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Carol Mahoney joins Warren Kucker to discuss Buyer First Is a Behavior, Not a Statement — Carol Mahoney on What Most Companies Get Wrong. Key takeaways include Buyer-first approach and AI coaching for sales.

EP. 12 35 min March 18, 2026 Recorded March 18, 2026

Buyer First Is a Behavior, Not a Statement — Carol Mahoney on What Most Companies Get Wrong

with Carol Mahoney

"Buyer-first approach requires actual behavioral change, not merely strategic positioning statements."

About This Episode

The episode explores buyer-first methodologies in sales, examines AI coaching applications for sales teams, and highlights mindset's importance in driving sales results. Carol Mahoney discusses understanding buyer perspectives, developing AI coaching technology, and how psychological orientation influences performance outcomes.

About the Guest

Carol Mahoney

Sales coach, Buyer First author, and Unbound Growth founder who transitioned from eliminating sales roles to becoming a prominent data-focused authority on seller adaptation to modern buying patterns.

Key Takeaways

  • ✓ Buyer-first approach
  • ✓ AI coaching for sales
  • ✓ Role of mindset in sales

Chapters

00:00 The Buyer-First Approach
10:58 AI Coaching for Sales
18:02 The Role of Mindset in Sales

Show Notes

Buyer first is something you do, not something you claim

Carole Mahoney, a sales coach, author of Buyer First and founder of Unbound Growth, started out running an inbound marketing agency with a mission to remove the need for salespeople. It did not last. However many good leads she generated, her clients' salespeople burned through them because they did not know how to sell to today's buyer. So she learned to sell herself, working with a coach through Objective Management Group, whose data set she now uses to evaluate and coach teams.

The gap she sees most is between what companies say and what they do. Almost every company calls itself customer centric, but when Mahoney asks who their buyers are, they don't have answers and certainly no documentation.

being buyer first is more about a mindset and a behavior than it is a statement that you make.

The contradiction shows up in hiring, when companies hire a competitor's salespeople who may not match their buyer, and in compensation, when leaders say "buyer first" and then tell reps to hit the number no matter what. Mahoney argues pay should reward winning the right customers, the ones who stay long and refer. It shows up in messaging too. She scores copy for what she calls the "wee-wee factor": how much a company talks about me, we, I and our products versus the words that matter to the buyer. One client struggling to show up in AI agents and search engines could not say what question their buyer asks first, so she typed it in to show them what the buyer was actually seeing.

Ask questions to understand, not to set up the pitch

Mahoney separates two kinds of discovery. One collects the information needed to pitch the product. The other tries to understand what the problem means for the buyer personally and professionally, how urgent it is, whether they should change at all, why now rather than later, and why the solution is worth the money. Buyers tune out sellers who only do the first.

A rep who adopts this approach inside a company that doesn't becomes "the thorn in the side" of the organization. Either they leave, taking the company's investment with them, or they regress into old habits and end up back on a plan. That is why her next books target managers and leadership, who have to build the culture and systems that support the behavior.

Onboarding should start with the buyer, not the product

Mahoney calls onboarding the most important step after hiring. A perfect-fit hire dropped into a bad environment will still struggle through the first 90 days.

Her version immerses new reps in the buyer's world before the product: meeting buyers, talking with them, watching videos of buyers on sales calls. Only then is the product mapped to each persona's problem, in small chunks that can be applied right away, so that by the end of week one a new rep can hold a short conversation that tries to schedule a meeting.

The loop then alternates between AI and people. Reps certify in a role-play simulation, take real calls, and work with a manager on what was going through their mind. The real call feeds back into the AI, which scores it, assigns the next small chunk, briefs the manager for one-to-ones and writes to the CRM.

There's no reason why people should be entering information into a CRM manually anymore. It's ridiculous.

Removing that repetitive work also changes span of control. Mahoney puts the ideal at eight to ten reps per manager and says that number can grow while each rep gets more one-to-one time.

The buyer knowledge is trapped in someone's head

Kucker asks whether reps misunderstand buyers because of poor training, siloed knowledge or knowledge lost altogether. Mahoney says it is mostly knowledge that isn't easily shared. It sits with a founder, product manager or engineer who is too busy to document it, and others don't know which questions to ask.

She gave a young woman joining a scientific startup as an early sales hire a list of questions for the engineers, who code for buyers' workflows and should know them best. Earlier in her career, at a company that built software for mapping the ocean floor, her best source was the chief technical officer, who went out on the boats to see step by step where users struggled. The company also kept geophysicists and hydrographers on staff.

So I would say the easiest play here is to hire your customer

Where that isn't possible, she has Harvard Business School students use AI to research a buyer's role, such as a chief innovation officer at Ford: a day in their life, how they are measured, what they need to know. Kucker adds a structural cause. Reps change jobs fast, often because quotas are too ambitious, while the sellers he sees do best stay 10 to 15 years in one industry, where there may only be 3,000 to 8,000 potential buyers.

Role play that learns from real buyers

Mahoney is building Learning Games because existing tools that link assessments, buyer profiles, practice and deal feedback are designed for Fortune 500 companies. Small and mid-sized companies can't afford them, so her platform lets coaches build the same thing for those clients.

