How a sales team books over $25M in new business per year | Lee Roberts

In this interview, Lee Roberts, Director of Firmwide Sales and owner at Bergen KDV, walks through how his company grew to generate over $25 million in net new sales annually. He explains the current sales structure—16 hunter‑type reps, 8 account‑manager‑type reps, team leads, and a sales‑engineering function—and how the organization evolved from a founder‑led, geographically‑focused model to a vertically‑focused, industry‑specific approach. Roberts emphasizes recruiting for business acumen, learning ability, and resourcefulness rather than just experience, and he describes an onboarding process that teaches reps to sell outcomes instead of product features across a portfolio of more than 60 productized solutions. He shares the metrics his team tracks—four new opportunities and four upcoming wins each week—as leading indicators of pipeline health, and he stresses the shift from activity‑based management to outcome‑based coaching. The conversation also covers prospecting tactics (phone, networking, drop‑ins, digital), allowing reps to play to their strengths, and the importance of storytelling that focuses on customer pain. Roberts discusses leadership mindset changes, delegating revenue generation to the team, and the need to build talent to increase enterprise value, especially for founders considering an exit. He recommends self‑education resources (Google, YouTube, books by Jeb Blount, Fanatical Prospecting, Challenger Sale) and highlights the role of the Independent Payroll Providers Association (IPPA) in industry advocacy and knowledge sharing. Throughout, he balances practical anecdotes with strategic insights on scaling a sales organization in the HCM space.
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I've ever received? Boy, that's an interesting, uh, interesting one. You know, I would, I would say, uh, you know, uh, this is a double-edged sword. You know, I think a lot of people have, have commented on my humbleness, and, uh, it's always something that, uh, you know, you never try to get too high in this business, never try to get too low. You just try to take it in stride. And I think that, uh, A lot of sales professionals would not get that tag, and I've always, always been proud to be recognized for that.
That reminds me of the interview question when you ask somebody like, what are your greatest weaknesses? They're like, oh, I work too hard. I, you know, care too much. I just, you know, I volunteer too much. And, oh man, awesome. Well, we appreciate you taking the time with us today, Lee. Excited to learn more about you and your journey. And we want to share some nuggets today on building out and growing a sales team and going from a founder-led bureau to having sales professionals in seat and beyond that. But why don't you tell us a little bit more about you and what you do so that we can have some context here?
Yeah. So in my daily life, I currently am director of firmwide sales. So certainly represent the HCM channel at Bergen KDV. I'm also an owner of the company and represent all of the different divisional lines. So I've got a lot to learn and I've got right now 16 sales professionals that are more on the hunter side. That are out evangelizing what we do. And then we also have a team of about 8 account managers that are looking after current clients and focused more on the nurturing and the expand side of the business. So if you kind of look at the predictable revenue salesforce model of specializing the salesforce and trying to get people focused on that, that's been a little bit of the journey that we've been up to. I started my career at Bergen as a producer. Didn't know anything, like many of us that get into this crazy industry, didn't know anything about it, but I've never left. So one of those as well. And, you know, really built, built my, my brand and my foundation at the old school grassroots level, one conversation at a time, one networking meeting at a time, and started running a small sales team a few years after I was a producer. And then really have been doing that ever since and just trying to grow it in quality and quantity. To drive revenue for the firm. Before that, I come from a very entrepreneurial family, so both my father as well as my grandfather were big into business, small business startups and the like. So it was a good foundation that we can unpack certainly a little bit more, but wish I'd have paid more attention probably to some of those conversations when they were hanging out with their business buddies. But it was a good foundation and I learned a lot, was brought up in those few of those businesses, and it was a lot of fun.
That's awesome. So, so you mentioned a couple of things I want to dig into here as we move forward. You talked about the size of that team. I want to hear a little bit more about how you lead and structure those conversations. Um, but you also talked about, and this is the first thing that jumps out when you look at your LinkedIn profile and something that I talked to Matt about, we had Matt Lovitz on, uh, a while back and talked about his, his sort of bag, what's in his bag, what's in his toolkit. You guys offer a laundry list of solutions. Like, I mean, there was probably 25 lines on your LinkedIn profile of all the different solutions you guys offer. How do you bring folks up to speed when you have that level of, you know, sort of variety of solutions? And what is your approach to getting a rep from, you know, those first 90 days to 6 months to getting them able to be able to sell the right tools in their bag at the right time?
Yeah, it's a lot to unpack there. And, you know, I think the first thing I would mention is that's not always a good thing. So there are days where, you know, I'm on one side of the fence with that versus the other. But I think it really starts with, you know, I do a lot of recruiting. And, you know, I'm looking for people to come join our organization that have high aptitude. And one of the things that I'm constantly looking for is just their ability to learn. As you know, this space specific to HCM has changed so much. There's a lot of same fundamentals, but, you know, it's always evolving and changing. And then you actually times that by the number of different offerings that we have. And it's funny, a couple months ago I was on a, on a program like this, and I think I said 26, and I kind of scratched my head afterwards and said, you know, I probably should go count at one point and make sure I'm not fabricating the story. And, uh, when you actually look at what we have productized now, it's over 60, uh, different products that we have to sell. And Counting HCM would be one of those, um, particular products. So it does take a person that isn't going to get lost in the weeds. But really, I would break it down to I'm looking for business acumen, uh, primarily. I'm looking for people that can understand business and how business runs and be able to communicate in a way that's focused on outcomes. And I think that's one of the things that we forget as sales professionals is, you know, people don't care about the feature, they don't care about what it does, they care about the result. And if you focus on teaching those people what to look for and what the results are versus all of the details that we tend to spend a lot of time answering, I think you can get them started quicker. Now, it takes a while to get someone up to speed, certainly, and we can talk more about that, but there's a lot of things you can do to shorten that time frame. And, you know, that's kind of what we focus on. But, you know, I'm really looking for people in the hiring process that have shown the ability to learn and create and do a lot of things themselves. So that kind of self-starter, high business acumen mentality is certainly someone that thrives here. If you're looking for a complete step-by-step 20-step checklist of exactly how you're going to do it, uh, Bergen is not the place for you. And I think that would be applicable to many of the same businesses here in the, you know, certainly in the HCM world.
