---
title: "From MLB Draft Pick to $25M ARR: How Tyler Molinaro Scales SaaS in Government"
episode: 66
podcast: "The LeanScale Podcast"
publisher: "LeanScale"
guest: "Tyler Molinaro"
guest_title: "Chief Revenue Officer, GreenSpark"
date_published: 2026-05-15
date_modified: 2026-07-22
duration: 00:59:29
word_count: 10406
topics: ["enterprise-sales", "ai-in-gtm", "revenue-operations", "sales-leadership", "gtm-strategy"]
canonical_url: https://leanscale-knowledge-hub.netlify.app/podcast/tyler-molinaro-saas-government/
source: "LeanScale Podcast Knowledge Hub — https://leanscale-knowledge-hub.netlify.app"
license: "Free to quote and cite with attribution to The LeanScale Podcast."
---

# From MLB Draft Pick to $25M ARR: How Tyler Molinaro Scales SaaS in Government — Full Transcript

> Episode 66 of The LeanScale Podcast, with Tyler Molinaro.
> Published May 15, 2026 · 00:59:29 · 10,406 words.
> Machine-transcribed and **not diarized** — speaker attribution is inferred, so verify
> attribution against the audio before quoting a specific person.
> Structured breakdown: https://leanscale-knowledge-hub.netlify.app/podcast/tyler-molinaro-saas-government/

## 00:00 — Cold open: from the Yankees to CRO

**[0:00]** Today, I'm sitting down with Tyler Molinaro, the CRO at Greenspark, a vertical Saas company selling into the metal recycling industry. Before Greenspark, Tyler was one of the founding members of Rubicon Smart City, where he helped build a GovTech Saas business from 0 to 25 million ARR in just 5 years. Doing something almost nobody does, selling enterprise software to government fast. Oh, and before all of that, he got drafted by the New York Yankees out of college. We're going to get into how he's running the same playbook at a new company, his contrarian take on hiring, and why he thinks a small team with AI could build a hundred

## 00:43 — Drafted by the Yankees, then a pivot to software

**[0:43]** million dollar company today. Tyler, thanks so much for being here. Really excited to dive in. You have so many interesting stories that I think we can start with, but one that stood out to me, it's very unique when we're doing Chief Revenue Officer podcasts, is the opportunity to play for the Yankees, actually getting drafted into the MLB. We'd love to hear that story and how you took that and pivoted to what you're doing today. Yeah, it's a great question. Honestly, I'm surprised you don't run into more, given how competitive the entry point to sales is, you get a lot of athletes in there. I'm surprised

**[1:21]** you don't run into it more, but yeah, sports has always been a really big part of my entire life, growing up all the way through college. Played everything in high school and got fortunate enough to play baseball in college. For me, it was always, I just want to continue to play the sport that I enjoy playing, or a sport that I enjoy playing. I had some really good moments in college and started to talk to a bunch of MLB teams, which is not something that I actually thought would ever be a part of my progression as a player. Ultimately, yeah, my thing was 2011, so a really long time ago now, got popped by the New York Yankees

**[2:02]** in the 11th round, I think it was. I was actually a sophomore in college at the time. The MLB draft is very, very strange. It's actually changed a little bit since then, but it's a very strange ordeal, and particularly a very strange ordeal for whatever I was, 19, being someone that was not really on my radar for things to be paying attention to growing up in terms of how to deal with being drafted. Ultimately, I chose to go back into school at UNC Wilmington, where I finished up and had an opportunity to play coming out of college as well, but was faced with the same decision that I think eventually 99.999% of athletes

**[2:39]** are faced with at a certain point, which is, what do I do now? Which is where I find myself here, period of day after whatever that's been, graduated in 2013. So 12, 13 years later, find myself here in New York City as a CRO at Greenspark. That's amazing. How, and when you said you're surprised, we see a lot of college athletes, high school athletes, very few that had the opportunity to play pro. So I think that's just another level of excellence that I'm sure you've taken in the work you do today. But we'd love to hear the tie-in. Anything that baseball or sports taught you that you applied to how you're approaching the role today?

## 03:23 — What baseball taught him about managing people

**[3:23]** Yeah, honestly, it's interesting. So yes, 100%. And I actually, it's from the management side. I think about all the things that I hated as a player, the way coaches would interact with me or coach me and all the ways that coaches really got through to me. And I carried that into the way I looked at, you know, one, build teams, but ultimately manage individuals and manage teams. One thing that I've always been really adamant about, particularly when I was an athlete and like still now in a professional setting, is there's more than one way to be successful at the exact same task. And I think I really struggled as a player and as an individual

**[4:05]** maybe in school or, you know, as I was kind of entering into the workforce, being asked to go about achieving a task in a very scripted manner and not having the freedom to deviate without some sort of recourse being applied. And, you know, when I started to have the opportunity to manage a small team and it grew and it grew. And now I think that that's something I really care about, you know, being pretty forthright. Like, hey, like, I think this is, you know, an optimal way to achieve an outcome. You know, maybe you disagree. If so, like let's have a conversation and understand why. Like maybe there's an alternative here

**[4:45]** that we come to that's in the middle. Ultimately, like I'm probably going to be biased to my way, but I've got, you know, guys who are in RebOps roles or sales roles who say stuff to me all the time. And I'm like, yeah, that's actually way better than what I originally thought we should do. So, yeah, I mean, I'm always really open to feedback. Maybe not initially, as some might say, but ultimately all I care about is getting to the right outcome. And, you know, I think that sometimes that gets lost as a manager is like your managing outcomes, the way in which you achieve those outcomes should be completely irrelevant.