The problem she wants to solve is measurement. Weight loss shows up on a scale; communication and negotiation habits only show up in lagging results, so students and clients keep asking whether they are getting better, and without that feedback they give up. Her answer is an AI buyer trained not only on a LinkedIn profile but on real calls: actual objections, facial expressions and tone of voice. As the rep improves, the scenario gets harder, and the insights gathered become a way to capture buyer knowledge that used to live in people's heads.

Kucker recognizes the problem. The cold call role play he warms up with keeps raising objections about why his product isn't as good as Gong's, which are not the objections he hears on real calls. A friend described Mahoney's goal as a holodeck for sales training, and the long-term plan is a video game interface. For now the team is building the AI first.

The project is also personal. Learning to sell let Mahoney design the life she wanted for herself and her kids, and she wants to bring the platform to shelters so others can do the same.

When bots talk to bots, the human conversation becomes the luxury

Looking two to three years out, Mahoney sees buyers using agents instead of search engines, and a rise in automated dialing, email automation and AI comments on LinkedIn. She hopes for labeling requirements like warnings on cigarettes, but expects bots on the receiving end to filter automated messages either way.

the human conversation is going to become the luxury commodity

What works now, she says, is small, moderated, peer-to-peer gatherings such as workshops and dinners where curated groups talk openly. She compares it to cheese: anyone can buy the mass-produced kind, but some people pay four times as much at the farmer's market and tell everyone about it. Those are the buyers to target.

Kucker agrees the cold mass outreach boom of the past seven years is largely over, but notes that being where buyers are makes it hard to build a hundred million dollar company in four years. Mahoney's answer is to become the place buyers want to gather. She also sees investors shifting from how fast a company adds customers to how many it keeps and how their lifetime value grows.

Full Transcript Show

00:14 Warren Kucker: Hey there and welcome to another episode of Selling AI. Today we're diving into the psychology of selling, why mindset matters more than activity metrics, and what happens when you build AI that actually coaches sellers on behavior instead of just drilling them on scripts. I have Carol Mahoney on the show today. Carol is a sales coach, author of Buyer First, founder of Unbound Growth, and she's been training and assessing sales teams for over a decade using hard and fast competency data. Here's what makes the conversation interesting. Carol isn't just advising sellers on how to use AI or how buyers use AI to evaluate products. She's building her own platform called Learning Games. It takes a seller's actual assessment data, their deal history, their market, generates training and role play scenarios for them. So in today's episode, Carol and I talk about why buyer confidence matters more than overall call volume, how she hires and trains sellers across wildly different industries, and where AI coaching ends and human coaching has to begin. All right, I'm super pumped for today's conversation. Let's get to it. Welcome to the show, Carol.

01:10 Carole Mahoney: Hey, thank you so much for having me, Warren. This is becoming such a fun conversation for me lately. I'm excited.

01:16 Warren Kucker: Awesome, I'm pumped. Our listeners are gonna get a lot out of this. just a little bit about your background. You went from like starting an inbound marketing agency, running it, and I believe it was HubSpot, correct me if I'm wrong, I think I'm right. And then kind of journeyed into being a sales coach. Maybe not a typical career culture, a move in that they're kind of two different skill sets, so impressive.

01:34 Carole Mahoney: Yeah.

01:35 Warren Kucker: Walk us through what pulled you into the sales world. Give us a bit about that journey.

01:39 Carole Mahoney: I mean, I was a bit pulled in kicking and screaming, I like to say the whole way. When I first started my marketing agency business, before I even became a HubSpot partner, my mission was to obliterate the need for salespeople, right? SEO, the new technology is gonna replace salespeople, sales is dead. Sound familiar? And it wasn't too long after that, that no matter how much good leads that I would generate for clients and their salespeople would take those leads and burn right through them. They couldn't close them, they couldn't... you know, do anything with them because they didn't know how to sell to today's buyer. And so even though I wanted to let, you know, remove the sales person from the equation because pushy, slimy, sleazy, nobody wants that, to realizing that salespeople are the ones that now need to adapt. We've done it in marketing. We've mastered inbound marketing. We can generate the leads with the right people who will raise their hand and say, I'm kind of interested in talking to you. Now salespeople who can adjust to that. And what I found is that so many struggled with it because they couldn't grab the concept of how to change the behaviors. It's always worked this way. Why won't it work this way now? And so if I was going to complete the other side of my mission, which was to help small businesses to grow and to scale and to create more jobs to further our economy, then I'm going to need to teach them how to sell. And if I'm going to teach them how to sell, then I need to learn how to sell, which means I also needed to change how I thought about sales and my own mindsets for sales. So I worked with a sales coach through Objective Management Group, which is the data set that I use to now evaluate and train with and coach with all of the teams that I work with and individuals. But the mission for me was then not to obliterate the need for salespeople, but to get salespeople to adapt in such a way that the perception of sales changes from the buyer's perspective, that we don't have buyer's remorse anymore, that salespeople cannot, they don't have to feel icky about the work that they're doing because they are truly trying to help people. I think that AI can be a major part of that for us, but I also think that it's a way we can also teach salespeople how to sell in a more, I don't know, user-friendly way. Like stop teaching people how to do things the way we did them in school and sit there and watch a lecture and then take a quiz and then try to apply it. That's just not how we learn anymore.

