The Innovative Revenue Leader

How can AI do more than save time for sales teams? In this episode of Innovative Revenue Leader, Seth Marrs sits down with Jordan Ledwein, Co-Founder of Sales Lift and Reinforcement Services Partner at Sandler, to explore how AI is changing sales coaching, training, and skill development. Jordan shares how organizations can use AI not just to automate tasks, but to help sellers improve performance through feedback, practice, and reinforcement.

The conversation covers AI-driven coaching, sales skill development, CRM adoption, conversation intelligence, and how revenue leaders can redirect time previously spent on administrative work into more impactful coaching and development activities. Jordan also discusses why continuous learning remains one of the most valuable skills in an AI-enabled world.

Takeaways:
  • AI can help sales professionals improve their skills by providing feedback and identifying opportunities for improvement, not just by automating tasks.

  • Revenue leaders should use AI to free up time for higher-value coaching and rep development rather than simply reducing workload.

  • As AI increases selling time, communication, storytelling, questioning, trust-building, and other core sales skills become even more important.

  • CRM systems are becoming more valuable to sellers as AI helps turn captured data into actionable support and insights.

  • Effective coaching requires more than checking boxes; leaders need visibility into how well skills are being executed over time.

  • Organizations can use AI to measure training adoption and understand whether sellers are actually applying what they have learned.

  • Continuous learning and adaptability remain critical skills as technology continues to evolve.

Quote of the Show:
  • “Be open to learning new things and be a continuous learner.” - Jordan Ledwein

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Ways to Tune In:

Creators and Guests

Guest
Seth Marrs

What is The Innovative Revenue Leader?

This podcast explores the future of sales performance, giving Chief Revenue Officers and other growth leaders the insights, tools, and stories they need to lead with confidence. Through candid conversations with top executives, analysts, and tech innovators, we uncover how to harness data, optimize talent, and build tech-enabled sales teams that win. Listeners will walk away with actionable strategies to drive growth, outpace change, and future-proof their revenue engine.

IRL - Jordan Ledwein
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Speaker 2: [00:00:00] Welcome to the Innovative Revenue Leader Podcast. I'm your host, Seth Mars. Join me as we deliver practical insights to help B2B CROs Find new and innovative ways to grow in this fast changing environment. The Innovative Revenue Leader is sponsored by Sandler, a triad company, empowering sales professionals and leaders to master the craft of selling at all levels.

seth-marrs_22_06-12-2026_150813: Hello, everyone. I'm really excited to introduce today's guest. He's a sales trainer, AI strategist, HubSpot expert, and a serial entrepreneur. He became the youngest Sandler trainer ever certified at just twenty years old and has trained thousands of sales professionals across hundreds of companies. He co-founded SalesLift, which is a, a diamond HubSpot solutions partner, ranking in the top three globally for installations and building CRM systems.

Really understands how the technology works underneath. He founded SellSmarter, where he helps s- sales organizations cut through the AI hype and [00:01:00] be able to build real systems that make reps faster, more consistent, and more confident. His current position, he's like a typical serial entrepreneur. He's a co-founder of two companies, SalesLift being one and then SellSmarter being two.

Jordan, it's great to have you on.

jordan-ledwein_1_06-12-2026_150812: Yeah. Yeah. Thanks for having me, Seth. Great to be here

seth-marrs_22_06-12-2026_150813: Yeah. Yeah, yeah. So let's, let's jump into the kind of the question we talk really around CROs and, and, and kind of the things that would be valuable to them with what's going on in, in the market. What, what's the most innovative thing that you've, that you've seen in B2B right now?

jordan-ledwein_1_06-12-2026_150812: I think there's, there's two things that come to mind. Um, the first is kind of where we are today, and I think there's some really exciting things happening with just what technology is possible to do today, let alone AI, but technology as a whole. But I see a lot of people talking about how AI can save you time, or AI can do this task for you, or AI can do that, which I think is super important and there's, there's value there.

But what I don't see a lot of people talking about is where AI can, can also help [00:02:00] you become a better version of a, of yourself, a better seller, a better, uh, sales leader, a better whatever position it is that you hold by not only just taking some things off your plate, but saying, "Hey, when, when you sent that email, here's a few areas where it could've been tighter," or, "When you had that call, here's a few ways that you could have done this section better." And actually, you know, having real-time feedback to a lot of things that we've never really had feedback on in, in the sales world.

Um, the second piece that's, is pretty different, but it's where I kind of see sales tech going, with the different roles that I, I hold, one of the biggest challenges I see when it comes to sales technology adoption

seth-marrs_22_06-12-2026_150813: Yeah

jordan-ledwein_1_06-12-2026_150812: of adoption, right?

