Kevin Davis: The Surfer’s Guide to Smarter Sales Territory Planning

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So I'm super excited to be partnering with them to give you an exclusive offer to get Otter.ai for sales today for free. Go to otter.ai, that's O-T-T-E-R dot A-I forward slash JBSales to get your free offer and start saving time and selling more effectively today. RevOps should be able to put those sales reps in a position for success. But it all starts with being able to quantify and consistently define what a territory actually gets. Hey, everyone. Welcome back to Make It Happen Mondays, where we talk about sales, business, entrepreneurship, personal growth, mental health, and everything in between with guests who I truly respect and I think make a positive impact on the world around us. Now, today's conversation is with Kevin Davis.

He is the co-founder and CEO of Boogie Board, a company rethinking sales territory planning with data and AI. Now, before Boogie Board, Kevin's journey started in the small Wisconsin town where he learned grip the hard way from shoveling snow and driving plows to working his way through a marketing grid. We talked about how Kevin stumbled into sales, then into operations, and why he believes he shouldn't ever have been in sales in the first place, yet that path gave him an edge on understanding both sides. He shares this surfer-not-hunter philosophy for modern sales and why the way we define and assign territories is deeply broken, which I couldn't agree with more. We also dug into why reps don't trust ops and how to fix that with transparency and how early career tactical mistakes shaped his approach to clarity and value-first selling.

This one's packed with sharp insights for anyone in sales, ops, or leadership trying to bridge the trust gap and build smarter, go-to-market engines here. So I hope you enjoy this conversation as much as I did. Let's make it happen. Kevin Davis, welcome to the Make It Happen Monday podcast. My friend, how are you doing today? I'm good. Thanks so much for having me. Pleasure to be here. Yeah, looking forward to this conversation. Especially as I went to, you know, I went to RevFest or RevOps a couple of them and really watching how RevOps is rising quickly in this, especially in this world of AI. So I'm really interested in getting your perspective on some of that. But as my audience always knows, I'd love to dive into the origin story first about what made you, you, right?

So parents, upbringing, all that fun stuff, the stuff that we can't find on LinkedIn. Give us a little bit of a background there and then we'll dive into the details. Yeah. I grew up in a small town in Wisconsin, a little suburb of Milwaukee called Heartland, Wisconsin, which is a very cold place, but a beautiful place, drenched with lakes in the summertime. And I lived there my whole life when I was a kid, all the way from the same house as a baby to when I was an adult. And, um, I had some, some odd jobs that you would expect for, for a young boy to get tasked with doing landscaping, shoveling snow. I even, if you can believe it, learned how to drive a snow plow and salt the roads at one point.

And so I did a whole bunch of that stuff, uh, growing up and, uh, then eventually went to the, the university, uh, of Wisconsin, uh, in Madison was sort of my, my genesis, uh, with the through line being the great state of Wisconsin. What, and I forget, what degree did you go for? I got a marketing degree, uh, which I grabbed because I, uh, initially got a, uh, was going to get a real estate and finance degree. Madison has a really strong program. Um, but it's, it's actually hard to do that. And so I was not up for doing hard things at that point. And so I kind of, uh, delved into the marketing world, nothing against, um, marketing degrees, but I did. That's the same thing that happened to me.

Yeah. I kind of, I started my, my first major was art. Because my mom was an artist and I was the best artist in my tiny little town of, you know, whatever, two thousand, you know, 10,000 people or something like that. Um, and then I was like, Ooh, uh, I, I went to university of Maryland, so huge school. And I remember sitting in my first art class, looking at the talent around me going, okay, guess I'm not an artist, uh, uh, next. Right. And then I went to like math and engineering. Cause my dad's an engineer. I was like, okay, let me try this. And then I hit calculus. So I was like, nevermind. Nope. And I, I ended up with marketing cause I'm like, ah, not, I mean, yes, it was easier, a lot easier than most of them, but it felt like it kind of combined a lot of my skills, if you will, like artistic plus communication, plus all these different things.

So, so I'm going to be at a little bit of a similar path. Yeah. Yeah. It was, it was more of a natural fit for me. Um, and I, I did enjoy it and I kind of did eventually help me get into the working world. So I, I, I can't, uh, shame it. Yeah. So walk me through the kind of the ops journey here, right? Cause you know, I mean, we'll, we'll talk about your, the company that you're, that you built, but where did ops all of a sudden start to become a highlight for you of, first of all, interest and also importance. Yeah, it was, it was mostly by accident. I, I started at a software company called NetSuite. I had your traditional, like out of college BDR job is actually in Boston, um, swelling and dialing.

And then I was a salesperson for a long time. I had various sales roles at NetSuite and Google. And, uh, during COVID I was living in Europe and we were about to have a baby, my wife and I, and, uh, we kind of needed to come home cause it was unclear how long we were going to be locked down. We had some issues with like the way our, our, our, our time there was set up. And so I had to live for a job and, uh, we're going to Google and there's a lot of jobs at Google, fortunately at that time. And there was one in operations and I always been ops curious. Um, and I, I jumped into, to the world then I had always been kind of a, uh, data driven and, uh, systems focused salesperson. But, um, that's when I actually bought into it was, was coming back from COVID.