03:47 Warren Kucker: Great segue into, let's say, our first topic conversation. So you talk a lot about a buyer-first approach to sales. What

03:54 Carole Mahoney: Yeah.

03:55 Warren Kucker: does that actually look like in practice? And when you're coaching a seller, how do you kind of coach them to have that buyer-first mentality?

04:02 Carole Mahoney: And one of the things that I find a lot of companies say is, course we put our buyers first. We put our customers where a customer centric organization, or as an entrepreneur, you think, of course I'm putting my buyers first. Like I'm talking to them every single day, but being buyer first is more about a mindset and a behavior than it is a statement that you make. And even though they will say that they are buyer first, if I go in and ask them about who their buyers are, they don't have answers. They certainly don't have documentation around that or anything that's built around that. So they don't have a true understanding of their buyers. Somebody has this perception, someone else might have this perception. And it's very rare that you also, you see that understanding, that deep understanding of the buyer. And then if they do have that, oftentimes they're not aligning who their buyers are to the salespeople that they hire. You know, they're hiring their competitors, you know, salespeople who might not be the same type of buyer that you have, or, you know, someone who has a lot of industry knowledge and they just need to learn how to sell. is actually matching that with their buyer and focusing on their messaging from the buyer's perspective. What is their problem? What does it mean for them? What happens if they don't solve it, both personally and professionally? Is that important enough to do something about now instead of talking about their products first and their features first? Something that happens on both executive roles and enterprise roles, as well as small business owners. We know our stuff. We want to talk about our stuff and what we do and how we do it. easily do that in override and thinking about what is that the buyer actually needs? Are they even the right person for this solution? Maybe we need to tell them, go to do this instead. Instead, it's win at every cost, do everything you can. Oh yeah, we're of course, we're buyer first, but make sure that you hit your number no matter what. It doesn't align. And so being a buyer first is not just saying that you are and not just knowing about who your buyers are, but living and breathing it on a regular basis. interacting with them on a regular basis. That's how you also stay ahead of the trends of where your buyers are going and what they need and setting up your compensations and structures in a way that incentivize not just winning at all costs, but winning the right customers who stay long and refer us when those ones at all costs. And even in your marketing messaging, having it, I sometimes will analyze marketing messaging just for fun. And I'm building out a platform for that in the AI, but where I call it the wee-wee factor, where we look at how much are you talking about yourself, me, we, I, ours, and our products versus how much are you talking about your buyer and the words and phrases that matter to them? And then emails or web pages, whatever content there is. And so it's just amazing when I apply that filter sometimes to my clients when I'm training and coaching them, how simple it becomes for them. And for example, I'm working with one company and you know, they're struggling to get to bring in leads and they're struggling to show up on the agents and the search engines. And they're like, well, what do need to do? I'm like, okay, so what do you think the first question your buyer is asking themselves when they encounter this problem? And they didn't know. And so I typed in, how do I know when I need X, Y, and Z? And I'm like, this is what they're seeing. And so if this is not what you're saying to them, then you're never gonna get found by them and nor are they gonna really feel that you understand them. and you're gonna then impose a process on them that doesn't align with how they're gonna even make this decision. So it goes from that and all the way through to how your salespeople and how you interact with your buyers. Are you asking questions just so you can find out the information that you need to then pitch them your product? Or are you asking questions to really truly understand what's going on with them, where they're coming from, what it means for them, how urgent that is, why they should make a change if they should even make a change, why they should do it now and versus later, or maybe if it's too late. and why your solution is the right solution or not, why this type of solution works, why it's worth spending the money. If you can't talk in those kinds of languages and questions, buyers are going to tune you right out. You're just like everybody else. So it's, it's, that's a mindset that you have to have. Now I'm working on two other books. The next one is seller first, because I've worked with salespeople who have taken on this mindset and methodology and they become the thorn in the side to the organization. That's not truly buyer first. It's this constant conflict. so either the salesperson leaves to go somewhere else where they are, and the company loses the investment in that salesperson, sometimes top producers, or they regress back into their old habits. And then they get put back on plan again, and then they're not succeeding as well. And so that's why I'm writing the next two books for management and for leadership, because you also have to set up the culture and the structure and the systems that support this type of behavior and mindset. but I wanted to give it to salespeople first and small business owners first so that they at least know what they should do next rather than waiting for leadership to figure it out and to trickle it down to them.

08:37 Warren Kucker: Yeah, so, and that's actually a dovetail into where I wanted to go to. So when you engage with companies and you're talking to leadership, a decent amount of your consulting is around hiring and identifying the right people to sell your product or service, right? But let's say the next step in this buyer-first mindset, have you put in like tactical programs for them to be onboarding or training their reps to be buyer-first and what does that look like?

