Don't overthink it, with Scott Leese

podcast Oct 12, 2021


Repeatable Revenue Podcast #007 - with Scott Leese


What do addiction, athletics, and sales all have in common? In this episode, Ray connects with Scott Leese to discuss how to build a strong sales team from the ground up in any industry, what Scott's health issues and battle with addiction taught him about how to sell, and much more.

Topics include:

  • Startups and sales

  • Industry experience versus sales experience

  • Building remote sales teams

  • Bosses as mentors

  • Company culture

  • Recruiting talent

  • Building a network on LinkedIn

  • And other topics...

Resources Mentioned:
Book – Thinking in Bets by Annie Duke
Surf & Sales Event –



RJG: Welcome to the show Scott, glad to have you.

Scott Leese: Thanks for having me, man. And as I already told you, but I'm now going to tell all of your listeners, I am extremely jealous Ray's sitting in Mexico right now, feel like I can see the beach outside of his window, I don't feel good right now. Ray, I feel like I'm losing and you're winning.

RJG: I'll resist the urge to turn the monitor and show you. I was watching dolphins and whales from my office last week, yeah.

Scott Leese: That's not helping, right?

RJG: Yeah.

Oh, you know what? But is that why you wear the surf hat though?

Scott Leese: I mean, I always wear that. So I have like, how many of these I have two or three of these and, I just kind of rotate depending on my mood today is it's kind of a red, white-bluish five.

RJG: Patriotic surf.

Scott Leese: Yeah, yeah, for today.

RJG: We'll dive into a little bit more on surfing here in just a bit, man. But just kick things off for listeners. What's your sales story? How'd you get into sales and into sales leadership?

Scott Leese: Yeah, not the normal way maybe the abnormal way is the normal way now, meaning so many of us just fall into this profession. I wasn't a business person growing up. I was not like a high school kid who was entrepreneurial, like thinking of business ideas or any of that stuff.

And I'm getting up there in years and, I'm probably the last generation that got through college without having an email address. I wasn't computers, and tech was just like, not my thing, right.

I ended up in sales after a long hospitalization. I was 23 years old and had just finished graduate school and ended up super sick and spent the better part of four years in and out of hospitals across a couple of different states. Battling different auto-immune diseases and colon cancer scare and had nine major surgeries or lack of saving surgeries, two emergency surgeries and got addicted to opioids in the process and had to kick off with dope. So, I was 27 years old before I ever started a career and before I'd ever tried my hand at selling anything.

And I saw sales as the only vehicle I could think of legally where I could make up for lost time and how well I did sort of dictated how much I would earn, right. The better I did, the more I get paid. If I do badly, you get fired, and as an athlete, I played two sports in college for four years.

As an athlete, I understood that competitiveness, right? Like you do well, you get paid, you don't, you're gone. Well, that makes sense, let me see if I can make this work and, I had a friend or two, maybe even at the time who were in sales in some capacity, and they were doing pretty good.

I'm like, well, if so-and-so can make this work, maybe I can make it work. And then I went to a startup on purpose as opposed to a big corporate entity because I felt like I wanted to be a part of something, going back to wanting to be a part of a team I've been in teams my whole life.

Like I go to a little startup. I feel like I matter, I mean something on this team, I have access to different people. Maybe I can move up faster. Those were the things, kind of going through my head and so that's how I got started in sales, and I did pretty well pretty quick and got pushed into leadership pretty quick.

The rest is kind of history, as I say, I've been building and scaling sales teams, as an operator for 16 years or so. As a consultant and an advisor for a couple of years now.

RJG: Awesome, man. That's a lot of, a lot in there. One of the questions I was going to ask you, you brought this up, on the opioids and breaking that.

And I read that you did that like straight cold Turkey. I mean, just rode that out and, in the recovery at home, how impactful was that experience on where you are today?

Scott Leese: Very impactful in a lot of ways that I didn't know at the time. You talk a lot about resiliency in sales.

You talk a lot about setbacks and failing. You talk a lot about mindset and willpower, right? I mean, if you haven't gone through any kind of struggle with addiction, It's potentially difficult for you to understand the amount of willpower required, and willpower on its own is not enough for most people and it breaks you.

And so to have been so sick for so long and then have to get off of drugs, it was almost like going back to square one in a way like, oh, I just defeated this demon. What the fuck is this? This is like boss-level demon times too now, right. But I got lucky if I'm being honest because the medicine, the narcotics that I was taking were medicine to deal with the pain from me being in a hospital years and what I was going through, it wasn't me medicating or self-medicating, you know, to deal with emotional pain or trauma or things like that.

So I think a lot of the mental addiction piece didn't afflict me as much as the physical addiction did. So, by the time that I was healed and healthy from the illnesses and I just had the drugs to deal with, my mindset was okay, well, I have walked through hell for four years.

I know about drugs. If I stop taking these pills and drinking this liquid morphine that I've been drinking for four years, like I'm going to go through transporting for a couple of weeks, but my mindset was a couple of weeks it's nothing I can endure, I've endured so much, like what's the big deal about a couple of weeks ago.

And the hospital UCF hospital was like super adamant that I shouldn't try to cold Turkey and my mom was a nurse and was like, you shouldn't try to cold Turkey. I had to sign these, against doctor's orders, papers, or UCF. Yeah, I see your eyes raised. I had to sign them basically. So I wouldn't, my family wouldn't Sue if anything happened when I was trying to get off the drugs.

