Scaling Sales Through Coaching, Gamification, and Trust | TFOS E14

In this episode, Rick talks discusses the evolving landscape of sales enablement with Brian Trautschold, co-founder of Ambition, a leading sales performance management platform.

Brian shares his entrepreneurial journey—from coffee runs and copy machines at UBS to co-founding multiple startups and building Ambition into a company that transforms sales teams through coaching, gamification, and trust.

If you're a sales leader navigating the complexities of scaling your team or thinking about how AI and manager enablement will shape the next decade of performance, this is a must-listen conversation.

Connect with Brian Trautschold: https://www.linkedin.com/in/brian-trautschold-97518219/
Check out Ambition: https://ambition.com/

Connect with Rick Smith: https://www.linkedin.com/in/rick-smith-094b29b/
Check out Conquer: https://conquer.io/

Creators and Guests

Host

Rick Smith

Chief Customer Officer at Conquer, Host of The Future of Selling Podcast, Eternal Student

What is The Future of Selling?

The Future of Selling is the go-to podcast for sales professionals looking to sharpen their skills and stay ahead in the competitive world of B2B sales. Each episode features expert interviews, real-world case studies, and actionable tips to help you navigate the complex B2B buyer's journey. Whether you're dealing with long sales cycles, multiple decision-makers, or rapidly changing technologies, we’ve got you covered. Tune in to discover the latest trends, best practices, and proven strategies for closing more deals and building lasting relationships in the B2B space. Perfect for sales leaders, account managers, and anyone aiming to master the art of B2B selling.

Future Of Selling (00:01.859)
All right. Hey, welcome to the Future of Selling podcast. Appreciate you being here today. You know, in our podcast, we dive into challenges, trends, innovations, anything that's impacting the future of sales of the sales industry itself. My name is Rick Smith. I'm your host, and I'm so appreciative that you guys have joined us today. I would like to introduce our guest that we got on the on the show. Our guest is Brian Troutshield, and Brian is the co-founder and the CEO of Ambition.

And we want to dive into ambition. We know little bit about ambition because we have some clients that we share. So that's really cool. He's also co-founded multiple startups, including FirePlug. you're going to have to tell me if I say this wrong, but I'm going to say reticker. Did I say that right? Did I do that right? I did. Excellent. I like that.

Brian (00:51.199)
You're spot on. Yeah, absolutely.

Future Of Selling (00:54.311)
You're an alumnus of Y Combinator Accelerator program. So that's really around the entrepreneurship. So I'm excited to hear about that. And you've been instrumental in guiding and directing and growing ambition that you spent a ton of your time and really have an emphasis on lean operations, data-driven decision-making. So anyway, I'm excited about the conversation today. Brian, welcome to the podcast.

Brian (01:22.828)
Rick, thank you so much for having me. I really appreciate it and I'm looking forward to the conversation.

Future Of Selling (01:27.099)
Yeah, me too, me too. But before we jump into it, I always like to give a few fun facts that I pick up about people. You because you're, mean, you're, Brian and you're the co-founder COO. People might want to know a little bit more about you though. You know, who, who are you? What, what do you like to do? So one, you're known for your passion for startups. That's the first thing we picked up. And if you go back and look at your LinkedIn, you got like startup after startup after startup. So you've been in a few of them, right? So that's kind of cool. You're a huge Memphis Grizzlies fan.

Brian (01:56.878)
It's true. Guilty.

Future Of Selling (01:58.159)
Which, sorry about that. Yeah, but you know I was looking and prepping for the show today. was like, they made it the playoffs. That's good.

Brian (02:07.414)
Yeah, that's positive. We made it. We didn't last long, but we made it.

Future Of Selling (02:11.623)
Yeah, but you guys are in there get swept by Oklahoma City. don't know what I don't know what's going on with that team. They're awesome this year So anyway, you're big big NBA fan Memphis Grizzlies fan. I'm the San Antonio Spurs fan by the way and They used to be great One of your experiences also thought this was funny one of the experiences you have late on your listed on your LinkedIn is an

Brian (02:25.965)
awesome.

Future Of Selling (02:36.519)
Analyst intern and your description of what you did there was pretty funny. I don't know if you've seen this a while but analyze my ass off Disrupted traditional client management and communications. Okay, I like that master of coffee pot copies more copies so many copies There you go, did you enjoy that job?

Brian (02:44.525)
You

Brian (03:02.03)
you know, I mean, we can get into all of them, but it's funny because I have not seen that in, gosh, I mean, maybe a decade plus since I wrote that. and that is, that's right. That's how I, that's how I recall it. I remember making a lot of copies. remember calling clients, and that was, you know, my first, my first experience in a, know, kind of traditional corporate environment. And I was the like literal low.

Future Of Selling (03:10.811)
Yeah. Yeah.

Brian (03:30.21)
person on the totem pole doing all this stuff. Yeah, it was a pretty good experience.

Future Of Selling (03:33.745)
Yes. All right. Well, so, so is that part of what drove you into this? And we'll get, I got a couple of things to talk about, but is that part of what drove you into that entrepreneurial or did you already know at that point? I want to be an entrepreneur. I want to start my own company. Or was it working for a big company doing coffee pot and copies that you're like, Nope, I'm out. Not doing this.