09:00 Carole Mahoney: Yeah. And so hiring the right person is the first step. Onboarding them is really the most important step because you can hire the best salesperson who's perfect for the role as you've described it. But if you aren't able to onboard them well in the 90 days that they're going to be there to set them up for success, it's going to be, they're going to struggle. And then you're going to wonder why I thought they were the perfect fit, but you know, you can't take a perfect fit and put them in a bad environment and expect them to be able to function that way. And so having a onboarding program that is also buyer first. So instead of talking about your products first and what they do, talk about your buyers, immerse them in their world, introduce them to your buyers, have conversations with them, show videos of them on sales calls and how they react to things, embody it as much as you possibly can. Then how does your product and service align with that particular buyer persona's problem and all throughout the organization? and chunk it into small areas of information that they can apply right away so that they don't get overwhelmed in that information. So by the end of week one, they're able to have a minimal introductory, try to schedule a meeting conversation with that particular persona. And so buyer first, understanding their world, its application then to what products and services you offer and then get on the phones with them, real life. And getting those repetitions in, certifying that their knowledge, not that they just know what to do, but that they go in a role play simulation where they actually then have to pass that, just then get on the phone with the actual buyers that gives them coaching of, improve here. And then bringing in the manager when you have to deal with, okay, so you've practiced it this way in the role play, let's have the human conversation where you're not always, it's a different dynamic than talking with the best AI machine that you have, right? And have the manager do that and then work with them on the fine points of, right, what's going through your mind here? And where does that come from for you? And what's a better way to approach this for you? Let's practice that again. And digging into even the personal side with them of what might be getting in their way of doing a particular thing. And then having that human approach, do it on the call with that particular buyer. Take that call to then inform the AI of. What is it that went well? Score them on that and then continue to give them, all right, here's another microchunk for you to work on. Sharing that with the manager so that they know what to do in their one-to-ones with them. And even in their group sessions to group them in that way and feed it to that all that information back to the database in the CRM. There's no reason why people should be entering information into a CRM manually anymore. It's ridiculous.

11:28 Warren Kucker: Right?

11:28 Carole Mahoney: So all of that to be able to get them to ramp up faster. in micro sections that are focused on the buyer first and their world, and then bringing in the products and services that you sell when it's appropriate for them to learn those pieces. So stacking in the habits, interacting with both AI and human. And it's interesting is that if you can apply this type of methodology, then you think about how many managers can handle a team of salespeople. Like the ideal number is between eight and 10. If you take away a lot of the repetition and manual tasks that a manager needs to do, Not only can they spend more quality one-to-one time with their team, but you can increase the number of team members that they're under. So

12:06 Warren Kucker: Thanks.

12:07 Carole Mahoney: it's efficiency play, but it's also aligning with how we actually learn today and change those behaviors and focus first on the buyer. so that it's less of a overload of information under the pressure to meet a quota really fast. We're stacking that so that at the end of 90 days, they're walking into it like they've been doing it forever.

12:27 Warren Kucker: That's really a really good call out and I wanna dig into the role play piece of this and this question actually might take us into it, but it might not. So

12:34 Carole Mahoney: it

12:34 Warren Kucker: you talked about it earlier, like there's a gap in reps understanding the problems of people that are buying from them, right? In any scenario, right? Someone that walks into

12:41 Carole Mahoney: Mm-hmm. Yeah.

12:43 Warren Kucker: a showroom looking to remodel an area of their home, someone that's trying to buy a piece of software. That gap exists. There's a couple of reasons why it could exist, right?

12:55 Carole Mahoney: Yeah.

12:56 Warren Kucker: the training that's being done isn't good enough, right? Or there's actually not enough people in the organization that truly understand how their prospects work, or there's no one that truly understands how their prospects work. And in this scenario, I think what you run into is at some point there were people that understood how your prospect works and what they care about, but

13:17 Carole Mahoney: You know?

13:18 Warren Kucker: there wasn't enough of them. And it basically ends up happening where those people that even are still there, They're so buried in how they do it now that they forget how it happens alternatively without them. Do

13:28 Carole Mahoney: Right.

13:28 Warren Kucker: you feel that like one of those three things is more prevalent, a lack of training, a lack of like the knowledge is trapped in silos or the knowledge is just kind of lost altogether?

13:38 Carole Mahoney: It is, I would say it is definitely the lack of knowledge or the lack of knowledge that's easily shared. It's usually trapped in someone's head. That

13:46 Warren Kucker: Right, yeah.

13:47 Carole Mahoney: person is typically the founder or someone who's in the product management side or the engineering side. And they're too busy to then document that. And people don't even know what sometimes questions to ask them to really get the information that matters. Ironically enough, I was mentoring a young woman this morning who was trying to get into an organization. and she would be one of their first sales hires. And it's a startup, really cool application in what they do. I'm a science nerd, so anybody who's doing something scientific, I'm all in. And it's interesting because she's like, you know, I'm gonna have a conversation with the engineers and I'm like, perfect. Because if you're gonna have to go in there and start figuring out the documentation to figure out how to translate all of this technical to everyday language in sales and marketing, then you're gonna need to talk to the engineers who should know the buyers the best because they're the ones that are- coding for their workflows. And so I her a list of questions to ask about your customers and your buyers so she could extract that information to then like, is how I would go to market. This is how we would sell to them kind of conversation. And even in the work that I do at Harvard Business Schools with the students and we have millions of case studies, it's always if you can operate from the mindset of your buyer, put yourself in their body, in their world and think about. You know, in this case, we were talking about them selling to large companies who are doing prototypes for particular things. And I'm like, okay, so if you're the chief officer of innovation at Ford and you need to figure out what the next Model T scheme is going to look like for it to have the zero dynamics, what is it in your workflow that you need to fix? That's a challenge for you right now. So like really getting into the role and into the head to understand what that might look like and use AI to go type in the What is a day in the life of the chief in innovation offer at a company like Ford and how are they measured? And what are some of the certifications and knowledge that they need to have? You can find that information out relatively easily, at least a sense of it. And so if you can operate from that as a filter, everything else starts to become a little bit more clear and easier to figure out what to focus on, what to practice on.