I mean, I'm sure you've seen it, but,

seth-marrs_22_06-12-2026_150813: Totally

jordan-ledwein_1_06-12-2026_150812: some reps just aren't used to using the tools that a lot of reps are gonna have to use the next few years to be successful. But what I'm excited about is I see AI as not just another tool or type of technology to learn, but almost like an orchestration layer [00:03:00] that manages the technology for the reps. So what I mean by that is, let's say a rep is using a CRM, they're using a email and calendar tool, maybe they're using a database tool. They have all this technology out there that they have to learn, and that's hard enough as it is as a rep to do your main job and that. In the future, what I see is there's these tools like Claude or Codex by ChatGPT or whatever it is that you can connect to, and as long as you know how to ask for what you're looking for, it can go and do that work.

And I see that being a huge, uh, advantage as we look at how do we improve sales tech adoption so it becomes easier for a rep to integrate and, and, uh, operate with these tools rather than it just being another thing to add to their list of things to learn. those two things are where I'm, I'm most excited these days.

seth-marrs_22_06-12-2026_150813: Yeah. And like when you, when you think of it, isn't the cycle like if you, if you took the idea of being-- like using it to be the better version of yourself, I think that's so important because I think a lot of people treat it like old technology, where it's a thing that I ask it to do [00:04:00] something, you do it.

But this technology grows with you. So if you build it in the right way, it will make you a better version of yourself. But also it can also make you a worse version of yourself. Like if you use it to answer the questions for you and to do the work for you, the real thought, like thoughtful pieces, you actually will become worse and more homogenized.

But if you use it to take all your expertise or to build your expertise and explore it, you'll become something that is valuable beyond. It's kind of, it's kind of the belief. But I look at that like, if you can get people on the path of, wow, this is allowing me to be so much better, the adoption would hopefully take care of itself because it becomes that thing that is hugely valuable to you

jordan-ledwein_1_06-12-2026_150812: Yeah, I, I agree completely. And one thing I say to people a lot of times is like, if you use AI to replace yourself, you're gonna replace yourself. But if you use AI to amplify what you're doing, you know, now you just turned your efforts into what three people or five people could do instead of just you, right?

[00:05:00] So that's where I think there's a lot of value when people understand, you know, it's not like a lot of the other technology that we've worked with before. It's kind of something entirely new

seth-marrs_22_06-12-2026_150813: Yeah, it's d-- it's just, yeah, it's, it's there to help you. The other thing that is when you were talking about the adoption side, it's so weird too, because I mean, you do a lot of CRM implementations and, and the old school way of CRM was, I need you to log your activities and do that stuff. The new version is, I just need you to keep your recorder on.

That's it. And I just need to use y-you to use company tools, and I'll make your life better. Um, like so it's, it's interesting, the work part of it, everyone used to complain. Our salespeople used to complain, I don't-- I can't do this because you're making me do extra work. Now I just need you to make it visible.

What type of stuff do... Are you running into that? Are you seeing that change more and more, like as you go, where people are starting to buy into it and use this technology? 'Cause I know you talk very directly to sellers about how to use this to actually make their lives better and do all the things you're talking about, about being your best self.

[00:06:00] Are you starting to see that catch on with sellers where they're willing to kind of expose what they do in order to get value from these technologies?

jordan-ledwein_1_06-12-2026_150812: In some places I am, in some places I'm not. I just had an email actually that I looked at earlier this morning from a rep at a company that is in a more old school industry that you'd think of, like not super tech savvy industry where they're using all the tech out there. But he was asking questions about how do I integrate this AI tool and that AI tool into their CRM, which was HubSpot. And I was basically telling him like, "Hey, the things that you're asking for are exactly right, but you know, there's this functionality. You could use Claude to connect to it and ask exactly what you're looking for. There's a couple different options, but try it out and see where you get." And also his sales leader who he'd copied on it, I had taught him how to do it about two to three weeks before 'cause he was trying to figure it out and he wasn't thinking his team was gonna get involved with it. But then he chimed in and was like, "Hey, I'll show you how to do all this stuff." And now there's kind of some level of almost like excitement around these tools because it's exactly what's happening. The CRM is instead of being a burden to a sales rep, it's becoming a tool that they never really had [00:07:00] before

seth-marrs_22_06-12-2026_150813: Yeah, yeah. It's, it's actually valuable rather than more valuable for a company or a manager

jordan-ledwein_1_06-12-2026_150812: Exactly. And that's kind of what the CRM has always been, or even all sales technologies. It's like, who is this tool really for? And now it's, there's not that question anymore

seth-marrs_22_06-12-2026_150813: Exactly. Exactly. Yeah, that's awesome. Okay, so let's talk a, a little bit about AI in, in sales training, 'cause you have a ton of experience with this. I mean, you've grown up in a franchisee, in a, in a franchise for Sandler, been training for a long time. Um, can you provide a couple of ways you're using AI to make, to, to make you better, like as a trainer, and then also ex- and, and also talk to it from how it's improving the experience of those that you are training