So, I went home and, just kinda locked myself in my room, and it was a brutal couple of weeks physically. I had people who were trying to enable me, candidly, like, well here, why don't you take one to take this, take that like lessen the blow or whatever, and I'm like, no, you don't understand.

I don't even want to take a fucking Advil ever again in my life. That was my mindset. So all of that stuff paired me, I think, mentally for the roller coaster. The rejection, the threat of losing your job or losing your job, the starting of new ventures after you built something that was pretty successful and having to go back to the beginning and start over, and it gives you the perspective of like, what's the worst thing that can happen, right?

It's like I've already been, hopefully, knock on wood through the worst thing that I'll ever go through in my life. So what do I care if this prospect hangs up on me? What do I care if this deal doesn't come? What do I care if my boss fires me? Oh, well, I'll get another job, big deal. Right, and having that kind of mindset, I think, frees you up and liberates you and allows you to kind of move forward in life with a little bit less fear and take more chances and gives you some confidence, that's like, I can go through anything.

RJG: Yeah. And we all know the state of mind that you're in. If you're selling, when you're overly concerned about the next deal, overly concerned about losing your job overly concerned about it, just, it completely changes the way that you approach it.

I mean, congratulations to you, and it takes a lot of courage, especially to not take advice from doctors and then go through and barrel through it. Is there reflecting on what you went through? I mean, obviously, if I'm listening to this, obviously not the experience that I'm going to have, but if I'm going to try to prepare myself mentally for the roller coaster that is sales, are there any, is there anything you recommend, that maybe isn't quite as enduring as something like that?

Scott Leese: Yeah. Please, please. Don't go through what I went through right, to learn.

 I think everybody, no matter who you are. We've all been through shit and trauma and hell and the things that seem impossible. If you hear me talk, if I heard you talk about what you've been through in your life, it might sound impossible to me and I might be over here.

Like, I don't know how Ray made it through that. I couldn't have done that. So I think what you do, everybody does is you got to draw back on the hardships and challenges that you've already made it through in your life, right. And realize, probably dealing with the rollercoaster of selling is not that big a deal or not the hardest thing in the grand scheme of things.

Right, you're talking about people who've come from broken homes, survived addiction or abuse, or have moved all over the world, right. And had to like uproot their whole lives, all this kind of stuff. It's so much harder than selling.

So if you can kind of come back to the core of who you are and be like, yeah, I'll be okay.

I can get through this, so what if these people tell me no, I've proved people wrong my whole life, right. And give kind of adopt that mindset. Even if you have to create this chip on your shoulder, right. Where you're like the world's out to get me, everybody's trying to hold me down.

Like I, okay. I won't be stopped, right. Me against the world. If that's what it takes, I'm going to prove you wrong. All of those kinds of things I think can and should funnel into how you approach the difficult moments selling or leading sales teams and things like that, and as an athlete, I also always come back to how could they have to forget things, get to have a short memory.

Right, I talk about a quarterback who throws a pick-six, throws an interception. You better forget about that. Cause if you're still thinking about that intersection, Break huddle, next time you have the ball, you're in big trouble.

I played college tennis. Tennis is one of alongside golf, I think in my opinion, the most mentally taxing sports that there is, you have hundreds of opportunities, every single match to feel like dirt because you've made mistakes and you have no teammates to blame it on at all. Right. So you know, you miss a shot, you double fault like you gotta forget about it and move on to the next thing.

So I think if you can drawback on some of these experiences in your life, personal experiences or sporting experiences or whatever, I just think it helps give you perspective required to understand that, you're going to fail 99 times out of a hundred as a salesperson and that's okay.

That doesn't mean you're terrible that means you're going to be great if you just do it right.

RJG: Do you think? So you mentioned the athletics piece a couple of times and I did. I was in sports, I've done a lot of martial arts and I've noticed with there it's been, I think it's been a commonality with a lot of high performers in sales.

Is that something that you have found or that you would look for or is that?

Scott Leese: It has been a commonality for a long time, there's even been studies on it, somewhere I remember reading that, in sales, the sport that had the highest overall quota attainment was wrestling.

I don't exactly remember why, but individual sport spotlights on you the whole time, right. You win your praise, you lose, like you are publicly shamed because you just got your ass wrestling, right. But there's a lot of other disciplines or activities that I think lend themselves just as well. And some of those are starting to get more attention as they should.

There's a lot of people who were musicians who gotten into sales. You're on stage, you gotta perform. There's a lot of people who are actors who were in theater, you gotta go into character, you gotta read sales scripts, and why not.

Groupon is famously known for when they first got started hiring a bunch of standup comics in the Chicago land area. Why? Well, comics are charming.

CarMax comics build rapport, right? You make people laugh. So it doesn't have to just be athletics. There's just so many different activities like the debate club, speech and debate club. I've talked to a couple of people recently from Gong who had experienced in speech and debate, same kind of thing, crafting arguments competing.

Right, I think that's maybe if it's getting more, how do I phrase this? It's less about, oh, Ray's an athlete, we got to hire him and it's more about, what has Ray done and participated in that potentially shaped his personality, where he might be a successful seller and it could be sport, it could be performance, it could be all these different things.

