Sales Hustle is now Sales Transformation
July 1, 2021

Episode #113 Surf and Sales with Scott Leese

Joining Collin Mitchell in this episode of the Sales Hustle Podcast is Scott Leese. Let’s hear from Scott as he shares about the challenges he went through in his life that made him appreciate every opportunity, which later led him to share what he loves talking about the most: Building a sales org and how to be a VP of sales.

Scott Leese is the CEO and Founder of Scott Lease Consulting Inc. that works with both domestic and international companies on sales strategy, process, people, pitch and more. He’s also the CEO and Founder of Surf and Sales which provides an alternative to standard sales conferences by providing deeper learning, meaningful relationships, and an experience that will transform careers and business. 

He has a new book called More Than a Number: The Modern VP Sales Playbook. A powerful playbook for sales professionals that let Sales Directors discover how to prepare for the next coveted role; let VPs of sales find out how to thrive in high-pressure positions; and give CEOs/Founders the strategy to empower their VP of Sales for growth. 

You can find out more about Scott Leese through the following links below.

You can get a copy of Scott’s book ‘More than Number Modern Playbook at

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Episode 113 - Scott Leese

Welcome to the sales hustle. The only no BS podcast, where we bring you the real raw uncut experiences from sales makers across various industries. The only place where you can get what you're looking for. Uh, your sales game today's episode is brought to you by sales cast sales cast helps sales professionals transform the relationship building process and win their dream clients.

[00:00:30] I'm your host, Colin. What is happening? Sales hustlers. Welcome to another episode. I'm super pumped to have Scott Leese here today. Uh, he's a six time sales leader, three times founder, three times. Author has a new book and we're going to be talking about what he loves talking about most building a sales org, and how to be a VP of sales Scott.

[00:00:51] Welcome to sales hustle. I'm excited to be here, Colin. Thanks for having me. Yeah, man, for those who maybe don't know you and have been sleeping under a rock, why don't you just, uh, give us the short version of your sales story. A short version, um, got into sales, uh, around 20 years ago or so roundabout way did not study sales or business at all.

[00:01:12] Studied psychology and religion played two sports in college for four years. Went to grad school, got a master's degree in learning, um, learning theory and educational technology. And, uh, finished my master's degree. Got super sick at 23 years old, spent four years in the hospital fighting for my life.

[00:01:30] Nine major surgeries, four life-saving surgeries. Two of them emergency got addicted to opioids, had to kick and get healthy off of all this stuff started my sales career at 27 years old, a $30,000 base salary in San Francisco bay area. You know, making 150 calls a day, just like so many others. And, um, you know, quickly moved into sales leadership, and then building and scaling sales orgs as a VP SVP of sales for a long time.

[00:01:58] And, um, started a consulting business about four years ago, but a year and a half ago, um, decided to go full-time and been doing that ever since and run a couple of other businesses. One of them is called surfing sales. It's a sales conference down in Rica and where's the podcast that Richard and I, Richard Harris is my co-founder.

[00:02:19] A run called the surfing sales podcast and also started a business during COVID called Thursday night sales. It's now the world's largest and longest running virtual sales happy hour in the world. I'll pause there. That's a yes. Wow. I'm in the hospital for four years. That must have been brutal. Yeah, it was just, uh, I mean, what's interesting is you kind of forget.

[00:02:46] Some of the things that you went through when you were going through that, some of the way that some of which I think, you know, you repressed some of those memories and the pain, some of it, I was too sick or too built up to even remember shit that was going on, you know, the other day, uh, I spent some time with my parents for the first time in a year and a half since COVID.

[00:03:04] And my dad was telling me the story about, you know, when the priest came and talked to my mom, because they didn't think I was gonna make it. And my mom broke down and I'm like, I don't think I've ever heard this story before. Is that why, you know, You were there, you were, you know, like, damn I didn't, I didn't know that.

[00:03:19] So yeah, no fun at all, but you know, you don't go through something like that and not have it, uh, change you, not just like physically and emotionally, that can hopefully not in a negative way, but in a positive way. And I emerged from that experience, you know, with an extreme sense of, um, appreciation for every opportunity that we have.

[00:03:42] Uh, as well as a strong sense of urgency and that sense of urgency to get shit done, as it says right behind you and get it done quickly, you know, I think has been a bit of a superpower for me. So yeah, I was going to say that I was going to say, I imagine that that experience has really fueled your drive to be success.

[00:04:04] Yeah, 100%, you know, I, my health is perilous, you know, even today and just will always be that's just the way it is. So I'm sort of always operating under this premise of like, I feel good today. So I might as well get as much done as possible. Cause I don't know how long that's going to last. Right. And so that fuels me to create and be productive.