Brian (03:55.468)
Yeah, that's a fun question, right? Because I was probably, I was in my 20s, was an intern in college when I was there at UBS. And then I had my first experience outside of college was at HP, Hewlett Packard, like the big Hewlett Packard before it split. And I did not know, when I was at UBS as an intern, I did not know that I wanted to...

Future Of Selling (04:15.739)
Right.

Brian (04:21.876)
start a company, honestly, we can get more into it. But yeah, my, my experience of those companies just kind of opened my eyes to there were all types of things big companies are really doing that is really dumb, or like could be way smarter, could be way more efficient. You know, and maybe we'll get into that like whole entrepreneurship, entrepreneurship section later. But yeah, you know, as a 21 year old, you think

man, all these big companies with tens of thousand employees and publicly traded. And you think like, gosh, they must have it all figured out. They must be so smart. And like not to knock UBS or Hewlett Packard, but you get in, in your little tiny sliver of the company and you're like, my gosh, there's so many things that are messed up and no one has any idea what they're doing. And that was, that was like pretty eye opening for me, for sure.

Future Of Selling (04:57.254)
Right.

Future Of Selling (05:08.508)
Yeah.

Future Of Selling (05:15.579)
Right. So was it more because it frustrated you or more because you saw the opportunity that, know what, I can do this better on my own. Let me just find the thing I want to do and go do that.

Brian (05:29.887)
yeah, you know, it's kind of like the Jetsons. Like you remember like Jetsons cartoons, like you're growing up.

Future Of Selling (05:35.495)
I'm not that old, sorry. I do remember him, yes I do.

Brian (05:38.126)
I know the I know the cartoon. And like, you know, you think you're gonna have flying cars and robots that are doing work for you. And, you know, your meal is going to pop out of this pill from the microwave thing. And like, you know, what you come to find out is that the status quo is the status quo in a ton of places. And there are all of these, these are all these things as a as a young

person who was like pre career that you think are solved or that you think are working really well. And, you know, I mean, I still I find this every day. I know you guys find it at conquer to the system or the process is like stuck together with, you know, a paperclip and duct tape and a piece of chewing gum and no one knows how it even works like or if it works. And so yeah, I got I was I was fortunate to

see that, know, see that at a couple really specific levels and at really big companies. You know, I had no responsibility. No one was listening to me. No one was like, Brian, what's your idea? No one was doing that. Because like, I probably didn't have any ideas. But yeah, it was very it ended up being very useful later on to be able to pull from those experiences be able to be like, Oh, I remember how they do it here. And like, it's not

Future Of Selling (06:51.751)
It's

Brian (07:07.691)
It could be way better.

Future Of Selling (07:09.031)
Yeah, yeah, gotcha, gotcha. tell me about so clearly that was part of the journey that was part of the path to move toward the entrepreneurship, right. And pursuing that. So you've done a couple of companies to co-found a couple of companies. But really, it sounds like where you found your sweet spot is is ambition. So so tell us a little bit about ambition and why you guys co-founded that and what you guys are doing.

Brian (07:36.654)
Yeah, absolutely. So Ambition is a sales performance management and coaching software. We sell a suite of products all as part of one, you know, kind of under the Ambition brand that help large, complex sales organizations better measure, better manage, and ultimately get the best performance out of their salespeople. What we started as

is really simple and what we've become, think is really powerful. And so we started as a, idea. And like you said, Rick, I, myself, my two co-founders of an ambition, we had started two companies together prior. We actually had done a number of things together, really starting at the end of college. Uh, we all three went to the university of Tennessee in Knoxville. Um, and maybe talk about that in a little bit, but like we came out of the university of Tennessee, this is after the internship. This is, this is after that. We're like,

We should start a company. should do something. By the way, we're graduating in effectively the financial crisis. So the 2008, 2009, all the things that, know, kind of going back to the UBS and HP stuff, like going into school and kind of going through college from, for me, 2006 to 2009, you know, you're kind of like midway through college is like, actually none of those things you thought you were going to do existed.

Future Of Selling (08:42.705)
Yeah, tough time.

Brian (09:01.654)
Like you're not going to, know, these, these companies are not hiring. if anything, they're doing massive layoffs. And so there was kind of this awareness, midway through my college experience. That's like, okay, you know, the way that I thought my career after college was going to go may not be right, you know, and not that I was super wise about any of that stuff, but I think I was aware enough to be like, you know, maybe there are some other paths.

Future Of Selling (09:01.841)
Right.

Brian (09:30.624)
Long story short, like we started some companies happy to dig into that side, but we had started a consumer, kind of a consumer facing product that was very much about, interestingly, how to better aggregate and analyze the news you're reading, which I think actually is really relevant today. A lot of people are very siloed in what information they're getting, whether it's from Twitter or...

Instagram or Reddit or you know, whether they watch CNN or MSNBC, whatever you're getting kind of this very filtered view of what's happening in the world based on the based on where you read. long story short, we had started a company around that idea and it was great. It was great for two, three years. But what we realized is there was no business like the company and the product were fantastic, but there was a really challenging business model.

