AI Coaches Every Sales Call

Jake Aaron Villarreal: I'm Jake Aaron Villarreal, born and raised in Silicon Valley. I'm here to take you behind the scenes to share what it's like to be a startup founder, the journey they're on, the problems they face, the products they build in an effort to make our lives better. I'm excited to have with us today co-founder and CEO Matt Doyon of Triple Session. Matt, welcome to the show.

Matt Doyon: It's great to be here.

Jake Aaron Villarreal: Well, Matt, I'm excited to have you here. We had a call a few weeks back and it was fascinating of where you came from and where you're at and where you live in the world and some exciting stuff to dive into. But a little bit more for the listeners, Matt is not just the co-founder and CEO of the company, he's also the author of Revenue Revolution. His career spans 25 years in sales, holding positions as SDR, AE, manager, VP, and CRO at companies like HubSpot and Rock Content. So, Matt, I love your background. We talked a little bit about sales. I also came from a sales background at—we used to call it the big O but Oracle Corporation—and really enjoyed my time there selling and understanding applications and business-to-business sales. There's always a challenge of when you're leading sales teams to get them on board, to have them execute, to coach them up, but you can always find better tools and better ways to do things. So we'll talk about your company and what inspired you to build that. Before we do, give us a little background of yourself. What were some of your early experiences that shaped you into becoming kind of the person you are today and wanted to be an entrepreneur?

Matt Doyon: Yeah, so uh again appreciate being here. I grew up in eastern Massachusetts. So born in a city called Lowell, which nobody had heard of for a while. It was actually the birthplace of the industrial revolution in the US. So all these factories that were built all over the city, and always had a very technical underpinning to the city, and then it kind of fell by the wayside and then came back in recent years. And if anybody knows Lowell they know it because of a movie from Mark Wahlberg named The Fighter where he talks about a guy named Micky Ward who's a champion there. So, uh, born there, grew up in that area.

Early on, I mean, I owe a debt of gratitude, I think, first to my grandparents, immigrant grandparents from Italy, learning a lot about just kind of blue-collar work ethic from them, seeing them really build a great life for themselves, traditional middle class, eastern Massachusetts, blue-collar family. And then being raised by a single mom who was highly educated. She was a college professor and a journalist, an investigative journalist, and as a kid of a single mom ended up going to work with her a lot. So sitting in college classrooms, sitting in newsrooms in the late 80s, early 90s watching reporters do their thing. Um, I didn't think about it until far later on in my career, but how much of an impression that had in terms of sitting in classrooms watching people learn and teach and watching my mom, how she would break down a lesson, and how that really came into play when I was training and coaching sales teams. And then just watching journalists and the kind of questions they would ask to really dig in and understand what's going on in a situation. That's discovery. So, like, you know, I didn't piece together all of these influences until later on in life, but they really really marked me.

Jake Aaron Villarreal: Yeah. Yeah. Discovery is a big part of understanding someone's problem and how can you help solve that pain, whatever that is, whether it's a patient, you're a doctor, or you're a lawyer listening to someone trying to get through something, or you're in sales trying to understand how you can better serve your customers. Talk us through a little bit about you in terms of a leader. You've had roles at big companies that we mentioned, HubSpots of the world, as well as you're leading a company today. It's a jump to go from being an employee to being an entrepreneur. What was it that made that shift in you happen to say, "Look, I think it's my time to do this." And is this your first startup?

Matt Doyon: Uh, so not my first startup. I was uh previous to Triple Session, I was at another startup called Rock Content, which played in the content marketing space. It was a partner of HubSpot. All of these road map pieces that I've had in my career really bridged together. There was nothing that was ever a real big giant leap for me to go from one industry to another or one profession to another. It's always had the underpinnings of sales. That moment of, you know, "why now? Why me? You know, why start a company?" It really never was waking up one day. I was like, "Yeah, we're going to start a company," and that was that. Really with Triple Session specifically, it started with me being a sales leader at my last company, having a problem that I could not solve with anything in the market, and just looking to solve my own problem of sales coaching, sales training, sales enablement at scale. And again, really not finding the solution in the market and just grabbing the smartest developer I could find on my team and said, "Hey, you know, what are you doing nights and weekends here? Because I need to build something that I can't find in the market that will solve my problem." And it really started like that. Uh, and then with that gradually the pieces started to fall into place where lo and behold, today we now have a company and it's now serving hundreds of customers and now developing something that's really new and innovative in the market.