[00:04:29] I have a very short filter from idea to action. You know, if something comes into my head, boom, I act on it, you know, pretty quickly. And that's how I've, I've done stuff like, you know, get into sales, leadership quickly. The VP of sales, you know, move on when I, my time was done at a particular place and go start the thing again, you know, start writing books.

[00:04:50] I've written three books. Now start getting into investing. I'm an LP in a fund. I've done some angel investor. Uh, I have four companies that I run my consulting business, surfing sales, Thursday night sales, as well as a rental property company. I've a bunch of residential real estate properties. So I'm just always, I'm always moving.

[00:05:11] You know, my, my wife jokes that I have two speeds, full speed ahead and dead stop. That's it. There's no, no in between. And I think that comes from, you know, this sense of urgency and knowing what it's like to, you know, have nothing and lose everything. And wanting to make the most out of, you know, the time that I, the time that I have.

[00:05:31] Yeah. Wow. Uh, incredible story. Um, did, did didn't expect that? So, so, but I'm glad we spent a little time, you know, uncovering some of that a little bit and, uh, You know, so I want to shift a little bit now and just tell a little bit about the book, like how to be a VP of sales is kind of the context of the book, the good, bad, and the ugly, as you've mentioned before we hopped on here and maybe there's some seven there, they might talk some people out of wanting that kid, right?

[00:06:01] Yeah. Yeah. It very well might, you know, part of, part of what I, I felt compelled to write about. The, the experience as a VP of sales in particular at early stage kind of SAS startup companies, um, there's no real playbook or guide for how to become one, what things you need to know in order to get the role, uh, what do you need to do once you're in there?

[00:06:29] You know, how do you need to communicate with people? There's just no playbook for it. Um, and having done it, you know, half dozen times. I felt like I was positioned pretty well, uh, you know, to, to shed some light on the, on the subject. Um, I get pretty, I'm pretty Cammie, I'm pretty direct and like open and candid, you know, person.

[00:06:50] So, um, there's a lot of info in there. That's like, are you sure you want to do this? Because here's what it's like, here's what you're giving up. Here's what you should expect in terms of how you're going to be treated. Your neck is in the guillotine all the time. Right? That's the way it is. You got a 16.

[00:07:08] Life expectancy in this particular role, you lose the stuff that people don't want to talk about. Don't want you to know about taking that right? A hundred percent. Yeah. You know, I talk about stuff like, listen, when you're the first DP at a company and you take them to 20 10, 20, 30 million, you know what happens all the time?

[00:07:26] What happens all the time is you get topped off because they bring in somebody else. Who's taken a company to a hundred million or taken a company public before. And you know, you get. Sent sent packing a little bit. There was a I won't name names, but there was a unicorn announcement yesterday and they were original.

[00:07:47] VP of sales is a friend of mine. And, um, you know, they did a very good job building the foundation and getting them to their first, you know, 10, 20 million in error. And then they got topped off and they've been sidelined ever since. And the, you know, new CRO person. Is getting all the credit and that earliest VP didn't get the credit and I'm having conversations with them.

[00:08:11] Like, you know, Hey, this is the game a little bit. You've got good doc options. You don't camp can't hold it against anybody. Like you got to understand this is the game and this is how it's played. And so my mission is less to like disrupt the game and more to educate people. On what it's really like. So there's no gotchas, there's less surprises, right?

[00:08:35] So people who are in these leadership roles can be a little bit more emotionally protected from everything what's going on. Now, did you have a similar experience like this yourself? Of course, multiple hold time, multiple times over all of the things that I write about are born from experience. You know, I look, I was at a company as a, as a head of sales that, uh, Mid ish.

[00:08:59] Nine figure exit opportunity said no, because they thought they could go bigger and it didn't ever sell. I took a role. I was a VP of sales and I worked for a tyrant CEO who whipped me like a race horse and, you know, would never sign up for that kind of program. Again, I picked a company that I thought the product was ready, you know, and good to Brendan to be shipped.

[00:09:24] And we were going to be able to do this, turn out the product. Wasn't right. And I went there too early and I had to quit and get out of there. So I've made, I've made almost all the mistakes that you could possibly think of. I've also gotten it wrong right. Many times and learn from each particular place.

[00:09:40] Right? I mean the last company I was the SVP of sales at is worth multiple billions of dollars right now. And, you know, I hit a home run and I had a couple nice, smaller exits in between some of those missteps and this home run. So. You know, just sharing my experience about, you know, how to position yourself, to land the role, how to interview for it.

[00:10:03] Uh, what relationships matter, what kind of foundational things you need to build to ensure that you can scale how to recruit, how to build your brand. In the meantime, how to protect yourself. I talk about all these things and, and the, the name of the book is more than a number and, you know, pretty, pretty obvious, but it's trying to remind people that our values.