Why? So that's unique. So my COO always tells me that I'm a super anomaly when it comes to sales, because I have the ability to communicate and all that, but I am very, uh, detail, detail orient as far as measuring and looking at things objectively and that type of organized, quite frankly. Right. And usually that's not the case. Usually like you're just really good and you're not very organized at all, or you're really organized, you might not have the abilities to engage and connect with people. So was for you, was it, why did all of a sudden the analytics side become attractive or why did, you know, was there something about your upbringing or, or what you learned that kicked that analytical side in early from a sales standpoint, or did you understand it as you evolved in sales?

I think it's, it's much more natural to my personality. I think I actually probably never should have been a salesperson. I'm lucky that I was, um, but I remember, you know, my dad, if I asked him, Hey dad, what are we thinking for vacation as a kid growing up? He would show me a spreadsheet with 30 tabs, um, some sort of math that lands us on, you know, a great, uh, vacation with optimal time spent in each location. And so I think it was just baked into my DNA, um, that this is kind of how I think about things. I remember my wife early on in dating, telling me to stop texting her and bullet points. It's like, it's how I, how I kind of work. And so somehow I ended up as a salesperson, but it was much more natural for me to move over to the other side of the aisle.

Nice. So you were, and I want to dive into this cause I've looked through some of your previous interviews here. You hate the hunter whole label, right? Uh, you were a hunter, quote unquote, you know, we talk hunter farmer, right? Prospects, uh, SDRs, BDRs are hunters and AE or AMs or whatever, farmers, some AEs are both. Um, talk to me a little bit about that, right? And also your analogy of being a surfer instead of a hunter. Could you expand on that a little bit? Yeah. My, my thesis is that the, the hunter days are kind of over the ability to think of your customers prey is specifically what I don't like about, about that. Um, seeking them out, ultimately killing and eating them, right? That's what the metaphor more brings us to.

And I just, it was very clear to me early on that you just can't think of that, them that way. You are not in control of the situation. You have to come to them with this deep respect, this deep appreciation, almost like a worship or an immersion. And it felt a lot more like the way that a surfer takes on the ocean. They, they come into the abyss. They let the waves wash over them. They try to ride the wave in as respectful a way as possible through deep understanding. But they know that at the end of the day, that way it could crush them at any time. Hey, I hope you're enjoying the conversation so far. I want to take a quick minute to share with you what I'm working on these days with my new JB sales membership.

It includes live monthly training delivered by me on my two signature courses, which are filling the funnel and driving a close that cover all aspects of the sales process. It also includes monthly workshops that I'll be running on specific sales skills and different tech skills like chat GPT and how to leverage AI throughout the entire sales process. Finally, the membership gives you access to my entire online catalog with every course and every tip I've ever done. And as an exclusive offer to my podcast listeners, if you go to jbarrows.com, click on the individual membership link and use coupon code podcast at checkout, you'll get 25% off. Now let's get back to the conversation. So with that though, you know, look, I, I, I talked to a lot of sales, sales influencers and trainers, right.

And, and I don't want to name any names, but they all, you know, get them to come to you. And, you know, I don't prospect, I don't cold call cause I build my brand. And I'm like, look, you're a sales guy selling sales training to sales guys, right? Like I'm a crackhead selling crack to crackheads and I'm a crackhead, right? So it's, it's really easy for me to just let the wave come in and figure it out because I built my brand. I have, you know, the inbound stuff like that, but you know, and, and outside of the, the, the word hunter, right. Finding new business. How does a surfer hunt, find new business? Forget about the killing of the metaphor, but like looking at that, how do you succumb to the waves when you have to go out there and find that business because the business isn't directly coming to you?

Yeah. Yeah. I mean, if you've ever spent time on the coast, like sometimes, uh, there's a lot of driving around for surfers, you know, there's, there's, uh, waves that are, um, momentous at certain periods of time that are seasonal. Uh, there's, it requires an extreme understanding of, of, of the water. Of, of the weather of, um, your market, if you will. Um, I don't deny that that part of the hunter metaphor is, is correct, right? Like you have to be grinding out there trying to, to, to find things. I always just thought that the connection to the ocean was a little bit more of a beautiful one than the adversarial line of the hunter. So you're, so this is more about like, you know, obviously quality over quantity to you, right?

Like the mass blast. And I, I, I've been on that page for a while. Like, I think the mass blast is just dumb. Um, I, I, that's marketing, like let marketing do mass, like sales. We need to throw darts. We need to be super specific and personalized. So how do you scale that though? I think it's derivative of, of your customer. Like when I worked at, at Google cloud, we had, um, a leader come in who was from a different background and they wanted to set up a cold calling blitz, which was an ethos that we needed to an extent because we were a tech shop, a product shop. And so there wasn't that go out and get business, uh, mindset. The problem is Google cloud is entirely consumed by software developers and guess what they don't do.