Jake Aaron Villarreal: Yeah. Well, we're seeing a lot of services that are coming to bear from AI and helping automate and helping accelerate how companies do things, whether it's workflow automation or just in general better communication, better note-taking, better interviewing. A lot of really cool innovation. Let's talk a little bit about the coaching aspect. You know, there's so many different areas within businesses that need coaches. I personally have an executive coach and now that executive coach has got an AI coach. You know, so there's a lot of value in being able to call it 10x or 100x your time based on someone else providing content. What's the coaching aspect that you've identified in the space you're in?

Matt Doyon: So, the first piece is that any great coach is going to want data, whether it's qualitative or quantitative data. They're going to do a lot of talking to you about your background. They're going to know what your motivations are. They're going to know what your skills are, what's strong, what's not. They're really going to want to take the temperature as to what they're jumping into. So, piece one has to be starting and really moving forward with a coaching process with the best data that you could possibly have on the individual or teams that you're going to be working with. And what we found is just generally speaking, there's a big absence and gap in really complete data when we look at coaching. So, that's number one. We could talk about how we solve that later if you like, but number one is that piece.

Number two is really having the conversation as to how coaching should develop. I mean, oftentimes we kind of see teams jump into one-on-one coaching and working together without ever having that first conversation of "What are we looking to accomplish with this valuable coaching time, this one-on-one time?" So really putting a structure behind what coaching should be.

And then piece three would be a process. And in sales we talk about process a lot. If you think of discovery methodologies, there's an alphabet soup solution for whatever you want out there, from MEDDIC to SPICE to BANT to SPIN to you name it. And then when we get into coaching, it's like a free-for-all. Like whatever you want, however you want to do it, completely customized. And we saw that as a real big gap in having high-impact conversations. If we want high-impact conversations like we have in sales, we need a process that we can really learn and iterate and develop best practices as coaches. So that third piece of really instilling and really installing a coaching process is the third and likely the most important piece of what we do. It's just putting a formula behind coaching.

Jake Aaron Villarreal: Yeah. Got it. That makes a lot of sense. You know, we had a call before this a few weeks back and in 2020, your sales team was scattered working from home and you're looking at Gong and Chorus and Seismic and all these, you know, separate tools that should be talking to each other but aren't. Um, walk me through that frustration that made you say, "You know what, forget this. Let me go build something myself." What was that kind of final straw for you that said there's got to be a better way?

Matt Doyon: Well, I was using Gong uh and liking it, and I was really impressed by the data and the analytics, and then still finding myself and my managers sitting down and spending a lot of hours listening to recordings. So, that was the first hint that there's something slow and manual. "I still don't get a complete picture as to what I really want to learn when it comes down to how can I help my team get better." So when we think about really what to improve, it's never just looking at the revenue. We break the revenue stream down to individual process stages and those process stages down to the components of what goes into a great call. And then, you know, having to listen and spend hours taking notes and using spreadsheets... anything with a spreadsheet is an instant red flag for me that there's something going on here that's manual. It's data entry and likely not the best use of executive time. So, that was the first hint that, hey, there's something going on here that needs to improve in terms of a system.

And then the second piece was everything we were trying to do really came down to helping our individual people get better. 1% better week over week. And we knew if we could do that, the overall performance would improve, the revenue would perform, we'd get to where we need to go. And we were trying to do that in some pretty traditional ways. You know, let's review calls and figure out what's going on. Let's coach to that situation as best we could, even though the data was somewhat limited. Patching together CRM data and call data from listening. And then let's use training material, which we had a library of training material to pair that up and start to make recommendations and retrain and recoach and run role plays. But all these things were this constellation of separate initiatives that were just living in different places. And that was likely the biggest red flag.