And that's helping, I think with some of the diversity that is kind of coming into sales and into sales leadership. And it's a long time coming and there's a long way to go, but it's good to see some of this stuff happening.

RJG: That actually, it leads me to something that I've never heard you talking about recently, and it is the industry experience.

So when you're looking for whether it's an SDR or AE, even a sales manager, and there's a lot of must-have five years industry experience, but as you're pointing out, whether it's comedy or athletics or academics or so many other things that can shape who you are and whether you're going to be successful in the role other than industry experience.

Can you just, I guess for the audiences to tell what is your kind of your position on that approach to recruiting, and can you just explain kind your perspective on that?

Scott Leese: Yeah, I can do it in two words. It sucks. It's a horrible perspective, companies have for too long optimize for industry experience over acumen, over sales acumen, and I never understood that and it doesn't have to be just at the SDRA level.

Listen, the last company Ray that I was an operator as you probably know, is this company called quality cause a property tech company, you sold title insurance software to title insurance companies, real estate attorneys, underwriters people like this.

Let me ask you a question before I took this job, do you think I had experienced in the title insurance industry?

RJG: Probably not five years a bit.

Scott Leese: Zero, right.

Zero, I didn't even know what the fuck title insurance was, okay. So that company now we're worth a couple of billion dollars, okay. Now, when I'm figuring out how to pitch the product and position it and how to go to market.

I have to learn all this stuff, but it's far easier for me to learn an industry and learn a product than it is for me to learn how to sell. So as I went to hire and recruit salespeople for my team, do you think I tried to peel people from the title insurance industry? No, I'm looking for people who know how to sale, who know how to use modern sales, tactics, and modern sales tools, who've been in a startup and a fast-paced, high-growth environment before those are the things that I want. Cause that's way harder to teach them, to teach somebody about an industry, learning about the title insurance industry. It's like going back to school and taking a course.

It's just like, book-smart, I can give you materials and say, go memorize these terms. I can't say, Hey, go memorize like how to pitch, how to story tell and it doesn't work the same, it's much harder to teach. So I just, it absolutely sucks when I see those job ads. That's must have five years in the CPG space must have five years in retailing.

What the fuck are you talking about? Like if I applied for that job, are you not going to hire me? Because I have no retail sales. Like I've done a lot in my career, I'm pretty sure I could figure out how to sell retail if that is what is required of me. So I preach all the time, acumen, not in the industry experience.

RJG: And if you're a sales manager and you're hearing this and you say "this doesn't make any sense. I'm going to look for acumen". What is acumen? How do you define it for your unique business?

Scott Leese: Somebody who knows how to sell somebody who has stomach experience, demonstrable experience selling in a modern kind of sales environment, selling software or selling hardware with maybe a similar type of a sales cycle, whether it's transactional or more enterprise people who have experienced with a CRM and enablement tool, conversational, intelligent tool like gong people who've been in startup environments before people have been in large company environments before. There's so many other things, a history of quota attainment, good references or referrals, right. Things like that, those things matter way more to me than, "oh, Ray is like, been in the real estate industry forever".

Well, you know what happens if I hire people to quality, I had come from the title industry insurance industry. They've got 20 years of baggage and they're going to tell me it won't work that way, Scott. It always has worked this way and they're not going to be open to any kind of new ideas. When I got started at quality, everybody told me you cannot sell unless you are face-to-face in the title insurance industry.

And I said, well, that's interest, because I've built and scaled inside sales organizations, my whole career and that's what I intend to do here, and I don't think there's any ever been anybody like me, who's tried to scale an inside sales team inside this industry. So I'm pretty sure I'm going to be able to do it.

And that's what I'm going to do, and I saw, I hired people who didn't know any better. I hired people who sold inside, like me before, who had been at other tech companies before and we made it happen, and we defied all of those, like industry experts, right.

RJG: A blank coachable slate goes a lot further than the 20 years of experience, you know, it's the baggage, it's the way we've always done it.

If they haven't seen it done another way for 20 years if you're introduced, especially if you work with a lot of startups who are changing their disrupting markets. So bringing some of that old baggage in, I imagine is even less impactful in a startup.

Scott Leese: It's the opposite of what I wanted.

RJG: Yeah. Yeah. So you mentioned that you went to a startup on purpose early in your, in their sales career and one of the things that I've talked to people about is the small nature gives you a lot more leeway, you have a bigger impact, things like that. But the pushback I get is the failures.

I'm like, yeah, that's true. But I don't know how much money these, the startup really has, I don't really know what they're doing. The failure rates really high, then I'm going to be bouncing around. How would you pick a startup if you were looking for a role today or evaluator to just do some due diligence?

Scott Leese: I feel like I first want to rebut that whole argument that I will refrain from rebutting. The argument that no rebut it.

RJG: Absolutely.

Scott Leese: I'm going to get all fired up. How do I pick a startup? I think there's never, it's never been easier to know kind of the background of a startup like all of the financial information is available now.

Like 20 years ago when I was getting started, there was no like Crunchbase where I could read, has raised 10 million in a series a right. So not knowing how much money somebody has. It's kind of inexcusable to me like you had to, you just, haven't done your diligence, you haven't done your research.

So that's one thing that I look for is like, are they funded or are they bootstrapped? And what's their kind of cash position and situation depending on the size, I looked to see who the team is, who the leaders are, right. So if I saw your name as the VP of sales at this tech startup, to me, that's instant credibility and so now I'm more interested.

