S6E29 - Steve Bussey and Matt Bolian - The Surround Bound Sales Model
4 Aug 2025 · 54 min
Transcript of a Surf and Sales podcast episode (conversation-style) featuring hosts Coach Richard GPT, Scott Leese, and guests Steve Bussey and Matt Bolian (founders of Super Ed). The discussion covers Super Ed’s product (a CRM overlay that embeds process/documentation and enforces revenue workflows), the role of AI in sales (data quality, human-in-the-loop, last-mile execution), founder/early-stage challenges (anxiety, vulnerability, scaling from services to product), hiring and GTM topics (team quota, surround-bound go-to-market, hiring for full-cycle reps), and operational lessons from building products inside larger companies vs from scratch.
Chapters
Like, Scott always likes to start a conversation, and then he's like, oh, this would be really good on the podcast, Richard. Just go edit it.
And I'm like, you should just know by now to hit the record button.
I do, but, dude, then I have to edit shit, and that takes hours.
Yeah.
Yes. Right.
You don't. If you want to edit stuff, because I know how much you love fucking technology.
Yeah, no, that'll never happen. Nobody wants that for. For this.
All right, Scott, set everybody up while I set up the other stuff.
Yeah.
Okay. We're gonna probably record for, like, 45 minutes or so is my guess. 30. 45 minutes? Probably closer to 45.
We do these podcasts in a way that some people can interpret as being completely unprepared. We like to say that we don't prepare on purpose because we don't want it to sound fake or inauthentic, and we want to just spin the conversation wherever we go, and we want that to kind of show up.
So just so you know, there's no preset list of questions that we have or any kind of plan or anything like that. If there's something you want to avoid, like, you're tired of talking about the existential doom that we all face, let us know if we. If we. If we take us in a particular direction that you guys are not liking. Like, you use the chat in zoom and tell us, hey, can we pivot off of this? If there's something you want to specifically bring up that we haven't yet. Same deal.
Hit it.
Hit us in the. In the chat real quick and say, hey, do you mind asking about this thing?
Or here?
At the end of every show, we always say, how can we be helpful to you? Is there any questions that you want to ask us? So maybe think about, you know, one question each or something like that that you guys might want to ask us if you've got one. Richard needs to do a quick little sponsor thing at the beginning for Vasco and win AI.
What am I forgetting?
If you want the RAW files, I'll send.
Oh, yeah.
If you want to snip up stuff, go for it, man. We don't care. We'd love you to do it, but you're not required. And, you know, we're happy to get it to you. I can tell you this is going to drop on August 4th. Scott, we're ahead of the game now. We got two dropping on two Monday and then another two. So we're. It's going to help us. As I start traveling Again, Right. So, so this will go August 4th, so you'll have some time to, like, if you want to do anything creative with it.
I don't know if you've noticed, but these guys are not very creative. Their, their website's not creative at all. Their branding is not creative.
Yeah, well, that, that's a good topic. Let's talk about that.
That was actually the first.
This is me.
See, I don't.
You just need to hit the record button, dude. All this formality I can't handle. Oh, good. Really good. But this is actually, like, why I wanted to talk to them. Why I, I, I can't remember exactly how it happened, but I think I, I ended up on Matt's page and I was looking at the, the website and I was like, dude, this is so different. This is sick. It's like comic book style. I'm like, kudos for that. So. Yeah.
All right, well, let's roll into it because maybe I will use this recording just because Scott's. Scott's gonna buy her this week. That's really good, though. So welcome to everybody. We are back. We are live with no plan, no preconceived anything, any. That's what makes us cool, at least in our own minds, right, Scott?
Yes, in our own minds, we, we are quite cool. We used to be cool in our kids minds as well, but that era is gone.
Totally, totally gone. So thanks for joining us on the Surface sales podcast. As you heard Scott mention, big shout out to to ldad and Win AI for sponsoring the surf and sales event in Portugal, which is sold out. Might be the earliest we've sold out. Other than that one year right around Covid, where we sold it out before we even left the old one.
Yeah, that was the best. That will probably never be repeated, but no.
So thank you to Win AI and also thank you to our other sponsor, Vasco, where they are using AI to really just come in and connect all your systems, clean your data, enrich it automatically, and give you a really strong AI foundation that doesn't require coding or additional headcount back to this existential crisis that Scott's talking about. We do appreciate Basco and we will not blame them for the AI overlords taking over the world. So thank you for joining us. Scott, why don't you introduce our guests? Yeah.
We are joined today by two guys who have, I don't know, captured my heart, I guess basically, they're, they're, they've.
Done something that's pretty cool, by the way. Steel trap, like with the bottle locked, locks around it, and probably surrounded by nuclear fission and kryptonite to make sure that nobody can get inside his heart. So well done. And to the two of you, please, please provide the formula for which you did that, because I will patent it and then we will sell it and make money and we can all retire. Not worrying about AI. Go ahead, Richard.
Talking about being on fire. You're on. You're on fire. Well, they're from this company called Super Ed. And if you look at the website, it's all like comic book style, man. And I remember when I landed on the website and on Matt Bullion, who's here with us on his LinkedIn page, and I was like, this is different. And then Steve Bussey is going to join us as well. And these two guys are leading things over at Super Ed, based in Atlanta, Georgia. Welcome to the show, guys.
What up?
I can tell you the way to. The way to Scott's heart is by not planning to do it. It's like no plans. That's what we like.
That is by far the best answer I've ever heard. Even I have not come up with that answer. That is genius. Well said.
I love that. It's actually probably true.
