Scott Leese on the importance of getting sales ops right in B2B SaaS before hyperscale

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In this episode, Elias Rubel interviews Scott Leese of Scott Leese Consulting, LLC. A company founded with a focus on companies scaling from $0 - $25m ARR. Scott work with both domestic and international companies on sales strategy, process, people, pitch, and more. Listen to this episode to learn more on building and scaling a sales team.

Episode Outline

[04:39] Having the mindset of hustling and outworking everybody

[06:16] The purpose of writing his new book

[10:10] How investing in sales operations help scale the company

[12:04] Thoughts on recruiting and training people

[14:34] The bias and mistakes founders usually make

[16:35] How to communicate to your prospects in a way that is relevant to their needs

[19:22] The regret of not having a sales mentor or business mentor

Scott's Inspirations

Mike Lindstrom

Richard Harris

John Barrows

Kevin Dorsey

Connect with Scott




Surf and Sales

Scott Leese blog

Elias Rubel (00:02):

Hey there, all you cool cats and kittens and welcome back to another episode of best in SAS where each week we take you behind the scenes for conversations with some of Silicon Valley's best and brightest operators and investors. Crack a beer, get comfortable and join us on our quest to find the patterns and playbooks that accelerate the sprint to 10 million of that good stuff, that repeatable stuff, that stuff we call a R. R. All right, so today I'd like to welcome Scott Leese to the show. Scott is a six time startup sales leader, two time founder. He has a number one Amazon bestselling book and is a strategic advisor to tons of companies. I won't list them because there are too many to list among many other things. So Scott, welcome to the show.

Scott Leese (00:52):

Thanks for having me. Glad to be here man.

Elias Rubel (00:55):

Absolutely. So let's start like way at the beginning. I mean, you've, you've had like a storied sales career and it seems like it's only just continuing to, to grow like crazy. You've got surfing sales like what sparked your interest to begin with in sales? Like, how did your journey begin?

Scott Leese (01:13):

It's actually kind of born of desperation to be honest with you. And the lack of, of of alternatives and options. I, I never had a business mind. I never studied you know, marketing or anything like that. In my, in my youth, I mean all I cared about when I was in high school was playing sports and I played four sports throughout almost all of high school, narrowed it down to two that I was really good at, played those two sports in college. So I played college tennis in college soccer at a D two level. We had really good team. So, you know, I was playing all the time, traveling all the time, no time to work. And in school I was studying psychology and religious studies, so just like subjects that I thought were interesting, you know, not at all thinking about like, you know, making money, your business and this is like the late nineties.

Elias Rubel (02:10):

Right? So like the very boom. Like, I totally fucking had no idea what was going on because I was going to school in Marin County, which is like, you know, just North of San Francisco. But I, I was just absolutely not thinking about that stuff at all. Ended up going to grad school at Arizona state and you know, right when I was finishing grad school, I was 23 years old and I got super sick. And that began a four year battle in and out of the hospital, more time, more in the hospital than not. I usually tell the story as I basically spent four years in the hospital fighting for my life, got a couple autoimmune diseases and ended up having a series of surgeries. I've had nine surgeries in four emergency surgeries, two that were lifesaving, got addicted to opioids through all that medical stuff.

Scott Leese (03:09):

So I had to kick off of off of drugs. So, you know, here I am finally at 27 years old I am living in San Francisco. My wife is going to go to UC Berkeley for grad school and I have never worked. But like I literally have never had any kind of job that wasn't, you know, coaching sports or getting paid to play sports or something like that. So I looked around and were just like, I don't know what I'm going to do. My, my education is worthless. Like I, I haven't read or studied this stuff in four years. Like, where can I make money? The only thing I could think of was, well, I know salespeople get paid really well and I know that the harder you work and the better you do, you earn more. And I understood that as a, as a competitive athlete.

Elias Rubel (03:59):

And so that was my, that was my thought process. That was literally all I thought about in terms of why I decided to go into sales. It wasn't like, Oh, I might be good at this, or you know, this is really interesting, or anything like that. It was, where can I go make money? Because the one thing that I kind of felt about myself was I'm willing to outwork anybody. And I have literally been through hell for four years. So there's nothing that I'm about to face that will be harder than what I just dealt with. So that was it man. It's totally round, roundabout non traditional way to get into the, into the field. I love that.