## 05:21 — Managing outcomes vs. managing process

**[5:21]** Yeah, it feels like there's usually two schools of thought. It's managing based on outcomes and defining successes, outcomes or managing based on the process. But ultimately the process is designed to achieve an outcome. So if the process is flawed, you might not know it until you get to the outcome portion of it. So you run it out. You don't get the outcomes you're looking for. Then you know you need to go back and change your process rather than just hitting your head against the wall. Totally. And I'm done wrong. Like I said, I mean, we a big part of, particularly actually at Greenspark, was trying to actually build processes. And

**[6:00]** I think, honestly, process is meant to have, in my opinion, like it's nice to have to fall back onto. It shouldn't be the holy grail. And it's a safety net and particularly it's a good ramp exercise to create good habits and best practices. But the same way to go back to baseball that you see, you know, Aaron's judge stand in the box a particular way and swing the bat a particular way versus someone like Cody Bellinger, two great hitters on the Yankees, swinging the bat entirely different, standing in the box entirely different, being coached to do the same task and achieve outcomes entirely different. You know, I think a lot

**[6:44]** of that carries into the professional setting and, you know, good, good managers, I think not that I'm saying I'm a great manager, but I think good managers are able to tap into the best parts of their employees or their team. Ultimately, like, again, coaches are paid a lot of money to put the right players on the field in the right position to build the best total team. And, you know, at the end of the day, like, that's what leaders of businesses are meant to do. That's what managers of teams are meant to do. And you've got to extract, you've got to extract the maximum amount out of the personnel that you

**[7:20]** have. And it's not always the most talented businesses or the most talented athletic teams that wind up as champions or wind up on top. No, that's true. And I think if you look at, I don't know, maybe the past Super Bowl that shares a little bit as well, like nobody expected those teams to be playing each other at the end. And I think, yeah, just Sam Darnold's entire career, man. Yeah. I mean, it's indicative like, yeah, like he went from being the guy coming out of USC to thrust into a really challenging situation to almost just being completely forgotten. And, you know, it'd be interesting to get like an actual candidate

**[7:59]** answer from him if there's if there was ever like a moment that something clicked or it just started to become something where his self belief or the belief of individuals on his team or his coaching staff were freed him up mentally to play to his highest ability. But I'm sure we won't get that answer from him until he's out of the NFL and can give like actual answers because everyone just gives fake answers these days. But yeah, I mean, I think there it's you see it all the time. Yeah, we'll have to wait for the Netflix documentary to come out before he really dives into that. I think one thing I'd really love

## 08:33 — Rubicon Smart City: $0 to $25M ARR in GovTech

**[8:33]** to pick your brain on Rubicon, going from zero to 25 million in error in a very, very challenging sector to sell into. I've sold into government as well. It's the stereotypical 18 month sales cycle, a million different stakeholders. How did you approach it differently? And what clicked for you in that moment that helped you achieve so much success? Yeah. So Rubicon was an interesting company. So I'll just give a little bit of a little bit of context for those who probably have no idea what what it is we're even talking about. So Rubicon, I joined in 2018 at the time was an awesome company. I guess was peak like

**[9:19]** venture capital, Silicon Valley, the Uber of everything. What right? Like everyone's building the next Uber of insert industry here. Rubicon was really effective at capital capitalizing on on a lot of that momentum. They were really effective at raising capital in general. And they had built a really sizable competitor to the traditional waste management businesses. So like the companies that you may be familiar with waste management, the big green and yellow WMS company called Republic Waste Connections, like they kind of had a stranglehold on the waste management and sustainability services industry and still really do for

**[9:57]** them. I'm out in Phoenix. So I'm very familiar with the waste management open. Exactly. They need a lot of waste management after that event. Yeah, like I say the cleanup and suing I'm sure is great for them. Yeah, exactly. So yeah, so like, they had been around for I guess, about six or seven years, it was a very traditional kind of brokerage business. They had wedged themselves in the middle of, you know, waste producers and needing to distribute that that waste to a location is historically used, you know, those those companies that I just I just mentioned. And Rubicon had kind of wedge themselves in there as a way to do

**[10:36]** this with with technology. Ultimately, it still ended up being a bit of a human intensive business with less the technology. And so ultimately, they wanted to spin up a true SaaS piece of the business. And out of that was born Rubicon, Smart City, there was an individual, Michael Allegretti, who kind of spearheaded that and began hiring folks. And I was I was fortunate enough to be one of the very few that that got to start this business. So it was it was a unique opportunity, right? Like, at the time, I don't know, don't quote me on this, but I think Rubicon had probably raised close to $250 million. And here we are,

**[11:14]** like this startup within a privately held very well backed other big startup, which was a unique, unique experience in and of of itself, because we had access to things that like new startups don't like we had a really effective marketing team had, you know, motions in place and infrastructure in place. And we had, you know, pretty good capital to just get going with we were able to do things like free pilots for cities. Like I remember when we were just getting started, we, we would go to cities and be like, dude, I don't care how many, how many vehicles you have, we will we will let you put this in

**[11:48]** your trucks for free for for six months. And like, weirdly, it took a took a year or so to get people to agree to that. I think partly because they're like, that just doesn't seem legal. But ultimately, we, we got to the point where we had a really good, a really good understanding of what these these end users in the cities were wanting. There was very clearly a need, you know, they hadn't had a great experience, private equity had come in and kind of just derailed what they had been used to for the better part of the last 10 years or so. Technology as a whole really had it taken a step forward in the particular

**[12:25]** segment that we were selling into, which was, you know, waste vehicles and stuff, plows and street sweepers and things like that. And so there was just this really big appetite. What people don't realize about cities and government in general was like, on a varying degree of scale here, like I'm not saying they're all Google, they're they're enterprise businesses. Now they have more bureaucracy that they have to deal with as well. Like it's not it's not all fun games, but like they're enterprise businesses. There's a lot of really, really intelligent people running running these cities like the city of New