And so we kind of plateaued, had a great, we'd built a great team. We'd learn how to design consumer level experience, how to build that product, how to deliver it. So there was, it was kind of like a grad school for me almost. Like, here's how you actually do it in practice. Here's how you manage a team of people. but we were at this, what I'd call a plateau of, of how that company was operating. And we were like, we don't really know where it can go. Like there's not really a next.

step to make the business work. we kind of sat down, the three of us sat down, we had a really good group of investors as well. And we were pretty open. And I'd say honest of like, we don't really know how to take this further. You know, it's kind of this highly used app. It's got a bunch of it's got a bunch of engagement. But, you know, there's no way to make it make money at a high level. There's really limited way to grow it.

And we got down to the whiteboard, which is something I still like to do, which is take the ideas we have, take the challenges we're facing and try to put it in some type of box or some type of Venn diagram of solving a problem and coming up with a direction. And we honed in on this problem that other companies and a handful of us had experienced, which was the way that we're motivating

Brian (11:54.862)
salespeople and even the way they were measuring salespeople is not very effective. And this was at my experience at HP. This is my experience at US Express, which is a big logistics company. was, know, all of those folks were very reactive to performance. They were very much, you know, the way that you motivate people in a classic sales organization is on the floor. It's kind of hand to hand combat. It's like a great sales manager.

you know, trying to get their people going. And what we also knew was that those types of organizations, this is the type of customers that conquer surface today, as well as ambition. They know what, what needs to happen for those people to be successful. They know that people need to be doing these activities. They need to be doing this part of the sales process. They need to be this effective. They need to be this good at it for it to work. And

The challenge oftentimes is just getting people to do the work. I compare it to working out. I don't have a trainer, but if I had a trainer, they'd be like, you know, Brian, if you ran 20 miles a week, you would be a lot more fit. And like, just getting me to run 20 miles really hard. Spread it out however many days you want, five days, seven days. It's gonna be challenging. But the companies know that if they get those people to do that,

Future Of Selling (12:54.523)
Right. Yeah.

Future Of Selling (13:10.534)
Yes, I agree.

Brian (13:19.768)
kind of formula or a version of the formula that works for them, they'll be successful. They'll hit their quota, their quarterly goal or whatever. But motivating them to do that was real challenge. So Ambition, our original idea was how do we make sales fun? How do we get the process of sales, which is not the signing the document at the end, closing it. It's really all of the things that happened before that.

from a salesperson point of view, how do we make that fun? How do we make it engaging? How do we make it easy for 300 sellers at a company to show up every day and do whatever that looks like? And so, we called it fantasy football for sales. We had this kind of gamification, game-oriented approach. We tried to be very consumer-centric in our design. And that's how we got started. And so that was based on our

lived experience at those type of companies. was also, you know, taking a step back. was like, we're going to have to kind of make our own way. Let's find a thing that we like thinking about. I think that's very important for young entrepreneurs. Like what's a thing that you want to think about for? I mean, God, like I've done this for 12, 13 years. Like, I don't know how many hours that is a million hours. Like, you know, whatever the number is, find something that you want to think about for a million hours.

Future Of Selling (14:41.959)
Right.

Brian (14:46.958)
And then, you know, if you keep working at it, you can actually have a pretty big impact.

Future Of Selling (14:52.827)
Yeah. So I'm going to predict right now that that statement you just made is going to end up as a short that we can.

Brian (15:00.014)
Maybe I feel bad like the math may be way off on that. I need to like put it in Excel or Ask Chad GBT real quick, but it's gonna be a lot of time.

Future Of Selling (15:08.549)
Yeah. Yeah. But what a great, but what a great statement. You know, I mean, just you, if you want to be successful, find something you'd be interested in enough to spend a million hours doing it. I mean, that's, that's the, that's the key, right? I mean, it's kind of the law of curiosity, right? you know, as far as growth is concerned, I mean, that, which I'm curious in leads me to growth. If I'll just allow myself to be, to get beyond the

the borders, know, get beyond the next step that threshold. So, so yeah, I agree with you. so also, I love the question you asked, by the way, how do we just make sales fun? mean, such that's just such an obvious question, but it's such a great question to kind of get you started on the whiteboard and kind of, you know, working through the options and things like that. So it sounds like a good description of who you guys are. But the.

Gamification, you talked about that. How has that evolved over the years? what role do you think it plays in transformation for the sales team?

Brian (16:14.446)
Yeah, I'm glad you asked that because I do still think fun is important. I actually, if we kind of go through the evolution of ambition over that 12, 13 years, we started this very fun-oriented, gamification-oriented product. And we really evolved into this, what I think of as like a manager and leader enablement, as well as like really...

really what we're becoming is automation and AI around coaching. Like that is really what we're becoming. the massive gap in between was a series of things, but primarily, and this is for the folks who want to start their own company or be really early in a startup or something like that, you have to listen to your customers. You have to talk to your customers and really listen to your users. So this is a concept that's blurry for people, but sometimes there's the

The customer buys something that is fixing a pain right now or is giving them more value right now. But if you talk to the users, which are our primary users over the past decade have been the manager, the manager, the director of sales, the revenue operations person. It's rarely the front end seller is a user of our product, but the power users come from that front line manager, the director, the VP.