15:48 Warren Kucker: That's That's a great approach to this particular problem, which I think is prevalent and I don't think it's gonna go away because I don't think we'll take the right steps for a while to actually get there. I actually think the velocity at which people move around sales jobs makes this a little bit harder to kind of

16:03 Carole Mahoney: Mm-hmm.

16:04 Warren Kucker: corral. And most of that velocity is actually because people aren't making enough money because their quotas are too ambitious, right? So it's

16:09 Carole Mahoney: That's true. Yeah.

16:12 Warren Kucker: a structural problem that needs to be fixed. I've actually talked to a few people. that are lifelong sellers in the same industry. And it may not be the industry that they would have chosen to start or the sexiest industry from the outside, but after 10, 15 years, could sell any piece of technology within that industry. know every industry is smaller than you think. There's 3,000, 5,000, 8,000 potential people that could buy a piece of software in that market. Having

16:34 Carole Mahoney: Yeah.

16:37 Warren Kucker: that insider track really gets valuable, but it takes a long time. You can't hop between six industries in order to get there. So it's an interesting, it's interesting play. still think that people really struggle to understand the day-to-day workflow that they're trying to solve for. They just speak to it in a cursory level.

16:52 Carole Mahoney: Yeah. I think I've also, because I came, my first SaaS tech job was actually Salesforce 2.0. So SaaS was just beginning to be a thing. And so I

17:01 Warren Kucker: Okay.

17:01 Carole Mahoney: worked with a company who did a visualization software for mapping the ocean floor. So think of hundreds of millions of billions of data points between asymmetry and biometric and all of the different types of data sets that they would then create a 3D environment for scientists to fly through, to analyze the ocean floor, to lay pipes, to figure out where to dredge, to all of that. figure out where country lions are on the ocean floor. And what was interesting is that I was one of the first sales and marketing roles in the company. And what I found most helpful was I worked with the chief technical officer who would go on the boats to figure

17:35 Warren Kucker: Mm-hmm.

17:36 Carole Mahoney: out what is it that they're doing step by step that is causing them challenges, maybe that they don't even realize that there's a better way to do that. And he then took that and like, here's what we need to create, here's what we need to do. And we also had... geophysicists and hygrographers that were on staff as well that could do those things. So I would say the easiest play here is to hire your customer, you know, and go

17:59 Warren Kucker: Yeah.

18:00 Carole Mahoney: to work with them. And there's so many different ways that you could creatively do that to make that a part of your onboarding program. And, you know, I have this vision for learning games that we can turn it into something that is actually enables us to create that kind of an environment where it's almost like you can be on the ship with that person and see what their workflow would be like, and then be able to decide, what do I need to know about this in onboarding salespeople or anyone in your company?

18:27 Warren Kucker: Now, so that's a great pivot. Let's dive into a little bit of learning games. Tell us what you're building, like why you're building it, what problem it solves. Give us a little bit about learning games.

18:36 Carole Mahoney: I think I'm one of those, those tech founders who decided to create something because they couldn't find the, thing that they wanted the way that they wanted it to solve the problem that

18:44 Warren Kucker: Yeah, that's a way to do it.

18:45 Carole Mahoney: we had. And, you know, it's interesting because there are technologies out there right now that described what I just said. Like you, take an assessment. It's based on that particular profile aligns with who your buyer is, does that practice gives that feedback back to the, I fees it to the deal. And like most things, especially new technologies, it is primarily designed for the Fortune 500 companies, right? Where they have thousands of salespeople that they're trying to work through. The small business owner, the mid-size companies though, they can't afford that technology yet, nor would they even know how to apply it because they're not at that stage yet. So I've been trying to create a platform whereby... And in one area, other sales coaches or other types of coaches, executive coaches like me can use this platform to do that for their clients. They're small and mid-sized clients, whether it's teaching them how to be a veteran executive leader or negotiator or entrepreneurial salesperson or small business owner or whatever it might be. So creating a platform for them to be able to create their own. then using that, I want to be able to then scale it to the point where we can create, actually instead of a... of a UI where you're looking at something on a screen, that there's a video game behind that. Because the way that we learn in real environments, like how can we create as real of an environment where our buyers are as possible to immerse ourselves literally in their world? And then be able to use that to help people to learn faster, be engaged in that learning. So onboarding becomes more fun, becomes more sticky. People can ramp up faster in whether it's a sales role or a security role or an engineer role. by really immersing them in the world of the buyer and then how you're able to solve those particular things. And I have a couple of other crazy ideas after that, but I'll let you know once the patent's filed.