**[12:56]** York, the city of LA, the city of Houston city things like there's brilliant people in those in those cities that are putting systems in place and trying to make them a better place for their residents to live. And so their appetite for like valuable technology is really high. And they just hadn't they just really hadn't been given an opportunity to invest in a direction that they believed in. And fortunately, we were kind of the right place, right time. And then like, we could probably get into it. But like a lot of the work really came in for our to your point, like for us is like, how do we get through

## 13:29 — A symbiotic partner network: Sourcewell, HGAC, Samsara, Geotab

**[13:29]** these sale processes quickly? You know, ultimately, you can only reduce the cycle so much when you're dealing with, you know, laws and regulations that you have to abide by. But you know, through a lot of just general trial and error having conversations and ultimately partnering with a ton of external, you know, relationships, whether that was something like these things called source well, and HJC and finding partners is a great company called Samsara, that I'm sure a lot of folks are familiar with today. Geotab, we built this really organic network of partners that had a symbiotic relationship with us. And I would say by year two, we had

**[14:14]** kind of just figured it out. And it became a rinse and repeat cycle to the point where it was as repeatable of a sales motion in municipal government as I think you can probably get. And that's and that's saying something again, remember, we're selling into cities that have, you know, waste vehicles, we're not we're not selling like it infrastructure into the security department, or or anything like that. But yeah, it was it was a really, really cool experience. And like, I'm sure we'll get into the conversation. There was a lot of things that I learned as I started as you know, an IC, a role, move my way up

**[14:53]** to managing small teams, moving my way up to being, you know, ahead of effectively the go to market side that that I did an experience that are like, yeah, like this is this is how you do it. And then a lot of times I'm like, Oh, I probably could have done that way different. And having the opportunity to do that again, I would I would definitely change it. Where Where did the I think this is really helpful knowledge and context for somebody listening, because I work with a lot of companies that are selling into governments. Where were you able to get that sales cycle to? Yeah, then I'll stack one more question

## 15:25 — Hiring a deliberately heterogeneous team

**[15:25]** into it. How did you get the talent into the team and build the team to be able to effectively run the plays that you had? It's a I'm going to start with the second one first, and hopefully that'll dovetail it to too far. But Michael, Grady, who started it actually had a really interesting take on hiring talent. Initially, he hired someone that was a true salesperson, which was which was me, like, that was my background. He hired a consultant in with a sustainability background, he hired a lobbyist, and then he hired someone who worked very closely with more on the federal side, but very closely with legislative personnel. So

**[16:11]** he hired this like weird mix, not really knowing what would play well, in the actual sale, but ultimately wanting to create this culture of, like, not not a very non homogeneous culture, relative to people's backgrounds experience. So like, I was like the loud, you know, salesperson, and we had someone very pragmatic, and who's one of my best friends today, who comes from a consulting background. And then another one, like I said, we have two guys that that really had a bit more exposure to what it meant to work with cities. And it was intentional, or was this happenstance? Yeah, that was very intentional by by Allegretti. But one of the

**[16:54]** things that I took from that is there is not a one size fits all there is not an ideal cut from this cloth is a requisite to be successful. All of us were successful in our own right. And two of those three people I just mentioned, were with it through the end with me as well, and are, you know, thriving and crushing it, current state today, and, you know, in all of our various kind of trajectories and pathways. And so they're, again, I said, I think we'll probably get into this down the road. But hiring is something that I genuinely enjoy doing, particularly, and a small company, because it really matters. If you're running

**[17:37]** a lean business, like you run a really large company, yeah, one person maybe doesn't shake, shake it up too much. When you when you're hiring in a lean company, one person who's amazing can completely change your your life as a leader, your your business is trajectory, etc. So yeah, I really, really take that that function quite seriously. But to answer your question, going back on, how did we get the sales cycles down? And where did we eventually get them down to? Like everything they range, but ultimately, like we found ways to get them into, you know, four to six months, ultimately, the larger ones, you still play blazing fast

## 18:17 — Compressing government cycles from 24 to 4–6 months

**[18:17]** for government. That's very fast. In the larger ones, you still found yourself in a 12 month slog. But I would honestly say like they probably would have been a 24 month slog if we we didn't have some of the mechanisms that we ended up finding. And like I said, we had a really strong partnership with a company called Sourcewell. And if you're not familiar with Sourcewell, it's a it's basically a cooperative purchasing organization that allows cities to see what other cities purchase and say, if they're allowed to do it, I'm allowed to do it. And so it's this validation that's created. And it's it's way more intricate than that. I'm

**[18:56]** dramatically oversimplifying it. But that that's effectively what it is. And at the same time, again, we are very fortunate. Sourcewell is is is a business. And so this is how how they make money. They help transact these sales between public and private. And a competitor to them started up, which is HGAC by I was like Houston Galveston Area Council. It was also a cooperative purchasing. And it also happened to be in one of the better states as far as cities. Like if you just think of major cities, you've got Dallas, San Antonio, Austin, and Houston, El Paso is a top 20 city by population. So like, I'm speaking the obvious,

**[19:36]** but Texas is a phenomenal city state relative to, you know, government opportunity. And so we built a very strong partnership with with these two entities. And their their desired outcome is our desired outcome. And ultimately, through through that, and like I said, some of these these more traditional partner channels, partners like Geotab and SAMHSA are which are some telematic companies, very successful, telematic companies, we kind of built this army of Rubicon extension that all wanted us to be successful, because if we were successful, they were successful. And then as we grew, we built a, you know, a pretty meaningful

**[20:19]** network of what I would consider like more traditional lobbyists, we probably had four or so on our on our payroll that I just kind of like, you got stuck, they got you the conversation you needed your contract sitting on the attorney's office for three weeks, they they they know who to call to get information about what's what's going on. And so we just kind of created this way where we never didn't have an answer to what was happening. And I think that's one of the biggest challenges in sales in general, really in government sales is like a lot of it is a black box. There's a lot of ways that a deal can just go cold, even

**[20:58]** when everyone wants it to happen. I mean, I'd be lying, we still have deals where we got to like, yeah, we're gonna do this, like, we'll send it up sign. And then it's just, you know, in commit in the Salesforce for four months. And the only thing we're waiting on is like the city attorney to just put the stamp on it and send it back to us. So you still run into that. And like, I don't think you're you're ever going to be able to fully avoid that. But we ended up having a team that just understood the complexities, and then understood when faced with this problem, here are the things that you need to do to try to solve that problem.