And when you listen to your users, they tell you magical stuff that you would not know. And they will tell you, we used to call it magic wand. they'll say, man, if I, if I could only be able to do X, if I could only do this thing, and sometimes they'll say in your product, but oftentimes they're just like, I really wish I could do X. I really wish I had the ability to see this thing. And, that is, that is someone telling you whether it's a million dollar value or.

$10 million value or billion dollars. They're telling you like a secret. And if you can like capture that thing and you can say that solving for that thing this person told me is really the value. So to kind of re-answer your question, we start with this gamification thing. We're kind of solving. How do we get these people to do this thing that management wants? Management wants them to hit number. They have a model. They need these people to be productive. The managers, the directors of sales, they're telling us

Brian (18:37.934)
how do I orchestrate the whole thing? How do I have more ability to see what's happening and then change the behavior and really manage to this more dynamic plan? Like business is dynamic. It's every day is changing every, the plan you had at the beginning of the quarter is not how it's going to end up at the end of the quarter. And so you have to be able to really get on a man to man basis, just to use a sports metaphor and like, and be able to shift and change in real time. And,

learning that, hearing that from people for years, shifted our product focus from just gamification to this more holistic, how do we coach, how do we manage to drive that sales performance? Now, gamification is still really important. You need, you guys serve massive customers, Fortune same for us. You have these...

really widely scaled organizations. And so to get people to change their behavior, it is not as simple as saying, Brian, go run the 20 miles. Like that is easy from the top, but if you actually want that to come to fruition, there's a more comprehensive strategy to do that. So that's how gamification plays a part. It helps, you know, it really helps tap into the, tap inside of the, you know, tap inside of the,

the brain of an individual seller or a person in the organization. And sometimes you're pulling, sometimes you're pushing, sometimes you're trying to get them intrinsically motivated to do something. And I strongly believe this sometimes is giving them the information. A lot of organizations, the seller or the person who you want to change the behavior of, they want to change it too. They want to be successful. They may just not have.

the information or the guidance of what it will take to be that. And so if you can give them that with, you know, the gamification interface, you can give them the nudges on your watch to say you've got like, you know, 2000 more steps to your all time record. They'll go do the thing. You just have to give, you kind of have to give it to them so they can take action.

Future Of Selling (20:49.809)
think a big piece of it is, I was thinking about this before we got on, right? Why does gamification work? What is it, know, what is it, yeah, how does it get in the brain and make that work and make it more fun? You know, I think about and talk about sometimes and read a lot about just the flow experience, right? And to me, gamification kind of marries into that, right? Because if you think about, well, what creates flow? Well, there's a couple of things. One, you got to know what's important.

Okay, the goals that I'm trying to achieve, right? And not only I need to know the goal, I need to know what the target for the goal is. So what does good look like? Then I've got to have feedback. And the more immediate that feedback is, higher the likelihood that I actually step into that optimal experience or that flow. And then ultimately there's got to be some tension. If there's no tension between where I'm at and what I'm trying to achieve, it's no fun.

It's just not fun, right? And so as I think about the gamification piece, I'm like, yeah, that makes perfect sense. That's going to make sales more fun. You've turned it into an activity that I can kind of move into this flow. mean, what's your take on that?

Brian (22:01.198)
I think the flow description, those kind of four components you described, it's totally right. talk, we frame it, we framed it differently in our marketing speak. We framed it differently when we talked to executives, but you know, from an individual perspective, and I, I mean, we, don't know how far a field will get today, but I coach baseball for 10 year olds. Like they, we have the same thing. And when we, when we go say, Hey, you know,

today we're gonna go get in the cages and we're gonna hit 100 balls. That doesn't sound very fun. That sounds like work. When we say we're gonna have, we're gonna make this a game. We're gonna see who can hit, you know, pool side and go to the right of the pitcher and go to right field. And we're gonna see who can do the most of those across all you kids. We're gonna keep score. Now it's a game. Now it's a competition. Now kids wanna go more and they wanna take more than 100 swings.

Future Of Selling (22:37.671)
Haha!

Brian (22:59.094)
And so there are these little, you know, whether it's psychologically unlocking that, whether it's just framing it different. and you know, one other method I would, I would give to sales leaders or revenue leaders or anyone who manages people for, we talk about it starts with why. So like, why do you want to do these things? The seller doesn't most of the time, the seller doesn't, the why for them is not, I want my,

I want my division at Fortune 500 X to hit their number. That is not their Y. Their Y is like, I want to refurbish my house. I want a boat. I want to send my kids to this school. Whatever it, or I want to, whatever. Like it could be, it could be like a really noble thing, or it could be like, I want a new truck. Like whatever it is, like it doesn't matter. It's their thing. And then it's on, and same thing for baseball. Like those kids.

Future Of Selling (23:51.825)
Yeah. Yeah.