So if I'm just in my early career, I pay a tag, listened to podcasts like this, I'm on LinkedIn. I follow people who've been in the game for a while. I have my favorites of, you know, who's which people's advice I take and whatnot. I'm trying to go work for one of them.

I'm trying to de-risk it a little bit, because I'm trying to say, well, if Ray thinks this is a good gig if Scott thinks that this was a good. It's probably pretty good. So I'm leaning on some advice from elder statesmen, if you will and then specifically trying to learn from a boss who could turn into a mentor and a good leader there.

And then from a product standpoint, like I love looking for are older, sexy kind of, markets, title, insurance industry, right? No innovation in 25 years, no modern competition whatsoever. So now all of a sudden I've got a modern product, that's the best product in the market and very little competition to go after people don't build in that industry because it's a son of a bitch to sell to and building the product took years and it's super complicated.

So there's this big moat arounding that industry. So I like these vertical-specific kind of SAS plays in these kinds of less sexy industries because there's a big win there. So those are some of the things that I look for, you know, and on top of that, you're trying to learn what you can about the culture of the company, right.

Trying to figure out, what people who work there say about the company to see if it's legit versus just a smokescreen. Those are some of the things that I'm looking for

RJG: Okay, you mentioned in that the, a boss that can be a good mentor, and as soon as you said that, I thought back, and that was a game-changer for me early in my career.

Like I got lucky, I had a handful of just incredibly talented, great leaders that were teaching me that I was through osmosis, just catching some of what they were dishing out. Where would you put that if you're shopping for the startups? Cause I'm not sure that I would be anywhere near where I am today without the help of a lot of those mentors early on.

Where would you put that in the priority list for someone?

Scott Leese: And I'd rank it pretty high, to be honest with you. I really would. Again, because things are so transparent now, right? Like I can see a little bit about who you are and how you think and your philosophy on selling and management, just by reading all of your LinkedIn posts.

So I can tell a little bit if I'm going to buy with this guy or this girl, right. I can tell if I listened to this podcast and Katie, he is the RVP of sales or Nikki is the sales manager. And I'm like, I would love to go work for her. Right, she's got an energetic personality that comes through in her podcast.

Her posts are always super insightful and tactical. Like I can learn all that stuff. None of these platforms existed when I was coming up, right. There was no fucking LinkedIn, there's no podcasts, right? There's no blogs. There was nothing, right. So I just, I think it's super important. And it's one of the great regrets of my career is that I had to learn all this stuff on my own.

I did not have a bunch of mentors and good leaders around me. You know, the closest thing to the mentor, I never had, was a sales trainer who came into my first ever startup and made an impression upon me, and I just kind of stayed in contact with, and we still talk to this day, and it's the closest thing I've ever had to a mentor, but I didn't have it on a boss-level whatsoever.

I could have got better way faster, right. I could have avoided a lot of pitfalls and mistakes potentially. I just think, I think people are making a mistake who don't put a lot of stock into who they're going to go work for, I think people put too much stock into, oh, I really like this product. I really like this industry. I'm very passionate about that for me. I don't care about that stuff as much, I care about the opportunity and who I'm going to be around. That's what I'm thinking of. If I'm getting started right now, I'm not somebody over here who's like, oh, I'm really passionate about marketing tech.

And I really want to work in MarTech. No, I'm a fucking mercenary show me industry and the product ripe for disruption, you used that word before, and let's go make it happen, that becomes exciting to me. That will lead me to be passionate about the product and what I'm doing, not the other way around.

That's just me. That's how I think about it.

RJG: Yeah, certainly, they've said about culture, the winning shaped the culture, when your team is winning and you're racking up wins, like that tends to be, it's very difficult to build it, a great culture and an environment where you're just losing and like you said, if there's a great opportunity and you're going to find the passion, I imagine. Yeah, you mentioned culture a little bit ago and what are your views on culture? If you're going to VP , sales, sales management role, you're not necessarily CEO, so you can't go right the core values necessarily but, how do you shape a winning healthy, productive culture and in your view?

Scott Leese: Well, first of all, I think you have a responsibility to do so. And I think too many people kind of pawn it off on the CEO and say, Hey, it's not my culture. I'm just doing my thing. I feel a responsibility and on some level of responsibility to create my own culture inside of the larger culture.

And for me, that starts with develop. It starts with giving a shit about my people and my job is to help them get where they want to go. That's going to be different for each person. How I get them there is going to be a little bit different in order for me to show that I care and try to impact them and help them get where they want to go.

I got to put in time in order for me to put in time, I got to be accessible. So I have to create a transparent, open dialogue kind of environment where people can ask questions freely. They can get answers to things quickly that they're looking for. I've got to put in time to make sure I'm training people.

I'm coaching them, I'm caring for them, I'm helping them succeed that's where it all starts to me. And if the rest of the company doesn't have that culture, I can't necessarily control that. But I can control my team and my department, and in my experience, if you create that environment and the rest of the company, doesn't have it, your culture can bleed over in a good way and start to make a positive impact on the rest of the company.

And so I see that in a sales-centric kind of startup, I see that as a core function of the role.

RJG: I have found for people that say culture has to roll downhill and I don't necessarily agree. It's harder to push it uphill, but it doesn't necessarily have to roll downhill.