Answer the phone there's it's useless to call them. And so there's this, this conflict then of, okay, we have to grind. We have to be out there. Um, but the phone doesn't work. So you have to get much more creative. And so, um, yeah, to scale, uh, that there's, there's social channels, there's email channels, there's more sales led growth through the product in that specific example. But as an ethos, I think it just needs to be really derivative of what the customer necessitates. Yeah. I think that's, uh, I've kind of had the same conversation with clients where, oh, build your brand. And it's like, yeah, but none of your clients are, none of your customers are on LinkedIn. You know, it's so, what are you doing?

I mean, if you're, if you're doing it for yourself and your own personal career and because you want to do advancement, that's one thing. But if you're trying to attract clients, like my wife sells to local governments, right? So she's a CEO of her own little company and she sells to local governments. Local governments are not on LinkedIn. You know, she has, she does some minor stuff on LinkedIn and whatever, but most of the local governments, unfortunately, are on X or Twitter, right? So that's where she tends to engage and, and that type of thing. So it's almost going back to the, the ocean analogy, right? Go where the fish are, right? I think blue ocean, when you, when you're trying to differentiate yourself, but stay in the red ocean where the fish are, if you're trying to fish.

Yeah, absolutely. You need to know where they are. If you don't, that's, that's sort of an extreme problem. It should be pretty obvious to you. So let's kind of evolve into territories now, right? Which is kind of your sweet spot with what you do. Territories have always been interesting to me, how they've been created, developed. I, I thought a long time ago that I had heard it, but I didn't see it happening as much where people would actually be hired and put into territory based on their profile, based on their social profile. For instance, like you could use technology to look at my 400,000 followers, see where the heat spot, you know, the, the he's, Oh, John, you are really influential in this region or with this persona.

So based on that, we're going to give you this territory where we're going to give somebody else another territory. The other approach, and that hadn't come to fruition. Hopefully it's starting to now, obviously. The other approach is, it's just kind of like, there's no adjustment at all. It's like, yep, here's your territory. Here's your numbers. Doesn't matter who, you know, what your skills are. That's yours. And you might have a good territory. You might have a shitty territory. So could you explain how and why you've developed what you've developed and, and what the challenge is with territory alignment right now? Yeah. The reason why we develop what we develop is because I felt this sort of extreme pain at the various companies that, that I worked at.

Like it was, I worked at great companies. Um, but there was always this time in January where I was like, okay, we're not going to have territories for another few weeks. When they do come, everyone's going to be angry. My friends at sales and other companies thought the same thing. It was just this weird thing. And everyone was like, man, we throw our hands up. Like they're, they're terrible. And, uh, so the ethos was what if we could build a suggestion engine to make this algorithmic, make this go faster and make sure everybody knows like what's going on behind the scenes. So that was the first thing that we, we built, um, as, as a company, what's underlying all of that is an explosion of, of data, account data, intent data that allows us to think about markets much more precisely.

And the thing that I really had to learn was what a territory means to different types of companies. Um, for some companies, it's mostly about your coverage, how you're covering the market. Um, for others, uh, it's about retaining reps to an, to an extent, like that's going to be a big factor. Others there's, there's massive, um, geographical, uh, considerations. And again, we try to think of it as, as derivative of, of the customer and trying to solve, uh, multiple goals, but that, that explosion of data has allowed for a lot more interesting type of territory development. So one of the things you said that, uh, struck a course is reps feel like they've been handed a bag of mystery meat. It's the fast food version of sales ops, quick, dirty, and no one trusts what's inside.

Well, so that's the frustration, right? Like I got my territory. I don't know why I have this territory. I don't trust why you gave it to me. Like I might subjectively feel like you're putting me in a bad position because you want me fired or something like that. And put me, so how do you align? Once you, once you understand the company's definition of territory and however that flows, how do you then look at an individual rep objectively to say that this is a territory you're going to be successful in versus this one isn't. And, and does that have to do with skillset, right? Because I've seen territories before where, you know, average reps will complain, this is a shitty territory. And then a good rep comes in and turns it all the way around.

Like, you know, I, my first job at Xerox, for instance, I sold state and local governments and I, apparently I interviewed well and I went through the onboarding well. And so they gave me the hardest territory in, in the company. It had had like six reps in three years. There was no trust and, and they hadn't gotten any business out of it. And they were like, yeah, I'm like, great, thanks. You know, there's a bag of shit. But then through my own approach, whatever, I turned it around to be in the, one of the best ones, right? So how do you look at that from a objective standpoint to make sure that you're matching the right sales rep in the right territory? Yeah. I mean, territories are always going to be a hypothesis.