Brian (23:58.69)
They want to, they want to hit dingers. They want to go hit the ball hard, like whatever, like it's, it's your thing. The why establishing the why. And then like you said, like to that flow state, then you're working backwards. Like you're, you're working from the absolute goal of that individual to, okay, what's, where's the tension going to be? The tension is going to be in the day to day, the activities, the process, the quality at which you're doing them, the type of focus you have where you're, when you're in that work.

Future Of Selling (24:04.049)
Yeah. Yeah.

Brian (24:28.588)
when you're in the cage doing a hundred swings, like that is where you build the ability to go achieve the, the why. And, it's really challenging. I think a lot of folks, especially over the past decade or two went from a top down, I'm going to push you to do these things because you just have to do it to let me figure out strategies to pull you. And the pulling means that you're the individual is going to go.

Future Of Selling (24:49.756)
Yeah.

Brian (24:57.899)
Execute the thing.

Future Of Selling (24:59.003)
Yeah, got it. So you guys, so that makes perfect sense. So gamification for the sellers, right? Get some motivated, make sales fun, creates that tension, that flow, all the things we just talked about. But then also you guys are evolving quickly and maybe even, I mean, maybe you're already there, I think, to a coaching and development platform as well. So talk just a little bit about that piece of the puzzle for me.

Brian (25:28.342)
Yeah. Thanks for framing that up. Yeah. I think we have evolved. What's it called with the, you know, caterpillar to the metamorphosis has happened. Like, and like that has been the, it has been driven by our customers. It's been driven by our users, but it's seeing, it's seeing the holes. You kind of talked about this in my early career, the hole that we saw when we're serving our gamification solution to people was that the manager, the frontline managers, we call them.

Future Of Selling (25:37.756)
Yeah.

Brian (25:58.166)
the second line manager, which is typically that like director of sales, occasionally a VP. The tools at their disposal are much less robust and much less invested in than what a seller would have. And so a seller would have this whole kit of tools they could use. Like they were overloaded with stuff. And this is, you know, I think actually improving now, but there was all types of tools for

marketing for the seller and when you got into the manager you're sitting with a person who is managing eight to now sometimes more like 12 13 people and you say well, how do you do your job? What what was the setup for you to get the most out of these eight ten twelve individuals? What you find is this shockingly, you know ragtag

of training, of experience, of tooling. And when we go talk to leaders, the CRO of Fortune 500 companies, and you ask them, what's going to be the key to change this initiative? What's going to be the key to sell more effectively or hit the revenue goal? They'll say things like, our managers, our frontline managers, us pushing down into the field, what the new messaging is or the new strategy.

Future Of Selling (26:58.374)
Right.

Brian (27:23.342)
And then you go to the managers and they're like, well, I was just the best rep three quarters ago. I got promoted. I've had no management training. I have like seven different reports that I have to refresh every couple of days in Salesforce. have, you know, no real template of how I talk to my people. They're just making it up and they're doing the best they can. And they're this core lever for whether or not the organization is going to meet the expectations or miss.

Future Of Selling (27:42.343)
Yes.

Brian (27:52.158)
And like, by the way, every single week or every other week, someone's asking them for a forecast. Someone's asking for a stretch. Someone's asking how they're going to go, you know, take the next hill and they have nothing, largely. And, so we understood from those folks, they're like, man, they're serving these people is really important. It is a huge leverage point for the organization. And it is really this. Not only under invested, but like a black box of how does it happen? And.

So we started to your point, we started chipping away at adding functionality for that. And I'd say, um, it kind of coincided with two parallel lines for us. was how do we serve the manager better as well as how do we serve the enterprise better? And those two things are highly interrelated because in the enterprise, whether you've got a thousand salespeople, 3000, 10,000, we live in all those environments. That means you've got somewhere between, you know,

200 to a thousand managers who are this leverage point, this fulcrum of whether or not you're going to be effective. And that is kind of been our focus. we've, like I said, we've, I think, fully changed the company to gamification is an element of how you can do it. It's part of the process, but really what it's going to be about is this sales performance driven by

Future Of Selling (29:02.054)
Yeah.

Future Of Selling (29:14.683)
Yeah.

Brian (29:21.418)
largely the manager, frontline sales leader, second line sales leader, and how you get that consistent all the way through, you know, a pretty massive organization.

Future Of Selling (29:31.023)
Got it. Got it. Okay. Do you any chance you've got like maybe an example that you could, and you don't have to say the company's name. It's no worries, but maybe an example where you guys have gone in and you've kind of seen the difference, right? By putting your technology in place.

Brian (29:49.558)
Yeah, absolutely. talk about a, I mean, I want to the to keep us out of out of trouble. You know, no one wants to censor your podcast, but we work with one of the largest telecommunications companies in the United States, Fortune, sub 200. They have literally multiple thousands of salespeople using ambition and managers and what they

their mission was, was we have to change the process of how we sell. And that's came from the, this came from really, we look for initiatives. And so for all the salespeople out there, like initiatives and pains are what we sell into. Initiatives are how they're going to change and grow their business. The pains are like something is broken or breaking and we have to help fix it. And we look for initiatives. The initiative from the C level was we need to

We need to turn from a inbound order taking organization that sells one product to we need to turn our salespeople who are effectively taking orders into an outbound cross selling organization. And this is, think, I got a little, little balloon thing. this is, this is common all the time. Like some changes happen where the CEO has now tasked the CRO or the SVP of sales, whatever the title with.

