Train. Practice. Win. How Top Teams Actually Improve | James Santy, Founder & CEO, The Sales Dream

Bio:

James Santy is the founder and CEO of The Sales DREAM, with more than 20 years of experience spanning frontline sales, sales operations, and executive leadership. His career has been defined by a consistent ability to transform sales organizations, build scalable infrastructure, and deliver measurable growth.

Summary

In this conversation, Marc Crosby interviews James Santy, founder and CEO of The Sales Dream, discussing the critical aspects of effective sales training and coaching. They explore the common pitfalls of traditional sales training, the importance of experiential learning, and the role of leadership in fostering a culture of continuous improvement. James emphasizes the need for organizations to invest in training and practice, especially in a challenging market, and highlights the potential of AI tools to enhance sales coaching. The discussion also touches on preparing for diverse sales meetings and the future of sales training, advocating for a more structured and supportive approach to developing sales talent.

Web Links

The Sales DREAM Website: https://www.thesalesdream.com/

James Santy LinkedIn: https://www.linkedin.com/in/jamessanty/

Takeaways

Sales training often fails due to lack of application.
Experiential learning is crucial for retention.
Continuous practice is necessary for skill development.
Leadership involvement enhances training effectiveness.
AI can provide valuable coaching insights.
Sales reps need to prepare for diverse audiences.
Investing in training is essential for growth.
Sales training should be a core organizational tool.
Effort is a key indicator of sales success.
A culture of practice leads to better performance.

Sound bites

"Adults need to experience things to learn."
"Training should be rooted in deep application."
"Effort is the leading indicator of success."


Chapters

00:00 Introduction to Sales Transformation
03:09 The Importance of Effective Sales Training
05:48 Engaging Experienced Salespeople in Training
09:03 Leadership's Role in Sales Training
11:53 The Need for Continuous Coaching and Role-Playing
14:54 Leveraging AI in Sales Training
17:57 Frameworks for Successful Sales Processes
24:01 Tailoring Sales Strategies for Different Industries
25:46 The Importance of Preparation in Sales Meetings
28:00 Navigating Economic Challenges in Sales
29:37 Investing in Sales Training and Practice
31:58 The Future of Sales Training and AI Integration
35:41 Rapid Fire: Burn It or Build It?
42:46 Mindset Shift for Sales Leaders

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Views expressed are our own and do not represent any organizations

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Transcript

Digital Rebels Consulting (00:00.915)
Welcome in. I am Marc Crosby and this is Burn the Playbook. My guest today is James Santy founder and CEO of the Sales Dream. With more than 20 years experience spanning frontline sales, sales operations and executive leadership, his career has been defined by consistent ability to transform sales organizations, build scalable infrastructure and deliver measurable growth. Welcome James. Great having you.

James Santy (00:22.764)
Hey, thanks for having me. Appreciate you.

Digital Rebels Consulting (00:25.663)
So tell me a little bit more about what you do at sales dream, your little background and how'd you get started.

James Santy (00:30.594)
Yeah, so I spent 20 years at one company, sales rep all the way up to executive sales leadership at that organization, experienced a ton of stuff and 20 years in, I just decided I had to get out of corporate America and I always wanted to try my own little thing and so started the sales dream. Really we focused on consulting and sales training and helping organizations achieve better growth. Solarpreneur, I think just like you, so you know, try to get after it and you know, make an impact where I can with other organizations.

applications.

Digital Rebels Consulting (01:01.951)
Nice. Love that. I also see the opportunity that a lot of organizations, whether small, mid market enterprise organizations that could use help as far as just sales marketing optimization, aligning sales and marketing teams. At the end of the day, I think it also comes back to just how you onboard new team members, especially for sales training. So, where do you see as far as just the basic and why sales training typically fails at organizations?