You don't totally know how they're going to manifest. So I think as a baseline, you got to quantify what a territory is to you, what set of variables consist of and make up a territory. And then what is the expected health or, or, or kind of opportunity in this territory? So that now when I'm grading you, John, coming into my company, your achievement in that territory, um, is, is rated higher because we thought it was going to be more difficult for whatever reason quotas can then reflect that in things of that nature. But it all starts with being able to, to quantify and consistently define what a territory actually is. Uh, reps use the word fair a lot. It's not fair. Is it possible to create fairness when it comes to this?

Yes, it is. Um, you have to have good enough account data to, to know, um, you know, what the opportunity is in some accounts, um, um, but your approach to designing a territory can absolutely be fair. And if not fair, uh, very equitable, right? If I know this territory is a one and this territory is a 1.3, at least by my math, I can give you a 30% higher quota. Give this person, um, you know, a 30% less quota, uh, and go from there. So if you lift the veil and you, you don't, um, allow them to say, well, this is fair for this reason, or this is fair for that reason. It's like, if we've anchored our territory with a definition of what fairness is and how we're thinking about equity, you can, you can argue with our process.

We can invite your feedback into that process so that we improve it over time, but you can't say that what we did wasn't fair. So a lot of it, yeah, and I think this is the, the falter of most leadership is, is to your point of the, the transparency of it, right? Of, of lifting up the covers and saying, look, this is why we've done, this is why we did it this way. And here's the objective criteria that we are using. We can discuss the, the, you know, your opinions of the viability of that objectivity, but like let's, let's show you, right? So, cause I think another one you said was you say good design fee, uh, makes feedback a discussion, not a war. Yeah. And so are you really trying to create as much objectivity into this process as possible?

And how does that, um, how does that lead to much more constructive conversation? Yeah, I think it starts with the fact that this process is usually, usually done in under duress. The sales leaders and the operators that are doing this are working in spreadsheets. And so by the time it's done, they actually don't totally know what happened. And when they then try to unveil it, they're just so busy that like it, it kind of gets washed away. So we try to take a complete opposite approach. We've got a very specific process by which we're inviting feedback in early through surveys. So people feel like they're part of it. We're, um, you know, demonstrating what's happening throughout our algorithm is equitably designing the territories in the most, most mathematically kind of efficient way.

And then when we announced it at sales kickoff, we're giving all of these people credit for all the TLC that like went into this massive process because they really want to put sales reps in position for success. And sales reps will listen. I think sales reps better than most will understand that the world is imperfect and that account data is going to be imperfect. But if you can show them that you really cared and tried, I think they're responsive to that. Well, I think that's the challenge, right? So, I mean, there's rev ops and there's enablement and I've spent, you know, the majority of my career working with enablement. And the challenge that I always see with enablement is they're trying to, you know, lead a horse to water and make it drink.

And the reps rarely drink because, you know, the, the feedback loop isn't there. The integration isn't there. The, the, you know, it's, it's like, here's our program. We're going to, we're going to start. So it's the same thing in territories. I think there's a lot of distrust from sales reps because of what we've been through over the years. You know, I call it like, you know, the methodology book of the month club, right? Where, oh, we're doing challenger this month, this quarter. Oh, we're doing, you know, this, this quarter we're doing this. It's like, yeah, whatever. I'm just going to do the bare minimum. So I don't get yelled at here because I know another one's going to be here in six months.

So how do you, like, what does that structurally look like for you to, to align with sales and make sure that there's that connective tissue there, the feedback loop and everything. Like, I mean, tactically here, is it, you know, are you weekly meetings? Is there, is there SWAT teams basically that you're using? Like how could a company create alignment between RevOps and sales so that sales does listen and does appreciate the work that RevOps and enablement to a lesser degree bring to the table? Yeah. So the inputs that go into territory designer are pretty regular. So there, there's accounts and then there's attributes about those accounts. So simple questions like, Hey, do you have a list of 10 accounts that you really, really want to keep?

And you take that into consideration and maybe everybody gets to keep three or, or whatever it is. And you do that early on in the process. You kind of invite their eyes on, on what's happening and just demonstrate that you care. Then you might ask him, okay, what are five other companies in the market that you really want to sell to? And why really good data mining from people who are on the front lines or maybe have a personal interest, um, in an area. And then as far as the project is concerned, yeah. Extreme transparency. This is where like really boring stuff, like having beautiful project management documentation, a really clean, like SKO presentation where I was like, I always get so emotional about it because I can tell I'm in like founder mode.

I'm just like, we, we, we want these to be so good. We want this territory to be incredible. I'm always worried that I'm like a Chris Farley, like smothering his, his role. But I just, if you tell them that, that you really, you really cared about these, they tend to be receptive. Where have you seen it fail, right? Like rollouts fail of territory planning. And, you know, it's the same with training in a lot of ways. If there is an alignment top down in some way of making sure that we're tracking and integrating and all that stuff, it's, it is what it is. You know, you'll get the typical, Hey, everybody's excited. And then they'll all go back to what they're doing. So where have you seen the pitfalls of, whether it's with your solution or not, of rolling out territories and, and what are some things to avoid?