Future Of Selling (31:07.431)
Ha

Brian (31:18.816)
I need a different level of performance. need a different process. And the CRO there understood, he basically identified, we don't know how to manage our sales team very well. We have no standard process. We don't have standard visibility into both what the reps are doing and we cannot drive them to this new behavior. And we don't have a standardized management process. like we've got

literally thousands of people and every little 10 to 15 person unit is kind of doing their own thing, depending on their patch and their territory and their thing. And so we came in, they've established a very clear standardized process of how they manage, which is a cadence. It's kind of this orchestration process where every few, they're talking about, know, topic X on one week, topic Y on the next week. They're doing a forecast on week Z.

Future Of Selling (31:54.789)
Yeah.

Brian (32:17.422)
So they're moving through this cadence and all the people from a seller point of view, they're managed to the same expectations that meet their goals, roll up to their quota. The managers are also measured on, are you doing these conversations? Are you actually having a management one-on-one or a forecast one-on-one with your team, with your individuals? And so what you've seen there, to my point is you've got 2,500 people who are now

Future Of Selling (32:27.964)
Right.

Brian (32:46.062)
marching to the same drumbeat. They're running the same process. They know every single week the challenges they're facing if they're cross-selling. If the manager has met with them and talked about their forecasted opportunities, they have now standardized that across the organization. And what that is leading to is the CEO level change, which was we have to become an outbound sales organization that can sell into our existing customer base.

Future Of Selling (33:00.977)
Yeah.

Future Of Selling (33:14.651)
Yeah, that's huge. mean, you basically you you kind of help them create what does good look like for us, right? Not not and not a thousand answers of what does good look like. Not everybody answering for themselves, but for our organization, we want to go from an from an inbound, you know, so that's selling one one product to, know, this more comprehensive approach. And this is what good looks like, guys. This is how we get there. Right. And that's that's pretty phenomenal. Yeah.

Brian (33:22.551)
Exactly.

Brian (33:44.62)
And it, yeah, thank you. It's different for every, every organization is doing a different initiative. but like, you know, what we believe is it's kind of, you know, the war metaphor is like, it's very easy if you're sitting in the Pentagon to come up with this plan, the plan is to do whatever people in the Foxhole in the, in the trenches actually have to go execute the plan. And that is where companies I think oftentimes are struggling. because, know, it looks great on paper.

what's it actually look like in the field and how do you make sure the field is doing the plan is very different.

Future Of Selling (34:20.071)
Yeah, got it. Got it. So what do you see kind of, you know, as we look for future sales, right? I mean, what kind of emerging trends do you see that are coming and kind of shaping technology in sales, right? And I saw you guys are working on AI, I saw that on your LinkedIn, I everybody is, right? But what do you see happening? What's the future look like? And how are you guys working into that?

Brian (34:47.222)
I, yeah, I know we, I know we are in a conquer is and we've been, our strategy has really been like trying to solve very specific challenges for the manager, for the, for the leadership. and what's amazing about AI, like, and I'm not going to try to, you know, go too hard on this, but it's going to radically change how we gather information, how the information gets to us, even how we analyze it. And so like to, hone in on a more specific point of that.

Like I said, you've got in these organizations, we serve hundreds to thousands of managers and the manager is oftentimes ill trained or under trained. they may not have, you know, robust training framework there. they may not have, all of the data they need or to make good decisions, to do good, leadership. And you know, what I, what I used to say, and it's become radically better solved now that we can deliver it is.

The manager is not an analyst. there's, you know, there's these organizations have a whole revenue operations or sales ops group. Oftentimes they have data analytics groups somewhere else. they have these different teams of people and what is not next to the manager's title is analysts. and what they, what they need to know is when they, know, when Rick is coaching Brian and our weekly check-in, you need to know how I'm doing.

Future Of Selling (36:04.455)
Sure that.

Brian (36:14.83)
And the way that that actually looks for most of these organizations is that's across multiple reports. may be across multiple systems. You may not even have access to it. so AI, you know, in our world, delivering AI capabilities that can do that work for the manager so that the manager can be the best possible human with the most possible information and then give guidance, set a challenge for that person, help, help.

change their behavior or change their approach so that they can, you know, better reach the customer, better engage with a customer. We believe right now, just to kind of take it now one step up, like, I'll take that back. We are enabling the manager to be better at their role right now. I think as we go into the future, the two things that are going to be true as we have more AI automation and more AI interacting across our sales organization.

is that the human to human connection will be more important. There'll be lots of AI driven outbound, AI driven responses to inbound, AI analytics on what's happening, what trends, what do we suggest you do. You guys and us tap into all that. But I think ultimately what is going to be really key is that when a customer and a seller are at the late stages of a deal, the human interaction is going be more important than ever.