Well, it's interesting to hear because with a company your size, much larger than a firm like ours where, you know, same thing, we're interviewing and looking for resourcefulness. Resourcefulness is that one box that if it's checked, I know we're going to have, you know, at least our, our feet going in the right direction when I bring on a new teammate. And that really goes for any position on the team at this stage of the game for us. Now, let's go back to that team size for just a moment. So you got 16 hunters, 8 account managers, Any other sales leadership, any sales engineers, anybody helping with demos, any SDRs, anything like that?
Yeah, so basically, uh, you know, a couple of years ago I think I had 14 coming to me, uh, with everything, and that was obviously a little bit too linear. So we put in a couple of team leads, um, that we've got. So I've split the team into kind of two disciplines. One would be more of those generalists that have, uh, you know, the high, uh, business acumen that represent the whole bag, if you will. And then on the other side, I do recognize that there needs to be some specialization and some people that just understand the HCM world or some people that just understand the accounting software world or the technology world and the like. So that's more of my sales engineering team that, you know, that helps out with those. But, you know, really what I've done is, you know, honestly, I'm not stroking your ego here, but I've had my sights set on a vision of going to a vertically focused industry-based sales team for a long time. And it took us about 8 years to get there. So when everyone says, you know, you want it to happen fast, sometimes there's some foundational building blocks that you gotta work through in order to get there. But, you know, moving from that geographically focused team to a team that really understands the audience that they're talking to, I think helps you have a better chance of doing what you asked earlier, Matt. And that is, you know, if you can apply narrower audience to the problems you're trying to solve, I don't think that big bag of products to sell seems as daunting because it's a lot more aligned than spending time with a healthcare provider one day and a bank the next day and a financial services company the next day. So that's another thing that we've been up to.
I love that. Well, I want to dig more into that here in just a moment, but you touched on the thing that we struggle with so much, especially we're going to talk about these founder-led folks and oftentimes people start a bureau and they're on more of the processing and fulfillment side and they know, hey, I can execute how to actually fulfill this service. Some come from the sales world and then they've got to fill out the fulfillment side. And, you know, I don't know what the magic is. You know, it's probably better to have a multi-person founding team. I didn't have that luxury. But, but one of the, one of the biggest struggles is like, you know, if you're not from the sales world, you don't know how to talk in terms of means, does, is, right? You're speaking in the terms of is and does. Hey, we offer this great HCM system that does Ben Admin and timekeeping and payroll processing and and all that, but you can't really speak in terms of means, or you can't really speak in terms of means that's actually compelling, right? Which is where great storytelling comes in as well. Um, and I'll be interested to hear your perspective on how you guys weave stories into your sales process, if you do. But I think that's, that's always been the biggest disconnect for me with people, especially, especially even just some new folks, trying to get them up to speed on how do you actually keep pulling this back up out of the weeds, even during a demo, right, where you're tending to get down in the weeds a little bit, and they can off set you off on a tangent very quickly. But, but let's, let's kind of work to, um, you know, sequentially here, and let's, let's pull that thread a little bit more of hiring, uh, sales folks. So you, you've hired, led, and grown a sales team now up to 24 folks. You've got sales leads in place. Let's talk about some more of the key characteristics you look for when hiring a sales team member and bringing somebody new onto your squad.
Yeah, I think, you know, it's the, the thing I would tell you is, uh, you know, I don't hire people I don't know. And I know everyone gets mad at me when I say that, like, oh, there's no way that I can, you know, learn and meet everybody that I can know. But, you know, honestly, I've kind of flipped my mindset. And I think that's one of the problems with founder-led teams is, you know, those folks are so successful and they're such good creators and they just know it. And what oftentimes happens when they do recruit someone and bring them in, Matt, is You know, they keep all the warm stuff for themselves and they say, Matt, you go find it. And when you find it, I'll help you out. And the first thing that happens is Matt comes in and he finds it and he's excited. And you bring that to that particular person and the person says, geez, Matt, I'm sorry, but you know, that's just not what we're looking for. Go try again. And you know what I'm trying to look for in the recruiting process is I'm trying to look for people that I know that represent the values and that resourcefulness you're talking about that I want them to bring to the table. And I'm watching how they operate. And, you know, that's my advice to any young person, you know, that wants to be an owner someday or wants to be a leader. They're always like, you know, what's that one thing you tell me? And I just tell them, just be great at what you're doing. Just, just don't look over there. Just be focused on what you're doing and be the best at it. If you're the bottom person on the rung, be the best bottom person on the rung that's ever been on the rung. And I I promise you, someone is always watching. And that's what's happened to me in my entire career. The reason I'm here is I just kept working. I didn't stop. And there was plenty of things that didn't go well for me. And that's just some of the types of things that I'm looking at when I'm recruiting people. And when they get here, you know, I don't always know what I'm going to get. I'm not 100% by any means. You certainly are going to have some things happen that don't go that way. But I think it gives you a better chance for when you make that investment as an owner to say, I'm going to bring someone into my organization. I'm not a person that brings in 5 and hopes 1 or 2 stick. That's just way too much work to me. I want to bring in people that I'm going to invest in, and I want to change my mindset from I'm going to still work my stuff and then I'll help them out occasionally, really to be I'm their coach, I'm their leader, I'm the person that is going to grow them into someone that is going to drive a lot of revenue. And last fiscal year, you know, our teams together combined put up about $25 million in net new sales. Huge numbers, okay? I can't do that by making more calls. I can't do that by making more sales. I need to do that by growing the team and their capabilities in quality and quantity. And that's just a fundamental shift. That's tough. Are you gonna violate that as you're going through the startup? Absolutely. I violated it 1,000 times. But you gotta have your sights set, in my opinion, on growing that team up, delegating and elevating, and making sure that you're spending time on the high-value activities that you can. And at some point, you'll realize the rewards of that. And that's super cool when you watch not only what these teammates have been able to produce, you watch the income levels that they can achieve, you watch their personal lifestyles change, you watch them starting to do things where you're all of a sudden a little bit in the back of your head like, geez, they're, they're, they got more skills than I do. And, uh, you know, that's a very humbling time as a leader when you get to that, uh, to that front. So that's a little about kind of how I approach the recruiting and just the mindset that I take into it.