There's two, two main failures that I see. The first is lack of executive sponsorship. If the sales leader, if there's a perception that that person distrusts the operations crew, or they see them as just analysts, or they're not involved strategically in what's going on, that culturally will permeate down to complaining and distrust. The second piece is account data. If you have not clearly sung from the hilltops, here is what we are trying to do with our account data. Here's why the world of account data is not perfect. It doesn't exist perfectly in the world. Here are all the things we're trying. We'd love your feedback. You'll just get people saying our data is bad. So you can go use boogie boards algorithm all you want.

It's doing it on bad data. And so it doesn't matter. Yeah. That's what I keep saying that I thought AI was going to solve the, the garbage in garbage out scenario, right? It's like, Oh, it's disparate data, whatever. Throw AI in there. It'll make sense of it. It's still the same. It's, it's still garbage in garbage out. Like if you have shitty data, AI can, is going to produce shitty results for you and shitty insights. So it still is about that. And so do people and like, where does, I guess, question for you in general, like most people's data is super messy, right? They don't track the right way. So how do you start creating a culture of, of tracking in a way that is information that is, is valuable enough to be able to use, to be able to be more precise with, uh, territory planning and everything else.

Yeah. So we generally come when people are at least that like kind of a phase two of their, uh, account data journey. If they are in like, uh, dire straits, we will maybe come in and help them with that or recommend a partner who could, who can help them with that. Um, the, the steps in that journey tend to be shrinking, shrinking the problem down. Um, I think companies sometimes feel that they have to have their whole TAM perfectly enriched with, uh, various, uh, account data attributes, uh, and intent data signals that it seems like everyone else has perfectly. Um, and they don't. And so shrinking the problem down to what do I need to be able to make my serviceable address will market polished in Sierra so that I can design territories.

Um, and then we recommend things that we see from, from other clients. You know, you can actually go and get this data. It's actually publicly available now. You can get it cheaply. The data supply chain has, uh, expanded, but it, it does require someone, um, doing a lot of diligence in that work. Yeah. Yeah. And I think that's the rev ops, the power of rev ops, right? It's like, you got to crawl before you can walk. And I think it's having somebody in rev ops come in before they start implementing anything is get in there and get your hands around the data. And why is, you know, what is it? What do we have? How accurate is it? And then being able to, because you build on a house of cards, you build on a house of cards.

What's, I'm curious with all the territory stuff you've seen right now, this is, you know, less about, you know, the tactical side and more just your thought process on what your, what you think the model is moving forward here. Because I, my contention is the predictable revenue model is, is dead. It's a joke. It always has been, but it was tolerated because we were grow at all costs. Money was free. Who cares? Right. But it's never been a customer centric approach. And now with SDRs not even staying in their companies for a year and a half, the, the promise of the SDR becoming the AE and all that stuff is, is out the window. So, you know, you hear a lot of talk about pods, right? Where a territory has one or two SDRs and, you know, five or six AEs and a marketing liaison or something like that.

Where are, A, what's your favorite? And B, what do you think? And I know there's a billion variables here, SMB, mid-market enterprise, blah, blah, blah. But in general, where do you think we need to evolve to from a territory standpoint with ABM and all these cool tools so that we can put ourselves in a position to be successful moving here or sales orgs can put themselves in a better position moving forward? Yeah. So the word I use is focus. That's what you're trying to achieve. I pause at my least favorite because I've been in a pod and all of a sudden each person in that pod now has like four different managers because the most senior person in that pod has to tell the most junior people what to do.

The junior people also have to care what that person's manager thinks and their manager thinks it's just very, very confusing. So I'm not a fan of pods. And I think territories in the modern era are an efficiency angle, right? How many times have you been to a sales conference? Someone puts on the slide, you won't believe how little time sellers actually spend selling, right? Every sales conference ever. And so it turns out we maybe don't care about that or maybe we should. And the way that you do that is by stopping having them hunting around on the internet, Googling which accounts are good ones. And so having a rev ops person in the seat who is understanding of the new data tools that are available, able to elevate accounts that are good or likely to buy so that when a seller is in that mode of approaching those accounts, it's done a lot more thoughtfully and done spending time on the right accounts more often.

That takes a lot of business acumen, like an understanding. And so we're talking about analytics, we're talking about data, we're talking about insights, but then the variables is the sales reps' ability to think critically with that information. I'm a little concerned right now that business acumen is gone and we've over-operationalized, we've over-scienced everything about sales and we've completely lost the art of sales. How do you balance that? How do you balance the objectivity and teaching younger sales professionals the art of conversation, the art of the subjective pieces of this? Because I can science out everything, but there's always that human interaction. And if we aren't developing, I think the AI, my biggest challenge right now is I feel like the AI is stripping away all the learning, actually.