It will make the, I got my balloons again. It's going to, yeah, it's going to make that point in the conversation even more important. The seller has to be fantastic when you get to that human to human one-on-one. Are we going to make an investment in your tool? Are we going to invest in buying something? They have to be ultra well-prepared and ultra effective in that moment. And then what we believe is how they're going to get there.

Future Of Selling (37:45.559)
I I like it, the way.

Future Of Selling (37:59.271)
Yeah.

Brian (38:12.096)
Is there manager is going to have put them through, whether it is one-on-one training, whether it is asking them to do specific guidance from the organization, whether it's talking through a deal multiple times, the human interaction has to be fantastic so that when they are in that situation, they can excel. And AI is going to do a lot of the, the grunt work, the heavy lifting, the analysis, maybe even suggestions of how we can get there.

Future Of Selling (38:22.513)
Yeah.

Brian (38:40.536)
but the human has to be, the human's gonna have to be better when you get into the moment of I'm coaching this person or I'm at the finish line of this partnership.

Future Of Selling (38:52.667)
Right, right. Gotcha. Gotcha. And that's, and that's kind of the thesis that's driving you guys forward, right? Is using AI to get the information. They don't have to be the analysts, but I'm trying to make them be the best human they can be. I'm a leader, how do I be the best coach I can possibly be? Not that I have to go figure it all out, look at all the data, but it's going to give me the data. And then I just be the best coach. can be the best leader I can be. If I'm a seller,

I'm focused on building relationships and establishing trust and credibility and moving opportunities forward. Not, again, looking at the minutia necessarily.

Brian (39:33.494)
I think trust, I'm glad you said that word because I think trust is going to be a, that is going to be the highest value currency in kind of what is next. You know, you may get an email and you don't know if that's a human being or, or, or not. Like you may get a call or you may call into something that you want to buy. You're not going to know, but at some point there's going to be a human in the loop and that person has to establish trust with the customer.

And the seller and the manager have to establish a very high level of trust. And to do that, and when we do that, should say, you know, they're going to have a much better chance of partnering with that customer or having that, that seller succeed. versus I think a lot of the, yeah, a lot of the other, minutia of what happens. and we talked, we've talked about this for years, like how much time of a seller is not.

actually talking to a customer or how much time of a manager is not doing anything directly with their team. That I think that stuff's going to go away rather quickly. And then I think it is how do we, you know, frankly, how do we now scale? How do we, how do we effectively scale the work now that we may have more bandwidth to do that? How do we make sure that the rep has the most possible conversations with the customer? How do we have a manager who's excellent?

have the broadest influence over more people. I think that's a big one for us is like, span of control is going to continue to increase. So a manager may have 20 direct reports in the future rather than eight or 12. So I think all those things like scaling excellence is gonna be more possible with AI at our fingertips.

Future Of Selling (41:09.191)
Great point.

Future Of Selling (41:19.367)
Gotcha, gotcha. No, it's So you guys are doing some really cool stuff, clearly. Let me change gears though, just a little bit, if you don't mind. Cause I know we're getting short on time, but I always like to find out about you, right? As kind of guest on the podcast. Tell me about you as a leader. What does that look like for you? mean, kind of, you know, how do you lead people?

What's your kind of go-to? You have a framework that you use typically, is it just more of a, you know, how do you do that?

Brian (41:55.598)
yeah, people probably would say I just operate on vibes. no, but I think I have a bit of, you know, there's probably a consistent, I have folks who report to me on multiple departments. So it's not just like one team. I run operations here. That means that finance rolled up to me at times marketing has rolled up to me. All the revenue reports stuff into me. Those are all different. They're all different. you know, objectives of those teams, they're different parts of the process.

I think the thing that I look for most, and this is more of a startup mentality, is I oftentimes don't know the answer. I don't know the best answer of how we should do X, Y, or Z thing. I typically, I think, have a pretty clear idea of what is our objective. Our objective is to do X this quarter, or maybe this year. And then I want to establish what is the objective of the leader of that group, or the team lead, or down to the individual sometimes.

How do they play a part of that? Back to that like why? Like the why for me may be this big objective of us hitting our revenue goal or us delivering this new product. But there's a team effort. It's not one set of hands doing that. So I really look for people who are comfortable with ambiguity, comfortable with being very flexible.

I am not going to tell them the exact way to do the thing. I don't have the recipe. You may have to make up the recipe for the thing. And I really like people who are, I say like people, but I like managing and working with people who can like manage up to me and say, here's what I'm thinking about. I know we have this objective. I think that maybe this is the recipe of how we get there. Let's sit down and talk through it. And then I feel like we can establish these.

points in time or like what do we want to achieve on the way to get there? How can I be put to work? I love that stuff. So I don't have like a crisp framework, but I try to surround myself with two types of people. Like I said, one who operate ambiguity and two who are very like linear, here's how we go do that thing. And that's partially because I suck at that. I'm not very good at like the linear task management. I live in the...

Future Of Selling (44:15.9)
Yeah.