Mm-hmm.

jordan-ledwein_1_06-12-2026_150812: the opportunity to do that the time now.

seth-marrs_22_06-12-2026_150813: Yeah. It's, it's like it nonstop and it's also weirdly in the world of AI, non-invasive for a seller. 'Cause I can do all this stuff on my own. I don't need a manager to be critiquing me because I think a lot of people, it's like, if my manager is doing this, they're, they're also helping me, but they're kind of exposing me [00:08:00] too.

jordan-ledwein_1_06-12-2026_150812: You

seth-marrs_22_06-12-2026_150813: Yeah.

jordan-ledwein_1_06-12-2026_150812: Vulnerable as a rep to do that with your manager sometimes. And even more so, like what's the, the worst fear of a seller that has to role play is he's got to do it in front of the rest of his teammates or his company, and he's thinking about that, or she's thinking about this, and you can't actually just be in your own environment like you normally would be. Now you can't.

seth-marrs_22_06-12-2026_150813: It's awesome. It's awesome. Okay, so one thing that, that we've talked about a lot kind of internal working at, at, at Sandler is a term that we call progressive scoring. And, and basically for what, what that is, is that's the ability to score how you're executing skills on a call when you're working with a customer, with the idea being that I don't really care if you can tell me how to execute training.

I want you to be able to execute that training on a call with a customer under pressure where you're trying to really deliver, uh, deliver. Can, can you provide like a little bit more around your definition and k- explain-- 'cause you've done a lot of work on the [00:09:00] structural side of making this work. Can you talk a little bit around your definition of what that would be, um, what, what progressive scoring is, and kind of explain a lit- go in a little bit more detail than I did on, on what it does?

jordan-ledwein_1_06-12-2026_150812: Yeah. Yeah. I think the reason progressive scoring is, is so important is because, like you mentioned, it's not just taking a shot in time like today or that one meeting, but it's looking at a rep and their growth over a period of time, which is a lot more reliable than looking at a single call,

right? We all know that we have bad calls.

I still have bad calls. If you were to score one call today versus a different call today, they're gonna be vastly different.

So you can't really understand what's going on until you look at it from a progressive standpoint. So I think that's really important. But I think when we-- when I think about it from a holistic view, and this is kind of scaling way out, but I'm, I'm thinking about two things. When someone's learning something, when I'm learning anything, the question is, one, are they doing it? And then two, if they're doing it, how well are they doing it?

Right. It's like Going to the gym. Number one is do you go? Second is, okay, [00:10:00] how is your form when you're doing it? Same thing here. So it's how are sellers doing as far as actually deploying the new skills or techniques that they're learning? That's A. And then B, when they're doing it, are they doing it well? Are they doing-- Is it going the right direction? And what I think is exciting too, that we've talked about is the data that we're getting here and the value behind it when we can start to tie it to other metrics in the company, that's what's exciting because you can say, "Hey, when we really dive deep into pain and we get this score on, you know, finding the actual impact of the pain, this is what it does to our close rate," or,

"Here's the change in revenue across the reps that do that and the ones that don't do that."

That's what I'm kind of really excited to get to where we have all of that data and can say definitively, this is where we should focus

seth-marrs_22_06-12-2026_150813: Yeah. And it's, it's interesting, right? 'Cause you said, uh, one thing I said that, that, I mean, I loved the gym analogy, right? Like, it's one of the... Did I get to it? Like, or, and then when I went there, did I just kind of chill in the, in, in the locker room and talk to people? [00:11:00] Or did I actually work out and get some value from it?

And I, and I think that really tracks nicely because it takes multiple technology pieces to do that. One is to identify a skill, 'cause not all skills are used on, on all calls, and the other is how did you do doing it? Another thing you brought up that I think is worth kind of expanding on is it's not about like uploading a transcript and analyzing a transcript and then you're done.

It's about time, after time, after time, after time, after time, and looking at how you're performing in, in aggregate. That I think it's really hard to do, but that's where the value is. 'Cause I w- I don't, I don't-- It's great that I-- It's helpful to do it once or twice, but it's really important where I could see my progression

jordan-ledwein_1_06-12-2026_150812: Completely. Well, and I think you brought up something important because like, you know, I think a lot of people have tried or even thought about like, hey, I'm just gonna throw a transcript into ChatGPT or Claude and kind of see what it says. And ChatGPT and Claude are great at giving a response for anything that you give it, but the accuracy of [00:12:00] that response is, is another question, right?