But the next one that would come up is like, why aren't these systems talking to each other? Why can't I just see a call, understand exactly what's going on, recommend what needs to improve on the call, and then look at rollup data to say, "Overall, this is the stuff that you at the individual level should be thinking about in terms of improving your game, and oh, by the way, here's all the stuff that we've got on demand to improve it." Nothing was really connecting all those pieces together, even though we were trying to do it, we had it internally. Most of the teams I'd seen and worked with and talked to all had those assets themselves. They're just disconnected and scattered and not really working together as a force multiplier. And that was really the light bulb moment for me that this needs to change. It's just too inefficient when it's sliced up and spread around.

Jake Aaron Villarreal: Yeah, I hear you. Let's get tactical here. You're using AI to analyze every single sales call and automatically serve up best practice clips for top performers. What surprised you most about how sellers actually responded to AI coaching?

Matt Doyon: So, the first thing was I thought they were going to look at it like Big Brother. I thought they were going to say, "Hey, wait. You're looking at everything. You're calling me out. You're throwing the flag. You are pulling apart the stuff that I'm missing on calls and that's really uncomfortable and I don't like it." So, initially I was just skewing to the negative and thinking, "Ugh, people are going to hate being called out on the stuff that they miss." I was pleasantly surprised that they loved it. They wanted to know what the misses were. They wanted to be able to jump in and control that. So, a lot of the teams that we work with and a lot of the AEs that we talked to would actually want more assistance from their managers than they could possibly get because there are only so many hours of the day. So being able to deliver the gaps in their deals and really flag what was going sideways early so they could control it and jump in on it... They loved it and they love the assistance they were getting from it. That was clearly early stage the biggest pleasant surprise that we got.

Jake Aaron Villarreal: So when you hire new people that come in and you talk about how you're going to operate and the systems you're going to use and then you begin to give that to them to use, kind of visually for the audience, walk us through what it looks like. Are you logging into a system and is there like a coach, a video coach you're looking at or is it audio? Is it voice AI? Like walk us through the detail. This is for our new customers.

Matt Doyon: Yeah. So everything is set up on the back end with sales enablement, sales ops and sales leadership where on the back end we plug in the call system. So wherever meetings are happening, whether they're VoIP meetings, say like an Aircall, or video meetings in Zoom, Teams, Meets, we plug everything together with admins, and then we set up the scorecard structure that follows the playbook call by call. All of it done on the back end, and then we integrate to CRM. So by the time your onboarding analyst or customer success manager is actually logging in, the entire system has been set up and integrated, and they just log in and they start receiving the feedback reports either directly to their inbox or into a Slack message served up directly to them without them having to do anything.

So, we grab their call, we automatically connect it to whatever scorecard logic matches the call. We deliver the feedback report and make the recommendations and then nudge them over time with, "Hey, you know what? Jake has some calls that these clips show him going really deep into business impact with clients where they're great examples. Four minutes from this one, seven minutes of this one, six minutes of that one. Your calls are showing that that could be some area that you could improve in your game. Check out what he's doing over there." So now you can learn from others who are doing the job at a high level on the stuff that maybe you could improve.

And "Matt, we could see that you score high on these areas that Jake could use some help with. So, you know, you're always nailing down a next step at the end. Even if it's open, you're really getting the customer to commit to that. Jake doesn't always do that. So, we're going to grab those clips and serve them over to Jake to say, 'Hey, we can see from your scores on calls, Jake, you should really nail down next steps. Listen how Matt's doing it with three minutes at the end of that call, two minutes at the end of that one, four minutes at the end of that one.'" So, it really turns this engine of learning on from the best resources you could possibly get, which is actual people on your team playing the game at the highest level.