Well, a few things there, and it's interesting, before we jumped on, I shared with you, so this is a very topical, um, sort of episode for me in the respect that we just hired our director of business development. He's going to be laying the foundation for building out our sales team. We're going to be putting 8 reps in territory over the next 90 days, and so he's got his work cut out for him. And, but, but one of the first things that always comes into your mind, and you, you're a liar if you're a founder and you say otherwise, is just had a great inbound lead for a PEO prospect that I know the owner, you know, then this is a nice, you know, lead that's going to be a nice little revenue generator. And so do I hand it off to my new director of business development? Or do I keep it for myself because I don't want to pay commission on it? Right. And so like there, there's the, the conundrum that you're stuck with, but the right answer is always to hand it over because that little bit of commission, A, is going to keep that person around because they're going to get some early wins. You're going to help them. You're going to nurture them. And then secondarily, you kind of touched on it in there a little bit of like the number one use of your time as a business owner. Once you have a team of any amount, 1, 2, 3, 4, 50 folks, is developing your people. The more time you can spend in your day pouring into your people, pouring into your staff, pouring into the processes that help them to be successful, removing roadblocks from their day, like that is the number one investment of your time because otherwise you cannot create exponential movement in your business because you're always going to get in the way instead of serving people. So great nuggets in there. I love that. Let's talk a little bit about, you know, and I'll go back one more thing on, on looking for some of those key things for, from my side, sales team members. Like, granted, we want a diverse staff. I remember sitting around a table once of, of, you know, nothing but white former college athletes who, you know, 8 of us around a table going like, oh, not a lot of new ideas going to come out of this room, right? Like, we're all like carbon copies of each other. And like, you know, once you start to get some diversity of thought, once you start to get some, some, some different and unique opinions at the table, things change always for the better. That being said, I still, you know, if you were the captain of your college softball team and you're a shortstop, like, I'm gonna hire you 9 times out of 10 if I get the chance because you've proven leadership in an area where you've excelled above a bunch of leaders, right? And so like, that to me is like the ultimate, like, wow, you were a leader of leaders on a college, very uber competitive team. You were the shortstop and a captain, like, damn, deal done, right? So, so that's, uh, there's some easy things for me, some easy boxes to check. But what about some red flags? What are some things you this year, or have noticed over the years where you look back— and this is hindsight, it's always 20/20— I hired them and then I started thinking back to the interview process, like, dang, I should have realized that was going to be an issue. What are some of those things you've had with your sales teams over the year?
Yeah, so I think, you know, the number one thing that I've learned in my time in this business, specific to HCM, is a lot of folks hire people with, you know, experience. And that is a really double-edged sword, meaning what one of the things that I really have learned to ask a lot more questions around is, you know, not only tell me about a win or a sales success story, you know, Matt, to use that as an example, but how did you actually find that? Where did it come from? Because in my company, we've got a long ways to go on the effectiveness of our marketing. And getting the inbound game to be where we want it. We're making great strides on that. We're always going to work on that. We're going to try to automate and change our best and do those things. But really what it takes is it takes people that can go out into a competitive marketplace and create. So we talk about creation versus fulfillment, and that is the number one thing I look for. If I've got an inbound lead that says, hey, Matt, I've got a few employees, I need to get them paid. Can you help me out? I can throw a rock in any direction from where I'm standing and I can train 500 people on how to answer that question and do that. It's not invaluable. That's not what I'm saying. But what I'm looking for is I'm looking for people that can go out into the marketplace, that can help cut through the prioritization that all these organizations have, can teach them about unperceived needs that they may not know in addition to the known needs, and can actually work them through a sales process. And that is a very difficult skill that a lot of people, I'm not saying all, there's a lot of great creators that work in enterprise and work in companies that have great marketing firms. But one of the things that I just really like is that grassroots grit because kind of work from that way into the inbound once you get your referral sources set up and, and kind of are in it for a while, if that makes sense.
No, that's perfect. It actually segues into a question I had for you of that balance between the sort of old school, high activity, and like focusing on, you know, niche target prospect customers. And it sounds like some of this is going into the verticalization of what you guys have done. But, but you just mentioned, and I want to gloss over this because when I had Matt on, I was kind of doing the same thing, going back over and over the numbers. For those of us who are, you know, selling into the small business space with, uh, you know, hearing your team produce $25 million in net new is like, oh golly, like there's not even a conceivable way, uh, with based on the solution set we sell. Obviously I know you guys sell a diverse product set, but, but let's talk about, you know, what are some of the expectations from your team as it relates to metrics? What are the things you guys track? What are those leading indicators, and how do you make sure that, that they're getting touched on?
Yeah, so I think, you know, the, the, like you say, the, the old school methodology of, you know, tracking activities and how many calls you made and how many appointments you had and all of that stuff, I mean, I think, I think there can be a place for that. I'm really big on trying to paint that picture to new folks just as far as some, some guidelines of what it should look like. And that's one big things that I'm big on when team members start is, you know, I tried— I was just on the conversation yesterday with a peer in the technology space, and we were talking about, you know, how do you onboard employees? And we could unpack that forever. But, you know, the best one I ever did, I personally had 6 discovery meetings that I set up for that teammate on day 1. And after we got the I-9 and the W-4 and the handbook signed off, probably, and we're blessed to do that, we went into meeting mode. And what I wanted to show them is, A, it was possible, and B, this is what your cadence of your day should look like. You know, there's a place for networking and doing golf outings and fun stuff. I'm not saying that isn't part of maybe a business development strategy, but a 90-minute lunch a day isn't going to do it. You know, you got to be, you got to be working and you got to be doing that. So once they establish confidence with me, I don't track a lot of that. I'm more focused on outcomes. But the one thing I do like to look at every single week is I like to look at really two things. The first one is what are the 4 new opportunities that you've created? So that's one of the things we do in a sales meeting. What's your, what's your next 4? So put them up on the board. What are the 4 opportunities that you've created where we've moved it to a discovery or a demo phase? And then the second thing I look at is what are the next 4 wins? That you're going to push across the goal line. Where are they at? What's standing in the way of them becoming a Bergen customer? And what is the next step? And those are really the things that I've learned to look at. If a person is having a problem, we might look at appointments, we might look at proposals delivered, we might look at some of that stuff. But I've just really learned that, you know, focusing on kind of less is more when you've established trust with those salespeople. You know, when I was a producer and, you know, I was putting up $1 million a year, I didn't like that stuff. So, uh, you know, I try to treat them the way that I wanted to be treated. And as long as they show me that they're self-starters and doing the things that go into producing the results, I let them have rope. Obviously, if there's issues, then we got to pull that back in, and they know that, and that's part of the culture that we're establishing.