And like, if you give it that same thing two weeks apart, is it gonna be the same answer? Are they gonna be variations of each other? Because I would argue that they're not gonna be the same exact response if you just put in a, a very short prompt. You know, the level of nuance that you have to kind of go into to get into, you know, are they deploying this skill in certain situations? How are they deploying it? Because there's, there's the hard skills and then there's the soft skills.

seth-marrs_22_06-12-2026_150813: Yeah

jordan-ledwein_1_06-12-2026_150812: skills are easy. You know, the upfront contract where we get purpose, time, agenda, expectations, and yeah

But it's the softer skills like the pattern interrupts or the questioning strategies or the pendulum theory or the things that are a lot more nuanced inside of Sandler that people deploy them in a lot of different ways, and you can't use a keyword tracker

seth-marrs_22_06-12-2026_150813: Yeah

jordan-ledwein_1_06-12-2026_150812: quick prompt to say, hey, they did or didn't do this

seth-marrs_22_06-12-2026_150813: So true.

jordan-ledwein_1_06-12-2026_150812: Be able to trust that.

seth-marrs_22_06-12-2026_150813: Yeah, so like, y-y-- you know this probably better than anybody because you spent a ton of... You were-- You played a lead role in making this happen in conversation [00:13:00] intelligence using, like within Gong, using trackers and scorecards, and then also on other, the other conversational intelligence work or the, the web conferencing stuff.

I think a lot of people think this is easy. Like, I go in and I, I put a result in, and I get a quasi-decent answer to be able to get it right. But like I've watched you do this, and I've seen some of the prompts that are like nine pages long to try to get this stuff working. Can you pri-provide just a, a little bit more detail around how difficult it is to get it, where you can not just extract a skill and give one prompt, but be able to do it in a way that it's so accurate that call after call after call, you get a consistent score, no hallucination, it's actually working, so you could build with it?

jordan-ledwein_1_06-12-2026_150812: Yeah. I mean, the more you think about the topic, the harder it gets when you

seth-marrs_22_06-12-2026_150813: Yeah.

jordan-ledwein_1_06-12-2026_150812: Think about it, right? You

seth-marrs_22_06-12-2026_150813: It's true

jordan-ledwein_1_06-12-2026_150812: like, wait, you know, the one thing I hear, especially in the CRM world when I'm building sales processes for [00:14:00] different sales teams, is I hear, "We're, we're a little bit unique," right?

seth-marrs_22_06-12-2026_150813: Yeah,

jordan-ledwein_1_06-12-2026_150812: every single

seth-marrs_22_06-12-2026_150813: Yeah

jordan-ledwein_1_06-12-2026_150812: right?

And there's truth to that. There's... Sales is not a, hey, you start here every single time this happens, this happens, this happens, this happens, that happens, and it's always that process.

seth-marrs_22_06-12-2026_150813: Yeah

jordan-ledwein_1_06-12-2026_150812: sometimes you're working with a new client, sometimes you're working with a current client. Those are two different sales processes, two different sets of steps that you go through.

So like how you actually deploy the skills, where you deploy the skills, how you're talking to a client that you have a relationship with when you take them through a pain funnel versus a, a new client, those are two different things. So we had to do a lot of, of revising and testing and, and, um, just taking a look at how are they scoring and putting in qualifiers and, and details to say, "Hey, when this happens, look for this.

When that happens, look for this," to where, you know, we've developed, like you said, these nine-page or very long and extensive prompts that kind of call out all the different use cases where skills can be applied, [00:15:00] as well as the watch outs, the things to look for, so that it's not just, hey, you know, did I take this person through a pain funnel?

But it's looking for the different steps. It's saying what it should look for and what it shouldn't look for. It's looking for what the buyer language and response should be to that. So it's a lot more, um, ideally a lot more accurate and a lot easier to trust that as a sales leader that if it's saying, "Hey, this rep is here, this rep is here," you can say, "Okay, well maybe I should focus coaching here for this rep and, and there for that rep." So you actually have something that you can, you can use.

seth-marrs_22_06-12-2026_150813: Yeah. It's not like, um, it's very easy to go into an LLM and get a summary back on something that'll give you generally decent feedback. It feels like the difficulty becomes when you try to tie that to a score and then tie that to a score across thirty calls, twenty calls, ten calls. Like to do that really well is very, very different than just like, "Hey, give me feedback."

jordan-ledwein_1_06-12-2026_150812: Completely. Well, and especially like, you know, I think we're a little bit lucky 'cause we're getting to do it within the, the realm of Sandler, and

most of our [00:16:00] clients are following some form of a structured process. But, you know, I'm sure a lot of sales leaders could even say, "There's a lot of my reps that take their clients through different sales processes on different days for different deals when they maybe shouldn't."

So there's a lot of just things that you had to kind of, or we had to account for as we built these. Um, but also we're able to at least help sales leaders identify with a level of accuracy, are they trying to do the skills? And if they're

trying them, how well are they doing them? Which I think is really the feedback that a leader needs to, to understand, is this training working? Is, is the investment worth it? And then what are we getting from it?

seth-marrs_22_06-12-2026_150813: Yeah, 'cause if they, if, if you were trained in... I mean, this, this-- companies do this today. If you were trained in Sandler, then you're trained in Sandler. So when I'm evaluating your performance, you're either trained in Sandler or not trained in Sandler. Well, if you're not ac- if you were trained and you did not pay attention, and you don't use any of the tools that you were given, then you aren't actually trained.

