E14: A systematic approach to GTM infrastructure and talent with CRO, Martin Roth

Martin, welcome to the show. Thanks for coming on.

Thanks for having me. Happy to be here.

Yeah, excited to dig into this topic. It's one that I am very excited about. So, uh, we're going to be talking about building SMB transactional sales teams today, a topic that's near and dear to my heart. Um, so really looking forward to it. Hello and welcome to the Revenue Leadership Podcast by Topline. I'm your host, Kyle Norton, CRO at Owner.com. And every Wednesday we dive deep into the strategies and tactics being used to drive success by the best revenue leaders in the world. So join me as I sit down with revenue operators to discuss actionable frameworks that you can implement in your business today with no fluff, no sales pitches, and no platitudes. But first, a word from our sponsors.

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Billion. By way of introduction, uh, Martin was, uh, the first sales hire at Levelset, was there for a decade, went through the run from $200K ARR all the way through to $25 million— or $25 million revenue, 350 employees. You guys bought— got bought by Procore for $500 million. You were the CRO by the end of that stint and owned a wide swath of all things go-to-market, which you can talk about. And, I'm really excited to unpack that journey. I have hired some of your ex-teammates who have all really impressed, so I can personally vouch for the quality of the machine that you built and the leadership and training. That was the thing that actually got me to send you a message originally was just to give you a shout-out and say thanks for training these really good reps. So we're going to unpack a bunch of that today.

Love it. And I, you know, first of all, I'm grateful to be here. It's— I listened to the first two episodes. You got like the godfather of SaaS, you had Lemkin on here, you had our mutual friend KD, who always brings like all the energy. And so I feel like I'm in rare air here. I just, you know, I'm a peon in this world of revenue leadership. So I'm just happy to be nominated. Glad to be here. There you go.

Well, I think this episode will be— will live up to the hype of everything else. So just before we dive in, give people like your 60-second background, a little bit about your journey. Sure thing. Yeah.

So I, I was the CRO at Levelset. I started as the first sales hire. I was employee number 7. When I joined, we didn't have any ARR. I don't think we knew what ARR meant. Couldn't spell it at that time. We had a transactional revenue model. Levelset was a platform for construction payments and construction lien rights management, which Nobody that listens to this podcast is going to know what any of that stuff means. But we found this wedge into selling across all stakeholders on a construction project, big market, big opportunity for, you know, for building a big team. And we had a lot of fun over the course of 10 years. In 10 years, you have a lot of different versions of a company as you scale up. And my role, you know, going from carrying a bag to building the first team to running marketing and customer success and revenue and sales. Um, there's a lot of learnings, uh, over the course of that decade, but my roots are in sales leadership. That's probably my wheelhouse. Um, but I've, you know, moonlighted as a marketing leader and a customer success leader over the years. And you've seen this in your career, Kyle, the org kind of changes with the business needs and then you bring in, um, you know, I had great partners across, across the leadership team, um, outside of just sales. And so that's, that's the run. I left, uh, Procore about a year ago or a little over a year ago. And I am, I'm working on some new projects, but in the meantime, I do some advisory work with early-stage founders or executive sales leaders, and I help implement the playbook, the stuff that we know how to do as revenue leaders and help them avoid many of the same mistakes that I've made. And I love working with early-stage companies. I write about it online. And so I'm sure, you know, especially with SMB sales, which is a topic close to my heart also, you know, I, cut my teeth on selling $3,000 and $5,000 at a time. And I think it's an amazing platform for career growth and for leadership growth. For anybody who knows SMB sales, you know what I'm talking about. So I guess that's my intro.

Martinroth.com. Bingo. Yeah. Check the billboard. Yeah. So a lot of the discourse online and in podcast land is really enterprise focused. There's more PLG and vertical SaaS stuff today in the last 10 years, but not a ton of really awesome playbooks and frameworks still. And oftentimes, what I read online, it's not delineated between the two. It's just like common things. And I think these two businesses have enough uniqueness that really need to be considered separately in terms of what we're building. And like you said, it's, you know, SMBs and it's an amazing place to, if you were a passionate people leader, to like go build careers and to go build a platform for others to succeed on. But from an investing perspective, it has not been any near, it has not been nearly as popular as enterprise SaaS because the economics are tough, making the LTV CAC work. Can be a challenging endeavor because churn is high, rep turnover is high. It can be a people, like a very people-heavy model. And a lot of these things can scare people off. And so in order to do it really, really well, you need to be a different type of operator and be able to build system and structure. And we're going to unpack a lot of that today. To help people figure out how to go from SMB traction to maybe SMB scale. Just before we dive into that topic, so since leaving LaFayette, you're now consulting, advising. What's the most common mistake you're seeing earlier companies make? For all the founders out there that are going from founder-led to like first handful of sales reps, maybe their first head of sales, Where are the big stumbling blocks you're most commonly identifying with these types of companies?

Yeah, it's glad you said founder-led sales to building your first sales team. That's, that's the, maybe the most important transition that any revenue team has. You see this over and over again with early stage founders where they've helped close or been a material part of closing the first million or $2 million in ARR, and then they go build their first team, they bring in a couple of AEs, or hopefully they avoid the mistake of going and hiring some big name VP of sales who's going to come build it for them. Because like the, there's been a lot of words said and written about why that's not a good idea. But the thing that I see that most founders make the mistake of is whenever they hire their first handful of reps, they fall into this position where they want to hire good people. You know, they spend a ton of time with a rigorous interview process and they get down to their final candidates and then they bring the people on and then they just leave it to those new hires to go figure out how to sell. Right. It's almost like they are leaving it to chance. We're going to hire good people and we're going to get out of their way and let them do the work. Not founder mode. Not founder mode. Yeah. Whatever founder mode is, I don't know, but that's absolutely the wrong thing. And here's the way that I think about it. I think you and KD touched on this topic last week because you were talking about, uh, about playbooks. If you know what success looks like in sales, then you have a responsibility to write it down and give it to the person who needs to go do that job. Because then there are no questions. Here's what success looks like. Go do this work and you'll be successful. And if you do this work and you're not successful, then I can coach you on how to do it right. Or maybe there's something wrong with that playbook, but at least I've written it down and given you the blueprint for success. There's a responsibility for, for founders and for executive sales leaders. You have to raise the, the floor of performance. That's how I think about it is that your best sales reps, the top 10%, they're going to be top 10% no matter what. Stick them into an organization that has no collateral, no structure, undefined ICP, can't explain the product, and they're still going to go figure out how to sell it and go get customers. But as you, you know, as well as I do that when you're scaling a team, it's just, it's a numbers game. You cannot get top 10% people every single time you hire. Yeah. I don't know what yours— this might be fun to trade stories here, but what was your success rate? We probably hired, who even knows, 100 and something reps over time, like in total hires. And then you have attrition for the SMB team. We were probably at 50, 55%, maybe 60%, depending on the cohort or class. So think about that. If you're a founder and you're going to go hire 2 AEs, at best, one of them is, or on average, one of them is going to work out, but you're almost guaranteeing that both of them are not going to work out if you have not written down what you want them to do and you're just expecting them to go figure it out. That's the number one mistake I see with early stage founders. They don't write it down, write down what success looks like, and then hold them accountable to doing what you told them to do.

Yeah, my experience has been a little different just because I'm building this company at a different part of my career. Like, I think we've only had one AE mishire out of maybe 16. Wow. Because, you know, I had done this once before. I came in having already built a bunch of personal brand on LinkedIn. The company had a bunch of buzz. So the reps that I got to hire in, even in those early days were all like pretty freaking good. You know, like I hired people from your team that were highly successful and came over after the acquisition. Then I hired like President's Club performers from other people in restaurant tech. So we've been lucky in that regard. Um, with just like candidate quality and talent, but I say the exact same thing. Like you can't judge the quality of a revenue leader by their top people, or as a revenue leader, you can't consider yourself, you can't grade yourself based on your top people. You have to grade yourself based on that, that middle cohort, because like you said, like the best people will be, well, they'll be great no matter what. Um, but it's your ability to drive consistency with other folks that it's like, it's a lot more indicative of the system that you've built.