Yeah, that's great. And that's very well in line with how we view this too, right? Is like, what new opportunities are you creating? How much pipeline does that include? Because, you know, I mean, look, you're going to close a third of your valid pipeline. So it's just, it's just an easy way to look at what are these leading indicators. You know, we're going to see and understand, you know, are you doing the activity to make these things happen? But in reality, I don't care if you make 5 calls and set 5 appointments or if you make 500 calls and set 5 appointments, right? Like the 5 appointments are what matters. And to that end, you know, it's funny because my last job I ever had, I was, I was on and leading an enterprise sales team and the The thing with it was, going back to your earlier point on creating versus fulfilling, these guys would sit around all day and twiddle their thumbs waiting for the next lead from their SDR. And, you know, they'd be out playing golf and doing everything else going, I just don't have anything going on. You know, nobody's, nobody's giving me any appointments. And I'm like, what the heck are you talking about, dude? Like, that's not how this works, man. Like, you go out and set appointments. Like, and, and so, yeah, that's a nice luxury to have an SDR get a few for you, and those should be gravy on top. But geez, man. And it was interesting. Interesting mindset that I just wasn't familiar with, kind of coming from, you know, the ADP background where we were running a lot of appointments. Aerotech, good grief, we were running a lot more appointments there, you know, back to back to back. You know, the expectation was more in the 10 to 20 appointments per week range than, than kind of where we were, uh, once you start moving upstream a little bit. So what about— what are you guys doing? So this one, uh, is a question coming in from our sales leader on, you know, Thoughts and strategy on the sort of in-person check-in, dropping off information, cold calling in person. Is that something you guys are still doing during your prospecting process?
Yeah, so it's, you know, it's interesting. It's another question that gets asked, probably the most common question, you know, when you really break down the what do you look for, um, you know, in a salesperson. And I've learned over my journey that, you know, there's just a lot of ways that people can be effective, and we're all, we're all more gifted at certain things. Dropping by unannounced and having a conversation with someone, uh, is something that I'm perfectly fine doing in my social life, but in business life, that is the most uncomfortable thing for me on the planet. But I have two teammates that love that. And, you know, I was always very good on the phone. I was decent on video, uh, and using some of the more digital ways to, uh, you know, obviously generate interest and get people to kind of raise their hand and say, I want to have a conversation. I was also really good at networking, but they, they couldn't be more scared of those tools. So I've just kind of learned to, you know, let people, uh, and really teach people and make sure they're exposed to what is working, and then kind of let them find a little bit of their own voice. So it's not that there's 300,000 different ways to prospect or 300,000 different ways to sell this stuff, but I think we all are gifted, uh, in some unique ways with regards to how we do that. I've got one teammate, he's a master networker, and I don't think he's made a cold call in probably 5 years. He sells a couple million bucks a Uh, it's just he's got his network set up. They know what to look for. They feed him and he feeds them back, which is why it works, honestly, is he gives as much as he gets. And that's a big missing piece, I think, for a lot of us. So, uh, when you look at that, um, yeah, it can be a successful tactic in certain markets. You know, geography is a little bit different, type of industry is a little bit different. But, uh, I'm a big believer in just trying a lot of things and not doing 100 of anything in one day. That's just how my brain works. I like variety. And I like to make some calls, like to have people send some emails, make some videos, do some, you know, cold outreaches and other methods. And, you know, really, I think the fundamental thing that people just struggle with is, you know, are they not interested in meeting with you, or are you just not very interesting? And I think the number one thing that we forget in this business is that people don't buy HCM because they really want to. They buy it because it solves problems for them. That's why they buy it. And it's like you talked about, about where you're focusing your messaging. We focus on the wrong things far too often. And I think when you look at the good producers in this space, they tell great stories, they can relate those stories, and they're always focused on, you know, how do you make things better as you go through this sales process? And come along through the sales process with me, and we'll see whether or not it makes sense at the end.
Yeah, and you nailed it right there, right? You got to be Tylenol, not vitamins. And so if you're just saying, hey, you you know, come over to us, we can do the same thing, maybe a little bit better, then you're fighting a losing battle there. You need to solve a pain, and you need to make sure they feel that pain. And you need to make sure, even though you feel like you're saying something blatantly obvious to somebody, to help kind of put some salt in that wound, twist that knife, however you want to put it, you got to make sure they're feeling the pain and that they're, they're verbalizing that as well, which I think is also a big miss. People just make assumptions wildly throughout the sales process. But that's one I see over and over again, and I made it a million times myself. But, you know, whenever I'm asking for feedback, if we get off the stage and we're pitching and we're talking about what I do, it's almost always like, I didn't feel the pain. Like, I— like, you know, you touched on it and I get it. Like, I understand small businesses struggle with these things, but like, what does that mean? Like, what— like, how bad can it get? And so don't be scared to create— you know, people get a little hesitant on the fear, uncertainty, and doubt these days, the FUD. I get it. Like, we don't want to be doomsday folks, but at the same time, like, you got to make people feel the pain, or otherwise you're just, you know, just another voice lost in the crowd.
And I think another point on that too, just, you know, quickly, I've got a meeting right after this, uh, with a group that I took the next meeting, but honestly, I really don't remember why I took the next meeting. I mean, and I think, you know, as a busy executive or as a busy leader, I mean, I think that's very relatable. So Matt might have had pain a week ago, 2 weeks ago, but, you know, that's now— that was the old news. And now there's new problems that are going on. And like you say, when you're bringing it back and tying it back, I think that's one of the opportunities that I've seen the really good ones do. Is they're always tying back and reminding them of what that situation was, what the impact of that situation was, and let's not let that situation happen again, and talk more about that than about the actual features and benefits. And I think that's where you can win kind of that emotional game.
