a computer programmer, right? So for me, it was a series of events, series of decisions. I was really good at programming in high school, and I liked it. It was satisfying. It was a logical, obvious path, and that’s what I went to school for.

Darryl Praill: And maybe sometimes I didn’t give all I should have when I was at school because it came so easily to me, I kind of fluffed off a lot of the classes. I probably could’ve got better marks if I had tried. I relied upon my own talents that were just innate. So I didn’t learn discipline, shall we say in high school or in university because I just had talent. And then, I got out in the working force and I liked what I did, I was coding. Often, I was on site doing custom-coding for certain clients.

Darryl Praill: So that had given me a variety different… And I recognized early on, I really liked that variety, that variety was cool. And then I changed jobs and careers. And when you’re young, you don’t really know how to, you know, qualify another a job, it’s more money, okay, I’m in. And then I’m sitting at a desk all day, and all of a sudden, I’m like, “I don’t like sitting at a desk all day.” And then before you knew it, I was like, “I don’t wanna go to work in the morning.” So that’s about four years into my career, and I’m like, “Is programming for me?” Holy smokes, and I had to figure it all out.

Darryl Praill: So eventually, I took a job as a sales engineer, and that’s kinda how I got exposed to sales, first and foremost. And I was the guy they would come to and say, hey, make the product do whiz bang things to impress the prospect, answer all their questions, so they know it’s very capable. You’re the sales engineer that’s what you do. And I’m like, “I’m in, no problem.” And so it leveraged my skill sets. It leveraged my skill sets, but in different application.

Darryl Praill: And, that got me exposed to product, to the product side. I was still in high tech, but I was now selling as well. And so I liked all this. So then they said, “Hey, you should do product management, “where you actually define the product roadmap.” And then they said, “Okay, that was great, “you did a good job there. “There you should do product marketing, “take it to the market.” And then they said, “That’s great, there you should do marketing.” So I did some marketing for a while. And then they said, “You should do sales “cause you’re really good at the messaging “and the audience.” So I did sales.

Darryl Praill: So here I am, I’ve done my full journey. What can I tell you? What did I tell this young person who asked me that very question, “I’m I happy with my career decisions?” And I can think of this, sales and or marketing both, both, both of those careers cause they’re really revenue, revenue, the pursuit of revenue, changed my life. I’m very happy at what I do. I would have been bored stiff as a computer programmer, a good computer programmer, but bored stiff. I love my job, I love my life, I get up every day with a bounce to my step. I work with great people, and I wouldn’t change this for the world.

Darryl Praill: So, I ask you right now, are you in a situation to love your job? Can you let your occupation, can you let the job of sales change your life? Or are you still not quite sure? Well, you know what, that’s a legitimate question.

Welcome Scott Leese

Darryl Praill: So I said to myself, who can I bring on to help talk about this journey, about how sales can change your life? And I thought, well, but I looked at, maybe a guy who’d had six startups where he was a sales leader. And along the way, he’s won over three awards as the top Inside Sales leader at the AA-ISP. He’s had two roles where he’s founded organization. He’s a best selling author, and best of all, a strategic adviser to a whole bunch of people. Well, I said that guy, that guy could talk to my guys, my crew, about how sales can change your life. Everybody, welcome to the show, Scott Leese. How you doing today, sir?

Scott Leese: I’m doing great, Darryl. Thanks for having me.

Darryl Praill: Now if you’re not watching the video guys, if you’re on the audio, Scott’s got a big ass grin on his face. And he’s got a wonderful picture behind him of a surfer walking down the beach carrying his board, and footprints in the sand the whole thing. And I think that’s kind of symbolic because we know Scott, not only is he part, and he’s got his own gig Scott Leese Consulting, which by the way, is annoying cause check this out. on G2, he’s got 4.9 out of five stars, so that tells you something. And then I mentioned who is the best selling author, so he wrote the book, “Addicted to the Process” 4.9 out of five stars. Everything this guy does is 4.9 out of five stars. But also, he’s part of the Surf and Sales Summit. I think he’s teamed up with Richard Harris for that one where they go down, I think it’s Costa Rica this year, I don’t know if it’s there every year, but they go somewhere nice and tropical, where there’s some surfing and then there’s some selling to physically grow the skills. So I think this guy’s got it all figured out. Have I captured the essence of your pedigree and your lifestyle, Scott?