That's really not going to argue.
Oh, really? True. Yeah. Yeah. I don't like people who try. Basically, they try too hard. It's out. Tell everybody about what you've built, why it's so cool, what problem you guys are solving. Give people some context here for what you're up to.
Gosh, Steve, do you want to do it? You want to try? Give the first try.
I.
Last time I tried to do this, Steve, we had this whole. I mean, Scott, we had this whole plan and we were on the plane, we were talking about it and I did it. The. We were dressed up. I had to dress up and go places and oh, it looks so cool. What do you do? And I gave my pitch. And she goes, what?
I'll let Steve go first.
Yeah, well, the other thing is Matt had a great pitch and then he. When she asked him what. That's when it just all went out the window. The new one was made up. What I like to say is we help people learn to use software and to enforce their processes. So we're specifically focused on revenue teams, although it's not only revenue teams.
And basically think of it as like an overlay over top of the CRM and we help put the processes that people have right in front of their sales reps. So instead of like wondering what it is that they need to do, it's right there. The, the really cool thing though is especially with, with AI and stuff the way it is today, like having your data clean is super important. So one thing we do is like if you have, let's say you had like some type of business logic about how you want your deals to be run, if there's a problem, it's going to be a big red message at the top of the page that the rep has to see. And they can't say, oh, I didn't know that I was supposed to have it in that way. And so that's like one of the big source selling points that people like is taking the process but then actually saying, hey, you've done something wrong, here's how to go fix it and then give them that jump off point.
Not afraid to red line.
Yeah, there's a lot, there's a lot of red sometimes.
Yeah, yeah. What my favorite part of this, of what you all are doing is the fact that the CTO Steve has a better pitch than the CEO Matt.
That is correct.
This is, I don't know if you know this, but this is a unconventional situation that is not, not the norm. Not the norm at all.
Well, Steve not an old person, so it's, it's very helpful. Yes, Steve, like 80% of sales loft. Nobody knows that, but that's okay. There's a. If I was adding to what Steve just said. So you, so we're, so we're hearing it is.
We can get off track on AI for a second. But I have felt existential threat where everything I do, everything I say, everything I feel like I am doing feels wrong right now. Like as if I, as, as if I, I do something, I just have this underlying anxiety that it's not good enough and that it just means my prompts are poor. And I've gone for the last six months, quite frankly, I've gone on this like what is happening? And I've landed in this. And you look at our product, our product's always been this way. It is your process, is your prompt. And I think we're, we're headed towards this whiplash. Where is there's going to be for the next 2, 3 years? AI will underd deliver and it will over deliver and what will happen is we'll do a whiplash of natural language is so simplistic. It seems like it's helpful, but it, it is not. There's like a last mile issue of getting the humans to do the right thing. And so what we solve is we're the process layer between tools and we solve last mile delivery specifically for revenue teams, where we create the prompt that will give the context, the AI to help the process cause the process and the data tell the story. And if it's wrong, your AI will hallucinate.
Do you worry, though, that.
We'Ve historically been able to run the last mile? This is my belief. We've been able to run the last mile because we ran the first few miles ourselves. So when you don't have to run those first few miles and suddenly you're asking somebody, go ahead, finish the last leg of this race, how do I know that they're actually capable of running the last mile? How, how, how do we, how do we structure this process in guard rail in a way that doesn't d skill people to the point where they're just completely dependent?
Yeah, I, I would.
This is the problem we're trying to solve, and this is the reason super exist, is to make the humans better. So we, I mean, I like some of this thing that rethink of like, we are the.
Like, the human will win. I'm like, just not okay with a reality where a human doesn't win. And so I don't think AI will win. A human will win. So, like, what super is, I know it sounds a lot like what it does is you have a framework and we can pick one bant spin challengers, whatever it is you're going to do inside of your revenue framework, and then you have approval. Frameworks discount whatever it is we help. What does a framework do? By its nature, it prioritizes work for whomever it is. It then diagnoses the health and ties what you're supposed to do to action. And a framework teaches, it tells you what's right, what's wrong, and by that.
It'S implemented the right way. I agree with you.
If it's implemented the right way. Look, so like super is it helps you implement it because it standardizes your framework in a way that tells the reps you did something bad, you did something wrong. And then it puts the documentation literally where they are. They never have to leave the screen. It embeds documentation and it tells them in real time that they're doing wrong.
Right.
And I know we're not doing product pitches, but, you know, I'm kind of dumb and Scott's slightly smarter than me. He's kind of dumb plus one compared to Richard. And what does it mean? It provides the documentation because I do want to, I Do want to understand what super does to to. For the context of the rest of the conversation, what do you mean documentation? That sounds like a CTO word. You guys need to change titles.
In the.
It is in its most basic form, it's the words on the screen that tell you what to do. It may be the images on the screen that tell you what to do, or it may literally be like a blinking dot that tells you exactly where to click and why. So documentation. It has many forms.
So does that mean you're. Does that mean you're helping the CRM engagement or is it going to tell a rep what to do and what to say? That's. That's where I'm trying to figure out.
Where to do, not what to say. It tells them why you're doing the next step. So it's often in the updating of the record or the here's what's wrong with the like, here's what hasn't.
Let's.
Let's pretend we're using Win.
It's a reverse prompt. It's prompting the human versus the machines and widgets. So like.
And what's.
What.