Elias Rubel (04:37):

So this is totally off topic from what we're supposed to be covering in best in SAS, but I'm going to go there anyway cause it's top of mind now, which is let's throw them out there. They're out the door. So you know, you, you basically when people, when people are picking their careers, air quotes, picking their careers, which for many of us happens multiple times over. You know, a lot of the time it's based on trying to figure out where you have skills or you know, you invested a ton in an education or maybe you didn't have an education and that therefore steers you into a certain path. But I mean, for you that was, you're just like, fuck it, this is, this is like, it maps, why not go for it? So do you think that sales just in general, is that like that the opportunity is there in sales as a field four, anyone that wants to take it?

Scott Leese (05:32):

Oh, a hundred percent. A hundred percent. It is one of the careers that you, career paths you can take to make a significant amount of money where you still don't need any kind of higher education to get involved is an extremely low barrier to entry. You know, you don't have to have any kind of certifications or courses or, or anything depending on where you apply. So I absolutely fundamentally believe that. And you know, it's one of the reasons I wrote my book. I'm addicted to the process. I wrote it for people who are looking to get into sales for the first time or who are coming younger and newer in their career because it's like a place where a bunch of people go when they don't know what to do with themselves. You know, honestly, and you know, we're not people who have law degrees and medical degrees and you know, haven't gotten MBA's often or like people who, you know, have some charisma and like to like talk our way into and out of situations.

And you know, we've got different type of type of smarts, but we've never known really where to apply it or how to apply it. So you think about all the people with all these liberal arts degrees like me who get out of school and they're like, well, fuck, now what do I do? Right? There's some crazy stat that like 60 to 70% of new college graduates will go into some type of sales role as their first job out of school. I just, I just was recording a podcast with Dr. Richard Condie, who's who teaches at university of Houston downtown and he was telling me this, this kind of statistic. And yeah, I mean, I totally agree that it is a career path people can take with very low barrier to entry. You don't need education to get into it. You don't need to have prior experience, you just have to really commit yourself once you get there.

Elias Rubel (07:25):

I have this kind of joke that I don't know if I've ever vocalized to a larger audience, but it, and it probably isn't super true, but I kind of joke that when I started my first SAS business and we raised our first big venture round the only reason why we did that is because they forgot to ask me what year, what year I graduated Stanford because I dropped out of art school and I don't fit the, I don't fit. So similar, similar, but cool. So let's, let's now, let's fast forward, right? You were VP of sales at main street hub among many other places, and then that, you know, you grew that business massively before it was acquired by GoDaddy, so I'd love to hear kind of where, where in your journey was that as far as, you know, was that foundational? Was that leveraging a bunch of lessons that you had already learned and kind of how did that fit into your puzzle?

Scott Leese (08:22):

To me that was sort of going into the big leagues for the first time. Like I had had three head of sales roles, VP of sales roles, whatever the job titles were already. But the mainstream hub gig felt like just a different kind of a different kind of playing field, raise a little bit more money. I had relocated my family from the Bay area to Austin for the opportunity. We actually relocated the whole company from San Francisco to Austin. So it felt like, you know, there was a lot riding on it. I felt like I could see a clear path to a particular kind of revenue number and potential exit. And I absolutely felt like I could leverage my past experience you know, building and scaling sales org to make this happen. It was, you know, kind of an SMB transactional sale.

I had had experience doing that. I had grown teams from zero to almost 200 before in, in multiple States already. So I felt like I had like the playbook and the pedigree kind of down and I felt like, okay, these last couple of gigs I had had, they all just prepared me for this one right here. And I think that really helped me a lot. What I mean going full cycle through acquisition to go daddy. Now looking back on that experience, are there any takeaways that you bring with you as best practices or as playbooks you didn't have in your belt before going through that, that full cycle experience? Yeah, I mean I can, I can tell you the most important one to me is investing in sales operations.