You aren't using the [00:17:00] skills, so the investment you made is not being realized. So this allows you to see whether your investment's being implemented. And then you can say, "If it's implemented, now I, I can tie it to value."

jordan-ledwein_1_06-12-2026_150812: And I think the best part of it is, is that, you know, most Sandler clients, if not all of them, are clients because they believe that the level of investment that they've made is worth it, right? And I think you can get a lot of wins from Sandler with very, very marginal changes to your

people, right? It doesn't have to be that they follow the whole process. They could just start using upfront contract and see some wins from it, or, you know, hear one rule. I remember we had one, one class where, um, one of the clients heard, "You can't lose what you didn't have," right? And so she goes, "Oh, I'm gonna go make that call." She closed an $80,000 deal on a, you know, a couple thousand dollar boot camp.

There's the ROI right there, right? So you're still gonna see that. But imagine if you could do it across every skill in the Sandler

portfolio,

and you can actually amplify the investment that you're making from time and money perspective and get so much more out of it if [00:18:00] they were really using the whole system as a whole.

I mean, that's just what makes me excited about where we can take this and help our clients even more than we do today.

seth-marrs_22_06-12-2026_150813: Yeah, 'cause now you really know and now you'll really be able to see, tie it and, and turn those into the results. It, it is kind of, I think we've talked about this a lot. It is enablement becomes the new driver for growth. It's, it's, uh, and you should be able to use it. When it's structurally set up this way where it's measurable and tied to an outcome, you really can drive growth

jordan-ledwein_1_06-12-2026_150812: And the measurable piece is, is huge because it's been almost impossible to do that in sales until today

seth-marrs_22_06-12-2026_150813: Yeah, forever. Yeah. So like we talked about it earlier around the uploading the transcript and asking it for feedback based on methodology. Can you talk just a little bit more around how different that is? Like the-- if I'm doing just the, "Hey, I..." You know, you can upload it. Even if you tune the model to a methodology where it's gonna give you a fairly general, it's gonna fair-- give you a good answer on it.

[00:19:00] Like what are some of the... Like how is it different, what we're talking about versus that?

jordan-ledwein_1_06-12-2026_150812: Yeah, I, I think no matter how much you tune it, it, it's still not gonna be exactly what you could build if you were to build each skill individually. I mean, you know, 'cause when you think about it, the amount of prompts that we have, I mean, across maybe fifteen to twenty skills, we're talking about sixty to a hundred different prompts and like three to five prompts per skill.

Like it's very granular. Most folks who are, who are doing this on their own are doing one prompt. Well, it might be long, it might be tuned a little bit for the transcript. Now, again, I think you can get something out of that and say, "Hey, this is better than not, not

seth-marrs_22_06-12-2026_150813: yeah, for sure

jordan-ledwein_1_06-12-2026_150812: But what I worry about in that situation is AI seeing something that, especially if they're Sandler trained.

You know, Sandler trained people or Sandler's methodology, we say it's 180 degrees away from traditional.

seth-marrs_22_06-12-2026_150813: Yeah

jordan-ledwein_1_06-12-2026_150812: do things that AI does not think we should do,

right? Like Going negative on a deal.

AI does not think you should do that, and it's gonna flag that. And even if you tune the model a little bit, [00:20:00] some of that is gonna, gonna step in there to where it's, it's flagging things it shouldn't flag as bad behaviors that are really actually it's a skilled seller that's deploying skills that it doesn't know it's supposed to be looking out for.

seth-marrs_22_06-12-2026_150813: Yeah

jordan-ledwein_1_06-12-2026_150812: it's gonna give a bad seller a good score because they hit a keyword or they said something, but they might have done a terrible delivery or it was just a talk track and, you know, they, they lost the deal anyway. So I think it's, it's sometimes even adding more confusion to what's going on rather than helping you get a clearer picture of where your reps actually stand.

seth-marrs_22_06-12-2026_150813: Yeah. It could give you almost a false sense of security because of the generality of it, and it doesn't give you the specificity you need to really go in to know what worked and what didn't

jordan-ledwein_1_06-12-2026_150812: Well, and the other problem, like you'd mentioned earlier, is it's, it's not progressive, right? It's point in time. We're looking at one call. We're not-- And you can look at a couple different calls, but like, if you wanna get a realistic sample size that's gonna give you data that's reliable, it's gotta be progressive

seth-marrs_22_06-12-2026_150813: The old way, like when [00:21:00] CI came out, like I, I, I... The, the thing was go listen to your salesperson's call. So I got call recording, so you'd have sales managers like listening to their calls on their way to work and really trying to provide feedback. How, how does progressive scoring give that more... I mean, we talked about it a little bit, but give more accurate and consistent set of information so as a sales manager, so take it to the sales manager view.