All right, so let's say right now you're the founder, you're talking to a founder, you're talking to me. I'm the only salesperson at my company, and I'm not a sales professional by trade, like I've never sold, I'm just new in this industry. What book or books would you recommend to me to start to understand how to position my product and service in the market?
Oh man, there are so many. I mean, the thing that, the thing that I tell, um, all of my people that are sales professionals, even so, let alone you not being one, but you know, if there is any skill you're lacking, any skill, there's, there's two things you can do. There's G-O-O-G-L-E And there is Y-O-U-T-U-B-E. And you can learn if you put your mind to it, you can learn any skill that you want with regards to prospecting, with regards to asking better questions, with regards to presenting better, with regards to, you know, closing, handling objections, how to network, how to communicate, how to be interesting, how to use video, how to do all of those types of things. So I think you just got to kind of look at, you know, where are you lacking? Is it a lead thing? Then I think you should focus a little bit more on the marketing side of the house. Is it a sales thing? The variety of publications, you know, and books that I'm reading is very, very diverse. The one that, you know, I would probably say that's still just, you know, tried and true that I really, really enjoy is I like the Jeb Blount stories and the books that he has just as far as, you know, how he's always, you know, taking the tour and he's always looking for that pain and how to relate it and just, just how he operates. I enjoy— I've enjoyed a number of the speakers that we've had at IPPA events, you know, throughout. But, you know, I'm just always— it's kind of situational for me, honestly. It's, it's— I kind of follow that they ask, you answer theology of, you know, when I hear something or have a situation that presents me, I go research that and try to figure that out. And I think that when you look at the good ones, they're a little bit paranoid. They, they, uh, they always are worried about getting overtaken, and they're always looking for that little edge to try to figure out how they can implement it in their game and just be a little bit better. But that's what I would tell them, is this stuff is all learned. I mean, even a good sales professional— it's not like most of these people went to school to be great salespeople. That's not what they did. And they figured it out. They learned it. They learned it. They learned it. And you do not need to be an extrovert to be great in sales. Going back to how do you create, you know, most people don't know this about me, but I'm actually an I on the personality side. And that's why I love going and sitting in the deer stand for 14 hours all by myself and not talking to anybody. I can function and I enjoy talking to people. It's not that. But as far as what I really— what really fills my bucket is, you know, being alone and being solitude and just kind of being by myself.
So especially in this world, right, we talk so much all day. I feel like that's the one thing that even though we feel like everybody from the outside like, man, they're so extroverted and they're always, you know, on. And it's like, dude, the last thing I want to do is talk to anybody after 5 PM, like, other than my family. It's just like, go home, do my thing. But, um, so, so a couple things I want to touch on there, because this is— I want to put a big freaking asterisk on this, uh, something you pointed to earlier. And that's like, hey, look, I let my team kind of pick and choose their prospecting methods, uh, and, and do what they're best at. Now, the converse of that that I've seen over my years in sales leadership is that people will use that as their crutch later on when they're not succeeding and they're not following the playbook and they're not doing the right things. They're like, you know, geez, I'm just so great at email, but nobody's replying to any of my emails, right? Or whatever that thing is. So, so you nailed it in the respect that you got a fish in each of the ponds, right? You got to be doing email, you got to be doing phone calls, you got to be doing drop-ins, you got to be doing whatever the things are that are creating opportunities. You need to do all of them. If you, if you single down, double down on one single channel, You know, you're leaving yourself open for possible issues there. And I never found an underperforming rep that was hitting all their activity targets. It just never ever happens. Because to your point, like you talked about going to college for this, dude, quite the opposite, right? Most of us went to college for something completely unrelated. And, you know, we obviously aren't going to be engineers, doctors, accountants. So it's like, all right, what can I do to make the most amount of money without curing cancer? Oh, I can go in sales. Like, that's a pretty easy route to go. Um, but not easy and nobody wants to take the path typically more than not. And so that, that's the beauty of it and where there's such great career opportunities there, but I'll go back and of the Jeb Blount books as well, Fanatical Prospecting, I feel like is a great one. Yeah. I mean, I absolutely love it. I couldn't stop nodding my head throughout, but like it gives, for those of you that have no sales background, this gives you like the rabid dog version of getting after sales where you can then understand like I'm like, oh, okay, like this is the level of attention to detail it really takes to be successful and crush selling. And so I like that one. You know, some lighter stuff on like Jeffrey Gitomer and the Challenger Sale is great because it exploits some of the old, you know, uh, misconceptions about what it takes to be a great salesperson, creating relationships, all that fun stuff. So, so like to your point, YouTube and Google probably have more and you could do, you know, quick synopsis of each of these books and be on your way in an hour.
But exactly.
All right.
Life. The pipe is life.
That's right. It's life, baby. So you talked a little bit about going industry-centric versus the territory and kind of moving towards that model. Tell us a little bit about what went into your decision-making process, how you guys are rolling that out, what that's going to look like.