**[21:36]** Do you think you could have had similar results if you focused on direct or, hey, these partnerships were critical to even unlocking the opportunity? Yeah, no, it's, I think it's like, what is the saying, like, go fast, go long, go far, go together, like, yeah, I think we could have, I think we could have like cherry picked some wins. But there were the scale at which we were able to grow would have been near impossible without without that network. And like, I'd be lying if I was saying like we were selling the the greatest software like these, was it was it certainly better or improved than

**[22:18]** what these cities were used to? Yeah, like, for sure. Was it like step change different? No, we we we found a way to build trust and validation very, very quickly. Because remember, cities don't work with Rubicon, like they don't we were we were actually in their mind, we were a two year old company, or a one year old company, when we started talking to them that the six, seven years that Rubicon had built up in the private sector were meaningless to to the city. So, you know, we had to build trust and validation in a segment where that I mean, it's pretty paramount, as with it is in most segments, I would imagine, but

**[23:00]** yeah, without without the network that had gotten built, I think the pathway to trust and validation would have been much more challenging. I think a lot of people significantly under invest in their partner channels. And I know, so since starting LeanScale, our partner motion has been incredibly helpful. We sell a lot through VC and PE firms. Once we get into one port code, it's very easy to start moving into the other port codes. We sell through some technology platforms. Clay has been an excellent partner of ours. So those partner referrals account for around

**[23:40]** half of our deal flow. Wow. And I've worked in a lot of companies where that's a significant portion of the revenue. It takes time, though, and a lot of people want to scale fast. So do you have any markers of how to know is this a successful partnership? How do you evaluate if you should really go into feed or just tiptoe around? Yeah, that's a great, great question. So I'll give a give a good example. We when we were building Rubicon, we needed like telematics devices, you like stick them in the truck and it kind of tells you where it's at what it's doing. And we had historically used a

## 24:17 — Turning competitor Samsara into a co-sell partner

**[24:17]** product in a company called Geotab. They're coming out of out of Canada. They've been around really long time, very well trusted. But we started to we started to run up as like in as a competitor into against this company called Samsara. In fact, like we used we were in the city of Atlanta. At Rubicon we never lost we never lost a contract. The only contract that ever churned was the city of of Atlanta, who we ultimately ended up winning back, but we lost them to a company called Samsara. And it like kind of rocked us because our our headquarters at Rubicon was was in Atlanta. So it wasn't a good look.

**[24:55]** And we were just kind of like, well, who is Samsara? And what are what are they doing? So they kind of became persona non grata for us for a better part of two years, really. And ultimately, I was working on a really large deal. And I knew Samsara was talking to to the same same place. And I, I just made a point of it to walk up at one of the very large industry conferences and asked like, hey, who's who's over this this region and this account? Like I actually want to have a conversation. And they're just like, didn't want to give me the answer. I'm like, no, seriously, I think I think there's a really

**[25:34]** unique opportunity here. And so I ended up getting in touch with them and the guy I still still talking today is phenomenal, a phenomenal guy, really smart. His name's Brian Galoiak. He he and I just struggle conversation and was like, hey, look, like I actually think this is an opportunity for us to do this together. And if we go against one another, like ultimately one of us is going to lose. And I was like, to be fair, like actually think you're probably going to lose because you can't do some of the things that we can do. But I was like, you can actually do a lot of things that we we would like someone else to just do for

**[26:10]** us. So I'm actually happy to to just like go in this together and prove out that there's a partner model here. And he eventually this, you know, made its way to the executive channels. Their company is not public. They're an awesome run business. And we we we started doing this and that that exact sale went through exactly how we we intended. And it happened to be an enormous sales, like, you know, five million dollar deal for for us. I'm not sure what it was for for their side. But it proved out that there is a really large appetite in the market for integrated solutions. There is a a model that can be replicated in co-selling

**[27:03]** into the same account without, you know, pushing each other out. Like it is challenging, right? Like if you don't have if you have competing products, like it can certainly be challenging. So like there's there's an element that has to exist there. But it very, very quickly built out a repeatable model and very quickly built trust between two companies that I think, you know, six months, 12 months prior were viewed each other as, you know, existential threats to one another. So it was it was a pretty significant turning point, honestly. I think it's all about finding that mutual trust. It's great that they approached you

## 27:41 — Moneyball vs. buying the Yankees: the hiring debate

**[27:41]** too. It sounds like they were maybe more of the incumbent. So then kind of like inviting you into that opportunity is huge. I want to I want to go back to the hiring philosophies that you have if we can. And when we were talking about, hey, getting a heterogeneous group, different people, different backgrounds. I think the one thing to play devil's advocate is a lot of the companies, especially if you're well funded, you're racing after some incumbent, you're trying to grow fast. Do you have time to play that moneyball game? Yeah. Or do you need to just go buy the Yankees? It's a it's a great question. I would say I've just maybe

**[28:30]** been unfortunate enough that I've not had a war chest big enough to say, let's find out. I've just seen it go wrong, I guess. So it's not a sure bet is another way to put it. Is it maybe have a greater possibility of a positive outcome than playing the moneyball side? Maybe. I don't know that I'm intelligent enough to answer that that question, honestly. But yeah, I mean, I see I see it a lot. I mean, I'm in New York. It's it's an awesome environment to be in. If you're in really anything like I always say it's like no one comes to New York to be second best