Very conscious effort. That main street hub too lobbied very, very hard to get a sales operations hire as soon as humanly possible. And I had been devoid of resources in, in my prior three VP of sales roles from having no tech help to know personnel help or whatever. And I just sort of, you know, I drew a line in the sand for myself. I'm not going to work any place anymore unless the first person I can hire is a sales ops manager or a head of sales ops. That's, and I've stuck with that and I continue to teach and preach that I, in fact, I've, I've had multiple conversations this week with VPs of sales from big, huge companies all the way on down to ones who are building out their sales work for the first time right now. And like, I can't stress enough how important that is.

You know, I as an early, the VP should not be spending my time trying to figure out how to build, you know, Salesforce reports and workflows and all this kind of stuff. Like, that's not my skillset. No. There might be some, some VPs who had gotten good at this. That's not me. I need to figure out how to sell this product. I need to recruit, I need to train people. I need to build the whole process. I know what metrics to look at. I just don't want to be the one building all that crap. That's a big lesson. And we were able to implement that at main street hub and I've carried that on in my career. So it's interesting your, your thesis around, around the advising and sales work that you do, the consulting is almost identical to what we do on the marketing front.

Elias Rubel (11:51):

As far as you know, you're, you're all, you're focused on the revenue sprint from zero to 25 million error. And look, just looking at your roster, always hired hooplah stratify prodigy software. So I'm curious what, what is it like when you go into these companies, what are the, the most common mistakes that you see? Like a series a well funded, nothing but opportunity ahead of them. What are the most common mistakes you see them making? And you don't have to give us names, but if you could dive into maybe some of those stories of specifically like what you see commonly fucked up.

Scott Leese (12:37):

So it's interesting is, is how often the company fuck up the same thing. So one of the things I find myself saying all the time is, Hey, don't feel bad guys. Like you're not the only ones who have fucked this up. Well, one of the, some of the things that they do, you know, they have no idea what their ICP is, their ideal customer at all. Reaching out to God. No. And God knows what location. But Scott everywhere, everyone wants their software. I just need to hear about it. Everybody wants it. They've all been dying for it. Yeah. Yeah. So that one drives me nuts. The worst possible sin though is they just don't know how to, how to sell candidly. Like, do you just call you up and say, Hey Eli my name's Scott. I'm with a company called main street hub. This is what we do.

We'd love to show you it. And I'm just like, what are you doing? I did that pitch and approach and I see it all the fucking time. It drives me nuts. I wrote a whole book about it. My life experience kind of taught me that selling was very similar to the recovery process. Like, I'm not going to get you to buy from me if I don't get you to admit that you have a problem. If you don't understand why that problem is important. And if you don't feel any kind of urgency to address the problem, then and only then is somebody going to be interested in this solution. And salespeople and founders who are selling fuck this up all the time. All the time. I see people higher, you know, in AA pay them over a hundred thousand dollars as their initial like sales person because they quote unquote don't want to hire an expensive sales leader, which is actually not that much more expensive than some markets.

They have no kind of process whatsoever. They, they, they don't have any kind of repeatable, scalable pitch or approach for anything. It's all just very haphazard. Founders in particular make the mistake of thinking everybody is going to be enamored with their little baby the same way they are. So inevitably I have to simplify the pitch all the time and try to explain to them, look, just because your toy can do a hundred things doesn't mean your buyers care about those 100 things. Okay. I often tell the story of like me going onto a car lot to buy a car because I'm not a car guy at all. I I drive like two hybrids. I've had like three different Prius's in my life. All I care about is like the gas mileage, like the color maybe. Okay. And maybe is it like say for my kids, if I go onto a car lot and the sales guy starts talking to me about the breaking speed and the tire size and the weight of the engine and the zero to 60 like you're just fucking losing me, dude.