Jake Aaron Villarreal: It's so so smart. You know, when it comes to trying to get better, there's two approaches. One is you can get better after you make the mistake and then someone tells you what you did wrong and you just lost that million-dollar deal. Or you could have the preparation knowing ahead of time, "This is your weakness, and this is what you should consider doing or trying." So, you're bringing down your probabilities of failing big time and you're also preparing yourself to execute with success in that next call or that next meeting, which is great. So, it's really... it gives you the proactive insights about what you can do to get better, it sounds like, as well as practicing and then executing on those future sales calls. Is that correct?

Matt Doyon: Those two pieces. And then the third is because we flag things so fast—it's literally in your inbox two minutes after the call ends—it's like, "Hey, you didn't nail down who that key stakeholder is that is critical in that next call. You know, either get on the phone and say, 'Hey, I missed something here,' or before you send that summary email, put in bold right there, 'Hey, one thing that we didn't talk about is you mentioned that RevOps is going to be critical here. We should include them. Who next is the person that's best to include in that next meeting?'" And really start to shore up some of those gaps early so it's not just learning for the next deal. It's really starting to adjust the one that you're in before it gets too late and it goes sideways.

Jake Aaron Villarreal: Yeah, really cool. Yeah. How much of this that you're building is AI related?

Matt Doyon: I mean, most of it. Now, when we talk about constructing scorecard logic, we use a lot of call data. We use examples of top-ranked calls and we customize everything to the customer's process. So, when we look at version one AI, it was always big data. It was things like talk time and keyword analysis and cadence, things that are fairly easy to read today. The hard work is, what does a great early stage discovery stage one call look like in your company in the mid-market queue, not enterprise, not small? Like that one type of conversation is very unique even inside your business, let alone your industry, let alone sales at large. So we use AI to really craft really high impact scorecard logic. That's number one.

Number two is we need AI to really deliver output that's going to read those calls and get as close to having a great manager do that analysis as we possibly can. Sometimes we do even better than the managers because we catch stuff with AI that managers won't because they just lose attention. They get distracted. They can't do everything at scale. That's number two.

Number three, slicing up calls and putting them into a library of internal best practices. We call it the Moments Library. That's what I described a minute ago. Call clips from negotiating and overcoming objections and going back and forth against a certain competitor or business analysis or discovery or metric, whatever. We use AI to curate that library. So, it's automatically built when customers come in.

And then finally, AI roleplay is this whole new area that we've really gotten into this year and it's really gotten scary good at how close you can get to a customer conversation to practice but with AI. So with all of that, I mean, there's AI all over our product.

Jake Aaron Villarreal: Yeah. Really cool. So it's business-to-business. You're out there selling. If you are a prospect out there hearing this and you think, "You know, this is something I want to try," what's the business model? Is it subscription-based? Is it based on the amount of coaching calls you run through the system? How does it work?

Matt Doyon: Yep. It's a blended subscription with usage product. So, it's very similar to a lot of what AI teams are doing right now to make sure that we maximize impact but minimize waste. So, we look at the contract as a subscription. So, we want to install it for the agreed-upon timeline and the number of users that need it. But the usage-based is you pay really for calls that are running through the system and being evaluated and scored and given feedback. So we come up with a package of data that's going to be needed based on call volume and really build it out that way. So if you don't have as much call volume, you'll roll over and not pay for that. If you have more and you're getting even more value than we initially had projected, we'll look at that at the end of the renewal and start to customize based on that. So again, the idea is keep something in place that's easy to talk about internally with budgeting and finance and really stake what you're going to spend for the year, but at the same time not pay for just seats of users that might be on vacation for three weeks and not getting any value. If they're not using it for three weeks, you're not paying for three weeks. So we really flex to the new model of usage-based while still making it very easy to understand as far as seat-based.

Jake Aaron Villarreal: That's great. Matt, talk a little bit about the company. How long have you now been in the market? Have you gone out and raised funds? How big are you?