Let me ask you this. You said there's this interesting, and it makes sense. Like if you've got a brand, you're getting your filter for talent is going to be different. The demand you have is going to be different. We're going to talk about demand in SMB sales, but just think about demand from a hiring manager perspective. What does the top of your funnel look like? You're probably getting a better a better group of candidates than certainly what I was getting at 25 years old, you know, building a sales team for the first time and still trying to figure out how to go higher.

I was 35 and had, you know, a whole alumni network. So my first big cohort of people, they were all related to me by one degree or they've worked for me in the past. Yeah.

But the one that didn't work out, what, how did you, We'll maybe touch on this later with performance management, but what, how did you know? Like, why? Let's separate, like, you know, yeah, maybe, maybe we don't want to put anybody on blast. Maybe we can skip that one. That's okay. If it's only one person, then never mind.

We're going to clip this part of the podcast out.

Yeah. Don't worry. Yeah.

And so, um, I, I, I very much agree with the point there, but, um, The talent manufacturing question is one that we're going to spend a bunch of time on. So last sort of warm-up question before we dive in, what have you learned from your consulting work that now you're like, man, I wish I knew that when I was an operator? Yeah, the world has changed.

Look, even in just a year and a half, everything is different, or almost everything is different about how you would build and scale these teams. So one thing that I see with some of the companies that I'm working with, or even friends that are founders that are building teams, is that the productivity per rep, it's so much higher now if you're running a team the right way. And I think when I look back and if I'm self-conscious about the team that I built, I just, I don't think that I was demanding enough or structured our team in such a way that it required people to have a high productivity per rep. And by that, I just mean total bookings divided by total number of reps that are carrying a quota. That's one thing that's certainly different is that the team does not have to be as big as what it used to be. And probably I didn't need to throw as much headcount at our revenue number as I did. And I certainly can share some more stories about challenges with that. I'm sure you've seen that in your own career. But that's a learning is that I'm seeing teams that are producing, like punching way above their weight class with a productivity per rep or bookings per rep. Because I think you, it's possible. And 5 years ago or even 3 years ago, that level of performance wasn't possible for an SMB sales team.

Yeah, the data, the tooling, everything available. Yeah, for sure. Also more talent density, you know, as a bunch of companies have thinned out. You know, one of the challenges of XRP is you, you were, there were so many more companies that had funding that probably didn't deserve it that were stretching talent across such a broader ecosystem of companies that it was hard to get like amazing people. Now, in our market, in restaurant tech, there's been such a consolidation, such a downturn with many of our competitors that we've been able to go pick off like the best people because there's not 7 companies that are all crushing it. It's only a very small handful. And I think you're seeing that in in a ton of markets.

Well, and owner's like the bell of the ball too, that the company that's got a lot of gravity, it's a rocket ship. People want to be on, on that ship and that, that bodes well for the hiring. The other thing I'll mention that you probably remember this, but in the, you know, 2019 to 2021 timeframe, there was a ton of title inflation. And so it was really hard as a hiring manager to know if somebody actually had the skills and experience to match the title of their last 1 or 2 or 3 roles. And so, you know, we did all of the, same things that other companies do, which is if you see a rep or even a leader that was 9 months here, 12 months there, 18 months here, it's like, you know, run away. They don't have, there's, they don't have any loyalty or maybe they just can't stick a job for that long. Um, but it was hard. Look, when everybody was funded and everybody was hiring and there was a ton of competition, you had, you had two problems. Number one, the hiring manager, it was really difficult to know whether or not somebody's experience was consistent with the title that they held. The other problem was you had this inflated expectation of comp where a rep comes in, they've got like 2 years of AE experience and they're like, I want $180,000. Yeah. $180,000 OT. And I'm like, it's not happening. Like, I don't, you know, there's, I don't see the level of experience. I don't see the talent here. And so that's maybe this is a good segue into, into building SMB, you know, we, Levelset was founded in New Orleans. I live in New Orleans. Nobody thinks of New Orleans as a major tech hub, right? So we had to get really creative about how do we build a mint? That's what I would call it, like a mint, like you mint coins. We had to mint sales professionals, and I knew that I couldn't mint them into going and running $50,000 or $100,000 deals for our enterprise team. I had to get good at getting people from being Uber drivers and bartenders and selling vacation packages for the Marriott, right? To come and learn how to do SaaS sales and SaaS sales for construction, which is like, they don't know anything about this. And so the reason we did that is kind of a market response to going out and trying to find talent and just being frustrated or disappointed with the quality of talent relative to the context. Comp expectations and the title expectations. And so, you know, we, whether it was the market or the product or just the nature of the talent that we could attract and put to work profitably, we found a way to build an SMB team that really was the bellwether of our entire go-to-market motion. Even though we had other segments, our core business was SMB sales and SMB go-to-market inbound and outbound.

And then that talent powers the entire career journey in the upper segments over time. Yeah, for sure. I have so many examples.

I mean, dozens of examples from within our team of people who came in that were like going door to door selling Cox cable and came in and then within 2 and a half years, they're making like real money as a sales professional with infinite job prospects if they decided to leave Levelset, but we built a culture so that they never wanted to leave because they saw the career growth within our own org. So I'm not trying to skip ahead in the lesson plan. I know we have a lot to talk about, but you hit a nerve here and just these things are all connected, right? SMB, I just believe in it so much as a platform for changing. If sales is a possible avenue for anyone in their career, starting in SMB sales is such a wonderful platform to change your life because like literally you can get on the fast track to making $300,000 or $400,000 a year within 5 years. If you are good and you do the work and you keep your head down and you choose good companies and good leaders to work with, like you.

Yeah, for sure. So before we get into the details, I think, like, just frame up how you think about building SMB revenue engines differently than enterprise. Like, what are the distinguishing, um, identifiers there?

Well, first of all, enterprise is way sexier, right? Everybody loves enterprise sales. Everybody wants to close, you know, $500,000 deals, million-dollar deals. And don't get me wrong, those are really fun to close. But if you knew what work is required to go manufacture those deals, you might think twice about how sexy you think enterprise sales is. SMB gets a bad rap. It's like the low-status version of sales. And anytime I hear low status, I'm like, that, you know, I'm from New Orleans, like where there's a scrappy resilient town, give me low status all day long and let me go prove you, prove you wrong kind of mentality. And the difference other than the obvious, like sales cycle, deal size, sophistication of the customer, um, those things are just objectively, those are different. I think the mistake that people make, a mistake that we made was how you go to market. For an enterprise customer versus SMB customer are like night and day, even with the same product, the words you use, the messaging, how you generate demand, the sales process. I mean, the list goes on and on and on for all of the differences in the logistics of how you actually build a revenue engine for different market segments. You know, I'll share a quick story. So in the first, uh, when I started at Levelset, so carrying a bag, most of my compensation was commission, right? It was basically like eat what you kill. And we had this idea, we wanted recurring revenue. So let's go find recurring revenue. So what did I do? I went and found the top 100 companies that we could ever sell to. And I just started smiling and dialing, right? And within 18 months, we had closed 6 or 7 customers. I could probably name them all like by name if I thought hard enough, but we closed 6 or 7 customers and it was about $1.5 million in ARR. And it was land and expand. You started with a region and then you expanded and we were learning a lot about how to sell to these big organizations. And then it was like we caught a tiger by the tail. Once they started expanding, we had to figure out how to support these big organizations. You know, we have to go onboard 140 end users over the next 45 days because they wanted to do national expansion and SOC 2 compliance and all of the other things that they throw at you whenever you're selling to real enterprises. And we said, hold on, wait, I don't know, like, We need to make sure this is the business that we want to be in. And all the while we had been producing and putting content out around the problem that we solved in construction payments. And we had this pool of inbound leads that we just, we weren't working or we weren't working with them well enough. We were working them toward a transactional sale. We hadn't even thought about the packaging for the SaaS product. And so we kind of, moonwalked into this wonderful go-to-market where we could sell these inbound leads on a low average deal size SaaS subscription that was really valuable for these small businesses, contractors, roofers, electricians, plumbers, like, you know, just to give the audience like an idea of who we were selling to. And it totally changed our, our thought about how we were going to scale revenue. So we really, we shifted because we were struggling. Enterprise is lumpy. You have these big quarters and little quarters and big quarters and little quarters, as, as opposed, um, as you're building the, the revenue org, is the forecasting is hard when you're early. Then we found SMB was a lot more consistent. Um, and we shifted our go-to-market. And then we made this mistake where we were trying to run both at the same time, trying to fly two planes at once. We were trying to go upmarket and downmarket. And this gets back to the heart of your question, Kyle, which is what's the difference? The words you use, the value prop, the impact, the demo, the sales process, the stakeholders, they're totally different when you're selling to the owner of the business, like the owner of a $5 million plumbing company in Sarasota, Florida, as opposed to selling to a senior director of credit at ABC Supply that is one of 5 other senior directors of credit across the country. Totally different. And we, we tripped on our own feet so many times. It took us years to really figure out the messaging and how to go after those markets differently.