James Santy (01:24.75)
Well, first off, I'm not sure every company does sales training. So number one, if you're not doing it, like I think, you know, you're missing the boat for sure there. I think too, a lot of training that I've been through and I've done at corporate America before, and I see in the marketplace today is very skills developed. Let's do an objection workshop. Let's do, you know, focus on a minute skill or minute process of the sales process. And I think, you know, in a lot of cases people walk in and walk out and be like, maybe I took 5 % of the overall content and I walk

away going, right, that was an event and, you know, it's not an applicable piece of learning that I take into my business and I take into my sales process. So I think first and foremost, one, do it. And if you're not doing it, I think you should be focused on sales training. We'll talk, I'm sure, a lot more about that. And then two, if you're doing it, don't just do the traditional sales skills like, hey, let's do a discovery workshop where we're going to get better at discovery or, you we're going to get better at closing or whatever those things are. I think it's got to be more broad based than that. And certainly it's got to be applicable back.

into the business because if you don't have applied learnings you're going to be in big trouble.

Digital Rebels Consulting (02:29.994)
So what makes a hands-on training better than like a lecture or a workshop? What's the frequency if I guess if a company does have sales training, how often should you be doing it?

James Santy (02:39.95)
Well, mean, there's a couple of things. There's a adult learning theory and I'm certainly not the author by this, like, you know, lectures, like 5 % retention rate. And, you know, so if you have somebody in there and at the top, you know, they're, coming in and telling you about stuff. It's not really going to work. think, you know, adults need to experience things in order to learn it. I use the analogy all the time. I probably used it with you before, but like, if I'm going to build a picking table and I go to a seminar on how to build a picking table. And then a month later, I got to build it. The ability to like remember and

that's not very good. But if I pull open a YouTube and I like watch it as it goes and I do it as they're doing it, you know what? My ability to build a picking table goes way up and my ability to keep that like, you know, knowledge in my knowledge base is really high as well. So I think, you know, the number one flaw in a lot of these is like, look, I've got a lecture base. I might do a little bit of like application in there, but if it's, if it's not rooted in deep application and practice and experience and letting the seller like pick it up and play with it.

I think you just don't have the retention rate you want. So it's a wasted investment. If I spend, you know, 500 bucks to bring everybody in from my organization from all around the US and I pay a facilitator to come and do it and I have lunch for everybody, like I've got a lot of money wrapped up in that whole thing and I'm walking out with basically every rep kind of going, well, I'm not sure if that was any useful and I'm not sure if I'm going to use it and I'm not sure I'm going to apply it. So I think you got to really make sure you got applied like experiential focus into your business when you're training.

Digital Rebels Consulting (04:09.293)
Absolutely. And you got to build that picnic table more than one time, I think, in order to have it stick and remember. I mean, I don't know. I mean, I've built a lot of things around here. I have a bunch of kids and I built things once. And if I don't do it, you know, every few months, then I'm going to forget how to do it. I'm out to go back to the instruction manual and remember how to do it. So, I mean, you got to do it, I think, with a certain degree of frequency, no matter how inexperienced you are or how experienced you are. What do you find as far as just experienced salespeople and the approach?

to get them to take training seriously, I just have this feeling that, know, there's a lot of people out there that think they know everything they've been selling for 30 years. You can't tell me anything new. I've been around the block. So how do get those people, you know, even if it's just a workshop to come in there, take it seriously and not be concerned about, know, what they're having for lunch versus actually walking away with something.

James Santy (04:58.744)
Yeah, think a couple of things. One is I don't know that you're going to reach those people. Like I would say there's 20 % of the sales organizations world. There's 20 % of the sellers that are like, I don't need this. I walk. I'm fine. I walk every day in this. I'm good. I don't know if you're ever really going to reach those people. And so I would argue that, you know, be careful with them because you're probably never going to please them and make sure they're not dissenters in the sales process, right? Where you're like in the room and they're like, I don't need to be here. And then if that's the culture and they're the best reps, then

guess what, every one of your other reps are gonna be like, I don't need to be here, because if Suzy doesn't think she needs to be here, because she's the best rep in the company, then that's gonna be pervasive. I would just check the, I'm not sure that you can ever reach some of those people. I've met a lot of those people too, like yeah, I'm fine. I'm the best sales person in the world.