What I think we're all getting. Not that we're getting wrong about AI, it's just what I've. I've tried to prompt AI and maybe I'm dumb, I just can't get to work the way I want it to work. It's that it's because the underlying data is wrong. And yes, we're going to get things from. Well, so what you see happening. What I see happening is you have a lot of conversational intelligence and it could be Ask Elephant, Wind, AI, it could be fathom, it could be gong. What they're all doing is they're taking unstructured data, trying to structure it so we have more context on things. And you're trying to auto feel stuff so reps don't have to do it.
Yeah.
What, what that misses is the framework. Why is it working? What do you say on the call? How do you do. It's. It's. There's things that still have to occur that make the framework run and then AI sits on top of that and you can actually ask insightful questions if the data's correct.
Got it.
So the one thing just to add, because I think it's important with the documentation, like the word documentation, people, people that use our product, we don't write that for them. So we're not like creating their like process for them so they can put whatever they want on that screen so they could put a call prompt. You know, here's how you do X, Y, Z. And I think it's important. Not. I'm not, not like in a pitch way, but it's just important because it's like.
They have their own processes and they have their own ways that they want to do things. And it's so important that they can customize it for exactly what they need and not have like, let's say, you know, like, we work with HubSpot a lot and let's say that HubSpot said, here's how you should do X. That's probably not going to be relevant to like most people. At a certain point they're going to like, maybe they're like on board with that, but then they're very quickly going to have their own process. So they have to be able to define it exactly how they need it and want it. And that's like so important to the, to the idea.
Yeah.
I got a. I have a question for you, Mac.
You said something and I interpreted it at a different level than the technology answer you gave, but I feel like it's relevant particularly to this human part that we're always talking about. Right. The humanity. You said for the last six months I've been feeling like I'm doing everything wrong. Right. Do you feel that at the human level, not just like the business level. Right. Like, that's. Which is part of the startup game and the founder thing. Like, you're just, you're, you're just, you're hustling as fast as you can. I interpreted that as. Oh, I wonder if he means like not just work, but outside work. Like, just because so much chaos is going on and it doesn't have to be that. It was like, it could be totally work. I was just curious.
Like, the answer is. The answer is yes, is. I've been.
There's a.
There's a. There's like I. I had a song in my head that I was. I was listening to this morning. Like, gave it to me. Is on the solid rock I stand on Everything else is seeking sand. And I've just felt like life is sinking sand everywhere.
Everywhere. Right.
Like, and it's a bit about AI. I'm like, we have, like, we don't know it's for dinner. Why don't we chat? GPT that and I have it all. Like, we could all. We could literally just have all this figured out why and we haven't done it yet. And it's like feeling of just so. Except like it's just I feel so. But I feel behind everywhere because of AI.
So how do you, how do you manage through that? Because for me I, that I have this issue, right? And I bought, I've had it for a long time and I have my own mental health stuff I talk about. But anxiety can be paralyzing, right? Whether it's work related anxiety, personal life and then you know, you know, you know, it can all blend together. How do you as a human and Steve, I'd ask you the same question. Scott, you the same question. How do you work through it? Other than the, well you just gotta take one step at a time, right? And maybe that is the answer. But I'm just curious to how different people handle that part.
I guess I have a, I have a very specific answer for this that's like. And this is specifically like with the business side. Although I share, I'm, I'm like pretty open with Matt. I'd just be like. One thing I've gotten pretty good at is like, I may not know how to say something, but I'm like I'm feeling something. And I'll just like tell Matt this is what I'm feeling right now. Not with the intent of like him to do anything about it, but like he may have, he may give me a different perspective on it. And I'm just like super open to like if I feel that way, I'm just like, oh man, I gotta. And you know, same. I'd say something like that to my wife, but like in the context of like business going to someone saying like this is how I feel right now, I don't really know what to do with it, but this how I feel. And then we'll like talk about it and just like work through it a little bit. But that's like for me personally, that's how I, I deal with what I, what I like.
What I like about that is it frames whatever you're going through as temporary rather than a permanent state. Because I feel whatever you feel right now is going to be different five minutes, ten minutes, five hours from now. So I think what Steve's talking about is actually really, really important for people to listen and pay attention and try to implement. Because it's not saying I am this thing which is more permanent. It's saying right now I feel this thing or this particular way. And for me at least.
That becomes less heavy. The, in the impermanence of that. It's a temporary thing. I don't have to worry about it quite as much. For me, that's my interpretation of what. Of what Steve's talking about there. Matt, you want to give an answer to that?
Such a big question. It's like a life question. Richard, why we don't.
That's why we don't plan this podcast.
Yeah, that's a big life question. I have two things I'm a big believer in frameworks.
And one of those frameworks is five dysfunctions of the team. And Steve, this is something like we've done from very beginning. And one of those in the first one is everything falls down if you can't be vulnerable. And I think there is so much.
There's just so much done that on every level when you can say, lord, I feel unseen, I feel not known, I feel behind. Here are the facts, here are the narratives I'm telling in my head. And I help me. And there's this level of. Of we're in it together. Whether that's a life. There's a life part like my life partner or Steve, my business partner. And we can just be vulnerable. And that vulnerability and being. Doing pain together. I used to be in the military, and this is what they do, like, make you go through pain together with people on purpose. And it just creates this. It sucks. They call.
If it ain't.
If it ain't training, it ain't rain. If it ain't raining, we ain't training. You know, like, there's like a. There's a reality to all things are hard. I'm glad I'm here with you. You know, like, there's a. There's a reality to that. Like.