You know, you think it's going to help with learning for the right people, but it's actually stripping it away because it can do all the preliminary stuff that junior reps used to do way better. So I'm curious, like, where that foundation comes from now, where the business acumen comes from in this model. So how do you, results, alignment, fun, but keep the engagement from an education standpoint, a development standpoint, a business acumen standpoint, and an EQ standpoint in this world of analytics? Yeah, yeah, I think your point is spot on, expecting a junior sales rep to now perfectly know why, you know, this is the right customer. And then now they have a message to say to them, they can also demo the product at an extremely deep degree.

It's like, we're definitely like not there. My thinking specifically from a territory standpoint is if you are elevating more of the right accounts to them, they're going to be spending time in an area that's more conducive to success. They're going to be having the right conversations. And they should be having similar styles of conversations. I mentioned not cold calling in one of my previous examples, but I'm still a huge proponent of as much time as you can possibly spend with customers in the market. I'm a huge proponent of in-person events now. I think the boomerang has swung totally back on that. That's not a nuanced idea, but I'm a big fan of sales reps spending time in that market. So I think it's about that partnership.

RevOps should be able to put those sales reps in a position for success. So they're not spending their time saying, actually, this account is in the Philippines and just doing like manual data work. They're actually on the phones with these companies. That could be a good fit. It's not going to be perfect, but they're getting more reps that way. Yeah. I mean, I think the people always, you know, I think again, we've over swung in various, we always, you know, everybody does all this and that, right? Sales isn't a numbers game purely, but it is a numbers game. The more at-bats you get, the more understanding you have about the interactions, about what works and what doesn't work. So at a certain point, yes, it is a numbers game, especially early in your career.

To me, it's quantity early and quality later, right? Because I always say as a manager, when I was managing reps, there was two levers I could pull to improve your results. One was quantity and quality, right? And the easier one for me to figure out was the quantity one. Can you do the job? Do you make the 50 dials? Do you make, you know, because I know the equation and if it, you know, pumps out, if you do these activities, it should do this, right? Then if you don't hit your numbers, my question I always use is, well, did, if you didn't hit your revenue targets, it's like, well, did you do the activities? Well, you know, I only did 250 versus four. Well, then go back and do fucking 400 calls, you know, like that.

Because I can't, I can't figure out if it's a quality or quantity thing at that point. But if you hit 400 dials, for instance, which was my numbers early days a week, now I know it's not an issue with your effort. Now I know it's quality. Now let's take a step back and now I can educate you. But I think so many people are trying to skip that step and jump right to the quality. It's almost like teaching a, this is why I hated challenger sale, teaching a 22 year old kid challenger sale, are you out of your fucking mind? You know, like that's like giving a 10 year old a shotgun and saying, yeah, go ahead, shoot over there. Like what? So there's that learning curve that I'm nervous about here. And I'm trying to figure out frameworks to address that, to improve the business acumen and all that grit that is necessary to have the context, to have the quality.

Yeah. Yeah. It's funny. I remember sitting in a challenger training when I was like very young and I was going to be selling to CIOs and developers, which I just, I probably could not have honestly held a 15 minute conversation about Google cloud at that time or software development generally. And so like, drowning them in a sea of rationale was probably not the right move for me at that point. And so, yeah, I resonate with that. I use that exact analogy. I'm like, yeah, tell it, go ahead and tell a 22 year old, see what happens when 22 years old, 23 years old, go challenge as an IT professional. Cause I was at two, like, I didn't know about challenger sale when I was right, but I kind of tried cause I had sat and started, I used to sell IT services.

And, and so, you know, I'd always go with my engineer cause I didn't know what the fuck I was talking about, but I would sit in server rooms and I would ask questions. So I kind of picked up on the lingo a few times and I was like, I got a little cocky and I was like, all right, I don't need an engineer. Right. And I remember like going to the CIO and kind of, Oh, let me tell you. Right. And it's, and looking back on it, it's a, it's hysterical because almost all of them are like this. Oh, look at this little door of a little sales rep. Oh, he's cute. He's trying. Right. And they, they give you almost just enough like rope to hang yourself. And then after a while they're like, okay, anyways, pep, pep, pep, pep.

Right. I'm sorry. I didn't mean to do it. So it's challenger sales always been a challenge for me. Um, but let's, let's talk about your evolution from a sales standpoint. Cause you talked earlier in your career about being too tactical. Right. And, and I'm wondering a, what the shift was there, but then you, with, um, boogie boards, first customer, it was a very kind of value relationship oriented thing. So you went from super tactical to seemingly a lot more strategic a, when did you make that switch and B, how do you scale that first customer interaction engagement that you had so that you can replicate that with the rest of the team? And what I've been calling it internally internally, uh, here is, is clarity selling.

This might be nuanced for, um, you know, an early stage company, but when I started boogie board, I would go on these sales calls and I would try to pitch our product in. I actually didn't know what the product was at this point. And so that came very clearly to these people right there. And I would listen back to these calls and I just put my head, my head in my hands. I go, my goodness, what did you just say? And so the first boogie board customer that we got, I was just, I wanted to learn as much as I could about these revenue operations, people that weren't from my world. And so I would just sit in forums and try to answer questions, try to meet people. Someone posted that they wanted to, uh, they, they had to do a, um, territory related question for an interview they were about to do.