[00:10:24] Is not just our productivity. Like we're more, we are worth more as humans and sales leaders, then your ability to hit this ever increasing target though. That's, that's what it's all about. And kind of who the target audience is, is anybody who's interested in maybe being a VP of sales, you know, one day.

[00:10:44] And there's a whole section in there for founders talking about how founders should look at their relationship. With somebody in the VP of sales role in order to make sure it's healthy and successful as well. So, yeah. Yeah. And so any, any tips for trying to avoid getting into a situation similar to some of the ones that you explained there for somebody who's maybe, you know, looking at VP of sales positions right now?

[00:11:10] Like what are some things they should look for? Yeah. So one of the things that I have learned over the years, The complexity of the interview process and the length of time, it takes them to make a decision is a reflection on how they operate internally every single day. Meaning if I get put through the ringer and have eight different interviews, and this process has been going on for six weeks and they're still trying to make a decision to present me with an offer to me that tells me they can't make up their fucking.

[00:11:47] And every decision that we go to make, if I was to work, there would be an absolute grind and it would be agonizing. Right. So I look out for, for that. What does that interview process, you know, look like? Um, I'm very keen now on the founders' backgrounds and what they're looking to do. So I had conversation during the interview process once where founders told me, you know, We're looking to get this business to, you know, 30 million in revenue or so, and sell the business for a hundred to 150 ARR.

[00:12:23] We're not trying to build some big, huge billion dollar thing. I didn't do good enough diligence. Cause what I didn't know is this founder's parents were very, very loaded and I didn't put two and two together that like a hundred and something million dollar exit for this particular founder, what it seemed like.

[00:12:44] To him and his financial situation and his family. And like I, at one point made a joke. I'm like, if you sell a business for 150 million, your dad doesn't give you any kind of credit. It's like, you're not even a success. Whereas me, this would be the first million I ever make. So I have urgency around. So thinking about that in your stage of life, right?

[00:13:06] Like if you're trying to make your first million and you're looking for a quick win, it might not be the best idea to hook yourself up to the wagon next to somebody who wants to be in this for 20 years and create this legacy, you know, $50 billion kind of organization or the opposite of that. Right. I turned 44 years old and in, uh, another couple of weeks and another week, And uh, if I was going to go back in a CRO VP of sales kind of capacity, I'm now no longer interested in somebody who's going to try to do a quick flip, where I make a million dollars.

[00:13:41] I'm now much more interested in somebody who's trying to build as large a business as humanly possible. So I can make generational life-changing wealth, not just for me and my family, but for my kids and their family and all this kind of stuff. So I'm trying to take a bigger step. I didn't understand those dynamics 5, 10, 15, 20 years ago.

[00:14:04] And I understand them. So I'm looking out for, you know, things like that, negotiating things. I can't tell you how many VPs of sales don't understand options and equity don't get any or get very little amount. So, you know, I think I saw you post something recently kind of breaking down some, some examples of that.

[00:14:26] I just did a little bit of like crappy napkin math, just to kind of get straight to the point, you know? And, um, the point was, you've got to have a sizable chunk in order for you to make, you know, high six for, for it to really matter. And either, you know, there's like, it can matter in the sense that it can buy you a new one.

[00:14:50] It can matter in the sense that it can buy you a new house, or it can matter in the sense that it will change the lives of you and everybody in your family for at least a generation. And you know, too many people, whether they're AEs or sales managers or VPs get one little stock grant of a couple of thousand shares.

[00:15:12] And they're like, I'm going to be a millionaire at this company. No. Yeah. Um, and so I'm just trying to, you know, do my small part to help people understand some of how that works. Yeah. Yeah. I think number one is like figuring out where you're at in your career path and what matters to you. Right. And, and, and, and then being able to identify what, you know, Spot maybe is right based on that.

[00:15:38] Right? Like what matters to you today might not matter to somebody as much, that's maybe younger, not trying to create that generational wealth. Um, and so I think that's probably a good place to start. And then, and then obviously picking up a copy of the book to figure out like, Hey, do I even want this damn position in the first place?

[00:15:58] Yeah. Yeah, because you give up, you give up a lot when you go into a VP role and go into. Your work-life balance disappears compared to being an individual contributor. You know, it is a mind fuck the first time that you, that your compensation is no longer determined by just your performance and your compensation is determined by everybody.

[00:16:19] Else's. Um, if you're somebody who massively craves stability, A VP of sales role is probably a bad idea for you. The average tenure is 16 months right now, down from 18. Well maybe, or maybe even sales in general. It's not for you. Yeah, maybe you would in general, but in particular, in the VP of sales kind of role, right.