We've talked a lot about what the, like, just kind of technically how it could work. How would this translate to, to making a sales manager what I believe they could do, which is a better coach to their seller in less time? 'Cause I don't have to listen to the hour call anymore

jordan-ledwein_1_06-12-2026_150812: I almost think about it like, I'll use somewhat of a sports analogy and pick whatever sport you want, but like you might have like an athlete and their baseball card or their football card or whatever, and then you have their attributes, right? And you have all the different things that they're maybe good at, like offense, defense, et cetera. it's almost giving a sales leader kind of their, their [00:22:00] team's attributes across their team, right? Like, where are my sellers good? Where are they maybe have some room for improvement? What direction do I need to take? Because just like we see in training, a sales leader sees in selling, all of his reps don't have the same problem,

right?

They'll have very unique things that they may be working on. You can't coach them all the same way or go through a one-on-one the same way. It needs to be more targeted if you really wanna get the lift that you're looking for. So it's actually giving sales leaders a roadmap for when they do those one-on-ones or those check-in calls or ride-alongs, they know what to look for and what skills to work on with their rep, because most sales managers I know don't get a lot of time with each of their reps.

So they need to figure out how do they amplify the time that they're spending, and rather than using that time to say, you know, "Where's this deal at? Where's that deal at?" Or what a lot of people are doing in their one-on-ones, it's like, "Hey, I saw that, you know, you're not doing-- or you need some, some help on, you know, the investment piece of the process and how to have a good investment conversation after you get through pain.

You

know, where, where, are you getting hung up or how can I [00:23:00] help you kind of maybe role play that in a, a tough situation you're dealing with right now?" And that's gonna be way more valuable for the rep than like, "Hey, yeah, everything's good. This deal's gonna close next week," et cetera, which is what I see a lot of these

seth-marrs_22_06-12-2026_150813: Yeah.

jordan-ledwein_1_06-12-2026_150812: Being

seth-marrs_22_06-12-2026_150813: Yeah, if you approach it for just a general listening, it's different than if you're given targeted feedback that you can action, snippets you could look at, those types of things. It's just very different

jordan-ledwein_1_06-12-2026_150812: And you, and you have-- You said it earlier too, like it's, it's less biased, right? Like one thing that I saw, I was doing this two years ago with simple just AI scoring on calls and the feedback I was getting, you know, my father runs the, the Sandler franchise that I work for. If he would've came to me and said, "Jordan, you're not going deep enough in the pain funnel," I would've said, known this since I was 16.

I'm going deep enough," you know, whatever.

seth-marrs_22_06-12-2026_150813: Yeah

jordan-ledwein_1_06-12-2026_150812: But I told it to me and I heard it a couple times and I was like, "You know what? After three or four calls of seeing this, I'm probably not going deep enough in the pain funnel," is what I told myself, right? And guess

seth-marrs_22_06-12-2026_150813: Yeah

jordan-ledwein_1_06-12-2026_150812: a sales manager, that's so much [00:24:00] better that the sales rep is saying that rather than it being your idea because we all know it's much better when it's their idea than

seth-marrs_22_06-12-2026_150813: Yeah

jordan-ledwein_1_06-12-2026_150812: right?

So I think it plays into a couple different places there.

seth-marrs_22_06-12-2026_150813: Yeah, and that's-- you're able to do that because I, I think the, the way that a human who's trying to consume all of these skills and give you feedback all at once would say, "Oh, he asked one or two questions on pain. He, he worked the pain funnel." No. Like, this is like... See, it's been crafted in a way that consistently pushes you to go deeper than those things.

So you can't just take it off and say, "I heard the skill, so they must have done it at the level that's, that's satisfactory." You actually have to go deeper, and it seems-- that seems to be a thing that comes up over and over is, yeah, okay, if I'm on a call and I hear you give a part of an upfront contract, then, then I tick the box saying you did it.

But the reality is you didn't really do it because there's layers to this that you have to execute that are-- you're not evaluating as a human, or you forget to [00:25:00] evaluate, or you evaluate at different levels

jordan-ledwein_1_06-12-2026_150812: And it somewhat takes the sales leader out of being the judge of it. You know what I mean? So they don't have to be the one that's holding the gavel and that kind of could be the bad guy in the situation. It's like, "Hey, based on the data that we're seeing, this is kind of what we're seeing. You think that's fair?

You know, what do you think you need to work on it?" It's working through it with the rep, so they're actually helping them kind of get to that next level, which is what I think most sales leaders are trying to, trying to accomplish.

seth-marrs_22_06-12-2026_150813: Yeah. So true. So now that sales managers don't need to do that type of stuff, like what are some things that you'd recommend to level up their coaching? Like what do... I, okay, I'm, I'm, I'm not listening to the five calls. I mean, we can debate whether to listen to them anyway, but those who are doing that, now I could redirect those hours into coaching.