Yeah, I mean, I think it's like I said, it's, it's been an evolution. And, you know, I make fun of a lot of my colleagues that have been in this longer than I have. And, you know, they've got a little bit of that. This is the way we've always done it. And, you know, we're going to stick with that. And I make it very clear to people that I bring on board with me in the recruiting process, you know, that things are going to change all the time. So if you're averse to change, this is not the place for you. We're going to change something every year. And it's a little bit about breaking the boring, you know, I mean, it's as much as it is strategic. I mean, we're always looking for a strategic edge. That's primarily what drives it. But, you know, I think sometimes as humans, just changing things up can get people, get a little bit more out of people. So, you know, we basically, and many of us in this industry, right, why were we successful? We're the local player. We're the independent that's, you know, in the community that we're serving and we're winning business because of that. And that absolutely will work for a long period of time. I'm not saying that, but it was probably about 2014-ish, I would say. And what I started to hear was, you know, Matt, you guys are great. You've done everything you've asked for. You know, you're right down the street, but— and the but was always generally followed by this business spends more time in our space. And, you know, I'm like, well, we're growing this sales team in quality and quantity. I know that they've got a lot to learn about a diverse product stack and a lot to learn about the number of businesses that they're going to be prospecting into. And, you know, when we looked at what makes the most sense as far as the impact, you know, I studied a lot of other people that have been at larger organizations than me that have done that. It's taken them a lot of years to go on the journey. I've looked at other more boutique businesses that just focus on, you know, trucking or just focus on something. And, you know, you just look at what they're putting out and putting in front of clients and it's tremendously different and it takes a lot of courage. I commend my team for believing in it and rolling with it and, you know, giving an opportunity to self-select into spaces that they wanted to learn.. And, uh, we've been on that journey for about the last 4 and a half months, and, uh, we flipped over for 100% on 7/1 of, uh, 2022. So we're brand new into it, but we've got people that geography just doesn't matter anymore, and, uh, we want those folks to become really in-depth and, uh, spending time around where their audience is hanging out. And I think it's going to allow us to hyperfocus and do some things. I think it's also going to for those operational folks on here. It's going to help us develop better products and be able to pick our places where our stack fits better instead of trying to be these generalists. And I know all of you out there have stories that are not successful or somewhat successful where we've tried to put our solution into something that kind of worked, but, you know, it was a stretch and we probably should have said no. And I would tell you, Matt, you know, going back to the other thing you said about pipeline, You know, when you can nurture a salesperson and get them to have a big pipeline, those deals stop showing up. Not always, but those marginal deals, they act totally different when they've got a large pipeline with a lot of opportunities than when they have nothing. And I think that's the number one thing in sales I've learned is that the, you know, the more desperate you are to build pipeline, the harder it is to do it. And there are times when the implementation team is full and they're saying, Matt, stop selling, we can't take on anymore. And you don't even need to call those people because the universe just flips and they're calling you now and saying, hey, Matt, I want to buy, I want to buy, I want to buy. So you got to try to balance that and, you know, make it happen. But, you know, that's kind of a little bit of how we approach it.
Yeah, it's funny, the ebbs and flows. I think about it like baseball. I always go back to baseball. It's like you step up to the plate. Confidence is 80% of the battle, right? Your mechanics can be flawless. It doesn't matter if you walk up to the plate and you have no confidence and you know you're not going to get a hit, like it's just not going to happen. Same thing with sales. And I also go back to, you know, I always tell these stories about about if I'd go out and make 25 drops in a day, 25 cold calls in person, I almost never went anywhere. It was just kind of one of the, the steps in my process of, you know, I'm going to touch this person 3 or 4 times. But sales karma, the sales gods would shine on me, and I would end up getting a lead that would call in or something in my inbox while I was out in the field. And it was just like, it was about putting in the time and making sure that you're getting those multiple touches along the way. Um, but man, I love this. And, and for those of you that haven't listened before, You know, I'm a big fan of the niches. You know, we did an episode on The Riches Are in Their Niches. If you think about so many of us partners with CPAs, and when you go in, you talked about providing value earlier to your partners, your referral partners. And when a CPA tells me like, oh, we serve everybody, like, you know, just any old company, and it's just like, well, who the heck do I refer to you? I don't know. Like, do I refer a 5-person construction company or a 5,000-employee construction company? I don't know, because you do everybody. So you're all things to nobody. In my mind. Whereas if you're like, dude, we really specialize in the dental industry and we have a nice construction department and we have a professional services department, I go, oh cool, like they specialize. And this just happened to me. We're, we're currently talking to new CPAs and the first thing is like, hey, have you worked with companies that are doing X, Y, and Z in this way? And those are the important things. I want to know that you've got that experience. And that resonates with the reps as well. Their, their messaging gets sharper, their ability to have great conversations. To your point, they're going to get up to speed faster because getting up to your speed getting up to speed on the solutions is one thing, but getting up to speed on 50 different industries and understanding all these different types of businesses is a real challenge for people. And you can kind of look like a fool if you're out there talking to a nonprofit one day and a manufacturing company the next day and just trying to understand what's different about how they're trying to grow their business. Um, you know, we use the example all the time, like if you call me and you say, hey man, I provide general liability and E&O insurance for payroll companies, I'm going, dude, come on over here. Like, because my current provider is not specializing in payroll companies, and I know you're going to know more than them. So I'm happy to welcome you in and see what kind of insights you have. So I love it for sure. Let's talk a little bit about that kind of like transition before we start to talk just about the industry as a whole here in the last few minutes. But so as I'm moving from, you know, either sole founder to my first— in, in just a little bit more context here, y'all, of the people that are selling their firms right now there's a very high density of, I've been the sole founder, I have no sales personnel. We started to plateau at low 7 figures, whatever that number is. And now I either need to start building out a sales team and I'm too tired, or I don't want to be that engaged to do that, or I'm just going to move on and sell the thing. So, so these are decisions that you got to make either in the earlier or later stages to say, hey, are we actually going to build out a sales organization? And so when I think about that as an owner and a founder, what do you think are some of the key things I should be thinking about whether or not I want to build out an in-house sales team?