20:26 Warren Kucker: That will do.

20:28 Carole Mahoney: I want to change the way that people learn. And I also want to change the way people learn specifically for sales to start. And the reason is because when we think about behavioral change, it's difficult for us to measure, right? Like if you think about losing weight, that's a... A behavioral change that you can measure. can measure yourself, can measure your weight, you can track your calories and things like that. But changing like communication behaviors, changing how we think kind of behaviors, how we interact and how we negotiate, those aren't as easily measurable outside of lagging things that tell you whether you did it well or not. And so I want to be able to give people that kind of feedback because one of the questions that I get over and over again from students and from clients is, am I getting better? How do I know if I'm getting better? because we need that encouragement to keep learning and to keep growing and to keep trying. And it builds our confidence with every improvement that we make. And so like, let's use losing weight. If you're doing all of the exercise and you're eating right, and you're doing all the things that you can do, but the scale isn't moving, what's going to happen? You're going to give up. So

21:29 Warren Kucker: Okay.

21:29 Carole Mahoney: how do we do that for behavior? And when you focus on it from a sales perspective, it's measurable in the activities and the outcomes. And so if I can take that knowledge and apply that to other types of behaviors, knowing that it works in here in a high stress situation where money is on the line and you can't get much more high pressure than that, how do we apply that to other aspects of our behavioral changes in life? So I have that kind of dream for it. And then it ultimately came to life because it was more of a personal legacy project. And when I When I left my ex-husband, who was, let's just say, not a good person, he told me I'd never amount to anything. Without him, I'd end up flipping burgers at McDonald's somewhere. And what happened was, when I learned how to sell, I was able to design a life that I wanted for me and my kids, not a life that I had to settle for with someone like him. And so now I want to take this platform, and I want to take it and put it inside of... like shelters where women or anyone else who is coming out of an abusive situation can go and can learn these kinds of career skills so that they too can design that kind of life for themselves.

22:36 Warren Kucker: Great.

22:36 Carole Mahoney: So it has a personal mission to it as well because I want to make it accessible to everyone, not just those who can afford it or who can go to Harvard Business School to get the education because we teach it there or any business school, but it can be taught to anyone, anywhere.

22:52 Warren Kucker: Right, right. No, I mean, it's always great. It's great to have a business idea like this rooted in a personal mission. Both on your emphasis on small to medium business and then like, again, rooting this in shelters or people that are less fortunate and don't have the ability to spend the time or the access to the platforms to help them develop those skills.

23:12 Carole Mahoney: Mm-hmm.

23:13 Warren Kucker: the role playing side, you kind of mentioned that like you built something because you knew there was a gap that you experienced yourself. This role-playing piece is like, always kind of like, for the past few years, been out there in the ether, but like hard to execute.

23:26 Carole Mahoney: Yeah.

23:26 Warren Kucker: Where do you feel like maybe it fell short in the past? And what do you think is the key that you're kind of like putting in front of people now to make it effective, fun, and like measurable in the ways that you talked about it? What do you think the leap is here that's really valuable for folks?

23:41 Carole Mahoney: I think the leap is here is the role plays are getting better. But I want the role plays to also get better because they're learning based off of the data that they're getting from their buyers. And so training the AI to act as the buyer, not just based off of the input that the salesperson puts in. That's a start. Like, you know, what's their LinkedIn profile, scanning through that, you know, other social profiles so that the AI can gather information about that particular buyer. But then also using the calls that they have with those particular buyers to also train that AI. to act more like their buyer? What are real world objections look like and sound like? What do they look like? What are their facial expressions? Their tones of voice from wherever. And so being able to use that data so that even as they're doing it, the AI is learning and as their skills increase, the AI starts to make it a little bit more difficult. And so it's stacking the difficulty and the efficacy of it as it does it more and more. And then I think ultimately too is that you can then use a lot of those insights. We were talking before about how difficult it is to sometimes get that information about your buyer out of the heads of the people, that's where that information can now come from. And so instead of trying to extract it out of the heads of those people who have it or who can only apply it because this is how they did it then, now we can take real world insights from this to understand what is it that our buyers are actually saying and needing and what their world is like. Because the salespeople are not only getting better at asking the questions because of the practice, the AI is learning and getting and gathering those insights as well.

25:10 Warren Kucker: Absolutely. I couldn't agree more. That's really good approach to tackling this problem. And I'm looking forward to seeing the ways that you solve it. So that's fantastic. I think the access to current conversations and transcripts and feeding that in so it's not a stale. I think part of

25:26 Carole Mahoney: Mm-hmm.

25:26 Warren Kucker: the reason that role play doesn't work very well is you role play two or three times with the same, let's say, AI. It

25:33 Carole Mahoney: Yeah.

25:34 Warren Kucker: just gets repetitive, right? So there's a cold call role play that I use. It's great, I use it to warm up before my cold calls. The objections it gives me are always about my product and rather than like typical objections. So as soon as they get into that part, I like kill it. And I only took like

25:47 Carole Mahoney: Great.