[00:16:41] You've got to end up reinventing yourself every couple of years and building something from scratch again. And then there's different stages. There's this phrase that I use called stage appropriate VP. Like there's a very different VP that a founder should hire. Who's trying to get their company off the ground versus somebody who's trying to get a company from 50 million to a hundred million, right.

[00:17:08] Those dashboard managers and the VPs of spreadsheets who are just thinking about strategy and tinkering, looking at numbers all day. They're in their high ivory tower and don't want to get into the mud and into the trenches. So I would never hire that type of VP to try to get me from zero to my first million in ARR, very different type of person.

[00:17:29] Right. You need somebody a little more scrappy. Yeah, yeah, yeah, yeah. I have that kind of dive bar kind of personality. Right. I use I'm a big music fan. So I use this analogy all the time. There's two times the VPs, right? The early stage and the, and the late stage. Okay. To me, the early stage is like, you're the Ramones.

[00:17:50] Okay. You're this like shitty little punk band in the shitty little dive bar in New York city. Right. But you're paving the way and you're like, seminally more important and matter more ultimately then poison or Motley crew playing this arena. Right. Getting all of the, you know, spotlight and, and maybe more of the cash and accolades and all that good stuff.

[00:18:15] Like you're a, you're a hair metal band. No, like I don't, that's not for me. So I knew that about me. So I always skewed early on, but there's some people who are like, no, I don't want to be the Ramones. I don't want to do all that crap. I want, I want this glam band kind of situation. So you got to know that about yourself and if you're a founder, you sure as shit better here.

[00:18:36] Because making not a hiring mistake, you know, can be the death sentence for your company. Yeah, yeah. No, that's, that's a, that's a good topic. I'm glad you brought that up. So from like the founders lens, right. Is how do they identify those two different types of VPs? The easiest thing to do is ask him, you know, what resources you need, how you plan to get started.

[00:19:01] Right? And if somebody has immediate answers, I need all these pieces of tech. I need all these hires. Uh, I gotta put all these, you know, plans in place. That's somebody who's operating from a much larger kind of purview. My answer is, well, I got to figure out what the hell we do come up with some type of like V1 pitch.

[00:19:28] And I got to start building some pipeline and see if I can sell this. And if I can figure out how to sell it myself and build pipeline, then I know I'm onto something. Then I want you to let me hire a couple people and see if I can teach a couple other people how to do what was working for me. Then if I can do that now I know we're onto something.

[00:19:51] So they're very, to two very different types of answers. And those are, you know, paraphrasing. Yeah. Those are the answers that you're going to get, depending on who you're talking. Yeah. Yeah. Um, awesome, man. Hey, thanks so much for, for coming on. Um, tell people where they can find the book and anything else you want to let them know.

[00:20:13] I mean, the book is, uh, is on Amazon. Of course you can also buy it off of my website. Scott leaves, and, um, you know, today's Thursday. So it's top of my mind, you know, if anybody ever wants to check out this, uh, virtual sales happy hour it's Thursday night It's free. It doesn't cost anything, couple hundred people.

[00:20:33] Every Thursday usually join and it's a good time and you might learn something and network, and we share open jobs and all this kind of stuff. And a couple thousand people, um, in our slack community and over 15,000 people have come to the happy hours in the last. So that's awesome. Uh, so we'll drop. Yeah, we will drop the link there for the book in the show notes, sales hustlers.

[00:20:56] We'll also, uh, drop the link there for Thursday night sales as well. So you can check it out. Uh, Scott, thanks so much for coming on. Really appreciate this topic. It's one that we have never dove into yet on sales households. So I'm pretty pumped to get this one out there. Any final thoughts before we close it out?

[00:21:14] Final thoughts? Um, I think that. This is totally off topic, but I think that we've entered an age where the employees have just as much power as employers and it's time. And that we recognize that as employees and stand up for our ourselves and make sure, you know, um, that you're creating the life that you want.

[00:21:37] You don't have to go to the office five days a week anymore. If you don't have to, you don't even have to go the office three days a week anymore. If you don't have to, you deserve to work for a place that understands. Work-life balance and integration and respects you as a human and cares about you as a person.

[00:21:51] Um, you don't have to work for, you know, the old school slave driver type, uh, you know, institutions that work you to death and treat you like nothing, but a number. So employee over employee. Yeah, I think that's still on topic.

[00:22:13] That's awesome, man. Thanks so much for coming on. If you enjoy today's episode, share it with your friends, write us a review and as always we're listening for your feedback. Thank you for tuning in to this episode of sales hustle. Are you a sales profile? Looking to take your sales career to the next level.

[00:22:30] If the answer is yes, then I want you to go over to sales,, check us out. And if you feel that you are ready, set up a time to talk with me and my co-founder Chris, I'm your host, Colin Mitchell. And if you enjoyed this episode, feel free to leave us a review and share the podcast with your friends.