So messaging being a big one, operational rigor. So like your operational system is so much more important in SMB versus it's deal excellence. Like that's where you win in enterprise. Can you just be excellent and highly proficient at running like really high quality deals. I think those, those are the two things that are so different. And then one of the things that I want to unpack is manufacturing demand. Yeah. You know, like SMB lives and dies off of demand and you would trade ability to drive demand versus deal excellence any day of the week because SMBs tend to if there's product market fit, be closable without all the sophistication and multi-stakeholder management ROI stuff.

There's so much less politics with SMB. Like that's what I love about it is that it's really straightforward. It's more, it's the most quid pro quo version of, of B2B SaaS sales where we have this product, it delivers this value or makes this impact on your business. We've recognized that you have this need. And here are the commercial terms, right? Would you like to get— you want to do it? Yeah. And it's yes or no. And you have comfort in the fact as a rep or as a leader, you have comfort in the fact that there's an infinite market to go sell to. You know, how many restaurants are there in the US? Yeah, like 300,000 that are A+ for us, which is that 300,000, you'll never find the end of that market. Like you can sell to your heart's content and owner will be a multi, multi-billion dollar company before you find the end of that market. That's the comfort you have when you're selling SaaS into an SMB space that has a big TAM. How do I think about demand? You know, for SMB, it's really simple. It's either inbound or outbound, like organic or inorganic, right? That's your matrix. And so for inbound organic, that's content, doing things like this, producing webinars, writing blogs, YouTube. I mean, we did every channel you could think of. We would produce content to drive in— we call them eyeballs, but to drive traffic to the website and then put them through a conversion funnel. And, you know, to be clear, most of our inbound traffic, they weren't coming in to download or— excuse me, they weren't coming to our website to request a demo. They were coming to our website to download resources. And we had to get good at turning that interest, them acknowledging pain, right? Intent. Turning that into a sales conversation. There's inorganic inbound, which is paid, which is fine up to $1 million. But as you know, there's diminishing returns with paid. It just ends up inflating your numbers and it's not a scalable model to, to drive, you know, spend a bunch of money to drive inbound. Although it is changing a little bit with some of the influencer thing. That's a difference that didn't exist. 2, 3 years ago, there are some affiliate models and some paid versions that are driving and working for scale. I'd be interested in hearing how you do that at Owner and how y'all think about that.

Yeah, paid works well for us. Yeah, paid is still a huge part of our overall pipeline mix. You have to be really good at it to make it work though. Like I have an awesome head of growth. Who is super dialed in and just like lives and breathes all things performance marketing and knows every— knows all the tricks of the trade. So it's still a big part for us. We're making big organic investments. There's just like a big opening in our market. Nobody owns the thought leadership position. And we've got a CEO who is great at it and like is an expert and loves it and is good in front of the camera. And so we de facto own that position already. We've only been doing organic for like a year, and I think we've got more followers on every platform than anybody else and more, I think, brand affinity. And then a healthy outbound mix and now like a quickly burgeoning partner motion. For us, it's It's diversification. You don't know, like you said about DemandGen, you don't know when that's going to hit that diminishing return. Like how many times can you deliver an ad to this same person before your CAC starts to bloat, before the real ROAS starts to diminish? We haven't found that yet.

Keep spending. Keep going until you find it. Keep spending.

And then, but then placing these other bets is a big part of it. So now having a very rapidly scaling organic engine and having this partner motion, we announced this partnership with US Foods. So they're the second biggest food distributor in the US. They'd be your top choice of any of them to partner with. And I hired a woman who's built this program twice at other companies like us, and it's just like flying on it. And we don't need that pipeline now. We are making a forward-looking investment because we want that as like, as another channel that will either lead us to smoking our 2025 number, or if any of these other channels falter or don't grow as fast as we think they should, then we've got some redundancy there. Revenue layers. Whenever I do that, add a layer.

I said revenue layers. Add a layer. Like that channel is, is another layer that you're going to need at some point in the future. Hopefully not soon, but eventually you'll need it.

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Yeah. And I usually think of things through these, these confidence intervals. So if my performance marketing, we're 70% confident we can scale it another 50% next year. Well, I'm going to take that expected value and like bake that into plan. And then I know outbound can scale. I'm confident it can scale to X. So let's take a 70% confidence interval there. And so you end up putting in enough redundancy into the plan because we all know things go wrong. You have to plan on things going wrong. I think one of the topics I want to cover on the podcast is just planning, annual planning. Maybe this is only exciting for me, but I'm still going to do it.

You're in the right audience. This is one of the many topics I can geek out on. Before we, before we move on though, Kyle, I want to, I want to go back to the original question just around the difference in demand from enterprise to SMB. So with SMB, I love that you brought up channel because I try to think about these things simply. So, okay, there's, there's 3, 3 methods of driving demand. One is inbound, organic or inorganic. Then there's outbound and everybody, you know, call it whatever you want, call it cold calling, call it whatever. You have to have some sort of outbound motion and figure out how to get it to work. And for us, you know, it took us a while to figure out the outbound motion for SMB to make the economics work. Because, you know, if you have a salesperson that makes, just use an arbitrary number, they make $75,000 a year in OTE and you want a 4-to-1 ratio. What is that? It's like $350,000 in bookings, $400,000 in bookings that they've got to get to make them profitable. Well, like you need to make sure that for them to make that $75,000, they got to close at least $35,000 or $40,000 at $5,000 apiece. That's 7 deals a month. That's if— how many leads do they have to talk to to get a 5% to 7% conversion rate? I mean, you can start to think through the funnel, and if you don't have your messaging tight and you haven't dialed in your ICP, and what you talked about is like the operational rigor, it is a system. It's not about getting one individual in the seats who just can can dazzle people with words and figure out how to go convert 100 leads into $25,000 in bookings. It's about how to do that across a team of eventually 100 salespeople who can do the same thing over and over again, because you've got 300,000 companies that you can go call on, right? Like that's the, in a revenue leader's mind, like that's what you're thinking about is scale. Outbound is really important. It's really hard to do for SMB businesses. And if you can do things like performance marketing, or in, or organic and inbound. If that's part of your DNA, then you, you, you can, you can run both of those channels at the same time. The third you mentioned is actual channel partners. We never figured out channel partners successfully. Um, they exist. Did you try? We tried. Yeah, we, we certainly did. It was never more than 10% of our bookings in any quarter or month. Um, we had channel partners. We just, we, well, that's it. That's probably a different podcast episode. We can, maybe we can save it for the end. On the enterprise side, Now we're in account-based marketing land or account-based sales land. And that's the, the, the method, especially in vertical SaaS, when all of these people talk, they're in the same city. So if you're going after an account, it benefits you to be super, super focused on a geographic area, or at least find out where these people hang out because they all borrow from each other, right? In the restaurant industry, in the construction industry, insert whatever vertical market, when you're going after enterprise, it's so, it's so account-based and we always had a named, a named account strategy. I guess that's what they call it, where we knew the market, we figured out which ones we wanted to go after, and then we would line up all of our efforts, the SDR team, the enterprise sales team, the field marketing team, which we were able to get that field marketing function to deliver a ton of ROI for us. Obviously, you have conferences and other things that you can spend money on. All of those things are kind of DOA if you try to do them on the SMB side because the same motions don't work. And so I just wanted to tie a knot on that point around the difference between structure and demand for enterprise versus SMB.