Like those aren't the people I think that are great for your culture anyway, but you know, they're out there and I don't know that I'd be worried about reaching them as much as like making sure that they show up the right way in the classroom. A lot of cases when I've been in the classroom with those kind of people, I'd be like, okay, well then use your experience to teach other people, right? Use those experiences to participate and be all in on this workshop, on this classroom so that you can become an expert, you can share your experience so that others can learn from you and be that leader versus maybe being the person that's picking up a bunch of stuff. You know, the other thing

for me is, you know, a lot of the training I've done in my, and I'm not saying my training is the greatest, but a lot of training I've done, I walk out and the best sales reps in the company come to me go, I didn't realize I was following a process. Like, because I lay out, you know, what we're doing and how we're doing it and the state, they're like, I do this. And I'm like, that's awesome. But they're like, I never knew there was like a methodology behind it. And so I think, you know, if you do it right, and you have got really great trainers, the other piece for me is,

I've been in a ton of classrooms where there's a facilitator that's never sold, okay? A teacher that's never sold. Stop doing that immediately. Burn that right now because as a rep, I'd walk in and be like, you've never walked a mile in my shoes. You don't know what I'm dealing with and you're going to tell me how to sell. Like you lost me with credibility before I've gotten to the room. And so I think the other piece I would say is like combat that is like bring a seasoned salesperson in that can actually sell and facilitate and knows what the

James Santy (07:12.332)
doing, that's going to go a long way for credibility and credentials in that room. And right away, those top reps are going to be like, that person knows it. This person's been there, done that. So you don't have this like, hey, I'm an L &D facilitator from my organization. That's like, I've never sold a day in my life, but let me tell you how to sell. Like just pretty quickly, you lose credibility.

Digital Rebels Consulting (07:33.605)
Yeah, I think we've all been in those rooms. then, with that, think, how do you, how should an organization tee up, you know, training, even if it's just a workshop, let's just assume that some companies don't have time to embed it and their everyday activities. And let's just say they're going to do a workshop, but how should a company position training sales training?

To a sales team before they even get into that room, is there a right way to do it or a wrong way to do it as far as just a positioning that that is going to be a beneficial outcome for them, whether it's a sales or their commission or their longevity and the organization, what's a good strategy for that.

James Santy (08:10.05)
think leadership alignment is probably the number one thing I would say.

I've been in a lot of trainings where, you know, you can't find a leader in that room. And so it's like, well, how serious are we taking this? Right. I've also been in trainings where the CEO of a big company is in the room and they're like, we're doing this. And so I think commitment of the organization probably is the most important thing to think about there. Like, is this a one-time event? Is this something we're just doing? Those are less impactful and maybe a little bit more inconsequential in some cases. So you don't get as much leadership in the room. So I'd be a little bit careful with those.

But I do think if you get a leader, whether it's your sales leader, a sales manager, somebody in the room that's like, no, I'm in too, right? I'm doing this, I'm with you side by side, shoulder to shoulder. It feels different, it's got a different gravity to it. So I would say number one thing I would be thinking about is getting my leadership in that room with my sales team.

Digital Rebels Consulting (09:03.269)
Yeah, that makes a lot of sense, especially just having those people in the room and kind of establishing a better culture. And, you know, add onto that, I think it all comes back to culture as far as just what you're establishing, you know, what kind of teams are you developing? What does your business stand for? Who are you serving? Those sorts of principles and mission, statements and values. I think you have to keep coming back to, or else you kind of lose sight as to what the purpose is, whether it's sales training or any other sort of training, all comes back to the culture from my perspective.