Yeah, one. One of the things I was reading that you wrote. I'm gonna. This is not going to be a perfect quote, but you said something to the effect of, if you're still delivering client work yourself, your company's not valuable. It's vulnerable. Tell. Tell me more about that. And that. That hits home for probably every. Every. Maybe everybody. Every knowledge worker sure as hell. Everybody who's in a training, consulting kind of role where you are the freaking product. Right? Tell. Tell me a little bit more about what you meant behind that. If you're still delivering client work yourself, your company is invaluable. It's vulnerable.
I. I have a question, Scott. That's a. I like that quote. It's like, did you. Did you AI and find that? Or did you just actually prepare for.
Nice doctor I stocked your profile.
Scott. Scott is a human, and he actually does. Do. I like it when he wants to learn something? He actually Researches it.
Heck yeah.
Before the whatever cat GPT. So great.
That was hot. Yeah.
I was like that's one of my. So before.
Before Super I started a consulting company called RevPartners and in the HubSpot ecosystem and we scale really quick to about 100 plus people and one of our.
And I think this is. It's not just consulting. It's not just. This is. There's a reality of like to have something.
That. So like right now I'm in Super. I. Right now I'm on p. I'm on parental leave. Like I just had a baby two weeks ago.
Congrats.
Congratulations.
Right.
And I'm still doing some work at Super. It's vulnerable. I can't take the time off that I wish I could right now. Like if so when I. When I'm saying there's a level as much as guys, I mean like as much as AI can get rid of some stuff we talked about in this. In future if you have to be the person that's the human in the loop we call it in AI whatever we call that human in the loop. If you're the person and they can't delegate and you start to do work, there's a vulnerability that just exists when you take time off, the product stops. And I think so.
But are you advocating to change that or are you advocating to lean into that and accept it and say that's okay, let's not lose that.
I I think when built with people my education of that because I. Because we help one of the things super does we help people do more like I, I help. We help people create margin. And what I'm. What I'm most. That statement's really getting to let's help people create margin and they can choose to do what they want with that margin.
And maybe that is build a large consulting org and you can have margin and.
And you're.
And that's profit margin but you're still working or that's margin where I can take some time off and I can be. It's not about growing a large org but it's about having margin in my life.
And I think the thing sort of unstated here because it gets really hard to describe what super is sometimes. Cause we do there's like two different people that we serve and they're very different. One of the like Personas that we serve is like specifically like partners in the HubSpot ecosystem and other ecosystems but like partner agencies are like the big one. And so I think specifically for that quote around, like, if you're work, if you're the one doing the delivery, you're vulnerable. It's like, the idea of, like, tech enabling your. Your agency or having a way to, like, scale your agency. That's not just. It's not about AI, it's just about, like, having technology to help you, like, scale up your agency. Because a lot of the agencies, at least in the HubSpot ecosystem, are very, like, human powered down to the, like, very core.
If you're. And it gets the core. When I talk about. We help people create margin, it's. If you are charging per hour worked money, we help people get away from that model, and that's what we help people think about and do. Only on the agency and consultant side. Yeah.
Are you charging by hour, Richard?
No, I never charged by hour. Like, wasn't I the one who taught you that?
That's why. That's why I didn't have. That was one of the first things. One of the first things I got right about what. What I was doing.
Yeah, yeah, yeah, yeah.
So I have a question. Are y' all both based in Atlanta?
Yes.
Okay.
And how did y' all choose Atlanta, or did you just happen to both be there? You met each other, and it just sort of was kismet. Like, you know, because there's different, you know, Know, there's Austin, there's Atlanta, there's San Francisco. There's, you know, silicon slopes in Utah. Like, why Atlanta?
I move. I moved here in 2014 out of. Out of college, actually, to start working at Sales Loft. That's what that was my first job out of college. And I moved to Atlanta because I did a semester abroad in South Korea. And I liked that Seoul had a lot of trees. And so I asked a recruiter to find me a place, a city on the east coast that wasn't north, that had a lot of trees and that had tech company. And I literally was like, well, you can probably do Atlanta or you can go down to, like, Florida. And I was like, I'll go to Atlanta. That was like, florida doesn't have trees.
Florida doesn't. But that's. But that. I mean, I think that's also fascinating of, like, you know, when I moved to Denver, my mom's like, why are you moving to Denver? And I said, you know, I like the skiing. I like the weather. And they have, you know, professional sports teams. They had bad football, and they had basketball, and they ran just getting baseball. And I'm like, mom, you go to the symphony all the time. I Want to go to sporting events, right. And so I got season tickets and all that kind of stuff. So we all have our reasons. How about you, Matt? How. How did you end up in Atlanta?
Yeah, part of the question was the implicit was, was there any reason starting Atlanta that's good for super? Like, was there any business reason? I mean, there's no business reason about being Atlanta for me. It just.
I am here because life caused me to be here and there.
I don't know.
I didn't even pick Atlanta. Atlanta picked me. I'm just. I'm here.
And what does that mean?
What do you mean, Atlanta?
Guys, I. I mean, I was in the military for, okay years. And when I got out of the military, I thought I wanted to go into a tech.
Tech job.
I thought tech meant, like, court, like, big, big tech. So I got, like, a job Twitter as an ae. Um, and then my dad got, like, a terminal illness, so I moved to Mississippi, where he's from, and I went and worked for a tech company in Mississippi, which. A tech company. Mississippi is a telecon company. A tech company.
Wait a second. There's a tech company in Mississippi?
Yeah, yeah, yeah, yeah, yeah. WorldCom was there.
Yeah.
They didn't last very long.