Yeah. And you have to be able to manufacture demand. I think you can hire enterprise reps that have good books, that know how to work their network. They can, they can, they can find a lot of their path to the number creatively. But I think in SMB, you need to centrally generate that demand in order to survive. And you have to be able to generate that demand consistently. And that is your gate. Like, it's not in enterprise. Oftentimes your gate is how many really great enterprise sellers can you hire? Yeah, because it's super hard to find them. Can they sell in your market? You know, how fast can you ramp them? A lot of enterprise success can be that. But in SMB, the thing that gates your ability to scale is, can you just generate the meetings in large part? For us, I can find good talent. We can scale it up pretty quickly. It's not a very complex sales cycle. People can figure that out. To get to a baseline, and then we want to get them to excellence. But like the really hard puzzle to solve is how do you generate the demand economically, which you touched on, and we'll unpack that as well. So in terms of like the keys, so we'll structure this, the keys to winning in SMB demand and demand creation and being able to manufacture demand in an economic manner is one of the really big big pieces. Operational rigor we've talked about, and we'll dive into systems and technology. But let's talk about people because I think how you manage is so different. If you tried to manage an enterprise seller like you manage an SMB rep with spiffs and contests and weekly coaching, like, you know, an enterprise rep will flip you the bird. So the people topic, I think, is really different. So How do you think about the people engine in an SMB business? Like what are the key pillars? What do people need to build around?

So we may come from different camps on this and I'd encourage maybe a Spartan debate on this. So, you know, I, if you're running an SMB sales team, I believe that you need to be in office. Call me old school. Call me a dinosaur. I don't disagree. Okay. But I know you have a distributed team, right?

We have a fully distributed team and it's working great. Right. Would there be an advantage to ramp and productivity and attainment in an office? I think there's a fair argument for that, for sure.

And look, I'll put you, you're a top 1%er, Kyle, with respect to your leadership and ability. And so the best leaders figure out how to do it and we all, had, we were forced to do this in COVID. Like we, from Friday, March 13th to Monday, March 16th on a dime, we all had to figure out how to be remote sales leaders.

So I didn't figure it out that fast. It took me a little while.

Quick, quick story. We, we actually onboarded a class of 14 sales reps on March 16th, which, yeah, that was a, yeah, it was a 2020 was probably the hardest year of my professional career. Uh, and for many others, like, you know, in, in And not to— I'm not a martyr here. Like, I feel very fortunate in my life, but like, it was tough as a sales leader to try to figure out how to go remote because we were very much an in-person team. Okay. Why do I say that? This is another thing that I think I get in trouble for, or people disagree with me, but like, micromanagement is a good thing. Now, I want to be careful.

So this is my reframe of micromanagement.

We microcoach. Yeah, we microcoach. Okay, I'll use your language. I think we mean the same thing, which is going back to my comment before about if you're a founder or an executive sales leader and you've written down the playbook or the blueprint or whatever word you want to use to describe the path that people need to follow to go achieve success in the role. If you've done that work and you've given them the tools to go be successful, well, then it's your job as a leader to go hold them accountable to that. And if you're running an SMB sales team, Let's be clear, this is a high velocity, high phone call, entry level sales position. It's a hard job. It is a hard, it's effort driven a lot. Effort means a lot. And the rep has to show up every single day and make, you know, somewhere between 50 and 100 phone calls just to generate their full desk AEs. They've got to generate their demand and set the meetings and run the demos and negotiate the deals and convert the deals. It's a ton of effort. And when you're scaling a team, I just never figured out a way how to scale it without being really deliberate about what I'm asking people to do and then coaching them to execute on our playbook. And when people deviated, it's like one of two things. Either you can't do it, in which case I'm going to show you, you know, I'll do it. We do it, then you do it. I'll teach you how to do it, or you won't do it. And if you won't do it, well then, hey, I love you, but you get to go be successful somewhere else. It doesn't mean that you're a bad person or that I'm a bad person or whatever. I just, I don't know how to scale this team other in any other way than just, we're going to run our system. I'm going to coach you to run this system the way we need to. And if you don't want to buy into that, that's okay. This is at-will employment. Everybody chooses to be here every single day that they show up. And by the way, a career in sales is an absolute choice. Like, you have to be a little crazy and a super optimist to choose a career in sales to begin with. And so if you have that right mindset and you join a team and you have a leader that's hands-off, it's like, run, because you're not going to get the microcoaching that you need to build the skills. The other thing I'll say about this, and, you know, tenure is important, like with SMB sales, uh, just categorically, there's higher rep turnover. And that's true across SMB sales for any organization. And it's because of the, to say it's because of the effort, I guess I'm paraphrasing. I'm using my own definition for that, Kyle. It's like, if you're going to go wake up every single day and crank out 75 phone calls and call business owners and interrupt their day to convince them that they need to buy your solution. There is a shelf life for how long you can do that work. Right. And it, for us, the average tenure for a successful rep, the average tenure was like somewhere between 1.5 and 2.5 years. I don't know the exact number, but if you had an SMB rep that was still in an SMB role 2.5 years in, and they hadn't moved up in the career, uh, the career, career planning or like the career ladder or they haven't moved up to and been promoted to a different customer segment or a different role, then it's a bit of a red flag. Now, the lazy sales leader in me is like, hey, this guy hits his quota all the time, or this girl hits their quota all the time and they're happy and they're, they're comfortable being here. You know, I want to keep that person on this team. That's the lazy sales leader. The, the real sales leader in me says, hey, what's going on in this person's life that makes, is it, is it maybe some insecurity or is it something a limiting belief that they have about what they want out of their life and their career? How can I go help them so that they can achieve more personal, professional, and financial success in their life? Because that's the individual contributor track. Or maybe they're better on a leadership track. And that goes back to, it's not micromanaging, it's microcoaching, and it's microcoaching the careers for each individual. You have to care about this stuff. I think if you don't care about the humans, the people that join your team, and what they want to do with their life and what their goals are, then it's just not worth it. Like, go do something else. Don't be a sales leader because that's the most fun part.

Yeah, right. The relationship is so much more personal in SMB because you're, you're working with these people in the infancy of their career and you have such a material impact on the trajectory. If you teach them the right things, the right mindset, the right attitudes, the right ways to show up every day, you can put them on a path to like achieving anything. If you, when you manage an enterprise team, it's much more transactional. Like this is a more professional relationship. Like we don't need to be buddy-buddy. Like you're here to try to smoke your number and make $600K. I'm here to do my job. The, the like relationship, I think, and the, you know, the personal investment, there's, that's the reason I like SMBs is I really, I got into coaching because I like seeing people progress and it's always like given me a lot of energy. And in SMB, you can just like see people, they get their first AE job, they smash their first quota and they get their first like $10,000 or $20,000 check. They get their first manager job. Like those are the most fun conversations to have and it's just so meaningful.

Can we touch on that real quick? So we had this, I'm going to let some of like our, my core values come through in, on our sales team. But one of the things we talked about often was this idea of bright spots. This is what you're talking about, by the way. The first $100K they book or the biggest, the biggest month they ever have, or they broke a company record or, or it has nothing to do with work. Maybe it's that they got engaged or they paid off their student loans or I mean, all kinds of things come into the workplace when you're running an SMB sales team because the relationship is so personal. You get to know everything about these people. And it's not just because you're working side by side with them. It's because you, it's, it's, you almost build this mini community of support and everybody's rooting for each other, for their, each other's success. And so we, um, we had this, this mantra of like, manufacture or just focus on the focus on manufacture and celebrate the bright spots. What does that mean? A bright spot could be anything. It could be, the $100K bookings target. It could be that they had some meaningful life event, but we made it a habit and we built skills within the organization of finding and rooting out the bright spots and elevating them and celebrating them. And this is really important because this goes back to one of our advisors and investors at Levelset was Chip Heath. If you've ever read Chip and Dan Heath, they did, right?