You know, it's kind of like sports. mean, there's sports teams where you know that, you know, if a good player gets drafted, let's just say it's NFL or something like that, and they're going into a good building, so to speak, you know, those players are going to thrive just because the coaches, whether it's the head coach, the general manager, the supporting coaches, you know, that's just a good culture to be in and they will thrive where you see some, you know, NFL drafts. Again, you see a great player go to a bad team. You're like, Oh man, it's not going to work out well for him just because you know, the culture and it's just toxic and they're not going to thrive. So it doesn't matter, I guess, what sort of training.

Those sorts of players get you know, I'll go back to the culture as far as them probably doing well or not But you know everybody's different, of course But you know, I think even going back to the experienced sales rep example, too I mean, mean and I guess to pull that sports thread a little bit further the best players continue to practice and practice and put those reps in every day no matter if they're the best in the business and Like Tom Brady for instance, he still put in the work probably harder in his last few years than he did

probably in the first three years, just because there's always something to learn, always somebody to help. And it doesn't make sense. And I haven't seen this before. I'm curious your thoughts as far as having an established like player coach within a sales team, as opposed to just putting all that burden on like the sales manager or the senior vice president. Do you embed those sorts of people? Have you seen that in other organizations having that sort of player coach?

James Santy (10:57.678)
No, not a ton. Look, I learned a ton. When I started my sales career and I was a rep, I'd find the best salesperson I could. I'd take them to every single sales call I went on and then I'd learn all their tricks and tips. And before you knew it, I was like, all right, I'm kind of done with you. I've learned all I can from you. Now it's time for me to fly, right? So I think part of this is up to the salesperson themselves to be like, hey, how do I go out and find the best salespeople and emulate what they're doing?

And I don't think that's a relatively easy thing to do, but it's hard to do. I haven't seen a ton of coaching. The problem with coaching in general and sales, I just don't think it's very good across most organizations. If you pulled every sales rep today be like, how good do think your coach is? I think most people would say it's not very good. And whether that's your sales manager or somebody else, but I think there's a lot of opportunities in organizations to help with sales coaching.

And there's probably ways to think about it differently. know, at The Sales Dream, we've got some AI tools these days that are helping coach. And those AI tools are built to not only just be listening to how you're doing when you're practicing and role playing, but also give you suggestions of how might it sound, right?

And let's be honest, I could be practicing with you right now and working on whatever part of my sales process. You might be like, wow, I've got some experience of like, hey, I tune this different, I do this different. And I just don't think a lot of reps get that. Now, the other part is I've also been in a lot of reps where I've done that coaching and I'll go after role play after role play, like, here's what you're missing. And then three or four deep, they're still not getting it. I want to be like, come on. I don't know how to tell you this anymore. I think you got to have some good

coaching, you got to also be a rep that's willing to listen and capable of listening and taking that feedback and coaching, which not everybody can do either. So it's probably both. I haven't seen a lot of great coaching yet in a lot of sales organizations. Look, just in general, sales, think, is broken. 50 % of people aren't hitting quota, probably, out there. You can look at stats. Maybe it's 40, maybe it's 60, whatever. But if half of my assets for sales aren't generating revenue to me, it's like, I don't think they're getting good coaching. I don't think they're getting good training.

James Santy (13:11.184)
can't look at this and say like sales organizations are killing it. You know, the economy is not great. You know, companies aren't growing. All this sort of stuff just points back to like, okay, well, my revenue engine is probably not doing what it needs to do. And I'd be taking a really insular look right now to be like, all right, well, what's my training? Like, what's my talent look like? Most of the executives I talked to, most of them say like they would give us their sales team a six out of 10. A six? That's that's a freaking deal. You know what saying? Like,

Digital Rebels Consulting (13:39.459)
You

James Santy (13:40.938)
they don't think they have the skills or equipment to be ready to go. So it's like, if I'm an executive and I know that for my sales team, like what am I doing about that and how am I progressing that? So I think it's pervasive. I don't know that there's a really good easy answer, but you know, I think we're at a state where it's like, look, there's lots of salespeople in the world and I'm not sure that they're effective as they need to be and that's a really big issue.