25:48 Warren Kucker: three times to realize that, that I'm gonna get an objections about why my product isn't as good as Gong's, which I don't mind those objections, just they're not the objections I get on cold calls, right?

25:56 Carole Mahoney: Right.

25:57 Warren Kucker: It's not going to change unless you evolve it, right? So that's a really good way to put it.

26:00 Carole Mahoney: Yeah, it has to be, yeah, it goes back to that it has to be as real world as possible. And, you we're gonna, it's gonna grow and scale from there, but I want it to be as real world as possible because that's what's gonna engage the person's brain to make it more applicable. And if as they're improving and we know exactly the AI knows exactly where to push their buttons that they need to improve on, then, and be able to then adjust for that as they get better. And I think that's the key for it. I laughed in one of a friend of mine, he said, So you're trying to like basically create the halo deck for sales training. I'm like, yeah, kind of.

26:33 Warren Kucker: like it, I like that approach. In that vein too, you talk about gamifying it, making it a video game. What are your thoughts, like how are you going to do that? Let's say in the sales context, I know you're looking at a broader context. How do

26:44 Carole Mahoney: Mm.

26:44 Warren Kucker: you make it so a rep actually kind of enjoys doing it? It's not just a kicking and screaming training exercise. And then

26:51 Carole Mahoney: Yeah.

26:51 Warren Kucker: also, again, you run into this feedback loop, which I think is just a continual problem, like how do I know it's doing anything, right?

26:56 Carole Mahoney: Okay.

26:57 Warren Kucker: How do you think you'll gamify it? I don't think you've done it quite yet, but how do you think you'll do it in the future?

27:01 Carole Mahoney: I've been the future. thinking that I want to it's basically you're changing out the interface. And so how do we take that interface and put it into a video game type of an environment? mean, I remember when video games were the click on the screen thing, you you went in to help to find the princess and the clues and all of those types of things. Like we've gone from that to like virtual reality. And so if we can design the game based off of what the AI is giving us to the input in, then we can create that kind of environment where people are, it's like you're playing a video game with your buyer. And And gamifying is it that way in the actual learning of it. So it's not just a learning management system, it's an application learning management system where they get to apply it in as real of an environment as possible. And so, yes, we're talking about how we can do that. We're at that first stage of building out the AI first, and then the next stage we'll be looking at how the interface actually works.

27:54 Warren Kucker: Awesome, that's great. Okay, cool. Let's say maybe a little bit of last question here, then I'm sure it's gonna be good a couple other questions, why I hedge

28:02 Carole Mahoney: Okay.

28:02 Warren Kucker: my bets there. You've been, I say coaching for 10, 15, 20 years and lead gen a little bit before that. How do you think things might shift over the next two to three years? Based on the way tech is going, how buyers are behaving, how sellers are developing themselves, what do you think might be a... moderate to major shift that happens in the selling or buying cycle in next three years.

28:25 Carole Mahoney: I mean, I think we're already starting to see it that people are increasing using agents to find things that they would normally go to a search engine for. So how are you being, how are you being found through agents? Number one. I think that's going to be a big part of it as well as people. The other thing I think that's also changing and I'm seeing both of these things already. And I think it's only going to accelerate is the automated dialing. the email automations, we even have AI bots now making comments for people on LinkedIn. People can still suss those things out. There's gonna become less and less tolerance, I think, for those things. And there's probably even gonna be, I'm seeing like, we have to put safety measures on cigarettes kind of thing. Like people are gonna be required to say this was generated by AI or something along those lines for the transparency, because I think people are gonna start to demand it. That's my hope. I know I would probably demand it. I'm still educating my family. Like that's AI generated. Nope, that's AI generated. So, you know, there, I look at that, I thought hopefully the legislators wake up and realize that we need to put some protections and guard rails in place for help to people to distinguish. Otherwise, this is just going to be chaos. And nothing is real. Nothing is believable anymore. And so I think that may happen. so as a result, anyone who's doing those kinds of automated emails or anything like that, the bots on the other end are going to detect that as being sent by another bot and they're never going to see it. The bots are going to start talking to the bots. And so the human conversation is going to become the luxury commodity in that when I look at how people are going to market successfully right now, it's not from mass outbound campaigns. It's not from mass marketing campaigns or social media campaigns. It's from gathering certain individuals together and having intimate conversations about the challenges that they're facing, open discussions that are moderated, are, you know, nice restaurants, nice spies, like an experience. They're looking for people to connect without all of the social media stuff that's being thrown at them with people that they can be trustworthy with and can open up to. That is what people are starving for at every level of every organization I've seen. And so that peer to peer moderated kind of a conversation where everyone is on the same kind of thinking and footing and understands what the other is talking about. That's the kind of go-to market that's being facilitated, that's being the most successful right now. Because the more noise that's out there, the more gets tuned out. The more we train our buyers not to listen to us. And

31:03 Warren Kucker: Thanks.