Yeah, I think it's, uh, we put on a session back in the Spring Conference, uh, in Vegas about it, but I think it's really, you got to think about what you just said. So what is your endgame? And, uh, you know, we've got another one that's actually, uh, coming up that's going to be a little bit related, uh, at the Fall Summit, uh, down in Florida that's going to be talking about this. And, you know, basically the, the punchline is whenever you create a business, no matter what you think you're gonna do you should be creating that business with the sole focus of selling it at any point in time that you want. And what people don't realize, and you mentioned it earlier, is that when we look at how businesses are being valued— we actually market and sell a lot of businesses now as one of our lines— the people component has perhaps never been a larger multiple put on that in kind of the extra stuff that's outside of revenue and EBITDA and those types of things. And that's how you create enterprise value. Value. So if your endgame is that you're just gonna sell to a large giant and a sales team's not gonna be needed and you're really gonna invest a bunch of money and, you know, at the end of the day, there's not gonna be a huge ROI trade-off in the additional revenue you're gonna get on board to sell, then don't do it. And just continue to ride it out and just no sweat. That's cool. That's an exit plan. But if your goal is to maybe sell to a strategic or transition that to someone else who's in the business or sell it to someone externally who wants to come in and run then building out that leadership team, not alone, let alone a sales team, but having good leaders that can run operations, that can run implementation, that can run client support, that can run sales is just very, very important to the business. And my number one thing that I'll just go back to is you have to stop committing one of the three sins of sales management, which is being that owner and being that visionary and also being the number one salesperson. Being the visionary and the owner is a full-time gig. And I understand that you got— it's not— we don't just forklift and flip the light switch overnight and all of a sudden you're not. It's a journey that you go on to get there. But it's just changing that mindset to be, okay, my job is not to be the revenue producer. And I know you got to deal when you got payroll to meet and all those types of things for your own internal stuff. I get that. But your sole focus has got to be, I've got to grow this team in talent. And they are going to collectively then take this business probably further than you can even imagine if you get the right people in the seats and get them going in the right direction and being that leader that can communicate a vision that they want to follow and go out and execute on. So that's what I always bring it back to is everyone shouldn't start a sales team. It's not, I'm not, it's not for everybody. But for the ones that want to embark on it, have some patience. Great rewards, but there's a lot of rough spots. It takes work, it takes commitment. And what you got to do is you got to get those folks confident, Matt, like you said right away. And you got to become a great teacher, and you have to transfer all of that knowledge and all of the stuff that you've learned, and you've got to get it over to your reps. The last training that I just put my team through, uh, and this was while we were going through channels, I actually put them through about a 6-week course on teaching business owners how to create enterprise value. Like, that was the course that I put them through, and they learned about everything from selling to a giant to selling to a strategic to doing an ESOP to transitioning it out there. And really what it was around is I wanted them to understand, you guys are out talking about selling payroll or selling timekeeping or selling HR. Well, what does it mean to the overall value of the enterprise to have bad HR timekeeping and payroll versus best in class? Does it matter? And those are some of the things that I think light bulbs came on in their head, just as far as what you were talking about, how you actually communicate the who cares and what's in it for me. And that's just an example of training that has nothing to do with our space. It has nothing to do with selling. It is everything to do with how do I grow the business acumen of the people that are out representing my brand? And that are having conversations with business leaders in our channels. We call them channels in our industry segments that we're out marketing to.
Man, I love it. So much to unpack there. But, but first and foremost, so, so if you started getting heart palpitations when Lee said, hey, I, you know, I need to be the owner and I need to hand things off and let people run with, with and operate their things, then you don't have A players on your team if that was really concerning to you. And you'll know the difference when you start adding some A's you. Things start moving faster. You don't have to micromanage. You don't have to sit over everything, and, and things just happen, right? And sales, it's no different. But you can't expect somebody to come in with no resources, no infrastructure, and pick up a bag and just start selling. So you need to start to create your business now as if you're going to sell it in 5 years regardless. And there are a couple of great books around this that, as you were speaking, I, I thought it might make sense to reference. One is Built to Sell. If you've never read Built to Sell, fantastic book, talks about a marketing agency that's a lot like what we described. They do all sorts of different work for different clients in different industries and different services. And then ultimately, by the end of the book, they refined on to where they're literally just making logos. And then they're more profitable than ever. They're getting the right clients because they know exactly what they offer. They know exactly who they offer it to. And they've got a very refined target audience and a very refined combined product. And so those are the types of things— well, I'm not saying you need to combine. I do joke all the time, like, I wish I would have just started dentalpayroll.com and not sold a single other thing to any, you know, other than payroll to dentists for the first 5 years, and just take that as far and as wide as we could until we deployed anything else. We took the other approach, which is sell everything to everybody early on, and that worked out like crap. And so, you know, learn from my mistakes. And then the other one—
we did too.
And then the other one is the email. So if you've never read The E-Myth, another quick synopsis for you here, but it's, it's build your business as if it's a franchise prototype. So what that means is I should build this as if it's going to be replicated in multiple other locations. And so all my systems and processes have to be able to be used as the blueprint. And so we think about that twofold. So we think about if we're going to go out, we're going to be this big proponent of HR, of culture, of creating an awesome place to work, of hiring, retaining, and developing top talent. Well, we need to walk the walk internally, right? We need to show up and we need to treat our people with respect and we need to pour into and we need to develop in them and all those things we're talking about. But also, yeah, we need to have great systems and processes in place where we can plug people in and out and they can use their creative energies for things better than processing payroll and, you know, cutting checks and all that good stuff. But, um, and I love that last thing you mentioned on— before we move over to IPPA, you talked about that 6-week course. Tremendous, uh, job by you guys pouring into your talent.. And so for those of you that are going, man, I can't afford a 6-week course. Well, I bet you can. First and foremost, like, first of all, Disney Leadership Institute has their classes online available now for like $200. Some of the— I paid thousands of dollars to go down to Disney and take some of these courses. They're online for $200. LinkedIn Learning has 30,000+ classes on it. It's a few bucks a month. You can get it free with a library card. There's just a million different ways you can get access to resources. You just mentioned YouTube, right? For a long time, it was just about YouTube, man. It was about finding the best sequence of YouTube videos to put together. To get somebody the education they need. So don't think that you've got to go spend beaucoup bucks for a consultant to come in and train up your whole team. There are a ton of ways to get there. So cut it with the excuses. But let's, let's transition over to IPPA, talk about the industry as a whole. So you are the president of the board of directors of IPPA, is that right?
That is correct. We are, we're taking on new duties. So we're excited. We're very excited. But yeah, the 12 months just started.
Yeah. So IPPA, for those of you not familiar, is the Independent Payroll Providers Association. Um, I, I forever stiff-armed the IPPA, said, hey, we're too innovative, we're building our own software, we're trying to do this own— our own thing. Like, we don't want to follow, you know, the local model where I just license software and grow a payroll bureau and then sell it in 10 years to ADP. We're doing something unique and we don't want to be part of that crowd. And then Matt Umholtz, you know, for the 18th time I'll probably mention him on here, you know, was like, hey, you really need to come to conference to just check it out before you join. And so I came out to the conference and I was like, hot dang, like, I've been— I am wrong, you are right. I should have been involved from this, from the start, and I have been ever since, and I can't be a bigger proponent of it. But tell me a little bit about you, what you've, what you've gained out of sort of volunteering, what you've gained out of being a member, and kind of why do you invest so much time into the IPPA?