And the one advantage I think sales always has is you're, it's easy to measure whether you're doing a great job or not, and if you're head of sales and you're trying to shape the culture and you're crushing your number, you tend to just, all right, well, let him do what he's doing, and then you, and you continue to do that and you continue to rack up the words.

 And you get a little bit more autonomy and you're right. You build a healthy subculture and it does absolutely bleed throughout the rest of the organization, I've seen it happen. How have you seen, I guess with startups specifically since the COVID thing for the past 12, 14 months, what changes are, what important changes have occurred in and what's here to stay, if anything?

Scott Leese: Well, I think that I think the biggest change and the thing that's here to stay is the adaptation to a remote workforce specifically around sales. I can't tell you how many engineering and product teams have been able to work remote for God knows how long, but sales has never allowed to because it's like, oh, you can't trust sales people to work at home.

They won't do any work. Well, I think what we realized in the last year and a half or so is that's not true. And salespeople and sales teams have thrived in many cases and companies have therefore thrived during a pandemic for God's sake. So I don't think that pendulum is going to swing back too hard in the other direction, frankly.

I really don't. I don't think you're going to find people willing to commute 30 to 90 minutes each way every morning, and every afternoon, when they've had this taste of a different type of work life, balance, and environment, right? People are getting more done because they're not in a car two hours a day.

People are spending more time with their family spending more time with their kids, exercising more, maybe right, learning, taking on new product projects and creating side hustles and things like this for themselves. Why would I sign up to commute? Why would I sign up to go get on the fucking train every morning or go sit in rush hour traffic.

So I think that companies who don't recognize that are going to have a really hard time with the talent wars coming soon, I think there's going to be a bit of a hybrid kind of switch where people are like, okay, you can work two, three days in the office for two or three days from home, and I think for a good while, that will work because so many people are just starved for socialization, but there's a lot of people who are more productive who are happier working from home.

And I think that change is here to stay, and it helps with recruiting it saves tons of money for startups. The biggest overhead for a startup is office space and people have, you're building a startup in New York city or San Francisco, and you're trying to hire salespeople. It's expensive. Right. A hundred and something dollars, a square foot, a hundred thousand dollars salaries.

You don't have to do that anymore. You can hire salespeople from anywhere and save all the overhead. and I think that's going to stay, I really do. I think that's going to stay for a good while.

RJG: How has building a remote sales team or managing a remote sales team? How's it different than in person, and I guess in a way of, if I used to have an in-person sales team for COVID, I did this, I tested this remote stuff, but, we're wanting to go back in the office because I've never managed a sales team remotely.

And so it just kind of intimidates me, how are you going to hold them accountable? How are you going to build a culture? How are you going to those things? If I've never done it before, what's your advice to building or leading a sales team remotely? 

Scott Leese: Well, number one, there's a million people for you to talk to now who have just done this for over a year and get tips and tricks from whereas pre COVID.

There was maybe a couple of hundred, I think, what you have to be aware of is like speed of response, and accessibility has to be at an all time high. It's easy for me to walk in the office and say, Hey Ray, I need help with something. It's a lot harder when I have to text you or slack you to try to get your attention and then get you to respond to it.

And then I have to be sitting there to read it as well, and I know I can't be distracted. So one of the things that I've told everybody is when your team messages you, you've got to be like, boom, you gotta be like, you got Hawkeye that thing, which is tough because you feel like you're always on. So my speed with responding to people, my quick ability to get blockers out of their way, my sort of sanity and mental health checks on people.

And my non-work conversation threshold is way higher than it used to be in an office environment a lot of, Hey, how you doing? What's going on in your life? How are you handling this? How I handled that. So I think there's a lot more humanity involved in the remote kind of situation, training and onboarding people.

You got to make sure you are not just throwing people to the wolves too soon. That was one of the things that held people back from hiring again, was they didn't know how to retrain people remotely. You don't want people sitting, watching a zoom call for eight hours trying to learn stuff. So it's gotta be smaller groups, it's gotta be interrupt, breaks interruptions, small focus, kind of blocks and segments utilize training tools like Lessonly or, those kinds of things. But I think that is a lot less hard than you imagine it to be, and for every person who's arguing, well, you miss all that energy on the sales floor and all that kind of thing.

I used to be in that camp too, but there was a lot of people who never liked all that energy and preferred their own quiet, private space. So, as you're trying to build your team, like if it's a remote team, maybe optimize for people who like remote, who are not Sort of whining for things to go back to the way that they used to be.

And maybe you'll have people who are a little more comfortable with this kind of arrangement environment now and are excited about it rather than frustrated with it.

RJG: Yeah, you've had, I've actually shared a post that you wrote a while back on LinkedIn about the full cycle, the full sales cycle versus the segment and say it having one person kind of go all the way through this versus SDR to AE to am.

And as opposed, I don't necessarily not just to just reread it, but can you elaborate what's your point of view on that? And can you give me a little background on this?

Scott Leese: I have always had full cycle sales reps. I've never done the SDR AE. Now I think if you're selling something that is typically a six-figure annual price tag or more, and you're in a long sales cycle or an enterprise sales, I can understand why the model works, but the predictable revenue STR a model was built for enterprise selling.