Scott Leese:  You got it man. I’m gonna hire you as my agent. That was a good intro.

Darryl Praill: But, you know, I do marketing on the side just saying, you know, VanillaSoft’s just a part-time gig, you know, I’m just kidding you. Alright, so we talked about this Scott, in the green room and you were so passionate when you said, “Sales can change your life.” So let’s just open-end this conversation for those who are listening. Why are you so passionate about sharing this message, about talking about the impact this career can have for you? I mean, I’m gonna guess you’ve seen people not experience that or people second guess it like, talk to me.

Scott Leese: Well, first of all, it comes from the fact that those changed my life in a massive, massive way. I never studied business, I never, I actually never had a job until I was out 27 years old, that didn’t involve playing sports or coaching youth sports. I was an athlete all through high school, played four sports. Played two sports in college. I had a top 10 College tennis team, top 25 college soccer team, and you know, went to grad school and kept playing Semi-Pro soccer in Arizona, just had nothing to do with business or making money or anything like that. Wasn’t even on my mind. And I got extremely sick at age 23 years old. I spent the better part of the next four years in the hospital fighting for my life. I got really bad autoimmune disease, ulcerative colitis, had a scare with colon cancer. I’ve had nine major surgeries. I have no large intestine. I have been through the wringer.

Scott Leese: And during that four-year period, I also got addicted to opioids dealing with pain. So by the time I’m 27 years old, I haven’t, you know, had a job, I haven’t worked, I don’t even remember the things that I studied in school or grad school, I have just kicked drugs, I’m trying to rebuild my body and strength back, and I picked sales because it was the only thing I could think of, where I could make up for lost time. And I could elevate my income to a place as fast as humanly possible. It was a complete strategic decision on my part, and it’s just incredible for me and for my family to see you know, how it’s transformed me, you know, as a person and as a leader, and the things that it’s enabled me to do for myself and for others. And so I’m passionate about it because I’ve seen the miracle that it works and I’ve lived it and I want other people to know that that’s possible and anybody who’s been through some shit, you know, or going through it right now that there is a way out and sales can be that vehicle.

Sales Can Be a Platform

Darryl Praill: What I love about what you’re hearing right now guys, is that Scott has been really vulnerable and really transparent. He’s putting it out there. And that’s what the show’s all about. That’s what we should be talking about, right? Scott, you made a comment. And I’ve heard you describe it this way before in the past, where you said, “Sales can be a platform.” And my emphasis is on the word platform. For you to become extremely successful, you said it here just now. And it can change your life. And of course, that’s exactly what you just described. When you say that, what do you mean it can be a platform?

Scott Leese: Well, it is a place where you get to really be your true self, and let it out and in a safe environment. It’s difficult for us I think, walking around in public, to be as confident as we wanna be. You know, the things that we dealt with growing up as kids or the insecurities that we have, or, you know, if we had rough upbringing or childhoods, those things, it’s difficult to kind of overcome those things without a lot of work, a lot of therapy and stuff like that, but when you walk into your job as a salesperson, you can be whoever you want. The people that you’re calling and talking to you that day, you know, they don’t know if you’re the number one salesperson in the company, or if it’s your first day on the job.

Scott Leese: And there was something very empowering about that for me when I first got started. And I was able to use some success in sales to really work on my own self-esteem, my confidence, my decision making, the risks that I take, and in time, as I moved away from an individual contributor towards leadership, it gave me the opportunity to, you know, kinda pay it back and it’s one of the reasons I’ve continued to do what I do is I love talking to salespeople who are early in their career and trying to give them the tools that work for me, so they can have the opportunity to, you know, feel better about themselves, to get out of some financial holes that they might be in and just transform their life.

Scott Leese: And it’s difficult for me to imagine too many other professions that allow you that platform to use your word that would allow you that platform to do just that. And you know, my dad’s been accounting professor for 40-something years at the university. I don’t know that he has that same platform, he can make an impact on kids, but he’s not changing the game, you know, financially for himself, for his family, and that kind of thing. And so it just seemed like the perfect vehicle, for me to be able to, you know, really in broad, broad strokes change the entire course of my life, and it’s led me to where I am now.