Digital Rebels Consulting (14:04.449)
Yeah, it certainly is. Whose job should it be to do role playing? I think that you touched on your AI tool and I want to hear more about that too. But I mean, traditionally should it be the sales manager's job, the frontline manager's role to role play with the reps or should they outsource it or what's the right answer?

James Santy (14:24.832)
Yeah, I mean, think the answer, you know, traditionally has been I've got to have either a friend of mine that's a sales rep. So if you and I are working for the same company, I'd be like, hey, let's let me call you up and give you my pitch. Right. And, you know, I've seen a lot of that and that's that's like traditionally the standard and best practice. You know, sales managers also are there to do that with you. And I think it should be there. I think the advent of AI and certainly we have that capability at the sales dream to to role play with with an agent. I think that is so much far along.

than where we are historically for being able to do this. Because again, couple things happen when you do role play human to human. First and foremost, I'm not sure how good you are at role playing. if I'm using you, I'm like, I'm not sure how good you are at, know, prevailing what my customer's needs will be and talking about what their challenges are and all this sort of stuff. So if you're not good at it, then my role play is already kind of not so great. And then two, if I suck, are you

really gonna tell me I suck? Probably not, because you're about to go next in role play and the last thing you wanna do is shred me, because then I'm gonna be so much tougher on you and your role play. So we get this like human nicety perspective and I live in Minnesota now, so you get the whole Minnesota nice. a really good job. Okay, my turn, right? Because I want you to tell me good job and I don't really wanna get into it. And so, you know, then there's this other piece of like, okay, well, if my role play is not very good and then the feedback I'm getting from it, it's an exercise of futility, right? And so you're stuck.

Digital Rebels Consulting (15:44.482)
Hmm.

James Santy (15:54.528)
in the mud, you're just spinning your wheels, you're not doing anything to actually improve yourself, you're just going through the motion. So I do believe that AI is going to take us way further in this. I think it makes it way more attainable. One of my customers sent me a video the other day of them at the bowling alley using the tool. And I was like, what are you doing after I got the tech?

He was like, man, my game's not up for a little bit, so I figured I'd rip this open and take some lessons and actually do some role play. So again, wherever you are, however you are, I think it makes it a lot more attainable.

I don't have to have scripts or structures around it. And then I also get good quality coaching on the backside of it. And so if I suck, I suck, right? And AR is going to tell me like, hey, here's some ways you can improve it. And then the last piece is you're only as good as the person in front of you, right? So if you called me and you said a lot of things and I'd be like, gosh, they don't sound great, but I don't really have any expertise to tell you how to sound better, then I'm stuck. And you know, what I'm seeing with agent AI right now is not

only and specifically our agent, I guess I'll speak to that because I know that more, but our agent not only will like critique you but it'll also offer you suggestions on how you might approach this differently based on the training that we provide.

So I think that's another big thing here too, to make sure that, you know, if somebody can't really correct you and offer you guidance on how to do it better, then we're stuck. Like think about it this way. And like I do a lot of youth coaching, maybe you do with your kids as well, but you watch them and reps, right? You watch what they're doing and then you go correct them to what needs to be done better. Imagine having a coach be like, hey, good job, even though they don't know it's good or bad, right? Like it's just, it's not going to work in that person.

James Santy (17:37.232)
or that kid's not gonna develop their skills at all. And so you just look at the coaching capability in front of you, I think is a really big limiter in a lot of cases of like, do you know how to do it? Do you know how to coach? Do you know what good looks like? Do you know how to give me better advice? And I think in a lot of cases, the answer is no. So that's a big limiting factor I think out there today.