They were like, here's the question. What do people think about this? And I said, Hey, I, I just started this company. You want to just meet for an hour and talk about it. And, uh, I did all this prep work and I showed her what I thought. Cause I just wanted to compare notes with somebody. And she was like, I feel like you just did my homework for me. Like, thank you so much. And, um, she ended up taking another job later on and ironically had to design territories and had just remembered that, um, I had just tried to be helpful to her, um, and had been clear in my ideas. And so there was just the simplicity of it that she trusted me because I helped her, um, was a relational side that I just, I had been too deep in it before to really understand.

So let's talk about scale, right? Because, and, and does scaling that really stem from quite frankly, the quality of the territory that you're aligned with, right? Because if it's a spray and pray approach, it's almost damn near impossible to, to, to do that, what you did there, right? Like learn about the business, be super targeted, be high value, right? So there's one part of, yes. Okay. If we got a right territory and it's aligned in my, you know, intent data finds the, the clients that are fit my tier one ICP, I can spend my time doing that. Right. But it, we're still in kind of, unfortunately in a world of VC backed. I actually, I didn't ask you like, you know, from a VC standpoint, but the pressure is there to grow.

Yeah. And, you know, let's go back to my Xerox analogy. I almost got fired because when I came into that territory, it was evident to me, I tried to do what all the other sales reps were doing. Like all my private sector, uh, client reps flipping copiers every day, you know, like almost immediately. Right. And I'd go into the secretary of state treasury and all these others. I'd be like, Hey, I'm willing to talk to you about your copiers. And they'd be like, get the fuck out of here. Like, we don't want to talk to you. We've had six of you in the past three years, like whatever, we'll see another one of you in six months. So I was like, Holy shit. Like I was forced into the design thinking version of sales because I couldn't just go top down and be like, Hey, I got this great solution.

You should buy it. I literally had to, we had one building. It was, it was, it was one Ashburton place in Boston, Massachusetts, right next to the state house. And I would, I would, every day I would walk to the top of the building and I shake hands, kiss babies, shake hands, kiss babies, shake hands, kiss babies. And I would sit down with the users and I would learn about their workflows and I wouldn't sell a damn thing. Like I wouldn't even talk to the executives. And, and then about nine months in my boss was like, I had zero results, like zero. I had one or two here. And he was like, dude, I thought you were some King shit. You know, we hired you to give fixes. And I'm like, just, and thankfully I'm a little bit Boston through and through.

So I was like, dude, basically fuck off. Like you gave me a bag of shit. Let me do this because it's the only way I know how to fix this thing. Right. And then what I did was about nine months in, I would go to each one of the executives and I would say, Hey, you mind if I get some time on your calendar just to show you what I've learned over the course of the past nine months working with your employees here? Well, you know, when I mapped out all of their territory, like all of their workflows and their, their office floor, I had like a handwritten, you know, office floor map with a copier here and a printer here. And I was like, look, these are analog. If you flip these analog to this and you do this and you're going to save some money and then it'll actually be more efficient.

And they were like, Holy shit. Yes. Right. And it was like million dollar contract, million dollar contract. And I remember dumping it on my, on my boss's desk and being like, see, right. That is a rarity for reps and for founders, for reps with management and founders with VCs. So how do you keep the VCs at bay, if you will, or the growth, aggressive growth targets at bay to create an environment where that quality is, is, is enforced? Yeah, that's a, it's a great question. We're, we're, we're entirely bootstrapped, but I've, I've worked exclusively. Okay. Good for you. Nice. Thank you. Um, I've worked at companies that are, that are VC backed and, and, and publicly owned. And to me, it's, it's entirely a cultural leadership ethos, right?

Um, if they're feeling that pressure and they think that to achieve success, what they need to do is to put that pressure down. Like then that's, what's going to happen if they culturally understand and they can quantify that the treating customers in a certain way will produce results over time. And they have enough confidence in that they can, they can set it up in a way that's not, you know, it's not relaxed. You're still are out there running from every office to every office grinding and that needs to be extremely measured. But to me, it's an ethos. And that's kind of like when I did back to the ocean, it's like these customers are absolute Kings. If you think of them out in Kings and Queens, if you think of them out there in the wilderness and our goal is to pray buckshot on them, it's just not going to work.

Yeah. I think that's the, that's why I tell reps when they're looking for jobs, uh, like new career paths or whatever it is, like you got to kind of get that leader. I think that's a partnership vibe here because, and I love engineers. Don't get me wrong. Engineers are fantastic. They make great products. But if sales is seen in two ways, one is if sales is seen as an app, like as a second class citizen, if you will, right? Because the product is that good. So it's an engineering founder products and saying, yeah, okay. We tolerate sales. I personally would not join that company because I, I've rarely seen companies fail because the product doesn't work or not fit. I've all, I've seen them all fail because sales doesn't work.