Matt Doyon: Two and a half years been in market. We raised a $2 million pre-seed round. It's all we've needed so far. We're pretty lean and efficient. We're running at break even now. Big in terms of revenue, we're just over a million in ARR. We've pivoted the business about a year and a half ago to this new AI coaching model. We first started as an on-demand academy of learning and then really graduated up that way. Uh and then we had just a recent breakthrough in the business in terms of demand generation which has now really started to flip the switch and really started to flow heavy deal flow. So it's great that we're talking now because I need to staff up the business. We're good in sales, we're good in product. We need to really build out our onboarding, our customer success teams.

Jake Aaron Villarreal: Yeah, that's great. You know, every company has to find their way, and you know, distribution is one of them. It's direct sales, it's partnerships, it's affiliates. What's worked for you?

Matt Doyon: Partnerships number one, far and away. We really found our niche when we were finding customers that were using a lot of the same tech stack again and again and again, but was non-competitive. So when we could see some of those same tech players popping up in our conversations and then integrated to them and then started talking to them, that's really what changed the game for us. Far and away the number one partnership that we have is with Aircall where we started to see Aircall come up again and again with our customers where either their entire sales flow was done just through audio only in VoIP using Aircall, or was a blend of "we're going to start conversations maybe with our SDR team or have Aircall and support but then our AEs and our AMs are all on video." We just plugged into those scenarios really really well and were able to solve challenges for those customers that nobody was really filling in. So we signed a partnership with Aircall that we are now their preferred vendor for AI coaching and enablement and that's really opened the doors for us for signing a number of customers and really signing our ICP. Uh it's just a great fit and it's easier to sign those customers because we know their system. We plug into it and we know the challenges that they have.

Jake Aaron Villarreal: That's great. You know, for first-time founders that don't really know how to approach those partnership opportunities, what's that process like? Do you identify and get a couple wins under your belt and then call them and set up a meeting and propose like, "Hey, here's an opportunity for a win-win," or what's the process you went through to strike that deal?

Matt Doyon: Yeah, it all starts with the end customer and really solving for the end customer in a complementary way that just fits together and delivers unique value to the end customer with the collaboration of the two products or the product and service and really how it delivers for the customer. That's number one. Uh number two, yeah, getting those wins early, getting case studies of, you know, I'll use Aircall as the example, "Yes, we have Aircall. We plugged in Triple Session and it's really changed the game. Now both of these products are far more valuable together than either one would have been separately." Hearing that from the customer is far more valuable than hearing it from anyone inside our business. So having that customer voice relayed internally, uh that's great. And the fact that Aircall uses us doesn't hurt either. So they know our product, they know our value, they see it, they use it, and really seeing that capability as a user and seeing their customers in there... that's really made the entire conversation go a lot smoother.

Jake Aaron Villarreal: Yeah. Well, I love the idea, the strategy, the partnership, the distribution, and where you're at as a company. Now you're in growth mode. You know, there's been a transition globally for companies that are starting, um you know, really from COVID where everyone worked remotely, then you brought people back in the office. We're seeing a lot of that transition happen now. You could work wherever in the world. You're building an AI coaching platform from Guadalajara, Mexico. Like literally in a territory that, you know, there's challenges and there's things going on. How does running a startup from one of the world's most dangerous regions shape your perspective on risk?

Matt Doyon: Well, as an entrepreneur, I'm pretty risk tolerant anyway. So with living in Guadalajara, when you live here and when you've been in the market, you kind of take it as tried and true. So, I've lived here a couple of times, just recently moved back from Boston. Honestly, you know, when we look at—and I just have, I think, a different perspective in terms of risk—I really don't see a lot of risk in either what I do professionally or personally because when you zoom out globally first as a startup founder, you have to look globally. When we talk about risk, what are the risks that we're really taking? We're not fighting a civil war. We're not living in dangerous parts of the planet. We're not one of the 800 million people on the planet that are looking for clean drinking water right now, otherwise they die. I mean those are risks. That's really a difficult situation. I'm sitting in a luxury condo in a very nice part of a city working in a SaaS startup. Any kind of risk I take is not, you know, a Navy SEAL who's jumping out of a helicopter into a war zone. I've talked to those guys. That's risk, right? So, that's number one.