It wasn't built for mid market or SMB or high velocity sales. So it just got blindly adopted and implemented in places where it made no sense it complicated any longer than the sales cycle. It provided a crappy buying experience for people as they got handed over from one person to the next, it increased your customer acquisition costs, increase your organizational complexity.

Also, I have a fundamental moral issue with teaching somebody apart of what they need to do in their job and not all of it. If you're brand new to sales and you're telling me I want to be a sales person and I'm a teacher, my job is to teach you how to sell, not how to open. I don't want to teach you a piece of the pie. I don't like that,

and as a teacher that bothers me and it upsets me and I consider myself a teacher, and then what happens is these people get pigeonholed in this role of SDR and they can't get out of it because they've been an SDR successfully for 6, 12, 18 months. They go try to be an AEE somewhere else.

And the company's like, you don't have any closing experience, I'm sorry. Well, how the fuck am I supposed to get closing experience? When I'm an STR in my current company doesn't give you as good a chance to close deals, right. So I think it holds people back and has held people back in their career at times.

So for all of those reasons, I just never adopted it. I want my salesperson to research, to prospect, to run the demos, to close the deals. Once the deal is closed, I'm comfortable with them handing it over to somebody in account management, customer success. But if I'm running a hunting kind of team, I want them to do everything.

I want them to know how to do everything. I think it's a better experience for them. I think it's a better experience for the buyers, and I think there's economic reasons for it to make sense for the business and it can be done, I just did it.

RJG: You do the recruiting side of this, so you know, a lot about the talent pool and how hard it is to find people at different levels. Is it harder to find specialized SDR, a E a M type of roles or is it harder to find a full cycle sales rep to go all the way through?

Scott Leese: What I would tell you now is it's harder to find people for full cycle because now you've got all these AEs who are, let's say lazy or lazy early than they used to be because they've been spoonfed appointments.

They've been spoonfed demos the whole time. They're all entitled, and they're like, oh, I already prospected I don't have to prospect anymore. So now how do I take this? A guy who spent the last five years having deals handed to them and opportunities handed to them by being supported by an STR or two, as well as them, and how do I tell him, Hey, you gotta run the whole cycle again.

So it's hard now to find people willing to do that, and I don't think that's good for the profession at all, and I think that things will switch around a little bit. I think change is coming a little bit on that front.

RJG: Yeah. It's hard to go back. I mean, when you give somebody years of spoonfed demos and say, Hey, we want you to start making some calls and setting your own stuff. It's very difficult to move somebody back once they've had that experience, unless it's gonna forced upon them.

You said earlier, you said if you've failed 99 times in sales, like if you've failed, I needed times out of 100, you're still on your way to success, which it reminds me. I don't know if you've read I think it's any, Duke's thinking in bets, when she talks about the process versus results and the example she uses that I would like to use is, you know, if somebody drives home drunk and they make it home safely without killing anybody, it's still not a good decision.

The result was okay, but the process itself was still a terrible process, and I know your first book addicted to the process. So I feel like there's you kind of probably subscribed to that, to a degree, but what inspired you to write addicted to the process and what are your thoughts on it?

Scott Leese: Well, there's kind of three things. Number one, I have practiced process over results for a long time, all the way back to my athletic days, and so I wanted to hammer that home.

Number two, I wanted to tell my story a little bit and what I had been through, sort of show people that, if I can make it, anybody can do it basically, right. Try to be somewhat inspirational maybe, and just show I'm nobody special. I don't come from anything special and I figured it out.

And the last thing is, I spent probably 75% of my career in SMB, kind of more transactional selling environments, and I still to this day get pissed off when people tell me that is not as hard as enterprise level selling, and so I felt like transactional sales has always been like a disrespected, a faction of the sales community.

And I didn't like that, I never understood it, and people wouldn't produce content specifically for transactional selling. And that was the environment I was coming from. So I sort of saw a gap in the market and I'm like, well, why don't I write it a book specifically to kind of I help people who are just getting started in sales, which is where a lot of people end up is in transactional sales when they're just getting started and tell my story a little bit and make sure that people understand that process matters.

And it was the combining those three elements is what led to the production of the book, and if there was anything else, I'd say there was a couple of people in my ear being like, you got to put this stuff on paper, Scott, you gotta take pen to paper, you've been teaching it and training it for years, like get it done.

So I finally made time to, to write it, and I've been more than shocked with how well that it's done and been received, and I'm just really grateful that people have resonated with it.

RJG: And how was that? So your recent one from sales rep to manager is a good one, and I would say a guide. I mean, it's a book, but it's a guide. Like if you're sitting in a sales rep position, you're thinking about going into leadership, from sales rep to manager, I think is great too. How different was it writing the first one versus writing the second one for you?

Scott Leese: There's a lot different, you know that the first one is there's a lot of philosophy and a lot of why this works and why it's done this particular way, and as you said, from the second book from rep to managers, like this is what to do. It's very tactical, very actionable. I feel like and a guide to use your words.

So stylistically it's quite different, and then I collaborated on book two, so that was helpful, Ryan Walker was the coauthor, he's the VP of sales at a company called beyond pricing. So that was kind of fun that lessen the burden a little bit, you sharing ideas and marking each other's writing up and one person handles the artwork, one person handles the editing.

It's like sharing of responsibilities, that's quite different. I wouldn't say you have to be like perfectly aligned in partnered up, but if you and I are going to write something together, you both want to be proud of what is coming out and people have different opinions and ideas.