**[29:12]** at whatever it is they're doing. Like you want to be ballet? Like you're here to be the best ballet dancer. You want to be Broadway? You're here to be a Broadway star. Like you want to be in technology? Like you're here to build the best SaaS or tech business in the world. And that just, you know, innately drives, I think, people who who enjoy that atmosphere. Like it'll certainly shoot to some folks up and spit them out, for sure. But you wouldn't be you wouldn't be here if if you weren't if you weren't hungry for something. And I've just seen a lot of companies that are pretty well funded or maybe just,

**[29:47]** you know, this is where their their founders mentality is from. Maybe they're they're they're from that blue chip cloth and thinking that this is the only way. And where I always come back to is like we're selling software people like I don't need an Ivy League education. I don't need, you know, a master's degree. I don't need a background in finance or biology or whatever it is you think you need at your organization. At the end of the day, you are quite literally selling software to an end user. Like in our case, we're giving software to scrapyards. This stuff is not rocket science. And I'm sure then there's some industries where,

**[30:27]** you know, maybe those backgrounds lend themselves to some validity and trust. And I'm not saying that that's that's, you know, completely incorrect. But to make that a requisite for your pipeline in a hiring process, I just think is missing out on on just a ton of really qualified and really talented individuals. And not to make this about about myself, but like playing sports, I had I had zero scholarships for any sport out of high school. I believed in myself that I was better than just about everyone else that I saw going to these these various schools. And, you know, what whether I

**[31:07]** deserved it at the time in high school or not, you know, who's to say? But ultimately, I had a lot of self belief that given the opportunity, I would I would be able to prove myself. And ultimately, like I said, I got got to college, got drafted, got a full ride in, you know, baseball, which, like at the time wasn't a thing. You had 11 scholarships for, you know, 35 people on a team that then got divided up a ton. So 100% scholarship baseball was was meaningful at the time then. So, you know, I just I carry that with me and whether that's a chip on my shoulder and wanting to see

**[31:42]** other people be afforded the same opportunity that ultimately I was both as an athlete and as a professional in some instances, I think is is really important. Are you going to swing and miss and maybe whiff on on some hires in that? Yeah, but like, I could also hire the number one graduate at Harvard. And like they might not be capable of selling software to scrap yards either. So I think that that hiring philosophy is is nuanced. And like I said, I'm sure there's way smarter people than me that that have this broken down into some data centric model that

**[32:16]** allows them to see it, see it by the numbers and not not with a little bit more nuance and a little bit more character assessment and a little bit maybe more intuition and gut involved in it. But yeah, I mean, I think that, you know, I maybe maybe one day when I'm, you know, running a business that's got a war chest of a hundred million dollars, that that mentality changes a little bit, but I actually don't know that it would. I think something that you're completely right on. There's risk baked in both. And there's reasons why both running either play can can go horribly

**[32:51]** wrong. I have seen that too. I've seen the war chest go out and hire 100 salespeople. None of them hit their quota. They burned millions of dollars on this. And then they have to start over. So I've seen that reflect down my own experiences. I, I, I feel like I have a nuanced approach to that because I absolutely have found diamonds in the rough that on paper resume made no sense for whatever we're looking for, but you bring them in and they completely surprise you. And then I've made some where I thought they would surprise me. I thought I evaluated like

## 33:26 — Hiring for problem-solving over pedigree

**[33:26]** the soft skills, the grit, those types of things. And then they just flopped. So I think the more I hire and the more I build teams, the more I get confused of how to do it. I always try to bring it back to one, one thing. And it's, it is, I think in general, very challenging to assess relative to sales. I just think it's problem solving. Like it's critical thing in a problem solving. And like, maybe that's like, Duh, like a yes, of course it is. But like, I talk to see that even if it's obvious, it's tough to really know when you're, when you're, particularly when you're

**[33:59]** running a team or a piece of a business or maybe the entire business itself, all you're doing the entire day is solving problems. And I genuinely think the people who grow the fastest, build the fastest, find success the quickest, but the people who can solve the most problems effectively the fastest. And ultimately what you need to build, whether you're building an engineer team or you're building a post-sales team or you're building a sales team or marketing team, whatever it is, like you're looking people who can solve problems in their domain autonomously, effectively,

**[34:37]** and reliably. And sales calls are that, right? Like you're helping customers solve their problems. You're identifying threats to the deal as they come up and solving that risk in real time. You're using critical thinking and experiences, whether that's failure or success to draw upon and try to build a repeatable model of problem solving. And at the end of the day, if you give me someone with zero sales experience and they are an unbelievable problem solver and have an internal drive to be successful, like I'll take that bet every single time. Yeah. You just need

**[35:14]** to find them. I don't know. You got to find them and make sure the problem solving that they're sharing in the interview or if you have references, applies to the problems that they're going to have to solve in this role and that they can actually execute. But I think you're right. I think those are the underlying things we're looking for when we're looking to build high performing teams. It's just difficult tactically to go in and assess those things, especially when you have to build a larger team quickly and maybe not like a hundred million dollar word chest team. But even if you

**[35:53]** have to hire five, 10 sellers, that means you're probably interviewing 50 to a hundred people. Completely. I'm in it right now, for better or worse. And there's moments where I really enjoy it and you meet someone and you're just like, there was something about that person that I really liked. We have recruiters that send us resumes and it really takes a lot for me to not take the interview, honestly. I almost feel bad about not, truly. If I say no, I ask myself, why am I saying no? Do they deserve the opportunity? It's hard. So it's very rare that I say no when a recruiter

**[36:35]** sends someone because you just genuinely don't know what is going to come across in a conversation when you meet with someone. And I just think everyone deserves a chance. And that's been something that I've always done. And I could probably, wherever we're hiring right now, I genuinely think that there's maybe been 50 applicants sent through and I might've said no to one. And it might've just been because I didn't see the resume come through on my inbox. I think that ties in really well to something that you've talked about where you left a bigger company to come in and do a startup. So now, as you're the CEO of Greenspark, running this