Darryl Praill: You know, Scott really hit on something here, that I wanna maybe drill down on a little bit just before we go to our break. And that is sales unlike so many other professions out there so if you’re sitting right now going, “Maybe the grass is greener over there “and this other occupation, other areas “or I’m not so sure.” Sales is, you know, using the word “platform”, sales is the one platform that you have all these resources available to you, not just the resources. So you’ve got 1000 sales books out there, just like Scott’s you know, best-selling publication on Amazon plug, plug, go there now, order it. You’ve also got a ton of YouTube videos where they just share all this stuff. You know, Victor Antonio, is an example, where he’s got massive followers. He’s just one guy. Just sharing sales. And you can watch him whenever you want to. You got LinkedIn, where you can go and just follow the cats, the guys and the gals that really resonate with you, who you identify with.

Darryl Praill: And read their posts and watch their how-to videos, and then read the engagement in the comments. And you can talk, you can have a dialogue, you can challenge, you can push back, you can ask for more details. And all of that is a community. Sales has a community, unlike anywhere else that you can support one another. For Scott to come out and say, “Man, this is my life, “this is my story.” You know, you guys didn’t turn off, in fact, you probably listened to more. That’s what the platform’s about. That’s why sales as a profession, as an occupation, as a community, can truly change your life. And Scott’s right, you know, if you develop your skills, you’re gonna make a lot of dough, you can’t make some real. Scott made the story. I had to start my career at 27. So how do I catch up? And catch up just doesn’t mean in my career, it means in my income, right? And my accomplishments. So he did all that. Now, that’s setting the stage. We’re gonna take a break and I wanna talk about all the tactics you need to do, so that, it will in fact, change your life. We’ll be right back.

Commitment Levels – There Is No Plan B

Darryl Praill: Okay so, the first thing I wanna talk to you about is, I guess, let’s talk about commitment levels. I question sometimes whether everybody is truly committed, or they’re kinda got their toe in the water and they’re just, they’re tryna feeling it out. Talk to me. I mean, does commitment matter? Can I half-ass this or not?

Scott Leese: No, I don’t think you can half-ass in sales at all. You’ve really got to go all in, especially if you’re just getting started, it can be terrifying. When you’re first getting started, you know, the fear of picking up the phone or getting rejected by, you know, 50 to 100 people every single day. If you’re not really there, if you’re not really putting in the time to improve your skill set, it’s not gonna end well. I used to tell people, it’s like having one foot on the boat and one on dock, and that situation is not gonna end well. So there’s never been more resources available to you than right now, in order to become an effective successful seller. There was no podcast when I was starting 15 years ago, there was no YouTube videos teaching you how to sell. There was none of this stuff. There was no LinkedIn.

Scott Leese: You have so many resources available to you now, that it should make it easy for you to get started, and get over the first couple of humps, but you’ve gotta go all in with it. You’re not gonna achieve the level of success that you really want and deserve by kind of thinking you’re gonna give this sales thing a try and if it doesn’t work, you’ll, you know, go back to doing this other thing. That’s not the way to do it. Go all in, leave yourself, you know, no alternative. You know, I had been asked before, what was I gonna do if sales didn’t work out? And I had no answer, none. I had no idea whatsoever. There was like no option for me. I had to make this work. And I think that level of focus and commitment is really what starts to separate really successful salespeople from those who, you know, are kinda mediocre and those who wash out of their profession.

Darryl Praill: So I have a question right now to the crew listening. How many are freaking out right now? And how many of you are high fiving? ‘Cause Scott said something, “You gotta make, “you gotta go so far in, “you gotta commit so much that there’s no plan B.” Right? So many are now going, “Yeah, I’m in.” And there’s gonna be a lot of you going, “Well, I kinda like a plan B.” And, but your point is right. When there is no plan B, you are in fact, forced to make plan A work. There is no other option. I’m curious, so you started at 27, how long did it take you to figure out that you had to fully commit? Like, did you start there because of, you know, the history of your health and the challenges you overcame? Or did you also kinda go in there kind of like, “Well, I’m gonna see if I like this or not.” Like when did that transition happen for you, you were like all in and committed.