What, what are some things that you'd recommend?

jordan-ledwein_1_06-12-2026_150812: I think it's, it's somewhat taking coaching they used to take sales calls when they were in a sales seat. It's like put the pre-call plan together for your coaching meeting. Take the time that you now have to actually prepare for these coaching conversations because [00:26:00] I think they're a lot more important than a lot of sales leaders

give them credit for.

Or even, not even that they don't think they're important, but they don't have the time in

their day to

give to that when they have so many other things to, to handle. So taking those conversations and, and really being able to develop a rep and making it so that it doesn't take 12 months to get a rep to where you need to be.

It takes three months or six months. I mean, if we can do that across the board at large companies, the numbers speak for themselves very quickly, even at small companies, right?

seth-marrs_22_06-12-2026_150813: Yeah, true

jordan-ledwein_1_06-12-2026_150812: it's the ability for, for, um, the coaching to become a lot more impactful. But also, I think it goes back into the skill development too, and I think this is on the sales leadership side and the sales rep side is when we're spending more time on the sales versus non-sales activities with all the stuff that AI is doing, if we go from 30% selling to 40% selling to 50% selling, means our reps are getting a lot more at-bats, which

means Their ability to sell is gonna become a lot more important.

If they have twice the time to sell, their ability to sell becomes twice as important, [00:27:00] right? So I think our ability to make sure we're reinvesting in those, those soft and hard skills that, you know, some people are worried about AI kind of, having an impact on

to make sure that our reps are staying sharp, they can communicate, they can story tell, they can ask questions, they can find pain, they can build trust. The things that AI is not really going to be taking over, let's make sure we continue to amplify and improve those skills while we're still using AI to support what we're doing.

seth-marrs_22_06-12-2026_150813: Absolutely. Absolutely. It makes total sense. It's an opportunity. Like, it's an opportunity for you to be, you as a sales manager to redirect your time to quasi-val-- what feels valuable into something that would be infinitely more valuable

jordan-ledwein_1_06-12-2026_150812: And ideally, I think this is true with a lot of the ways that AI works is I don't know many sales managers that just wake up on Monday super excited to listen to call recordings of their sales team, right? But it's, it's taking away a lot of the work that none of us really got a lot of enjoyment or value out of already

to redirect it to [00:28:00] more creative work that we can really use the, the human brain that we've been, been blessed with to, you know, do the job that we are uniquely qualified to do while AI helps take care of the stuff that we didn't really wanna be doing anyway.

seth-marrs_22_06-12-2026_150813: Absolutely. Okay, so let's take a turn a little bit to you. So you grow up in a Sandler franchisee, like, with your dad as a Sandler, Sandler franchise owner. Like, did you always know sales was for you?

jordan-ledwein_1_06-12-2026_150812: Um, I think when I was in like third or fourth grade, I wanted to be a police officer and then a firefighter. Um, I wanted to be a garbage truck driver at one point in time, just wanted to hang

off the back

seth-marrs_22_06-12-2026_150813: It's amazing how many times people say that. Like you say

jordan-ledwein_1_06-12-2026_150812: I don't know why, but, uh, that was just my thing. So I, I didn't really realize I wanted to go into sales until I went into college, actually.

I, uh, I was always told I should go-- I should become a lawyer because I think that was just my parents' way of saying I was good at arguing without saying that directly. Yeah. Um, but when I was in high school, I went through a boot camp 'cause my dad was, um, becoming a [00:29:00] partner at a, a franchise, and he had been a client for 10 years.

So we'd go on hockey trips 'cause I was playing travel hockey. He'd be playing the Sandler tapes 'cause they were still cassette tapes at the time. Um, and, uh, I'd be listening, half listening. So it's kind of always being

seth-marrs_22_06-12-2026_150813: Yeah,

jordan-ledwein_1_06-12-2026_150812: uh, at

seth-marrs_22_06-12-2026_150813: it's it's been great

jordan-ledwein_1_06-12-2026_150812: exactly. Um, but I really realized it in college. I was like, "You know, I think I have the skill set already kind of developed to do sales.