Right. Um, but then on the flip side, if they are sales, but it's like the grant card own version of shitty sales, right? Where you're just go, go, go and numbers, numbers, numbers, numbers, and numbers. And like, like that's a massive red flag that, that I would run away with. So I guess if you're a rep or even a leader looking for your next, you know, position, next challenge, how do you uncover that in a, in an interview for instance? Or is there something you can look at from the outside that says this company, this company gives a shit like this one, they're, they're growing fast, but they're doing it in a quality way because a lot of times we can't from the outside really uncover that to see is, are there indicators that you look at that says, yeah, this is a company that gets it.

That's a great question. I think there's, there's so much you can do now to figure out what it's like to work at a company before you step in, right? You have access to websites like rep view glass door. You can go and look at tons and tons of reviews. You couldn't hit up people on LinkedIn and say, Hey, think about working at this, this company. You might even be able to get them a referral bonus and they'll tell you exactly, um, what it's like to, to work there. So that'll give you like the, the soft facts, but when you're in a conversation and you're talking to the leaders and they're interviewing you, you have to turn the tables on them and see if they know what they're talking about. Okay.

What is my territory? They can't answer the question. They, they don't know what's going on. Right. Um, or what is, what are my expectations going to be around quota about being, in person about how often I'm going to be meeting with customers? I always like to ask, um, I was interviewing at a company one time and I asked what the guy's favorite, um, industry publications or books were. And he just looked at me like I was ghost, like, Oh, uh, yeah, he doesn't know anything about the industry. He doesn't read anything about the industry. And so to me, I was like a major reply. Yeah. Yeah. I think that's the problem is that we, as potential employees don't, uh, interview the company nearly as much as we should as, as much as they're interviewing us.

And I'll tell you, I tell reps all the time, like a, get core on your values first, like just understand what your core values are. And because once you do that, you can start to look for companies, businesses, leadership that align with those. And once you do that, you can do some special stuff. But if you aren't allowed on or aren't aligned on core values, you're going to, it's, it's never going to end well. So love it, man. Well, look, uh, in the interest of time here, we're coming up on it. Anything I missed or anything else that, uh, the audience should be paying attention to that, uh, that we didn't dive into during the call. Oh, you know, I don't think any topics that we missed. I just, I, I'm feeling super hopeful right now.

I know it's been sort of a weird time to be in sales. I've been specifically in the world of tech, but I, I sort of feel an undercurrent of positivity of some of these companies and products doing things that work. And so I just like to share that with the audience. Cause, uh, for me, we're out, we're out here grinding, we're trying to make a bootstrap company work, but, um, I think there's some, some good energy, uh, among us. So sending that out to all listening. I'm glad, right. Cause it's, it's hard to come by. Like it's easy to be pessimistic these days, uh, with all the stuff that you're seeing out there. And I have a, I have a slight alteration to that cause I am, I am optimistic. Um, but only for those of us that care and are willing to put in the work.

Yeah, I am insanely pessimistic for everybody else. The average players out there, the ones who are just going through the motions, you know what I mean? And trying to make a buck and do their thing or whatever, but don't give a shit and aren't willing to like open up their eyes and evolve and, and try things and, you know, that type of stuff like that. So for that, and unfortunately I think that's a much larger part of our population than, than the ones who give a shit. So yeah, the wake up call is, uh, is, is coming. There's, there's no doubt about that. It's not, it's not even, I, I, and I, I tell people, you know, if you don't think it's a problem, go into chat GPT right now and pretend like you're a potential client for your services.

In five minutes, you'll realize that you get more value out of that than some dipshit SDR that's going to ask them bank questions and flip over to an AE, just going to ask them the same questions, don't do a demo and then bring an SE in two weeks later. Right? So those are the ones that I'm saying, you better wake up now or else, uh, your time is limited, but everybody else, but the people who care and are like, Ooh, this is a cool opportunity, man. I think the sky's the limit, quite frankly. I love that. I love that. I'm here for that. Awesome, man. Well, Kevin, uh, it's been a pleasure talking to you. Where can people find out more information about you and what you're doing with Boogie Board and all that other stuff?

Yeah. Check us out on LinkedIn. Um, go to our website, boogieboard.ai. I'm on LinkedIn. If you want to DM me, I'm happy to chat with any listeners. Very cool. Awesome, man. Well, thanks again for coming on. I appreciate it. Thank you. Good luck. Absolutely. And everybody hopefully enjoyed the conversation as much as I did. Like I always say at the end of all these podcasts, go out there and make somebody smile today. Cause no matter how bad your day's going or how bad you think it went, if you make somebody smile today, you know, you had a good day and the world needs a lot more of that right now. So thank you all very much. And I will see you on the other side. Hey everyone. I hope you enjoyed that conversation as much as I did with your support and our incredible guests.

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