Brian (44:17.198)
I think a lot of founders live in the what if and like, you know, when I see the thing, I'm going to react to it. So I try to, I'd say we have defaulted myself, Jared Travis have defaulted over the years to try to find the blend of those people. And I think that's best served as well.

Future Of Selling (44:35.463)
Yeah, no, I love it. So I like that tells me a lot about you, right? As a human being, because one of the things I picked up out of there was, look, I'm not the knower of all things worth knowing. I know some stuff, but there's a lot of things I don't know yet. So I'm dependent on the people that I hire and to help me come up with a solution as opposed to me shoving a solution down the throat. I saw I like that about you. What makes you come alive? You know, whether it's work, personal, I mean, what is it that just like makes you get up every morning and go, I'm ready.

Brian (45:07.48)
That's a great question. I love competing. That's the thing. Like whether it is, like I said, like, you know, out in the market for ambition. I really enjoy that. That's why I do coaching baseball and stuff. I think it's fun. Even though I'm not part of it. I try very hard to remember like, I'm not part of this thing. I'm just like the coach out there. But I think competing is a big part of it. I also, what I love and kind of back to the million hours thing.

Future Of Selling (45:28.773)
Right.

Brian (45:36.148)
I love thinking through the scenarios and like, do we come up with this strategy? That part is super fun to me. That's why I like people saying like, how do I go solve this thing? I really enjoy getting on a whiteboard or a piece of paper and saying like, well, how would we go do this? How would we go become well known for X or, you know, the people would come to us for this problem. That stuff is, that stuff brings me to life. You know, I

And I think some people love that stuff. Some people are like, man, that's just like, you're making it up. And I like making it up and then seeing if it works. Yeah. So I'd say those two things, like the competing part and then coming up with the strategy and testing it and whether it works and, you know, being open to being open to it, not working and then coming up with a new thing.

Future Of Selling (46:11.142)
Yeah.

Future Of Selling (46:25.745)
Got it, got it. Who's been the biggest influence on your life?

Brian (46:32.28)
I've been lucky to, that's a great question. I've been lucky to start these companies or a handful of companies with two amazing people. I'd say that's a big part of it. have to, whether you're starting a company or you're joining a company early, you're going to be somewhat of a reflection of the people that you spend a lot of time with in that way. And so having high integrity, high trust, creative, energetic people alongside you, I think is key.

My partners, Jared and Travis, I think have certainly influenced me even as a peer, but I've also been really lucky to have fantastic investors who've not only put money obviously into our companies and our endeavors, but have really, you know, shared stuff, talked through hard problems, given advice at all types of times. And I find myself, you know, I find myself sometimes, this is a weird thing to say, but like,

As I have kids, I'm like, I know the answer. just can't like, when I tell my kid to do the thing, they don't want to do it. And I know that investors feel the same way about me. They're like, I'm telling them the answer to the test. He's just like refusing to do it. And so I try to find like those things where these people who've been through many, many more situations. And that's Ted Allen, Barry Large, Alan Davis, Phil Molnar at Primus Capital.

Future Of Selling (47:36.017)
Yeah.

Brian (47:57.734)
Sid Chambliss at NCM. Like these are guys who, you know, have been with me for years, decades at this point. And, you know, somehow still put up with me, but are fantastic, fantastic, company builders.

Future Of Selling (48:11.303)
That's awesome. That's awesome. Cool. Well, thanks, man, for the time today. I know we're up close to the top of the hour. I always like to end with a couple of key takeaways, right? So we've covered a lot of ground, kind of who you are and why that's important and influences on your life. Talked about entrepreneurship. We talked about sales and how ambition's making a difference. I'm sales leader and I'm walking into a new situation, right? And I've got the challenge of making a difference.

What are a couple of key takeaways that I should be thinking about? What are the top two things I should be thinking about when I walk into that situation?

Brian (48:48.386)
Well, if you're a new sales manager, think that you have the honor as well as the challenge of like, are a major influencer on whether or not these people are going to be successful underneath you and whether the company is going to deliver. So I think that's a big responsibility that is awesome for you. I would be asking, do I, every day, can I set up a consistent process to get the most out of my people? That's going to be, how do I understand how they're doing, both like...

metric driven, but also on trend. That's, you you can solve that a bunch of ways, but ultimately you have to have a system to do it. You can't just make it up day in and day out. And I would, I would really try to ask, you know, the kind of fuzzy questions of like, why are you, why is this important to you, salesperson? Why, why, why does being successful here matter? And I think if you really get the trust level high, you'll get answers that then you can

you can help work toward, whatever it may be. So I would start with that kind of how do I understand how to get the most of these people in their role and then why is that important to them? And if you get those two things together, I think you can have a pretty profound impact on those individuals.

Future Of Selling (50:04.667)
Cool, cool. That's perfect, man. Brian, I appreciate you being here today. Thanks so much for the time. Been a really good discussion and you know, hope to run into each other again real soon.

Brian (50:16.278)
I'm sure I'll see you soon. Rick, this is great. I really appreciate you having me on.

Future Of Selling (50:19.961)
Absolutely. Thanks, man. Talk to you soon. Bye bye.

Brian (50:22.51)
All right, thank you.