## 37:19 — Back to startup mode at GreenSpark

**[37:19]** company, running this team back into startup mode, do you enjoy rolling up the sleeves, getting your hands dirty, getting the weeds of things? Yeah, I don't think anyone who's in startup land knows you're just not doing this job if you don't enjoy it. And then there's probably on the flip side, if you're at a blue chip or something like that, there's a different set of challenges you're faced with that you probably enjoy that we're not faced with in startup land. But yeah, no, I really do. I enjoy selling. I enjoy RevOps. I enjoy sitting in an office with our CEO, strategizing some far-fetched

**[38:02]** hypothetical scenario that we're trying to game out and have alternative pathways to if and maybe this one thing happens. I enjoy the ups and I enjoy the downs. Ultimately, I think it creates maybe not the greatest work-life balance, but at the end of the day, I don't think people who want to be successful have a healthy work-life balance, whether that's being an athlete or that's investment banking or whatever it is your flavor of choice ultimately is. But yeah, I was very intentional in trying to find a Series A, maybe a very early B startup. Because one, I enjoyed it when we were in that moment at Rubicon. And two, I

**[38:47]** knew as I grew through Rubicon, I wasn't always like, you know, ahead of a team or managing people or VP at Rubicon, I was an accounting deck when I started there. And so I got to learn by trial and error as I moved into various roles and was afforded the opportunity to succeed and fail in those particular roles. But I knew, given the opportunity to do something similar again, that I would have a much clearer defined playbook, but approach to what we were trying to accomplish and how to go about accomplishing it. And so it was very intentional in trying to find

**[39:29]** the right spot. And I succeeded in finding the right spot. I absolutely love it here. The team is amazing. Gordon, the founder, and I have a phenomenal working relationship, very symbiotic, and a very top down lead by example. You know, we expect hard work, like we'll show you what it looks like type mentality. I think there's an absolute I've done a mix startups, Fortune 1000 companies. There's an absolute dopamine rush of feeling the momentum and moving forward every day and being able to make an impact. That is really, really tough to replicate, at least personal

**[40:10]** experience. Couldn't agree more than larger organizations. Couldn't agree more. Something about feeling your impact is very meaningful. And like I said, I'm not saying that's for everyone. I'm sure that there's a lot of very successful people at really large companies that do very well and are happy to just kind of be a piece of the puzzle. For me, I want to know that what I'm doing matters to someone. Like it might not change the world, but it's being felt somewhere by someone and you can do that here. You know, BDR is on our team. Like we feel their impact

## 40:47 — What RevOps means to a CRO

**[40:47]** every single day. When one of them has an awesome day or an awesome week, the business feels that impact. And that's just a really unique environment to be around. And it's obviously a fun environment to be around if that's your cup of tea. You brought up RevOps a little bit ago. I'm curious your take. If you've had experiences where, hey, I've had lights out RevOps. I've been without it. And especially as a CRO now, what does RevOps mean to you and your role? I'm probably, and my CEO probably said this, I'm probably too invested as an individual in RevOps current state. I find it to be one fascinating. Like automation and optimization

**[41:32]** by any means necessary, I think is just the coolest thing in the world, whatever it is that you're doing. And I've definitely been on teams where I've been on teams where like RevOps wasn't a thing. Like I remember when we were building Rubicon and we didn't, we didn't have RevOps. Like I just started getting really into, you know, finding out how to make Salesforce work better. And then, you know, befriending our Salesforce admin and learning about, you know, Apex and flows and all these other things that you can do. And then now with GPT, like, I mean, there's just, there's quite literally nothing that you can't do in Salesforce,

**[42:06]** regardless of your, your experience, the bear entry is, is so low. So yeah, I mean, I think that my, my involvement is probably a little too heavy handed, honestly. But ultimately, it's coming from a place of me actually genuinely believing there is a positive result in this for the go-to-market team, whether that's generating more, a quicker response to inbound leads, or just generating more inbound leads in general, or whether that's creating more clarity in a deal. We use, we use a ton of tools here. It's a very well resourced sales org for the size and scale that

**[42:44]** we operate at. And tools like Scratchpad and Gong and obviously Salesforce and a number of others that we use or just inject GPT, gosh, are, have kind of changed the way that I view running sales orgs for the better. And, you know, I think there's a world where you said it's beginning, I genuinely think there's a world where someone's building a hundred million dollar business in the next 12 to 24 months that might be them in a body or just them themselves. Because I think the barrier to entry into all of these functions that companies once required is so low now.

**[43:27]** You know, I recently just set myself up with codecs and cloud code and VS to learn how to do this because I genuinely think if you're not, if you're not investing in this as any individual, like not a leader of an organization or in sales, like you are running the risk of letting things pass you by. Like I am, I am teetering on the edge of going to get a Mac mini to set up Cloudbot, but, you know, I got to figure out if I'm going to get completely hacked by this thing first and the security requirements. But like, I just, I'm fascinated by finding more efficient ways

**[44:01]** to achieve the same outcomes. And RevOps is the tool to that, that success. And we have, you know, this is again, an example of, of hiring someone. We have someone that was once a BDR at Rubicon that I saw while during his time there was a phenomenal problem solver, always wanted to help. And he was, he enjoyed the same things that I enjoyed relative to, to getting into the systems and getting into the numbers and creating ways to surface insights that lead decision making down particular pathways. And, and, you know, we, we brought him here and he is just the ultimate problem

**[44:43]** solver. You know, he is here is a list of problems. I trust you to go solve them. And when you get stuck, you will surface it to me to find some support and we will problem solve together. And if I could have, you know, five of him, like I would have, I would have five of him.