And number two, in terms of Mexico, Guadalajara, everything that's going down here, you know, the news cycle will amplify good and amplify bad. And I could just say that on the ground, the amplification of what's really happening... is it real? Yeah. Is it, you know, a war zone? Not by any means. It's just a complicated time and a complicated country. And unless you're dealing drugs, which I'm not, you're pretty much okay.

Jake Aaron Villarreal: Yeah. No, I love Mexico. And everybody has their own perspective. When you really land and get into countries, you know, find out that the news isn't reality in a lot of places. I went around the world and went to 50 countries and it was... I never really saw any of the dangers. It was just like experiences and great times and a new perspective, a global worldview, and coming out of that helped shape our company, and we have people all over the world working for us. So, I'm on the same page as you and actually kind of jealous that I'm not in Mexico as we speak.

Matt Doyon: I'm a 48-year-old dad of three. I work, you know, in a WeWork. You know, I go to schools with kids. I go to soccer practice. Uh I go to playdates. It's like my life is not high risk.

Jake Aaron Villarreal: Yeah. I love it. What's the biggest challenge for I guess you right now as a company? You've got some momentum. You've got good progress. You've raised some capital. You didn't really need more in revenue. Things look great. What's the biggest challenge for the company currently?

Matt Doyon: Finding—and this is going to lead right into you—finding qualified candidates that can fill unique roles that we have in a unique business. Beyond sales. We're fine with sales. Obviously, it's what we do. It's where our network is. If we want to find a great salesperson, we can bring them in, train them up, and get them in place. Product, we're really solid as well, but some other very very hands-on roles, especially to deliver our promise to our client. Uh we need great people for onboarding, great people for customer success, great people for account management. And we deal with a unique client that has unique needs and is solving it with a very unique product. So, bringing people in that can understand our client, really know how to solve it, and really be savvy enough to solve it through our product... finding those kind of people is really where we need to lean into offers like yours to really help us out.

Jake Aaron Villarreal: Yeah. Well, that sounds very common from what we see. You know, there's like 1,500 AI startups launching monthly and they're all getting products into market and running as fast as they can. We're seeing a lot of go-to-market teams hired much sooner than we have in traditional startups.

Matt Doyon: Mhm.

Jake Aaron Villarreal: And also getting, you know, the right foundation teams in place and there's just a lot of demand out there, which is great for a lot of companies and it's great when you have the right strategy in place. What are the things that have worked for you in terms of hiring? You're really good at selling, you're really good at leading. When it comes to hiring, it's not always the same situation for companies. What are some of the things that have worked for you?

Matt Doyon: Uh, finding people through network really helps. Investors help. Uh, my immediate network. Again, I just mentioned I'm 48, so I didn't start my professional career yesterday. So, working with a lot of great smart people, they know other great smart people. And putting the flyers out on positions open, you can find a lot of people that get referred over to you that can fit a lot of those roles. So, that's number one.

Number two, just putting a process behind it. Um that's something I learned fairly early on in my leadership career. You need to be really measured and understand what are you looking to learn about someone at each phase of the interview conversation to really make a smart educated guess on something that you still kind of move relatively quickly when you're hiring somebody and it's a very important hire for the business. So being really careful about that.

Um and then number three, something I wish I had done earlier and I do now for everybody is homework. Like there has to be a project, there has to be an assignment, there has to be some qualifier that somebody's going to do throughout the process. Whether it's a role play in sales, whether it's building a process in our customer success or onboarding org, whether it's a product, um a product assignment in our development team, whatever it might be, it's like see somebody work in the small scale, something that they can't just fake in a verbal interview. That gives you a real clear window into how they think, how they work, how well they prepare, the level of detail they put into their work. There's nothing that can really replace that except asking somebody to do that work. It's been really really telling for us when we do that.