Yeah, there's no tech companies in Mississippi. And so then I. I worked there, and I. And then the president of that company, I ended up being the chief of staff for him, worked for him, and just got thrown at stuff. He moved to Atlanta. He's like, hey, Matt, will you come here and be chief of staff with me here? I'm like, sure. And because he gave me a job offer, I got fired in Mississippi. It's a very weird culture. Loyalty matters a lot in Cayman. Anyway, I got fired there because he offered me a job. So then I was forced to go to Atlanta, and thus I'm here. And so, like, I'm gonna say Atlanta picked me. Atlanta picked me. And it just. Any. What I have found any. Because I've just moved so many places in the military is I have found every place I've ever been I ended up liking. Like, is never, like, when you're with people, you can just make a place in a space because people are people. So I've just never not liked the place I've been at.
That's cool. What was. What was the epiphany for the two of you to create super.
What was the. Hey, this is a pain we need to solve or lead solving?
Yeah, we.
So.
I was in rep. Partners at. And one of the reasons we Were rep. Partners is. Is. We were in the HubSpot ecosystem. And I was. We were like, okay, I'm gonna do. We're gonna do. We're gonna create a. A service company that can help fund a SaaS company. That was the original thought when we started. But me and my. Me and my original business partner called Brendan Tolson and he.
And yeah. So we're just in it. So we just did hundreds, you know, hundreds of implementations in this ecosystem. I was like, okay, we can find some problems. We met Rob Foreman was. Rob Foreman is the co founder of Sales Loft. He was. We got. We got investment for partners and he was part of. Part of that investment. And he said. He just randomly came out one day and said hey, I got this guy that anything he touches I'll. I'll invest in.
I was like, what?
I was like, okay, yeah, sign me up. It's very like this. He doesn't say those things. And I was like, right, okay, let me. Well, here's. Here's some problems. And we had. We had like 10 different problems.
We do.
And I was like, let me find the hardest one. And I gave it to Steve as a. Like a test. And he built. He came back and said, here's why everything you built is wrong. And I built it right and here it is. And then I was like, we should like him. Let's just go build something. And that's about how it happened.
Is there. From my side.
The.
The.
The.
The other side, by the way, is. Cause I. This is. I. I knew. I know Scott a little bit because what I was doing before. Super. So between super and when I left Sales Live, I started another company. It was like the classic, like two years of effort and we had zero customers, like failure type of story. It was like very painful like depressing time in my life. It's like not. Not very enjoyable. Like.
Tuesday night sales or now I forget if it's Tuesday or Thursday. I'm like, I don't know what. Thursday night. Sorry. Thursday Naga. I was like, I forget what day it was. Started going to that and like it. I just opened my eyes to a lot of stuff. And anyway, as I was like leaving and I was talking to Rob, like a lot of those things I learned about like sales and like the. The like getting started founder side. I like saw that in. In Matt very specifically. And so that was like for me is actually like very helpful. Cause I don't. I don't. I have like a little bit of context, but like a lot of that is just like, learned pain from failing for so long.
So I got. I got one question. I got sc. Got another one. You said you saw some things in Matt as a founder. What were those things? Because I think everybody struggles to figure out that founder, right? Like, how do I know? I'm. Whether it's the employee being hired as a sales rep there or a partner like you, what were the things that you could tangibly say about Matt?
Yep, I'd say three things stood out to me immediately that were, like, very tactical. Things that, like, were, like, wow, that's really different. Like, one is his. Like, Matt is a very specific way of writing, like, recaps and, like, notes, and that's, like, translated into the company now. So a lot of people do that. But, like, I got these, like, notes as we were, like, initially talking, and it was just like, it gave me, like, so much clarity and organization, and I was just like, wow. I feel, like, empowered right now because I have all this clarity from the way that he, like, is writing this, like, recap about, like, the project that he was thinking about and, you know, like, him making a video and walking through the email so that I can, like, hear it as well as, like, read it. So, like, he did a really good job with that. Everything. This was, like, probably the most important trait to me in, like, almost like, in people now, but it's just like, doing what you say you're going to do. So, like, everything that, like, Matt said he was going to do, he did, which.
Went a long way for me at the time. It was like. It was like, going a long way for me. And then just like, seeing the, like, the. The.
The like, vision communication that Matt does on, like, social. Like, he was still doing that at the time, like, specifically around, like, HubSpot was sort of like his, like, messaging point. And I saw that and I was like, oh, he can, like, he can, like, message and grow something in the market. Like, so, like, he had. He had the. Operationally, I was like, okay, if I work with him, I'll probably like, working with him.
And.
And he can clearly, like, do the things that he needs to do, which is like, sell and hype and, like, market. And I need to do. I need to be the one that then takes the things that he's hyping and makes it the reality. That's sort of my role in that, is that.
Is that build different when you're building something from scratch versus inside a machine, if you will. Like, like, sales loft, I guess at the end of what I'm Getting at is like, is it? Is it? Tell me, tell us a little bit about the differences in building a product from scratch versus building a product from inside something that. Yeah, well, somebody else's vision, maybe.