## 45:03 — Inside LeanScale's fleet of AI agents

**[45:03]** I think that's so amazing. And I've been doing, I've been doing ops for about 10 years. This is a completely different paradigm shift. So I know everybody says that there's plenty of hype around it. All the hype is real. So it's very real at lean scale. We're all power users of cloud code. Great. We have installed a enterprise wide open claw instance across our team. Oh, let's talk about. So we have a fleet of agents that we are using and we are training them. We have them in their own groups where they're sharing information with each other. We have managers of the agents blared in and it is completely change the game for us. Like

**[45:49]** I can't even describe it. I am fascinated by, by all of it. Like I'm probably going to ask you what, what you have your agents doing right now. Cause like I am. Yeah. I just don't know how if you are a business of any scale and I understand everyone's like, yes. But I see it a lot where it's very surface level. Or like an AI function in a SaaS app. Yes. And like, I, I'll give you a good example. We, we had a, you know, everyone was commissioned and you got to find out how to pay people at the end of the month. It was like, it was horrible. The, the RevOps guy I'm talking

## 46:30 — Automating a 10-hour commissions workflow into 5 minutes

**[46:30]** about, it was chewing up, I don't know, 10 hours of his month trying to do this stuff because it was so manual. And I was like, okay, we're like, we've got to fix this. Cause I can't have you spending 10 hours on something that should take you 30 minutes. So, you know, I used GPT to code out a script in Google sheets. That is we've ripped reports out of Salesforce, press button, everyone's commissioned done, you know, a 10 hour project now in, you know, five minutes creates an export. You drop it into the, the, the HR platform done just purely to try to not get

**[47:05]** passed by. But the times I am download it all everything to get set up with codecs. I need to get cloud code. I know that everyone's going to be yelling at me and say, you need to be using Opus. I kind of like not using an Apple computer in tech. It's like, Oh, you're not using cloud code. It's not because the business uses cloud code. I just, they, they were probably like, no, you're going to, you're going to break something. If we let you have access to our get out and cloud code. So I was like, okay, fair. I'll do this on my own. But yeah, just start building this out in my own

**[47:34]** time to see if I can build an app that does the same thing. Not, not because I think it's going to change anyone's life or his life even, but because I need to build that muscle. And I'm genuinely interested in it. And who knows what happens after green spark? Maybe, maybe I'm the guy who builds an app. That's a hundred million dollar business by myself. I think you'll be pretty inspired the more hands-on you get. And you asked for some tangible examples and, and I'm happy to share some. So one, um, I did set mine up on a Mac mini, by the way, since then we've

**[48:08]** moved to, which is good. If you're setting up for yourself, I think that's the easiest way to go. Um, but if the way our CTO set it up for the whole company, we have virtual private servers where each one of them has their own environment. So that's how we set it up across the board. Um, a couple of things though. I mean, I got mine hooked up to Salesforce, QuickBooks, my email, my calendar, uh, we use to manage. Are you giving it, are you giving it your, uh, credentials or are you creating its own credentials for each of these systems? I created its own. So I gave it its own work email. His name is Ben. So Ben has his own email.

**[48:48]** He has his own login to all of these systems. Most of the time it's getting him the API keys, or getting connected to their MCP so that way he can do the things he needs to do. Um, but here's a couple of things. One, I have all my reporting on autopilot. So he takes a pipeline report, highlights any risks. Um, he can also like merge data. So I'll give you an example. QuickBooks, he'll pull the AR aging report. Hey, all these accounts, and then from teamwork, that's where he managed all of our projects with customers. He pulls who the, uh, architect is on that account because that's who owns the relationship.

**[49:26]** And then he can like assign them and then send a Slack to everyone to like follow up on billing. Sure. I use it for our SOWs and MSAs. So there's, it's trained on what our SOWs look like. And then I can just take a transcript of a call, feed it as a detailed SOP and creates the entire thing for me. Those are all kinds of examples like that. I want to use it. Uh, so we use GPT and Gong, uh, a lot, and I want to use it to cut the time between Gong transcript uploading, running into GPT and distributing the correct information to the right resources. Like for me as a manager, what I care about is going to be different than what the rep

**[50:06]** and I'm so different, but like the way it should be prescribed is different. And so, or like what's important to you in that transcript might be different than the rep. And currently the way it's now it's, it's all fragmented, right? It's deal by deal. So we'll have, you know, chats and GPT and folders for, for each deal. And you have to, you know, go through those and you're flipping through the entire chat as a manager or a rep to find a particular section, or you're going back into Gong and searching for certain things. I, I want to, I want to consolidate that in some fashion and automate it to where our,

**[50:35]** our sales manager is getting a daily brief. What, what's important today, what's important this week, what, what moved backwards relative to the recent calls, what's, what has the likelihood to move forward if executing on, you know, ABC, uh, and then, you know, same thing for, for me and our, our CEO. So like, I, I just see that as an obvious evolution of how you digest information in a much more efficient, efficient manner. And like I said, all you're doing all day is solving problems. So if you could find a way to spend less time doing things that, um,

**[51:10]** have a more optimal pathway, like you have more times to solve problems that you wouldn't otherwise, uh, be beginning to. So, um, yeah, I'm fascinated by, by that stuff. And like ultimately I just think that, um, if you're in a wing business, like I just, again, I'm saying the obvious things probably, but like you, you, you can't be successful if you're not doing this stuff. No. And it's one of the few places where you even have the opportunity to, because if you're working at some other company, they wouldn't even let you fire you for setting up a plot bot on there. I know. I mean, I have the luxury of, you know, I started the company,