Jake Aaron Villarreal: Yeah, we see that happen on the engineering side and product design and even on you know different areas within operations. So I do think that there's good options to put people through, whether it's take-homes or simulations or just you know whiteboarding, just something to kind of see what they can do real time. But we always look at three things when we talk to candidates and you know talk to companies that are looking to hire, is you know, what are the things that you value first? So we understand as a company, what are the things that you want that person to have when they join? And then ask the ask the candidates things. But you first want to understand—you know, we call it the three C's—what's their competency? Do they actually have the background that you need? Do they have the character? And you know the character is something that you might not really get a full 100% grip on when you're just interviewing, but you certainly can get a sense of, do you innately feel like you can trust this person when you're talking to them? Do you feel like you like them? Do you feel like you could hang out with them? Do you feel like they're telling you the truth in these questions that you're asking them? Are they smiling? Do they have good energy when you're interviewing them? Are they sort of uptight? Like that type of character, does that fit you? And then the chemistry, like do they actually fit your culture?

Matt Doyon: Mhm.

Jake Aaron Villarreal: And those are kind of three like high-level filters, but we kind of start there to understand, you know, first understanding the company and what they're looking for and how they operate and the type of DNA they have. And then do the people that we're talking to have at least those bare minimums? I, as a company leader myself, the three C's or the three things that I look for when I interview anybody is I call it CEO. It's, you know, do I believe they have the right character? Do they have the right energy? And are they organized? For me, that's important. So, you know, we've seen a lot of people come through here and they're not organized. It's just like nothing really works well. So, those are like the easy things that we look for, but there's, you know, a list of a dozen other stuff as well. But excited to see the growth that's happening for you and where things are headed. Looking at 2026, it's just around the corner. What's on the roadmap as you turn the corner here and look at uh, like what are you excited about on the product or just in general?

Matt Doyon: Yeah, so I guess generally speaking this partner relationship that we have and the number of partner relationships that are really starting to mature, we're going to continue to invest in those and make sure that we really really spin those up and get the max value out of those for first the end customer and then our partners. And obviously if we take care of those two pieces of it, Triple Session will be fine in the end.

In terms of product roadmap, we're really investing a lot more on the LMS side of what we do. So we've spent the last year and a half really going deep into AI coaching and conversation intelligence and really maturing that side of the product. We have an LMS. It's internal. It has great courses. We've heard a lot of demand from our clients: "We want our own stuff in there." And the problem that we've seen with LMS in the market is that there are great tools out there that let you build a lot of content and then it sits on the shelf and gathers dust. And it is the bane of existence for a lot of enablement leaders who do all of that great work and then they're constantly trying to push it out to people on the team and get them to use it and get them to value it.

We have the system in place that can automatically pull people in, not push them, but pull them in just with the stuff that's most important to them and what we are detecting is where the real need is at the individual level. We want to empower our customers to be able to get their own content in there. So, we have their call clips, we have our library, now we have the demand that they want their own library in there. We're building the tool set that's going to allow them to bake that in.

Jake Aaron Villarreal: Got it. That's really cool. Well, you've got a lot going on there. I like the progress and the momentum I'm hearing and um it sounds like the arrow is pointing up, which is a good place to be as a company. Last question for you. Think big picture. You've been in sales for 25 plus years from individual contributor to scaling 100 plus person teams to now building AI that might fundamentally change how sales happens. When your kids are working, what do you think the role of a salesperson even looks like then?

Matt Doyon: Hm, so that could take a couple different directions, and seeing that far over the horizon today with how quickly things are moving... it's real interesting. So the first thing is I think we first need to look at—before we look at sales we need to look at buying behavior, and I believe that sales will reflect the buying behavior more than just forcing any differences on the sales side. So number one is how much is AI going to really start to impact buying behavior first, and then what adjustments do sales teams need to make to match in lock step how people are buying as AI impacts that side of the process and as the conversations mature. That's number one.