This is this probably one of my biggest, like things that I'm cautious to people about that are looking for like a tech co founder and I, I don't want someone from Salesloft to listen to this and like, think I'm dissing on them. But like, realistically, out of like 150 engineers at SalesLoft, probably five could have created anything from like truly from scratch. So it's like there's just, there's so much stuff. And then people that try often realize, like, oh, there's a lot of stuff I took for granted. Like, there's just so much stuff that someone did eight years ago that it just sort of serves as a foundation that you don't have to think about. And then when you're building it from scratch, like, you have to be the one to go and figure all that out. I like design. I literally like built my life around. I will be starting a company and when I do that, I need to be able to build everything that I like. I need to be able to build everything myself so that I don't need to hire a team of five people to go and build it. Like, I need to like do it myself to keep cost down. So I like, that's how I structure myself at sales off. So that's like one thing is just like, there's so much stuff that you have to do that you take for granted when you've been in a big machine. The second thing I'll say that is just this was why I left sales off. But this is every single big tech I've ever seen has been this way. Like everyone that I've talked to that's worked in a tech company over a certain size, it is very, very difficult to build new things because people don't want to own it after it's built. And so for me, I'm the builder, I would come and ask the question.
Oh, they don't want to own it because they don't want to do the.
Work or they don't want to own.
It because of accountability. Like, if it doesn't work, then I'm out or something like that.
No, no, because they don't want to do the work of like, when I own this and there's a problem, my team is going to have to fix it, which is going to affect my roadmap Right. So for me, I'm. I've always been the builder. Even at Sales Loft, I would come in and be like, okay, we don't have a mobile app. And revenue has been saying we need to have a mobile app for a year and a half and pro and like. And the. And the response will just be, we can't prioritize that. No. Like, we don't have a way to own it. So finally I'll just be like, I'll build a mobile app, get a team ready so that when I build the mobile app and hand it off, they can like, own it long term. Because I. You can't have one person owning stuff like that. And that project went well, actually, but that's like how we had to run it. But there'd be other projects where we'd say, hey, we're going to build this really critical thing and another team's going to own it. And it was like, I, like, kicked their dog. They'd like, they like, hated me for it because they'd be like, this guy is building stuff. And even like involving them in the process. But, like, building stuff and having to like, now I have to go own it and deal with it. And I just think that's a bad, like, mental model of like the world. But that's like, that was very prevalent and I think that mental model was very, like, it was like, very across the board. And I've seen it a lot of bigger tech companies as well. And I think people that go from that environment to a startup, they have to just be able to say, like, every, like, I own everything. And I. I'm willing to add anything to my own pile and I just need to, like, own it to, like, do what's needed for the business.
It's a totally different. I think that's killer advice.
Yes.
Not just for people in product, but in any role really for a startup. And I think it's actually really insightful for salespeople and sales leaders in the audience who have been the ones asking product for a year and a half for XYZ thing and just can't comprehend why don't I have that yet? How hard is it? How complicated is it? And they don't get to interact with somebody like you or anybody in product, for example. I think that was a really great.
Find.
The person you can bribe, like, like sales leaders at Sales off would literally like bribe me with. Like, they'd be like, like, I need this for a deal. I will, like, I'm going to give you a Nice gift card to a nice steakhouse. If you build this. And I'll just be like. I'll be like, yes, I'm going with that.
Yeah. I think. I think we. I think we underestimate sometimes how easily manipulated we can be.
Or Sarah very much so. Yeah.
Like, oh, you want me to work on that deal? I mean, I don't know. I'm a little light today.
You gotta.
You got a couple dollar bills you can slide my way. Done. That's kidding. Yeah. Underrated strategy, Richard. For every salesperson listening, don't bribe. Go bribe somebody in product and tech. Yeah, I love that. Oh, we're. We're starting to run towards the end of the show here, guys. We appreciate you spend some time with us. I think this has been really insightful, both the tech side of things, the building side of thing, the how to pick a partner side of things, as well as sort of the existential piece that I think. I think Matt captured really well what everybody. To be honest with you, I've actually never heard somebody say this. I just feel behind all the time. And I'm just sitting here going, me, man. That is exactly how I feel. I can't run fast. I can't run fast enough. I can't catch up. I'm just. I have to punt on some of these things I'm supposed to learn. I don't have time to learn all this other stuff. I gotta punt on that. I think that that was a really brilliant way to phrase that. We end every show by saying, how can we be helpful to you guys? Do you have any questions for one or both of us? So we'll give each of you a turn if you want one. Fire away. How can we be helpful to you guys?
I have a. I have a question for sales audience, because I'm thinking about this right now is.
As you're thinking about. So we right now have.
We have.
We have a unique model, but we are still in founding rep or like founding sales.
And we've.
And we.
I really, really, really.
And I. I kind of like sometimes take on these.
These agendas and I like revolutions that I really want to do. And so here's one of them. And I just want to, like, I want you to get your opinions on it is we right now have a three sales rep team and we have a team quota, and it's founding reps. How in your mind is. Would we go about how long will team quota last and why do you think it's a good idea or a bad idea? What's your experience? What's your thoughts on it?
I'd love this. Yeah, I do too.
Love this.
I've always.
Let me rephrase. I love the question.
I. I'm a believer that.
Early on you need your team to be successful. Right. And quota isn't the most important thing overall. As long as things are getting done, that doesn't mean you let people coast. When I do start to formalize the commission or the comp plan, I think you can have both. I think you can have an individual quota and a T quota. I think that's important because you do want to try to recognize the individual for their achievements. Right. And you can also recognize the team because that officers the teamwork. Right. And so now where's the balance in that? How much of the quota is this or that? That might be a better Scott question than me, if. If Scott agrees with me. But I think. I think right now you're just trying to step them up so they stick around. They learn the product you don't. They understand the market and they're, you know, helping you get to that next round of. Of logos. Right. Are your 50 logos getting you to 100 is more important than, you know, if you might overcompensate someone by 5 or 10%. Right. Like, if that's. If you're concerned about that, you know, then you. Yeah, you need to look at your money and your burn rate, stuff like that. But that shouldn't be the problem. The problem is how do I get this from product market ideation to product market recogn recognition to product market intent to product market fit? And you're going to need a hundred customers to determine that fit. So. And so whatever you can do to support the team, I think is critical.