I don't care about all that stuff and I'm just going to be like go away. You just want to know if you can sneak into those whole foods parking spots like this. Quiet as quietly as possible. Know that's all I care about. All I care about. So I don't understand why it's why sellers and founders in particular, they're just like, I think there's too close to it, right? It's like people don't care about all these different features. You've got to find out what things matter to them first so you can know these are, these are some of the really common mistakes that I see people make at the beginning. How, how so I think a lot of founders out there who are listening to this are saying to themselves, Oh, I'm not that guy or I'm not that gal. Like that's not me. Yeah. Like we've got this down where they really do care about our product.

Elias Rubel (16:33):

Is there a, how do you help founders have that aha moment where they realize, Oh shit, like I've been talking about product and features and nobody's buying, or maybe we've luckily landed some relationship sales, but like what do you do to illustrate that to them? I mean, I think you just said it. You just ask them know where are your deals coming from right now? Yeah. Coming from introductions and relationships, then that is not a scalable process whatsoever. Okay. So you've got to get outside of this little bubble to test whether there actually is an appetite for yeah. And then one of the things that seems to resonate with founders is I try to explain to them like, look, you know, this market better than anyone and you know, your product better than anyone. Mmm. So you might be comfortable just add living conversations and you might be good enough and passionate enough to get a couple people to buy.

Scott Leese (17:37):

But that's not what we're trying to solve for. We're trying to solve for hiring five to 50 people in the next two years who don't know anything about this industry or product at all. Okay. Who have sometimes limited, if no sales experience whatsoever. And so we've got to get the information that's trapped inside of your head right now onto paper. We got to get it out of your head and onto paper so we can get everybody else to be, you know, somewhat as savvy as you are about speaking about this, this product and this and this industry. We've got to simplify it. Like, have you ever tried to explain to your grandmother what your product does? You know, if her eyes glaze over then it's a bit too complicated. If you can't talk to your significant other significant other about what what you do.

Scott Leese (18:32):

Mmm. You know, without them understanding it in 30 to 60 seconds, then it's too complicated. Well, you just got to keep working to kind of dumb things down. It doesn't mean you throw out all the information and all the detail, it just means you don't have to lead with it. Just keep that stuff, you know, in the back burner so to speak. Keep it in your back pocket in case you in case you do need it. So I really, for me, I just try to hit it head on. I'm just like, look, you know, okay, you might think that you've got this pitch down and everything, but like you're reaching out to me telling me that sales are stagnant, that you know, the couple of people that you hired has not been able to close deals the same way you have and you know, it becomes quite obvious to them.

Elias Rubel (19:21):

Sure. So as we wind this down, you know, I always love to find out what inspirations, whether it's people, mentors, even peers, just who are doing great work out there in the industry have helped pave your way or keep you inspired through your career. Okay. Yeah. You know there's a couple people that I've have cited recently and I know, you know, one of my, I would say my biggest mistakes or biggest weaknesses is that I've never had a good mentor sales mentor or business mentor. I mean, when I was getting started, there was no such thing as LinkedIn or do you know any of the other communities that are out there? There's no podcasts, right? There's, it feels like there was a lot, there was a lot harder to get access to people and information, so I really screwed that, that part up.

Scott Leese (20:15):

But you know, there was one sales trainer yeah, my first ever sales job named Mike Lindstrom, who he used to work with Tony Robbins and you're super motivating and, and like challenging and not felt like he believed in me. And so he was somebody that I still keep in contact with to this day. Mmm. You know, my, my, my business partner in surfing sales Richard Harris, I mean he kind of has pestered me for years now to stop working for other people and go into business myself. A couple of friends of mine, John Burroughs and Kevin Dorsey both kind of said the same thing to me and have given me some advice and guidance. So, you know, these are really sharp savvy people. Mmm. But there are people I think who would just kind of been in my corner and, and kept me motivated and you know, their belief in me has been helpful. You know, as I try to tackle new things and new challenges and build, build upon, okay. Past success to hopefully propel myself forward, do even better.

Elias Rubel:

Well, Scott, it sounds like things are, things are only just getting even started for you. I mean, you've already had an amazing career thus far and it seems like you just keep ramping it up and up and up. So super excited to follow along with your journey. And thank you so much for joining on the podcast today. Yeah, thanks. Eli's good to talk to you, man.