Like, 2 of my favorite authors. I'm reading The Power of Moments right now. It's one of the ones that I haven't read.

Wonderful book. Yeah. So they did Made to Stick, they did Power of Moments, they did Decisive. They have this book called Switch that's all about—

2015. It was in my first SaaS job.

And he talks about this is celebrating the bright spot. So we took that from his mouth or also from the book or however you want to call it, but we took that and incorporated it into the company-wide culture. But as especially on sales, because I'll go back to this, the job, it's a hard job. Like, it is an unrelenting, just labor-intensive job filled with rejection. And as a leader, it's really easy for me to go into a pipeline meeting or a one-on-one and just trash on everything and just being frustrated. Like, but that's not good for anybody. And as a leader, especially as the team gets bigger, your job changes. You become this, I call it a cheerleader, call it the chief marketeer. Like your job is to assemble the team, set the vision, assemble the team, create the scoreboard, and then be the cheerleader, be the marketeer. And you have to keep in your back pocket a handful of those conversations. You know how it is. Like you go miss, you have a miss on the quarter that you were not supposed to miss and you were committing and you fell short, like we've all been there before, you're going to have to have a hard conversation with the team, but you save those. And most of the interactions you should have as a leader with the team are around these bright spots. The question that you asked in the beginning, Kyle, was like, how do you build this success culture? What are some of the, like, fundamental, um, these aren't secrets, but like, what are, what are the fundamentals of building an SMB team and the people? You have to have a success culture that people adhere to, and they can see visual or tangible proof of success around them. Every promotion, every milestone, it all needs to be celebrated publicly.

It's super important. And you use the word tangible. And so I think one of the things that's hard in a remote environment is your success is very ephemeral. Like, oh, I had this big, huge milestone. I'm still just like sitting here at my desk staring at my little screen. And so it's hard if we think, if we go to another author I like, Daniel Pink, and his DRIVE framework, autonomy, mastery, purpose. Yeah. Like, how do you give people those milestones and guideposts along the mastery journey? So I was reading Power of Moments. Very jealous that you were involved with the Heath brothers. And just Chip.

I've never met Dan.

So full disclosure, just Chip. And so what we did, what I recently did, so we did like an awards trip to Cancun because the team hit this like crazy number in Q1. And I had these plaques made. So they're like glass. It's like a glass circle on a placard and it goes on the wall. And there's a slot down the circle and you can put in little chips into the plaque for every one of your milestones. When you hit your quota for an entire quarter, when you win a quarterly award, when you win one of the values award, you put in these little chips because I was trying to give a physical manifestation of people's success so they can sit there and look at it. They're like, Man, like, I got like a whole stack of chips in my thing. Like, this is a representation of all of the things I've accomplished because it's hard to appreciate it. Totally. I wanted to do a thing in Slack where after your name, you could put like little, like a trophy case, you know, like how in video games, they'll have like the badges and the whatever. And I wanted a Slack version of that. So, It was like Martin Roth, and it's got like bullseye, bullseye trophy, like whatever values plaque. And so every time somebody slacks you, they see your sort of tally of awards. It's not possible in Slack. I've tried. But this plaque thing is an idea because I think your bright spots thing, we've come to this. It's funny, we've never talked about this. Like, I have the exact same view around it.

Look, here's the deal. Like, it's all made up anyway. Like, if we're going to be real about this, it's all made up. This stuff is manufactured. But if we're here and we're trying to go build a company and go drive revenue, well, like, let's have some fun along the way. It's okay if it's made up. We're all, we're all a part of the game. And so you just got to do what's, what's works with your culture, you know? So there's this example. I talk about this. Analogy where if you're— I'm not a pilot, like I don't fly planes, but I have some friends that fly planes and there's this thing whenever you have your first solo flight. Do you know what— have you ever heard of this? When you have your first solo flight, cut your shirt, like your shirt sleeves, they like tear your shirt. It doesn't mean anything. It's a stupid thing that is part of this pilot culture and they cut off the bottom of your shirt. Yeah, they like just tear like a ring. Or what? No, it's just like they just rip the shirt. They tear your shirt. And so you have like accomplished pilots, naval aviators, they'll have like their shirt framed on the wall from their first solo flight because it's this memento. It doesn't mean anything. It's made up, but you give it meaning based on your culture. I'll give you a couple examples.

When I started, my brain is now I'm like, hmm, could I, should I have people cut their shirts on the floor?

I wouldn't go that far. I'll give you a few other examples that maybe you or other listeners listeners can borrow. So when I was starting out at Levelset, I was afraid to cold call. Not too scared to admit it. Right. It's nerve-wracking. I'd never had a sales role before, and I had read somewhere that if you carry a bat in your hands or like a golf club, then it subconsciously gives you confidence or whatever. So I bought a Louisville Slugger bat for $20 on Amazon, and I would walk around and it became like this caricature, like, oh, Martin is on his headset. Pacing around the office with a bat in my hand. And then, you know, the first, um, with one of the first AEs I hired, uh, Tom Stern, he's like, hey, when do I get my bat? Like, I don't know, if you, when you hit $100,000 in bookings, you'll get a bat. And that created this thing where now, and then we had this bat ceremony and we had like a custom deal with Louisville Slugger where they would do custom bats with like people's nicknames on them and the whole, we had bat racks in each office and That was just one stupid, silly thing that was like specific to our culture. Another thing we did was when you hit $500,000 in bookings, you got a record on the wall. And then for every $500,000, you could go like gold and then platinum and then double platinum and then triple platinum. And so we had this record wall that had people's names and the date that they hit whatever the milestone was. Those are two examples that are very public. You have companies that have the one-call-close chain. I love that one where one-call-close, that one floats around traveling trophies. It's very common. My favorite though, and this is really reserved for leaders. And if you don't do this, Kyle, you should do this. I don't want to tell you how to run your business, but you should definitely do this.

I'm ready. I'm sold going into this.

So I actually work with a mentor executive coach when I was at Levelset. His name is Barrett Foster, and I've learned so much of what I've learned is from him, but he taught me me this? And he's like, use it. You'll never stop doing it because it makes such an impact on your team. At the end of every month, I'd send out a monthly email. So we use Slack mostly in the organization, but occasionally you would send an email when it mattered. And we would, I sent an email to basically the entire org and it was, you know, congratulations on this bookings number. I want to recognize these individuals for their outstanding contribution. Here's some contribution from outside the sales org that contributed. And then I would publish the stack rank because I believe and transparency. In addition to that, every single person that hit quota, I would write a handwritten card and send it to their house. Cool. And every quarter for top performer, and I'd make it personal. I'd write something because, again, we talked about building an SMB sales team. You get to know these people really well. I have hair standing up on my arms as I tell this story because on more than one occasion, I've gone into a former colleague's house, somebody that I worked with. and on the side of their fridge is like 5 or 6 or 7 cards that I've written even years after we work together because it means so much to people when they get recognized. What's the— there's like that Napoleon quote that I'm going to butcher. It's like a soldier will march long and hard or whatever, miles and miles for a small piece of ribbon. The same idea is true if you can find a way to make it personal. As a leader. I just love handwritten cards because people don't do it. They just don't do it. They won't sit down for 2 hours at the end of a month and just say thank you to every single person that hit their number. You only get it if you hit your number, but you have to have these little moments and bright spots.

Yeah, I love it. We think very similarly on this. And for some reason, I hadn't read The Power of Moments. I don't know how it slipped by me, but I'm like in it now. And And so I'm planning a bunch of stuff around it. So let's transition quickly on the talent topic and talk about manufacturing talent because, you know, you mentioned you're in New Orleans, but I think regardless of where you are, you really, if to make an SMB model work and the economics, you have to hire your own, you have to groom your own people. You have to be able to build sellers from within because it's so expensive to hire externally, and then the hit rate is, you know, whatever it is, and getting somebody to take a lateral move into another S&P role. There's a bunch of complexities there. So what were the pillars for you to manufacture great talent, which I know you did because I've interviewed and hired some of your reps, and clearly you guys had something special there.