**[51:48]** so I can just kind of do whatever, but I think, uh, the past couple of months,

**[51:58]** it's just going to look completely different in like not even the past 10 years, it's been iterating slightly better. It's going to get parabolic here very soon. Yes. And we're seeing all the benefits of it and using it. So now our next thing is, I think we're probably going to need to get in a position where we offer this to customers. Like, okay, we've built this for ourselves and there's a, I'll share it with you after this too. Um, our head of education put together a great video on, uh, GTM cloud code use cases. So very specific to those, but I think

## 52:36 — Software as a competitive advantage in legacy industries

**[52:36]** the future is building those out, tailoring them, and then also building the data pipeline to make sure it's getting fed the right information and context. And then the security side that's, that's going to matter. So yeah, I agree. I think there's, I think there's an enormous appetite for consumable AI solutions in the, in the form you're talking about, not, not in the like, here's a software with an AI feature. Like you and I talking about cloud bot, like we're still very much in the, in the, you know, a rounding error on a spreadsheet to the rest of the population in terms of where, where they're at on this stuff. Like I genuinely believe

**[53:13]** there's an enormous appetite for what you're talking about. And here's why, like I said, we work with scrap yards. They have in general historically been very rooted in legacy systems, like sit software that was built in the, let's call it late eighties, early nineties, the largest enterprise businesses are this. We are seeing, and I've, I've talked to others and they're saying, we are seeing for the very, very first time, probably ever in scrap software purchasing history, people viewing their software as a competitive advantage. Historically, it's been a, a,

**[53:50]** a cost center at, at worst and a risk mitigation at best. And, and that paradigm has dramatically shifted because everyone knows that there is something happening. They don't know what it is and what shape it's going to take form in for our industry and maybe for a lot of industries as well. But they do know that if they're not careful, it's going to pass them by and their position in the market is at risk. If they're, if they are not cognizant about where this fits into their operating model. So for the first time, and again, there's, there's other factors or some

**[54:27]** private equity stuff happening in our industry and things of that sort. But for the first time, we're seeing companies that have been using the same system for, like I said, 20 or 30 years, exploring either like legitimately exploring or testing the waters for what else they should be considering. And I've heard this, heard this set in a few times, but on average, enterprise organizations pick your vertical name, your vertical here, about 5% of them are out to market in a given year to purchase enterprise grade software. We are trending in a direction where this year and next it's 50% of insert your vertical or, or searching for enterprise grade

**[55:12]** software. And so like a great time to be a sales rep in enterprise sales, I suppose, but yeah, there's, there's no, there's no secret why, why companies are doing this. And it's, it's very cool to see it in an industry like mine that has historically been, you know, pretty risk adverse and reticent of change in general relative to whatever that is software or other. If it's permeating that deep, I, I would, I, you know, would love to understand where, where folks who are, you know, have the appetite, you know, a bit more in a bit more formalized what that looks like. But

**[55:47]** yeah, it's very cool to see in real time. Yeah. And when you're saying it's a competitive advantage, it absolutely is. So take lean scale can call us an agency consulting firm, whatever label you want to put on it. But we have consultants that do service work for customers. And mostly it's time and outcomes of what you can do. And my team, since we've implemented these things can do things in half the time, sometimes less in simple, simple, practical things like, Hey, I had a call with a customer that transcript gets turned into tasks in RPM system where they don't have to

**[56:26]** cause before six months ago, the consultant would get off and then they would go into teamwork and they would type in 30 things and spend an hour grooming the board. Is that cloud bot doing that? Or is that something else? Yeah, it's an open claw agent. Each consultant has their own. So it's connected to their instance of teamwork and it's connected to their, we use fireflies for call recording. Yeah. So the workflow is set up within. Do you build the logic in terms of how the tasks are built out in terms of like, does each person say, this is what I care about, or do you have a kind of standardized, like this is how the business operates?

**[57:01]** We have a repo of skills and we call them, it's a lean scale term. So I don't know if this is a technical term, we call them SOPs. Okay. So they're just very long prompts. Okay. That gives more direction. Yeah. Yeah. So we have a repo and get hub of our SOPs and skills, and then they can take them and then they can modify them if they want, like, Hey, I actually kind of want to do a little bit, something special. I like, but they can kind of take those off the shelf and start using them. Yeah, that's awesome. Yeah, man. We, we might need to do that here.

## 57:32 — Outsized leverage and the AI money merry-go-round

**[57:32]** Well, happy, happy after the show. I can give you a look under the hood or get you connected. Yeah, I'd love to. But yeah, I think, I just think you're right. It's, there are going to be companies that get this outsized leverage, especially in the next couple of years, because so far ahead and who knows what's going to happen. Anthropic just raised, what was it? $30 billion today. Yeah. These numbers that are happening make no sense to me. Again, I know I'm a very small company and, you know, they're, they're operating with monopoly money. I get it. But yeah, the merry-go-round of where the

**[58:09]** money is moving in AI is truly doesn't make any sense to me. So it's fun to see from the outside, I suppose. Yeah, but we'll see. I think the future, the future is bright, at least in the next couple of years of people who harness it really well. And, and I think there's just so much opportunity to be had, but kind of tying this all together, it's still going to come down to people recruiting great teams, empowering people, inspiring people, finding those people with critical thinking skills and really applying them to whatever the problems of tomorrow are.

## 58:44 — Closing: it still comes down to people

**[58:44]** Yeah. And I just love how you've been able to do that. And you have such a cool story around it. And I appreciate you sharing it today. Yeah, of course. But, and excited to see what you do next. Yeah, no, I, I appreciate it, man. This was really fun. I'm glad, I'm glad I joined. Looking forward to paying attention to what comes out down the road. I think, like I said, this is a fun time to be, I think, in a lot of industries. It's a really fun time to be in sales and it's a fun time to be able to be in a business where you can expose yourself to all the things that potentially make the businesses of tomorrow run and grow faster.

**[59:21]** Absolutely. Well, thank you for being on the show. And I look forward to catching up with you soon. Awesome. Appreciate it, man.