Yeah, for sure. So he asked you 18 times, there's a sales lesson there, right? Sales lesson there, pay attention to that, right? And Persistence is good. It's not a bad thing. But no, it's been incredibly humbling. It's a great association. You know, really, I got involved back in probably 2010 to 2012, somewhere in that realm. And I remember meetings back then, Matt, where there was, you know, 30, 50, maybe 60 people, generally in a, you know, darker, lower-level hotel room, conference room with a low ceiling. And, you know, it was fun. But, you know, now you fast Fast forward to today, we got 400 people that are attending. We got speakers like Jesse Itzler, we got, you know, Anthony Annarino, Jeb Blount. I mean, just recognize names that we've been able to bring in. And, you know, I think twofold is what we're about. One is we want to make sure this great industry stays relevant, and we want to make sure we stay up on the government affairs side and be plugged into what's happening legislatively to just, like you say, the ship has sailed as far as oversight on our industry, and that's okay. It's probably well needed, but we want to make sure there's a balance, and that's very important to us. And then the second thing is really we want to make service bureaus better be after they became a member of the organization versus before. And a lot of that is just on teaching, it's on bringing ideas, it's on educating them much like today on how they can grow a sales team or how they can build a better client service team or a better implementation team more, you know, just all facets of the business. It's the number one differentiator we all have. We can all obsess about going to vertically focused, or we can go to geographically focused, or we can focus on a little button that our system does versus Matt's doesn't. But at the end of the day, teamwork is the only differentiator we've got. And it's how do you get all of the different functions that go into managing an organization's HR timekeeping Human Payroll to work together. And I'm just very proud of the content and the association's investment in bringing those ideas to our members. And it's incredibly fun, the relationships that I've built over many years. You know, Matt Umholtz, I was on the phone with him the other day, Friday before Labor Day, and, uh, you know, bounced the question off of him, and we were talking about getting together at the conference. You know, it's just there's, there's a lot of things that you learn and you don't know when you're gonna need it. But I promise you, it will show up. And I think for a, you know, nominal investment, it's just a good group to get around. And I promise you, whatever you're paying on an annual basis, you'll 10x your return on that from one little nugget that you get every single year. And I think that's what it's all about. And anyone that's not a member, we're continuing to increase membership. We want you to be a part of it, both at the Payroll Bureau level, as well as if there's an allied member watching this that may have a product or a service that wants to bring that into our space. We've got great partners. Many of those organizations have led to that success and the revenue that I talked about. We do not do this alone, and that's what makes this work.
And I've seen some of you at the last conference that are listeners that were introduced to IPPA through the show, which is, which is ironic given the fact, because you kind of nailed it. Umholtz and I were on the phone in the middle of COVID going, we just had this hour-long conversation. I'll never forget it. It was during COVID I was standing in my driveway. Pacing back and forth, and we were talking about what are we doing to sell, how are we going to position things, how are we going to change things in this COVID world. And I was like, man, we should have recorded that call, dude. You know how many people could have gotten value out of that conversation? And then that literally was— Payrolland was born right there. It was like, you know what, same thing that the IPPA has already done for me is kind of exposed. You know, everybody has this give-first mentality. Nobody's ever hoarding information and doesn't want to share it. Because, because while we may eventually run into each other out in the You know, I ran into Pay Northwest ironically in a deal recently, and I was laughing. Lori, I hope you're listening to this point. If you are, shoot me a note. And I was like, Pay Northwest, I'm in South Carolina, and we— and the deal we were on was in Massachusetts. So I was like, all right, whatever. But that rarely happens unless there's somebody, you know, regional to you.
That's—
it's rare to get East Coast-West Coast battles going. But, but the bottom line is that we, you know, we're all better together. This whole thing is about, you defeating the common enemy, which is the nationals, right? It's not us. It's, it's, it's about taking away from the market share from those folks that are, are, don't have the client's best interest at heart and give us all opportunities to create value for our team and for our companies. And so that's been the big thing for me is like the rising tide lifts all boats mentality has been huge. Everybody's so giving with their time, information, sharing, and, and there's just so many things to your point I've never thought of that, you know, pure operators know so much better than me. And so I've been like, dang, that's, that's genius. I can't believe I didn't think of that. So it's been awesome. And yeah, genuinely appreciate you coming by. Let's kind of end it with this. What's, what's the most exciting thing happening in the industry right now, or in your business, for you?
Uh, so I think, you know, the most exciting thing, um, you know, in the industry is, you know, I remember times where getting getting people to understand and believe in the ROI of why to buy the things other than payroll compliance in this space, I mean, was impossible. I remember fractional CFOs that were consultants that were running around selling consulting to HR directors to teach them how to communicate the ROI of HR software to the CFO so that they would buy it. Like, I remember those days when I was out producing, and I think that It's been so fun to see just the evolution of getting the software to actually work so that it can conform to real-life business and then seeing the results of those companies that actually go on that journey and implement it. And that's another big problem with businesses. You know, we don't— a lot of these things take a lot of time to get implemented in the clients that we're working with, and they don't always have the resources to see it through. Or decision makers change or whatnot. But for those companies that really get a hire-to-retire solution in place that can take care of a lot of those things, there's just great impacts on just the talent that they're bringing on, the tenure that people are staying, the reduced turnover rates, and just a number of those things that we're seeing. And it's exciting. And I think some of the things that you're going to see that are even more exciting on the horizon are going to be, you know, how does the workforce data that we all have, who's going to want that? And how are they going to start forecasting and predicting more on the business is going to bring some exciting partnership opportunities and some product opportunities, I think, to this space that's going to help you maybe be able to add a couple more of those things to your bag that some of you probably haven't thought of. So they're not as far outside of the payroll box as you might think. And I think you're going to just continue to see see these platforms converge as we go forward, and it's going to mean better results for our clients, which is the most important thing that we all need to be focused on. But it's also going to have a benefit to us, uh, in increased revenue, uh, and additional things to sell as well.
I love it, man. Appreciate spending some time with us today and dropping some knowledge on the crew. Thanks for your time.
Awesome. Thanks, guys.