So I'll repeat some of the things that I mentioned earlier is have a clear set of expectations and a blueprint for success, right? Don't hire anyone into a role where they don't have demand or have leads that they can call. Like, that's a prerequisite. The second is you need to have some sort of educational— I call it a course, call it an onboarding. I don't know what the right word is for it, but there needs to be a blueprint for success, and there needs to be some period where you teach them those things. I always preferred to hire people that were more raw or didn't have sales experience than to hire people who did have sales experience. For SMB roles. For mid-market and enterprise, you kind of have to go based on experience, but I always prefer to hire internally as opposed to hiring externally. I'd much rather someone who came up through our system to go take on those mid-market or enterprise roles. And so that's like my quick answer on manufacturing frontline talent. I'd like to take a moment if it's okay to talk about manufacturing leadership talent, because I think that's actually more difficult. I I would agree.

And I think the single most important role in an entire SMB go-to-market function is frontline managers.

Frontline management, without a doubt.

Everything lives and dies on the frontline manager. Without a doubt.

And the best frontline managers are superhumans and can do things. Full disclosure, I was not a great frontline manager. Like when I think back to my time as a front— now in hindsight, like I know how to do it. If I could do it again, I would do so many things differently. Um, and, and I eventually got good at it, but there were so many frontline managers that we had on our team that were much better than I was. And when I think about manufacturing that talent, you know, there's a few things that I think of. The first is there needs to be career pathing on your team. And for the people that raise their hand and say they want to pursue leadership, give them a path to pursue leadership. And it could be as simple as like a handful of books. I'm sure you and I share some of the same books that we like that teach some of the fundamentals around leadership. We used to, I'm seeing if I have it on my—

I don't have it pinned on my LinkedIn because people are like, hey, I want to do this thing. Great. Here's the book.

Read these books, right? Maybe I should do that. We are— our most basic leadership curriculum was this. There's an— there's a Harvard Business School book for— it's called For New Managers. It's orange and it's outstanding. And it's got 10 or 11 articles and it covers all— it has— it actually isn't about sales at all. It's really just about taking a high-performing individual contributor and getting them to shift their brain to think about what it takes to be a leader and be a servant and be someone who is there to support the people that you lead. So that's one piece is like having, having some curriculum to give to people that express interest in leadership. The other thing is look for the helpers. Like when you look at a team, it's so much easier whenever you have a team in person, but even remote, it's clear to see which individuals have gravity. In the team? Who do people go to, to get advice? Who do people go to when they have a question that isn't a manager or a leader? Usually in any team of at least 5 people, there's one rep that stands out as having a voice, having influence, and being a positive impact on the other people around them. You have to go nurture that. And so there's no science to this. I don't think that there's like a leadership development playbook. I'm sure that stuff exists online if you can go find it. I was successful at promoting some leaders internally. I was unsuccessful at promoting some leaders internally. I was unsuccessful at hiring leaders externally. Like, I've made all of the mistakes. What I learned, though, is if you have a curriculum, you lean into people's interests and you look for the helpers and really coach them into what it means to be a leader. They already have the tactical knowledge of how to execute in the role, you really need to teach them what it means to be someone who isn't there to go close these deals for people. You have to be there to coach the skills and you got to learn how to coach coaches. Um, so that's a note on that. I don't know. I mean, how do y'all think about developing leaders within the org? How do you feel about team leads? There's another question. I hate the team lead role. I'm a big, um, I, I am, uh, what do you call it? I do not support team leads as a concept unless like some very specific criteria are met. I just feel like team leads are a disservice to the individual because there's, it's a conflict of interest, right?

Like, yeah, it depends on the structure. I think on the topic of building leaders, I agree. So looking for the helpers is a piece of it. I think giving people, people who, if you've never managed before, you have to give them the experience of what it's actually like to manage. Because many people want to be a manager because it's a promotion, but they don't want to be a manager to do that job. And especially you can have like the best rep and it's like, why don't you give me a team, Kyle? Like I should have a team. Well, like you hate updating Salesforce. You don't like coming to like enablement meetings and like non-customer-facing anything. You always grumble about it. So basically all of the things that a manager does all the time, you don't like. And like this happens all the time because I know this is oftentimes because of the, the, you haven't given enough of a career journey for, and you haven't put the IC at a high enough level of like respect, like my two top sellers in like my top segment, they have just as much access to me and voice in the organization and give feedback on product as any of the managers. And because like they're super duper valuable and they feel, um, they, I would say both feel like they are like really true partners in building this business. But if you make it so that the managers are the only important people in the business, then everybody's going to want to be a manager and you attract the wrong folks into it. So I think giving people the experience to know what it's like, helping the right people opt in and making sure that the people who who really shouldn't be in leadership have an awesome path otherwise is important. And then it's all about structure. Like, I think the reason so many managers don't work out is we just say you were a good rep, we drop them into the role and we say go for it. And unfortunately, the craft of sales is a very bad platform to become a manager. CS is a much better craft to come from to be a manager because you're a helper. You're listening more. You're thinking about problem solving. In sales, you have to be a bit of a competitive psychopath. It's all about persuading people and convincing people of stuff. And you have to not convince as a manager. I tell my managers all the time, do not spin this. Don't try to tell somebody, hey, actually the quota going up is good for you because now you get to stretch and blah, blah, blah. Like, dude, the quota goes up because we're running a software or like a high-growth business and everybody's quota needs to go up for this whole system to work of returning capital to shareholders. Don't try to like, you know, blow smoke up somebody's backside about why like some, their territory getting carved down by 50% is good for them. Like, it's just, this is like not really that good for them, but it's good for the business. So just tell them that. And salespeople want to like make people happy and convince people of things. And so you have to like unlearn so much of this stuff. So if you just drop a salesperson into a manager role, they tend to do the things they're used to doing, which is actually the wrong things. Just given the craft and what's important as a manager. So, I try to give them a system. I have a 6-pillar leadership framework. Can you sell? Can you hire? Can you coach? Can you build? Can you operate? Can you engage? And we're now building this leadership academy where every single one of those things has 7 to 15 lessons underneath it. And a bunch of them have content already, but then we're going pillar by pillar by pillar, having a module for every piece of this journey so that somebody can go in and be soup to nuts and really understand it. And it'll take them a long time to internalize it all, but you need a system, especially as you go from, I was individually managing the managers, so I was the source of their feedback. Now, there's two layers between me and the manager, but I need to make sure that my system is the thing implemented. Not that those people leaders aren't awesome, but like consistency of system is critical. And so I need to make sure my system is in the sales leadership function, the launch leadership function, like everything needs to be tied together or else chaos ensues.

Yeah. Well, I mean, look, it's very similar. To how you implement sales process and sales playbook. It's just a leadership development playbook. The way you described it is like the, that's the capstone course at Harvard version. I was doing the down on the bayou version down here in New Orleans, maybe a little scrappier. But yeah, I mean, you were, it was inspiring to hear you talk about that because you're saying like, that's all the right stuff. It's obviously the right stuff because you're having success building leaders. Um, and it's so much about, like, I love the point you made with when you have a team of salespeople, they're ambitious, they want to grow in their career. And if you don't give them the career pathing for them to grow in their career, then they're just going to go mimic whatever they see the leaders in the organization doing. And if that's the managers who are getting respect, then that's what they're going to desire. I think it's a really important point. We didn't have career pathing for way too long and it probably hurt us. Yeah. And then we implemented career pathing and turns out retention went up, right? The ironically, I guess the onboarding and ramp timeline for new reps shortened because they just had more confidence in their long-term prospects at the organization. Career pathing, super, super important. Important, not just for the leaders, but also for the individual contributors. And by the way, it should be said, if you didn't already say it clearly enough, it is totally okay to be a world-class individual contributor and just go make a bunch of money. Every organization needs those people, and those people are world-class for a reason. Like, it takes a certain type to go make a million bucks or a million and a half bucks a year as an individual contributor. And that's a viable career path. Leadership isn't the only way. You just have to, you know, if you're a psychopath like me and you who are just, I'm like called to it. I couldn't help myself but to want to be in the leadership because, you know, I get a lot of value from it. And it's got benefits too, but that's, that's for another conversation.