And then number two, again, literally when my kid, like my oldest son is 13, so if he decides to take up the baton and get into sales in 10 years from now, what is the world going to look like? I think data is going to be at the fingertips and AI is going to be that personal assistant in such a different way than it is today. Like, we're not going to have to look on social for anything. It's all going to be delivered and packaged right up. We're not going to have to really do a lot of homework in terms of who our buyers are, what they care about, what their business needs are. AI is going to deliver all of that. So like the pregame early stage industry information discovery, we're all going to be able to be industry experts and customer experts at the snap of our fingers because AI is going to do that heavy lifting to prep us in a way that we can't be prepped today or maybe it's starting but it's really not completely evolved.

So it's like, "Hey Matt, before you talk to Jake, here's everything that you should know about Jake. Here's his history. Here's his business. Here are quotes that he has. Here's what his industry looks like. Here are the industry trends." And you can now be a force multiplier in that first conversation by being hopefully the smartest guy he's going to talk to all week, all month, because we've served up all of this information that's made it hyper customized on him, his business, his industry, and now you can start to piece together where you may be able to work. I think we're going to get there a lot sooner than when my kids are going to be selling. I think that's going to happen a lot faster. And I'm starting to see signals of that already. We're not there yet, but I think that's really where sales is going to go and really where we're going to be able to optimize conversations.

Jake Aaron Villarreal: Matt, you're sitting side by side with Mark Roberge at HubSpot in 2012, watching them build the playbook every SaaS company now copies. Take us to that moment when you realized everything should be connected because that insight eventually became your entire company.

Matt Doyon: Yeah, I mean working with Mark was pivotal in my career and really the biggest thing I learned from Mark was systems building and how everything is interconnected. Each piece impacts the others and you really have to zoom out, look at everything, and then come down to the components and then break everything down to really understand, from hiring the right people, what are the components that go into that? Onboarding the people that you've just hired, what are all the great components that lead up to great onboarding? Ramping somebody, what does that look like? How do you measure it? How do you support people? How do you get them off the ground and really make sure the company is doing its piece? And then ongoing training and coaching and enablement and understanding how to not only maintain that person, but improve them over time.

Like Mark had this really intuitive knack of understanding the system at large and then being able to look at it at its most granular components and how they all fit together. And it was, you know, largely part of the ethos of HubSpot. That's what HubSpot's product was known for, connecting everything together and looking at how all these different pieces are just working better together when they're talking to one another. So when I saw that from a sales lens that Mark looked at it with, that's really what changed it for me and that's... I carried that with me in my next role as CRO of Rock Content and it certainly colors what we do today at Triple Session. Oftentimes I find myself talking about Triple Session as the HubSpot for revenue ops and enablement. It's like you can do the conversation over there, the LMS over there, coaching living by itself somewhere else. Or you can really look at these as all pieces of the same conversation and make sure the systems connect just like HubSpot does with sales and marketing. So it certainly colored my career, how I look at the world, and how we are building a product.

Jake Aaron Villarreal: I like that. Well, exciting times ahead. If anybody wants to find your company, where do they go?

Matt Doyon: Triplesession.com, just as it sounds. Um, LinkedIn, I live on LinkedIn. Matt Doyon should be the only one that you're going to find out there. That way to connect and get in touch with me. And then everything that we do is proof of concept, free trial. We get people set up really easily, really fast, so they can see the value of what we're doing with just a couple clicks. So, if this matches anyone and they're interested in taking it for a spin, we'll get you in. We'll get you seeing the value fast.

Jake Aaron Villarreal: If you like what we're doing, don't forget to subscribe, leave a review on Apple Podcasts or wherever you listen, and follow us on YouTube where we go behind the scenes to learn what it takes to be a startup founder.