Scott Leese: In all honesty, it took me about a week. You know, I had made the decision to go in sales and this was the way that I was gonna get it, but like the very first day that I started, we had like, a couple hours of training. And then in the afternoon, we got thrown on the phones. And when I mean thrown on the phones, I’m talking to old school thrown on the phones, like, I didn’t have any leads, it was go figure out who to call, there was no script or sales pitch, there was no materials, nothing. And I got, you know, punched upside the face that day, and was questioning how the hell am I gonna make this work? And, you know, was reminded that night by my wife, like, remember, there is no backup plan here. And, you know, her saying that, in addition to me kinda telling it to myself, but her saying that to me, just like shook me kind of to the core, and then a few days, you know, I started working a little bit harder and just reminding myself like, “What is there to be afraid of here?”

Scott Leese:You know, I have probably already defeated the toughest opponent that I’m ever gonna defeat in my life. So why am I worried if you know, if I can’t be successful in sales? Or why am I worried if this person is going to tell me “no”, or hang up on me. And you know, I got my first sale my first Friday, and it was 9:30 at night in California. And I had called somebody in Hawaii, cause I was taking advantage of the time change. And I closed that deal. And this, you know, light switch went off, whatever you wanna call it. And that switch was not like, “Oh, this is you know, the most amazing feeling, “this is the best job in the world.” It was, holy shit, the only reason that I just closed this deal is because it’s Friday night, and it’s 9:30 and in the office still.

Scott Leese: And that light bulb for me was, this is how I’m gonna win. I have no choice but to outwork everybody else. All these other people in the office have experience or education for this game, I don’t have any of those things, but you know what I have, I have determination, I have a work ethic, I have fought for years to even breathe this air and be in this office, so I respect the opportunity in front of me. And that was the light bulb, you know, I’ll just outwork everybody, and that’s what I started to do.

Series Of Small Decisions

Darryl Praill: Now, I may be reading into this, well, almost what I’m hearing you speak to in that narrative, is you made a series of decisions, that got you to that point. Did that pattern continue over your sales career? Is that, you know, how do you make the right decisions so that you’re moving the ball forward, so that sales does, in fact, ultimately change my life? ‘Cause there’s a lot of people right now listening who wanna be just like you. So what do they need to do on the decision making front?

Scott Leese: Well, I just think that life is sort of a series of small decisions, and the more successful, small decisions you make, you end up going in kind of the right direction and that direction leads you to happiness and success, hopefully. And so I came up with these little, you know, super micro goals and choices, right? I have a choice today to get up early and get to the office by 6 a.m. So, you know, it’s only nine o’clock in the East Coast so I can, you know, get a little bit of an advantage. I have a choice today to go out to lunch with some of the folks in the office who I know are gonna go have a pitcher of beer, or, you know, I can go somewhere else by myself and kinda decompress and have some quiet time.

Scott Leese: Or I can work through lunch. I can stay late, or I can go home. I can come in on the weekend. These are all things that I did when I was first getting started and my life was structured in such a way that it allowed me to do that. I didn’t have have kids yet. My wife was in grad school, so she was studying and working like non-stop. So I had all this downtime, and I was like, I chose to pour myself into work during my downtime because I knew again, I had to make up for lost time. I needed to play catch up, I’m not gonna be able to support my wife and I on a $30,000 base salary in San Francisco, it’s just impossible. So these small choices, you know, I’ve made similar decisions as I’ve gone about my career. A small choice whether to stay or go from a particular job. A small choice to stay as an executive or move into leadership. A decision to stay in San Francisco or move to Austin.

Scott Leese: All of these, we build up these decisions sometimes and make them seem like the be-all-end-all of the world, but the reality is, you know, they’re not. That every decision is just one little stepping stone for you to kind of follow the path that you’re meant for and that you’re carving out for yourself. And, you know, just to go back to what I said before, like, if you make the wrong decision, it’s not the end of the world. You’ve probably been through something worse before. So stop being paralyzed, you know, and this like paralysis, and by analysis kinda thing. Like I just don’t, i don’t resonate with that at all. You know, I practiced making decisions quicker and trusting my instincts and being able to live with the results of those decisions later on and knowing that if I made the wrong one, I’ll be able to recover and it’ll be all right. If I made the right one, great, off I go, and I stay on the right path.