Good. So, let's talk about building infrastructure. So, so we've talked about sort of a bunch of the people stuff, success culture, manufacturing talent, the importance of demand being sort of the second pillar with people. But then the third pillar that we really want to unpack is operational rigor and the rigor. And I call it systems engineering, like the systems engineering of building SMB go-to-market. So maybe just talk about what were the most important things for you to build? Like, what did you have to get right in the business to try to unlock? Because what you're solving for is repeatability, the economics. What were the key pieces of infrastructure that you had to lock in to make this work?

Okay. Um, I'll make some assumptions here. So one assumption is you have product market fit, you're scaling a team, you have a sales playbook that works, which those are all big assumptions, but here we are. Once you have that, to your point earlier, Kyle, you have to make sure that there's consistent performance and people consistently following the playbook that you put in place. And so I think about it on a few different levels. The first and most important is what I call operating rhythm or drumbeat of the, of the revenue org. It's the meeting cadence and it's the structure and the content of those meetings. And I want to be clear, I just like most other leaders or top performers or whatever, I don't like spending time in meetings for the sake of spending time in meetings. Like, in fact, I'd rather the whole revenue-producing organization spend as little amount of time in internal meetings as possible because we're supposed to be meeting externally with clients or prospective customers to try to get them to purchase from us or expand their usage or whatever. And so being really deliberate about what the operating cadence is for the business is important And it's important for a few reasons. Number one, it's about how you get information into the organization from a leadership role, but also how you get information back from the organization. And we'll talk about that in a minute because there's other things that you can do outside of your operating rhythm to get feedback from the org. My operating rhythm was simple. And you don't have to copy this blueprint, like different orgs have different cultures, remote versus in-person, all those things impact how you run your operating rhythm. But there are some table stakes meetings that have to happen. For example, every frontline rep needs to have a one-on-one every week, no exceptions. And it can be 30 minutes and it should be structured and it's the rep's time. And the structure for that meeting is really simple. What's going well, what's not going well, and what's the most important thing for us to talk about today? Now, in the what's most important for us to talk about today, If the rep chooses that they want to talk about a deal or pipeline or something totally unrelated to their job, it's their time. Keep it to 30 minutes. Every rep has a one-on-one. You have to have a weekly sales team meeting. Ours was 15 to 20 minutes once a week. To kick off a month or kick off a quarter, we might spend a little more time because we would be celebrating bright spots or maybe announcing a new product release, or we would spend a little more time in of the team, but there needs to be some moment once a week where the whole team comes together. If for no other reason, then you're just helping people understand what the goal is and what your traction is toward that goal. Now, for the people who say, hey, this could have been an email. Yeah, sure. It could have been an email, but people don't read. People don't read. Bring them together and make it a moment. And it's on you as a leader to make the meeting engaging. If people say that meeting is pointless, well, make it more valuable. Like, that's just work. Like, make it more valuable, more entertaining. Give, give the team a reason to show up. Um, two other types of meetings, part of my operating rhythm. You need a forecast meeting. If you have a small team, right? And you're, let's say, a frontline manager and you have 5 reps, you need to bring that group together and talk about pipeline and forecast and commits and best case on a weekly basis. As a group. There's a level of public accountability that comes with forecast meetings that's really important for driving performance, especially when it comes to playbook adherence and running the plays on specific deals. You know, people learn from us most. It's super important. The last meeting that I have in my operating cadence is, um, is call camps. Uh, and this is an enablement, uh, meeting, which I don't know if you run. I'm sure you do, or somebody from your team runs call camps. You know, at some point I didn't go to— yeah, yeah. Call camp, just to, for the audience here, you, you have 1 or 2, maybe 3 calls that have been pre-selected that have already been reviewed in Gong, or now they have all these AI tools that do this stuff for you. And you get together as a group and you look and listen to the call together and you talk about how the playbook was run on that call. Uh, and it's really helpful to just hear how other people are running the playbook and working the deals. Now, if you're, if you have an underperforming rep, they're required to participate in call camps. If you're hitting your number, you're not required to go to call camps, but I'm going to notice if you're not showing up and I'm not taking attendance, but I also know that there's a direct correlation between a rep leaning into their own enablement and their revenue performance. And usually if they're starting to slip on those call camp or enablement sessions, then their bookings target— I'm sorry, their bookings performance starts to slip. And so those are the 4 parts of my operating cadence. And you set this expectation at the beginning when reps join so that they know, okay, these— this is the venue that I have with these leaders when I have a voice, when I can bring up specific topics that are important to me. Some are personal, like in a one-on-one, some are less personal and can be valuable to other people on the team. And that would be in a forecast meeting or, um, or maybe a call camp. I ran a daily standup, um, because that was my operating style. I think that's a little more difficult if you have a bicoastal team. Um, it can get logistically challenging, but there are some benefits to those parts of an operating rhythm. So that's like the first piece around systems and infrastructure. We could talk about tech stack, like you have to have a good tech stack running an SMB sales team. The leads come from the company. Like, I hope that your SMB sales team is not out there on Google trying to find their own leads to call. Oh, you would be shocked. I know that many companies do it, but like, please don't. If that is you and you're running an SMB sales team and your team is using Google to find leads, call me, you know, martinroth.com, and I will help you set up so that you don't have to do this. And that's not even what I do. It's just like, it's a major disservice when you have a team of sellers who get paid to pick up the phone and talk to prospects, and they're spending 50 to 60% of their time perusing Google to find good leads to call, like, that's no man's land. Do not be there. It's not just not efficient. It's, that's, that's not the way to run an SMB team.

Um, so we could talk about item number 1 in my SaaS workshop.

Uh, yeah, I go on and on. Get your ICP, get your lead list. And we've geeked out about this. Like we talked about some of the sophisticated stuff we did at Levelset. I know you guys are doing interesting things. You've got some good partners. I don't want to call out those partners. Like, I don't know if they're sponsors or whatever, but there's, I know there's a firm at a lane. No, I was going to say DataLane. Like, those guys are doing really interesting stuff for the restaurant space. And like, that's the kind of technology that you should be leveraging on the tech stack side. And then certainly, like, you need a CRM, you need someplace that's recording calls, and you need to be reporting metrics back. The second thing I'd mention around systems and infrastructure is You need some dashboard. It can be pretty, it can be not pretty. My version was not pretty, and that's because I'm not that smart and I try to keep things really simple. And I use a Google spreadsheet that I personally updated every single month on the first day of every month. And it just went through our, our, our entire funnel. And what it does, it was a forcing function for me to go into the systems and look at it. Cause if it was automated, I wouldn't pay attention to it, but I was hungry for the insights. So I had to go collect the data myself. I'd encourage every sales leader to get into this habit. It's not efficient, but let's be honest, it's like 30 minutes to an hour of your time once a month. And the level of detail and understanding you can get to by doing this yourself, it separates your understanding from if you just had an automated dashboard. And we had Salesforce and we had the dashboard. Reports, and that's all important. But having one, a one, I call it a one-page sales overview. I have a template that, you know, it's on my website. You can go download for free, but all it is is the funnel. And I got really detailed with this, every talk time, conversion rates per call, everything down to hold close rates. And, you know, when we added in the install-based sales team, we had metrics for that. So it can get to be a Frankenstein of a dashboard, which is not even a dashboard. It's literally a spreadsheet, but I could run my entire revenue org from that one spreadsheet because I could look at it month over month and I knew exactly where in our funnel and on the team I needed to go focus. And the number one metric I cared about was productivity per rep, which we mentioned earlier in this call. Productivity per rep was just for an SMB sales team. It was the number one signal for demand, rep efficiency, sales leader efficiency. If I was comparing 2 or 3 sales teams and how the leader was, what's the PPR difference? What's the leads that are getting fed? Just use as an example of how you would leverage a spreadsheet like that. And then I'll finish this out with the topic of forecast meetings, which is a, this is a I think people run forecast meetings poorly, usually. And there's a certain way to run forecast meetings. And I think there's this tendency for leaders to show up and say, okay, what you got? Like, what's your call? Yeah. What you doing? And that's just a recipe for bad insights. If nothing else, it's not a disaster. Maybe you can perform your way out of running bad forecast meetings, but If you're going to spend the time, just do it right. And the right way for me is as a leader, I'd never figured out a way how to run the org without getting really granular into the pipeline and going deal by deal and really understanding what our commit was and what our best case was. And in that forecast meeting, you let each leader, if it's leaders in the forecast meeting, you let them make their commit in best case. And then you have to bring up specific deals that you see that are not compliant with your playbook and dig into why we're not running playbook on those so that you can layer on as a leader. Um, I could talk about this topic for a while, but forecast meetings, that's your, that's your litmus test for operational rigor. Your forecast meeting tells you exactly from the team what's happening on the, on the floor and in the sales conversations so that you can take quick action.