I think it's a great question. Like I said, I love any question like this that completely flies against conventional kind of wisdom and practices. That does not mean that I would implement it. The, the. This can last, in my opinion, in so long as all three people are comparable in their performance. It falls apart the moment Steve and Richard are doing really well and I start struggling bad. Now, you know, if Steve and Richard do 105% Dakota and I do 87% Dakota, Steven, Richard aren't mad at me, most likely, right. They think I'm trying. They want to help me and everything. But if all of a sudden I'm hitting 30%, you know, of what I'm supposed to bring in, now they're looking over their shoulder like, what the hell, man? This guy's not Doing his part. And it's, you know, to me, it's very similar to a sports team in a way, right? I mean, I. I was a defender in soccer. My job was not to score all the goals, just to prevent goals and get in people's way and all this, this kind of stuff, right? Everybody knows that and knows their role. I didn't give. If I didn't score, you know, as long, as long as we won. The problem is, what if my strikers are not scoring and what if I, as a defender, suddenly I'm the leading scorer on the, the team? Then I start to get resentful on that type of stuff. So you're safe, in my opinion, as long as the three people's performance is comparable. And if anybody is bringing in less revenue, they're picking up the slack potentially in other ways. Right? And I don't know, that could be collateral. It could be they traveled to more conferences and events. Could be they spearheaded some, you know, conference thing or some marketing campaign. Or maybe they, if you don't have a rev ops function, maybe they're real good at, you know, dashboards reporting, lead scoring, whatever the fuck all these things are. But again, if the discrepancy, the delta between performances gets too big, you're going to see resentment will start to show up and it's going to be like, why is that guy getting paid the same as the rest of us?
How long that can last? I mean, you can add a fourth as long as they are comparable. You can add a fifth as long as they're comparable. But the more people that you add, the more impossible it becomes for the delta to not increase between top producer, bottom producer, middle producer, et cetera. I have implemented this. I don't know if you remember this, Richard, or not. I've implemented this at the sales manager level, actually, because what, you know, the traditional model has been like, you take a hundred sales reps and you got, you know, 10 or so managers with each, with 10 reps and all that kind of thing. And what happens is the manager only cares about the performance of their 10 reps and they spend no time helping the other 90. And that always pissed me off and drove me nuts, right? And people are not celebrating other people's wins and all that kind of thing. So I, at one point in time had individual reps, had their own quota, but the sales leadership team had the overall quota only. So they were incentivized to coach anybody and everybody. And that worked pretty well, actually, for a while, you know, again, until the delta between the good managers and the bad managers got too significant, that resentment crept in. So.
And that's happened, like.
And I can share that.
That's my answer for you. I don't know if that's helpful or not, but go ahead.
And I was, yeah, I was just gonna say I was one of the managers. Right. And you know, I, and Scott knows this about me. I'm always sort of like a good middle of the lineup guy most of the time. Every now and then I'll get to the top of the order. Right. But he recognized that in me. It just wasn't quite the right way for the way I manage people and do things that. That didn't work. So he moved me into a much more ops related role. Right. To where I was more on the. I don't know, I guess you could sort of call it customer success. That was before the word, right, Scott? That has been operational piece. But yeah, and that's the key piece is recognizing that. So you don't just throw the baby out with the bathwater. It's like, okay, so you got three. One's not performing well. Why would I throw him out? Just because he's all of a sudden not doing great in sales. Is there another place I can leverage his brain trust and not lose all that institutional knowledge he has about us? Right. And sometimes you can, sometimes you can't. But I wouldn't be like, oh, you can only be an SDR and then an AE. No, someone comes in. You know, I've always said SDRs and early stage salespeople, you're. You're the gateway role. Right. You get to come in early. And that means there's more opportunity for you to go to other departments if it makes a good fit for everybody.
Steve, can I steal your question?
You can.
I gave my question to crispy, so I actually have a crispy question. Unless you have a second one.
I have a question. And it's related to team quota and it goes to this other portion. I love what you all just asked Scott. This is like very helpful for me as I'm thinking about this. And so we, we had like 250. We, we've gotten very low. We got much larger with a very small team. And one of those is we do something called. We have a. We have a different go to market motion called surround bound. It's a fake word. We made it up. Doesn't really matter. The idea is anytime someone thinks about the thing we do, they all of a sudden start seeing us. And it's True. If you start thinking about you just get surrounded and we have this like a thing and it's not it. And the way it is is every, every one of their sales team hadn't we kind of we hire for this and like if you don't want to be a part of it, don't work here. You must post on LinkedIn with our point of view. You interact with everybody. If we only do warm outreach is the idea. So but in that mechan, in that mechanism, our sale like what happens and the problem set that that creates is what who owns the leads. Because every, because we often have three people all going after the same person and it doesn't matter who comes in because we're on team quota. So one of the things team quota is solving for is the ability to surround down. So how would you, as you're thinking about this, how would you like how do you. I feel like I'm put between am I getting up the surround down go to market methodology or if I get rid of team quota. So that's what I'm solving. So with that information, does that change how you think or no?