Darryl Praill: So I guess I’m challenging the audience. Are you making those micro-decisions? I love that statement that Scott talked about. That are causing you to not, to miss your goals, right? Life, your career, it’s a series of micro decisions. Scott set goals. Are you setting goals? That goal maybe I wanna do X number of calls in the next hour. That is a very near term goal. Are you setting goals? Are you making the right decisions?

Extreme Level Of Self-Awareness

Darryl Praill: Now, lemme ask you this, Scott, you talked a little bit about do I become an executive? Or do I, you know, stay as a rep? How did you navigate the career path? Do you have any advice in a nutshell for those who want the sales career, but they want, no they wanna climb the ladder? What feedback, what guidance do you have to the nurture that dream and that aspiration.

Scott Leese: You know, this is probably not what people are expecting to hear, but the first thing that comes to mind is, you need to develop an extreme level of self-awareness. And what I mean by that is, you need to know your strengths and weaknesses. And my opinion, you need to continuously put yourself in a position that gives you the greatest chance for success. So an example of this is, I am not a very patient person. This is something that I struggle within all areas of my life. I kind of operate with like extreme sense of urgency all the time. So for me early in my career, I went into more transactional sales environments because I felt like I needed that, that high rev, that constant stimulus. I can remember early in my career, I had the opportunity to go work for Chevron.

Scott Leese: And it was gonna be like 18 months sales cycle, you know, global sales environment. And I mentioned it to my wife and she kinda laughed at me and she was like, “You are, you’d be horrible at that.” And she’s right. Like, I don’t have the patience for that. I just don’t, I can’t come home and be like, “Oh, sweet, I moved the prospect, “you know, from stage one to two out of 100 stage process.” Like that wasn’t gonna work for me back then. You know, and I think sales reps screw that up a lot. You know, so be self-aware of your personality. If you’re very relationship-based and nurturing a longer sales environment might be better for you. If you need instant gratification and you know, the opportunity to close deals every single day, a shorter sales environment is gonna be better for you. If you really get more satisfaction out of teaching other people and watching their success, and you don’t care much about, you know, the credit going your way, then leadership might be the right thing for you.

Scott Leese: But if you’re concerned all the time about, you know, being applauded and getting awards and making sure you get the pat on the back, like, then leadership might not be the right thing for you. If you have a hard time being patient while you teach people, then leadership might not be the right thing for you. As you move up in your career, your hours and your stress are going to increase, most likely, right? There’s a different toll that being an executive at a, you know, technology company, probably any company, then you know, being just an individual contributor and a frontline worker. So, know what you’re getting into and know who you are and put yourself in environments that give you the greatest chance for success.

Darryl Praill: So let’s recap here. What I’ve heard Scott talk about is that sales can be a… It can change your life as it did for him. To do that though, you need to have, you need to commit. You need to make, you need to set goals. They can be micro-goals or major goals, but you need to set goals. You need to have the right mindset. So there could be some rejection along the way, but that’s okay, cause I got the right mindset, I expect that. You need to be self-aware of your strengths and weaknesses. If you’re self-aware, you don’t put yourself in bad situations, and in fact, you create a career path for you, that works for who you are, all right. And then finally, you have to basically, you know, lean into the community. Lots of resources available to you, take advantage of that. Best advice though, there is no plan B. If you’re gonna do this, do it. Stop hesitating, jump all in. With that my friends, we’re out of time.

Darryl Praill: I would suggest you do this everybody listening, go to website, go to, look for any excuse to join them, to join them and develop your skill sets and oh my gosh, sand, sun, surfing, one-on-one coaching. This is brilliant, the guy’s clearly got this all figured out. Scott, best way to reach you, is at LinkedIn, website where else, you tell me?

Scott Leese: LinkedIn is a perfect place for me to connect with everybody. I obsessively check my messages there. So shoot me a note and I will get back to you for sure.

Darryl Praill: Alright guys, that is Scott Leese. Rockstar, he’s 4.9 out of five. My name is Darryl Praill, This is INSIDE Inside Sales. We’ll talk to you soon.