Yeah, that makes a ton of sense. The, We don't run a forecast meeting at all. I just do a bottoms up. I called the number halfway through the month. We were at like 30% of our number because we had our sales offsite. There was a long weekend, like a bunch of stuff. And I said at all hands, I'm like, this looks dire. And I was like, but I'll tell you where we're going to land. And I was within 2.5% on my bottoms up. Because for our business, we generate demand in such a predictable fashion and you can just look at how are we driving demand, how much is in funnel, what are our conversion rates with that sort of age of pipeline. And I can get to the number, the bottoms up. We're true SMB. You guys had a mix of like mid-market and other, but in true SMB, 10K ACV, like 7-day sales cycles. I don't, I don't, I, it's not that I don't forecast, I look at it actually every day. Just because I'm, I don't know, I need to, I need to know, but I can see from the bottoms-up model, how are we tracking to it? And then we know it's okay, we need 42 ops every single day, the rest of the week to be on track to hit the number.

We need 47%. Yeah. So much around pacing when you're running that.

We just managed that. But I agree, like in a mid-market environment, like having a really like well-run forecasting process is good. Okay. We are out of time. So we're going to go quickfire. Okay. Couple of questions that I ask every guest. and we'll short answers. So what do you know now that you wish you knew as a young leader?

You don't have to be Superman. Like, you don't have to put all of the weight on your shoulders. If you can find, whether it's, it just goes back to hiring. If you can find good people to surround yourself with, it makes the job so much better. And I think it took me too long to to learn how to hire or to figure out what advantage or blessing it is to have really talented people surrounding you. I got a few others if I can keep going. If as a revenue leader, your relationship with marketing and CS is almost as important as your relationship with your direct reports, and you should treat those relationships in the same way. I did not spend enough time investing in those relationships until I learned that that's important. And that's, uh, I wish I knew that earlier or younger in my career. Um, it's not as bad as you think, right? Uh, not with just in the role of revenue leadership. I feel like I was, I had this unhealthy, everything was everything. Like I had this unhealthy dose of paranoia and in hindsight, I can look back and be like, man, it's like I wore, I'm 35 years old and I have all this gray hair for a reason. And it's because I sweated the number every single month. And I just, I wish I could go back and say, hey, look, take it easy. Like, it ain't that bad. Uh, and then look, I'll, I'll leave, I'll end with this. I have a bunch of other insights, but like, I'll end with this. Never lose your edge as a sales leader. Always be willing to get on the sales floor. Go take a deal, uh, not take a deal from someone. You can give the rep the commission, but like, do what you can to stay close to the front lines because once you get disconnected from the customer and the problem and the reps' day-to-day life, you lose your effectiveness as a leader. They always have to see you as someone who has the capacity to do the most granular things at a high level.

Yeah, that's a great one. What's the most common advice you gave to your leaders or mentees?

I say this in my personal life and my professional life, one problem at a time. Like, you can only solve one problem at a time. And there's a tendency when you're trying to build and scale, there's there's so many things to work on and you have to get good at prioritizing and figuring out what's the highest leverage, highest impact thing to work on and just go figure that out. And once you figure that out, then go work on the next thing and then the next thing. But we can't solve all the things at once. We can only do one thing at a time and let's do that really, really well.

You got to choose the fires you want to let continue to burn, as KD said on last week's episode. Um, what's the hardest lesson you had to learn?

Don't hire 16 new reps on the first day of a global pandemic. I'm just kidding. Um, that one still keeps me up. No, I'd say like, look, nobody's going to save you, right? Like it's your job. You're the leader. Um, for better or for worse, all eyes are on you. You know, in the board meetings, you're the first person they want to hear from after the CEO is the revenue leader. They want to hear about performance to plan. They want to hear if it was a hard miss or a soft miss or a good beat or a great beat. Like they want to know what's going on with revenue and nobody's coming to help. Right. And you may get help from your partners across the organization, but I think you have to have the mentality that like it's on you and all eyes are going to be on you forever and ever. And that's just the nature of the role. And nobody's going to come help because I've just, I've been in situations where I would get frustrated maybe in in my, you know, naivety or coming up in my leadership career where I, I wouldn't do this in a board meeting, but internally I'd want to point fingers across the aisle at product or wherever. And which is obviously like, you never do that in a board meeting, but I'm human. Like those thoughts creep in and instead of getting spun up and getting frustrated or getting burnt out about that, it's like, hey, look, just like in sales, when you're with a prospect, you can only control what you can control. And the same is true in leadership. Nobody's coming to save you. Control what you can control. Work with the tools that you have available. And if you can get help from other people, great, but don't count on it. You have to focus on what you have to focus on and you have to deliver the number. Number 1 rule of sales leadership, hit your number. Number 2 rule, see rule number 1.

Yeah. And what's the best thing you've read in the last 12 months?

A book. This has nothing to do with sales or leadership, but I have kids. I have 3 kids. They're young. And The Good Inside by Dr. Becky Kennedy is outstanding.

Sitting beside my bed. Yeah.

It's great. My wife gave me that book and I read it cover to cover and it's outstanding.

And lots of parallels to what we do. Sturdy leadership is such a good framework to bring into our world. Exactly.

Another two recommendations. These are blogs, not books, although the books that I read are boring to this audience. But, like, two blogs that I've recently gone down the rabbit hole on, Jason Cohen, A Smart Bear, like everything that dude writes, I'll read. It's great. And then, I recently rediscovered Scott Belsky's blog. I can't even remember. I think it's called Implications or I can't remember what the name of it is, but Scott Belsky. He's at Adobe. He's a baller strategy officer now. Yeah, he's like, just, he thinks about things in a totally different way than I think about them. And those are two online publications that I've gotten really into lately.

Sweet. This was awesome, Martin. I appreciate the time. You're the best, Kyle.

How fun is this? And wait, I'll finish with this thought. Whenever it's like the worst possible, you know, you're just feeling down on yourself, just remind yourself. How lucky are we that we get to do this? We make money on the internet. Like, it's amazing. And we get to sell and, you know, it could be a really lucrative career too. How— and we get to work with fun people. Like, how lucky are we that we get to do this? It's amazing. I'm so glad you, you brought me on this show. I feel, um, you know, I'm standing on the shoulders of giants here because you got some star-studded, uh, guests on the show, but I just— I'm super grateful, Kyle. Thank you so much. For having me.

And, um, yeah, good luck. This was a blast. Great. And that's a good message to end with. How lucky are we? Davenport says it every day.

We call him B-Bot because that guy is an absolute machine. B-Bot.

Yeah, one of, one of Martin's former managers who's on my team now, uh, brings that energy all the time, and I absolutely love it. So appreciate you, and, uh, we're gonna have to do this again. Thank you for listening to the Revenue Leadership Podcast. If you enjoyed it, don't forget to subscribe and you can find a link in the show notes and be sure to leave a 5-star review, share it with your network, and please join me next Wednesday for another great conversation.