So there's something kind of special with forging a relationship like that and partnering up and producing something, and one other differences I didn't print from rep to manager and we decided to make it an ebook only a digital only kind of book, a little bit just for speed of production and kind of digestibility.

And even my first book addiction process is like 90 pages, right? From rep to manager, I think it would be like 63, if it was printed out, I think in the same kind of format and bound in the book, I'm a get in, get out, kind of got like, I want you to be able to finish the book in an afternoon by the pool or like, if you fly from Baja to San Francisco, like you should be damn near able to finish the book in one flight.

Right? I don't got time for this 400 page novel of business books where somebody just repeats the same thing through different analogies, 500 times, nobody got time for that shit anymore, okay. So I tried to remove just like all the fluff from both books and I have a third book coming out that kind of completes the trilogy of UL for me, which is all about being a VP of sales.

It's called more than a number and should be out anytime it's finished and everything, and that book is like 116 pages maybe something like that. It was my longest, but even 116 pages is not very much. So my philosophy on the writing is like, get in, get out, be quick, be tactical, be inspirational, be helpful, and let people get on with their day.

RJG: Mentor mindset. You can most business books if you read the first, third or the first half, you've got it, because, so they took it to an agent somebody said yeah, it needs to be this many and they just start stretching it out and in different ways but I would.

Scott Leese: Yeah and I operate the opposite. This last book, the more, the number of books that I just finished when I wrote it, it was like 35,000 words, and I'm like, oh, my goal is to write like 11,000 words for this book. So I had to cut two thirds of what I wrote. It's hard as a hard process. It forces you to look at things like, well, I don't need to say that.

How can I say this shorter? I can cut this section here, this is all fluff, this is bullshit over here. I don't even remember what I was talking about here, get rid of that, right. So is it interesting that's that has worked for me is to just kind of morph it all out onto the page and then trim as opposed to try to keep it tight initially and then stretch it, as you said, that's not what I'm trying to do.

I'm not in fifth grade anymore, okay. My son's teacher is like, oh, this needs to be 500 words, and you only wrote 320. What? You're going to punish him for getting to the point faster, no, I'm not here for that.

RJG: Yeah. I had an English teacher in school that did, we had to do a report and then the next week the assignment was cut it in half and then the next week was cut it in half again, and it was brutal.

Scott Leese: That's more real life applicable in my opinion.

RJG: Stuck with me. It was the same English teacher who said, why are you using such big words? Like you trying to show off? Nobody understands that. But I mean, a lot of people say no fluff, but I mean your books kinda, I mean, all your podcasts, your messaging, it's like all the, none of the fluff, all the gruff.

Scott Leese: That's a compliment, I think, right.

RJG: Is, it's a company.

Scott Leese: Somebody told me a while back that I'm gruff at the time.

RJG: It was me.

Yeah. It was on an email, and I said, you know the word gruff comes to mind, you sent me back the definition I went. Oh, it sounds a little mean when I read it like that.

Scott Leese: Oh my god.

RJG: Yeah. I didn't read the definition before I sent it though.

Scott Leese: That's, it's on brand for me, right.

RJG: Your approach to LinkedIn, like switching just a little bit from sales specifically, is a little bit different than, what you would like. It's not necessarily, it's not daily posting, you have a really engaged following.

You have a big following and a very engaged audience and, there's a lot of different pieces of advice from people that I respect a lot.

Do you know what, I'm just curious, what would be your answer to someone if you're a VP of sales or something and you say, I've got to develop, I buy it. I've got to develop a personal brand, but where do I get started? How should I be posting every day? I mean, how did you build your audience or what advice do you give to them? What I'm sure you're asked.

Scott Leese: I actually built my audience specifically to help me recruit that was the impetus for it.

My thought process was I need to connect with every single person in sales, leadership every founder or CEO, basically anybody who I might hire or who might hire me one day, I need to connect with them. So I'm the very first thing I did was build the size of my network app, which is counterintuitive to what everybody else tells you.

Everybody else is like, oh, the size of your network doesn't matter and everything. Bullshit. It mattered a lot and it helped me recruit, it helped me save hundreds of thousands of dollars in recruiting fees, and also helped me explained to my founders why I was spending time on LinkedIn building my brand, because I was able to say, listen, I'm trying to save you all this money and recruiting dude.

So you don't have to hire a staffing firm, we don't have to hire an internal recruiter. Let me do my thing, get off my back, and they're like, all right, fine, fine, fine, right. And then I went from there to just kind of engaging with other people's content. So reading what they would write, liking things, showing up in comments.

And then I just said, all right, it's time to start, and it's going to be bad, I'm not going to be perfect, I'm going to test this out, I'm gonna test that out, see what happens, and I'm not going to be like everybody else. I'm going to speak my mind, like who I am on LinkedIn is who I am on this podcast and who I am in this podcast is who I am.

That's all there is. It gets me in trouble sometimes, but I think it differentiates me and so I started talking about things that a lot of people don't want to talk about, whether it's how equity works and how it can kind of hose you if you don't know what you're doing, how hard and brutal it is to be a VP of sales, how fucked up it is that founders fire you within 12 to 18 months all the time, racial, injustice issues, diversity issues.