31:04 Carole Mahoney: that also elevates the need and status to be not just pitching yourself, but showing that you actually understand the challenges that people who you're trying to help have. And through those kinds of speaking engagements, workshops, dinners that are moderated and conversations that you even have one-to-one with those people and being very selective about who those people are and curating that, that's the way to go, I think, in the future. It's kind of like I've been relating it to cheese. You can go to the supermarket and buy any kind

31:32 Warren Kucker: Thank

31:33 Carole Mahoney: of mass-produced cheese that you can think of is probably there. But there's most people... that I know anyway, that are gonna get up early on a Saturday morning to go to the local farmer's market to get the goat cheese, to meet the goat and the farmer who made the cheese, pay four times as much for it to bring it home. And they'll tell everyone about this cheese. Those are the

31:50 Warren Kucker: Right.

31:51 Carole Mahoney: people that are going to be the ones that you want to target, not the ones who are looking for it. Like there's a place and a time for that. But this is what I think at the real higher level, if you're trying to reach executives, go to market is gonna be coming from and operators.

32:05 Warren Kucker: No, it's great call out. think you're absolutely right. The bots are going to talk to the bots, right? Whether

32:10 Carole Mahoney: Right.

32:11 Warren Kucker: we get something legislated about this or not at some point, hopefully we do. But I actually think that you're absolutely right. The market's going to regulate this, right? Like as anything else, when something becomes commoditized, everyone does it and then it doesn't work anymore, right? Like

32:22 Carole Mahoney: Yeah.

32:24 Warren Kucker: this in sales, the cold mass outreach boom of the past like seven years is pretty much done, right? So like then how do you stand out, right? You have to be where they are. What

32:35 Carole Mahoney: Mm-hmm.

32:36 Warren Kucker: makes that harder is it's hard to do things at the scale that we're used to.

32:39 Carole Mahoney: Yes.

32:39 Warren Kucker: So like, it's hard to build a hundred million dollar company in four years when you have to be where your buyers are. Because you

32:46 Carole Mahoney: Good.

32:47 Warren Kucker: don't have the ability to scale their physical presence that much, right?

32:50 Carole Mahoney: Well, the answer to that is if you have to be where your buyers are, then make yourself a place where your buyers want to go gather and collaborate and go to, bring them to you. Don't go have to be,

32:56 Warren Kucker: Right? Yeah. Yeah.

32:58 Carole Mahoney: if you can get to that point in that level, then this, that hundred million is totally achievable.

33:03 Warren Kucker: Right?

33:04 Carole Mahoney: That the other thing I would also say is that a lot of times, and I'm starting to see this shifted a little bit in investing, is that the focus on the getting to X number of customers, as fast as possible that the focus is starting to shift on how many of those are you keeping and how much is the lifetime value of those customers going up.

33:24 Warren Kucker: Right.

33:25 Carole Mahoney: having a target market that you serve the best that you can have deeper, longer engagements with for more period of time, I think is also the trend that we're going to start to see. No more of this. How do we grow as fast as possible and burn insurance through everything that we have that is going to start being, I think, more targeted. Again,

33:44 Warren Kucker: Great. I couldn't agree more. Yes. Yeah. Fingers crossed.

33:45 Carole Mahoney: That's also my hope. Yeah.

33:48 Warren Kucker: Totally agree. Great. Well, Carol, it's been a great conversation as expected.

33:52 Carole Mahoney: Thanks.

33:52 Warren Kucker: I'm super excited to see where you take learning games and continue to kind of guide where the seller should be going, how they should be looking forward,

34:00 Carole Mahoney: Yeah.

34:00 Warren Kucker: and how to make a better experience for our buyers. Where can people find you? You said you're writing a couple of books. Anything imminent? Anything we should be looking for in the near future?

34:09 Carole Mahoney: so the next book is going to be called Seller First. And this is going to be targeted for small business owners and entrepreneurs who tried hiring salespeople or they need to hire their first salesperson. And they either burned through money or had a bad experience or just don't know what it is that they should do because their entire company is resting on this. So how do they do that first step in hiring the right person and onboarding them? And of course, that also applies to companies and enterprises, but not just how do you find them and how you hire them, how do you onboard them, but how do you keep them? How do you coach and develop them in a way that is going to lighten up with the kind of culture that you have, the buyer that you have, but also keep your best top talent longer through the coaching and training development program that you designed for them, that's designed for them to reach their own personal goals.

34:54 Warren Kucker: That's great. Can't wait to read it. That's awesome. Carol, it's been a... Okay.

34:56 Carole Mahoney: Yeah, it'll be couple years.

35:00 Warren Kucker: Great, great. Well, it's been a pleasure. I appreciate taking the time to speak with us today.

35:05 Carole Mahoney: Thanks so much for having me.

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About the Host

Selling AI is hosted by Warren Kucker, founder of Topiq. Each week he sits down with revenue leaders, founders, and operators to unpack the strategies, tools, and stories behind selling AI products and using AI to sell smarter.

Warren Kucker — Host of Selling AI

Warren Kucker

A revenue leader and entrepreneur who founded Basiq.work, focusing on conversational AI for sales teams. Previously served as VP of Sales and CRO at Series B companies, scaling revenue to $2M+ quarterly bookings. His exits include Shelly.ai (ML email automation) and Boxton (digital freight platform). Started his career at Apple managing a $100M shipping efficiency program.