No. And, and because you actually said the most important part in my opinion is you're hiring for this. So you have to optimize for the type of person that understands when I'm surrounding this account, it may directly benefit Matt today, but later on it will directly benefit me. And there's an element of selfishness, selflessness and understanding of the long game, if you will. Right. I'll sacrifice, sacrifice myself today. I'll comment on these 10 posts. I'm not going to close any of those deals. I'm not the point person, but my teammates are going to help me and it's going to come back my way. And you know, you have to optimize for that in the hiring process. And if you don't, it's going to blow up. But if you optimize for it and you got the right person who gets that philosophy and buys into it, great. You know what I mean? I would love that. I've never heard the phrase surround bound before. I've for years. I go back to 2016 when I was at Qualia. I basically taught my whole team like, this is how you use LinkedIn and everybody needs to start growing their network and everybody needs to start posting content. And I used to get people messaging me in dms, being like, I don't know what the hell y' all do, but I can't get on LinkedIn without seeing Qualia Posts. Yeah, that's exactly in comments. That's who he was. So I'm everywhere. Anything everywhere, all at once or whatever that that movie is. Right. But there's a. You have to be selfless and you have to play the long game. You have to understand that even if I don't win today, it'll come back to me. So that's the key is hiring for it, I think received.
Yeah, that's very helpful. It gives me some less since you've done the path before. So I'm like less trepidation as I'm. I'm.
You're not as behind as you thought you were earlier.
Yeah, I'm not as bad as I thought. I.
Thank you. All right, Steve, Bill, here's the crispy question before we get out of here.
So, and this, this might be a bit of. Because being a startup, having a small team, we have to like our sales team right now has to have that like hunt, kill, eat mentality versus like being fed leads and then like working leads. Like the SD model. We don't have that right now. We have like four cycle AES. So the question is like, how do you search for that hunt, kill, eat mentality in sales reps in the interview process? Prehire, go ahead.
I think you. I. Well.
I mean, it's even before the interview process, right? Like, you know, you literally put in there, you will kill and eat your entire weeds. You do not have FDR support, like period. Like just let them know before they even apply. Right? Because then it's going to become one of the very first. If it's that important, you know, then it's going to be one of the first questions, right. To the same thing of, you know, are you looking for people who already post regularly on LinkedIn? Right. Are those. There are reps out there that do that. The other thing I would say, and it sounds unique, is that you all feel like the kind of organization where that SDR has been in SDR for 6 months, 12 months, 14 months, needs their shot. And y' all can give them that shot because maybe they are already doing LinkedIn. They're already, they're already used to hunting anyway, right? Like that's the role. So can you narrow your candidate pool by getting a specific Justin jumping the job application description first and then you need to, you know, do your research to see if they really are posting or not and then do your research on with them on. Tell me about how you do it. Tell me how you feel about not having an sdr. Right. And and push them hard. To tell you the truth. That's the quick answer. Got.
I'll give a slightly longer answer. First of all, I love that that's your philosophy. That is what I always did. Never. Even when it was in vogue and everybody was doing it. Never did I have strae model. I always had full cycle.
So you didn't equal you.
I did not.
I did not know that. Okay.
Yeah, I did not. And everybody told me, you know, I was an ida.
You're powder to be.
Oh, they hated it all. They had all their VCs on them. You know, this guy's gonna lead you down the wrong path or whatever. And you know, we're worth a couple billion dollars. So you. Right. I must have done something right.
Okay.
Anyway, so I love that.
How many, how many sales leaders have they had since you left?
No comment.
No comment.
Here's. Here's what, here's what I would say.
You can optimize for this through your messaging and content that you all put out.
Yes.
So you can if you want to. You don't have to, obviously, but you can take a very strong stance on how you feel about the SDRA model, how you feel about SDRs and their worthwhile purpose in the new sales world. You can talk specifically about Surround Bound, for example, as a methodology. Nobody talks about that online. You can specifically call out things you respect about certain salespeople that you like, certain sales orgs that you like, and how you want to emulate them, copy them, what have you. Right. You can be very brazen and say, I mean, I'm going to make stuff up, put words in your mouth. It's like, we don't believe in inbound, period. Right. You're not going to get fed, period. Right. So don't come here. If you're one of those kind of people, you can take like a strong tact with all of that kind of messaging. And during an actual interview process, should be pretty, pretty smooth. There's a lot of salespeople, believe it or not, that would like to own everything, that don't trust an SDR with pitching properly and teeing up meetings. There's a lot of salespeople who are burnt by bad meetings and no shows and things like this. Right. So you're optimizing for trying to find those people. And last thing I'll say, by the way, is the market. Is the pendulum swinging back around toward, you know, the earth needs everything in balance. Right. We went all the way to SDR model. Those are going away more and more. People are trying to optimize for full cycle AES now not to hire a hundred anymore but it's like I need three AES that are as good as the hundred I used to have. To your engineer kind of statement about about your prior company. I had five engineers that could build something from scratch at 150 that you know were serviceable for other other reasons. Sales same way. So I think the best way to find those people is to be very overt in your messaging and put it out there everywhere. Like everybody knows that Superd is.
A full cycle shop the same way everybody knew Qualia was when I was there.
That's what I would do.
Received. Consider it done.
Thank you.
It's helpful.
Gentlemen, thanks for coming on. We appreciate it. As always. Really fun conversation. And also a big thanks to our sponsors, Win, AI and Vasco. Please go support them. We couldn't be here without our sponsors. And even though surf and sales Portugal is sold out, go to surfacesales.com Put your name on the newsletter list because we're going to be announcing 2026 and its location soon. And every now and then someone drops out at the last minute. So if you're a last minute kind of traveler, we'll, we'll contact you if someone decides to drop out.
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