I talk about all these things, pretty candidly. But I also recognized in me that I'm not a robot. I can't just sit down at a desk every single day and be like, this is my LinkedIn posting hour, okay. I don't operate like that, I am only posting things if the spirit compels me, like if I'm not moved and something doesn't flow out of me, I don't right.

Sometimes I'll post three, four days a week, sometimes I might post once. It just depends. Do I have good ideas or not? Or do I have something to say, I don't use any kind of automation.

I know a bunch of people at the top of the leaderboard on LinkedIn who plug things into buffer. They write their five posts for the week, every Sunday, and boom, it goes out at 7:00 AM central every single day. Nope, I don't do that, I know people who have spouses and admins and EAs who reply to comments and then keep the engagement flowing and reply to DMS. Nope, I don't have a single person to do that.

Anything I do is mine, and I want it that way. I want it to be authentically me, and I did that, from the start and over time now, I think it's distinguished me a little bit from the pack because a lot of people don't do it the same way as I do, which is what you said.

And one last thing for people who are thinking about getting started, do not overthink it, do not overthink it. Like I don't rewrite things, I don't edit, I don't agonize trying to make it perfect. You know, I get messages from my mom all the time, she's like you misspelled these words here, I really don't care about a misspelled word.

Right? Dumb. Some of my best posts are things that I've had an idea while I'm driving as soon as I get out of the car, I just post it on my phone. Sometimes I have an idea, the night before and I didn't write it down and I go get in the shower in the morning and the idea comes back, and boom, first thing I do is I sit down and I crank it out and I have friends who struggle, who like put lots of energy and thought into what they write, and I'm like, man, just stop overthinking it, just put it out there and if it doesn't do well, who cares? Nobody saw it, if it didn't do well, right.

Again, just, I'm a big believer in like shrinking the Delta between idea and action, like you have a good idea. Just do it. Just execute on it, don't overanalyze it, don't overthink.

It don't find reasons not to do it. So that's what I would say to people who are just kind of getting started. Like just start don't overthink it, just put something out there that you think will be helpful to people.

RJG: Seems consistent with working in the startup world too, like you've got to move, take action and if you throw a post up and no one liked it, it's a data point, right? Got it, if you're trying to optimize messaging, look at it and go, okay, that one was a bomb. We'll try something different.

Scott Leese: I figured out why, when I stylistically do it wrong, then I posted at the wrong day, the wrong time is the story boring. Is it not engaging? What missed? And a lot of times people don't get the engagement that they want because their network is tiny. So I always go back to just start with building a network, just reach out to people and be like, Hey Ray, a big fan of your podcast, love the episode with Scott the other day.

Not looking to sell you anything just want to connect with you and see if I can be helpful one day and hopefully I can continue learning from you. What are you going to do? Say no to that connection request.

RJG: Right yeah. I've found it's a lot easier to connect with people when you just let them know no pitch is comming. Let me just say no pitch coming, reaching out, saw this, whatever it is, it's so long as you don't follow it up with a pitch. But if you're actually legitimately trying to connect with people and just building your network, tell them they'll most people say, okay, that's fine.

Scott Leese: Yeah, I get messages sometimes, DMS in LinkedIn and somebody will say, "Hey, Scott, been connected for years, thanks for putting stuff out there and had a question for you". And I look at the message history and the last message is from 2015, and it's my connection request to them saying, "Hey today, looking to connect with sales leaders in Mexico, love what you're doing on the podcast, not trying to sell you anything just want to learn from you. Let me know if I can ever be helpful, hope we can connect". And I'm like, damn, I'm looking at my message.

Thing is you never know who might be able to help you, and you never know who you can help. So I don't subscribe to this theory of, oh, I have to know somebody in order to connect them.

No, you don't. Cause that person that I hadn't even had a conversation with for five years has apparently been getting value out of being connected with me and the things that I write and now the moment is right and they've reached out and I reply to them and I do my best to help.

RJG: Yep.

Well, I know we're coming up on time and I want to make sure we hit on, we come back to the surfing piece, we can chat about surfing sales or where can people find you?

Scott Leese: Well, you should check out and As well as the surf and sales podcast, we have two events in November of 2021. One of them is sold out, the other one is almost sold out, but we'll have some in 2022, make it on LinkedIn.

RJG: I said maybe in Baja.

Scott Leese: Yeah, maybe in Baja, that's right, and then you can find me on LinkedIn, I'm super responsive there. Also every Thursday night I host Thursday night sales with my co-host Amy bolus. It's a zoom virtual sales happy hour where we answer questions from people around the world and just kind of hang out and have some labs and some fun and a lot of other places, but I'll just stop at those too.

If you want to catch me there, you can find me there. If you want to hang out, get some private trainings and events and things like that. You could also join my Patrion group, we do these fun events called tequila Tuesdays, I have guests come in and talk to everybody. So those are the three best ways probably to get a hold.

RJG: Okay, cool. And the Patrion group, I mean, for anybody listening, I'm a member of it and it is vastly more value than what you're paying to be part of their every week, you have a great speaker.

Scott Leese: I'll add another zero onto your monthly fee Ray.

RJG: Well, I'll pay it. It's like even earlier this week was a really great one. We'll follow up on that, but I thanks for your time, man. I'm really glad to have you on the podcast. Look forward to chatting with you a little bit more and, really appreciate your time and your insights here.

Scott Leese: A lot of fun, thank you.



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