I already enjoy the things that's in- that's involved with sales. I think this is the direction that I, I do wanna go." So that's when I, I took a week off of classes in college, uh, to go get certified as a s- as a trainer. Uh, worked out in a engineering sales role for four or five years, uh, in North Carolina, and then came back, uh, kinda a little bit after COVID to kinda help support my, my father's franchise as well as, you know, look at where the world of sales is at and figure out kind of what's happening

seth-marrs_22_06-12-2026_150813: Awesome. Yeah, so it didn't come as naturally as maybe I would've expected it to come for you. But yeah

jordan-ledwein_1_06-12-2026_150812: I think what I knew I wanted to do is I [00:30:00] knew I wanted to talk to people. I knew I wanted to talk to people. I had a skillset around that. I always enjoyed it. Um, and at the end of the day, that's all we're really doing here, right? It's, it's the

psychology Of communication and, and having conversations to get on the same page. And so I'm still kind of doing what I thought I was gonna be doing, just in a different way. Um, but I don't think many people are surprised that I ended up in, in sales.

seth-marrs_22_06-12-2026_150813: So if you could go back when you graduated, like, and, and give people one piece of advice on kind of knowing all that you know now for what they should do with their career, like what, what, what would you say?

jordan-ledwein_1_06-12-2026_150812: I'd say a couple things. Um, one, and this is something I think I got lucky 'cause I kind of enjoyed it already. I was homeschooled for two years when I was in, like, middle school, and it taught me how to learn really, really

seth-marrs_22_06-12-2026_150813: Okay

jordan-ledwein_1_06-12-2026_150812: right? Like I, I didn't have someone teaching me in a n- natural classroom per se.

My mom was-- My mom were hands-off. She's like, "Hey, I'll teach you this," or, "Here's kind of the, the book. Here's some resources. Do you wanna kinda learn it on your own?" 'Cause [00:31:00] she knew that that's what I kinda like to do. So I learned how to learn really well, and I think that's helped me tremendously the last 10 years, is I've been very invested in continuous learning and investing in myself to take courses or to learn something new or to try a new tool or just to figure out what's going on.

Um, So I think just be open to learning new things and be a continuous learner is one thing I'd recommend. And the other piece is you don't have to be an expert when you get started, right? Um, you just have to be focused on becoming as useful and valuable as you can to the people around you

and being open to giving away that value to the people. Um, and I think that's helped me as well, is just how can I be valuable to the people around me? What skills, what knowledge, what things could I provide, uh, to be an asset in, in the place that I am? And if you know enough to be valuable, um, you know, it'll, it'll be worth learning that, that piece or that tool

seth-marrs_22_06-12-2026_150813: Yeah. And I mean, that doesn't, that doesn't change, right? If you're adding value, someone [00:32:00] will invest in you. Someone will want to have you as a part of their team is... Yeah, that's, that, that's the whole game

jordan-ledwein_1_06-12-2026_150812: And you can pivot too, right? Like if you, if you know how to learn, you know how to learn valuable things, if that thing goes away, that's okay. You're ready for the next one. You, you've already done this before, so there's less of a concern of like, "Oh, what if AI takes that role?" Or, "What if,

you know, I don't really enjoy doing that?" It's not as much of a concern anymore, I think, if you focus on those two things

seth-marrs_22_06-12-2026_150813: Makes total sense. So tell, tell people, I mean, you've got a couple things going on as a, as an entrepreneur. Tell, tell people where they can find you and a little bit more around how they can learn about, about some of the things you're doing with your companies

jordan-ledwein_1_06-12-2026_150812: Yeah. The, the best place right now is LinkedIn. Um, so Jordan Ledwein, L-E-D-W-E-I-N is a good place to find me on LinkedIn. Um, I also have a website, theaisalesguy.com or theaisalesguy.com, and I have sellsmarter.ai are the kind of the best places to find me. But most of my content goes out on LinkedIn, and I'm just trying to share things that I thought kind of, um, changed how I sell or my process and other people would find value.

And that's really, that's really where a lot of this came from. The whole, the AI sales guy concept came three [00:33:00] four years ago. I was sitting around and I was trying to figure out, you know, how do I take my family's franchise, at the time it was three or four people, and how do I turn it into 10 or 15 people without hiring, you know, six to 10 people?

How do I do that with just the three of us? And I realized that it's all automation and technology that can really help us get to that level. ChatGPT came out a couple months later and I was like, "Well, now is the time to really dive into this." Uh, and the timing couldn't have been better. Um, but the fact that I made myself teach it made me learn it, and I couldn't be more glad that, that I did that based on where AI is today

seth-marrs_22_06-12-2026_150813: Yeah. And I, I follow your stuff. It's fantastic. Lots of tips and tricks that you can use both in your job, but then also in just wider if you're using AI, how does it work and how can you use it? So

jordan-ledwein_1_06-12-2026_150812: That's, that's the goal. So we'll, we'll see if I can keep it [00:34:00] up

seth-marrs_22_06-12-2026_150813: Great. Jordan, thanks for having... Thanks for coming on. It's great having you

jordan-ledwein_1_06-12-2026_150812: Yeah. Thanks, Seth. Great being here

Speaker: And that wraps up another episode. Thank you for joining. For show notes and other episodes, visit us@innovativerevenueleader.ai. The Innovative Revenue Leader is sponsored by Sandler, a Trilia company. Sandler provides top corporate sales and business development training while empowering sales professionals and leaders to master the graph of selling at all levels.