Digital Rebels Consulting (17:57.826)
Certainly. I know with my kids, I try to coach them and they don't want to hear anything from me. They want, they need to hear it from somebody else. So maybe in that case, it's probably better to have AI, I guess, give you that feedback and give you those tools for improvement or recommendations just because, I don't know, sometimes I go up against a tough audience as far as telling them how it should be done and based on what I've seen. You had mentioned as far as, you know, people in the Midwest are probably too nice.

James Santy (18:03.648)
Yeah. Yeah.

You

Digital Rebels Consulting (18:25.13)
One of the things that I noticed with AI, I'm sure you do too, is that it also can be too nice. It tells you like, Hey, that's a great idea or Hey, great job, or Hey, I thought of this, you know, weird thing that I was going to develop for, sales and marketing. What do you think of it? And it typically comes back like, that's a great idea. Let me help you get started. So I guess for your AI toll specifically, how does it go about, you know, making those recommendations and maybe not being so nice or course correcting into, I guess, better avenues for success.

James Santy (18:54.38)
Yeah, it's great question. like, I think what makes our agents different is it's taken all of our training and knows the process and fundamentals that we're teaching. So it's the first and foremost thing it's doing is listening, like, are you following the frameworks? Because like, again, 20 years in the industry of selling, it's all pretty fundamental, right? Like, you know, if you follow some pretty simple processes, it works, right? So like, there's some hacks that you can do. So the first thing our tool is listening for, like, are you doing the hacks? And if not, it'll correct you. The second thing is our

uniquely is doing is we've got a lot of ability to customize the personas inside the tool that you can role play with your customer. So the entire time it's listening to like, are you hitting the things the customer cares about? Because we've done the research on the customer side to say, hey, this person likely struggling with these things and has these challenges. So again, if I'm not following the framework, that's one thing, but two, if I'm not applying what the customer likely needs to have. So we're basically testing for empathy, right? To say, can you walk a mile in your customer's shoes?

And can you relate what your solution does to the problems they have? If you can't, you don't pass go, you don't collect $200, right? And that's the same thing with every one of our customers. We've all been in sales.

If you don't get to the brass tacks right away, be like, here's the problem I can solve for you and here's how I solve it. Because again, customers only care about themselves and that's fine. But I think that's a stark reality. like our tool is not only looking for framework, it's also looking for like, hey, what's in it for me from a customer's line standpoint? And then coaching you and judging you on like, did you do a good enough job to create the shadow of doubt that I'm doing it right, that I should maybe come back and have a conversation with you? And again, it's not perfect. Like agents aren't people. It's not going to

Digital Rebels Consulting (20:14.048)
Mm-hmm.

James Santy (20:36.506)
simulate 100 % of the next call you'll have. But from the feedback I've gotten from my users, it's about as close as they've ever experienced. And hey, look, if I can get as close as I can to a real life simulation, then I'm in a pretty good shape.

Digital Rebels Consulting (20:50.431)
Yeah. I mean, practicing a little bit is better than not practicing at all. I think that you'd mentioned frameworks. they, sales dream frameworks or are you pulling in from other frameworks out there? Or what does that look like as far as like what's in the background?

James Santy (21:05.934)
Yeah, it's a great question. We do have our own frameworks. So after selling for as long as I've had and teaching thousands of people how to sell more effectively, I've got what I think is a pretty good playbook.

Yeah, mean, it works for customers. so kind of regardless of industry, it's a way to approach things a little differently, show up with empathy and get to know the customer deeper and then come back and share them. So I'm to go back real quick because I want to talk about like this analogy of frameworks, right? Because when I was first married with my wife, we were super start out, right? Like first house, no furniture, no anything right out of college. And I remember going to Walmart and buying like those like, know, kit furniture stuff, you know what

talking about, right? Like super cheap, hard to put together, but like effective for a startup, you know, kind of house, right? And we get those and imagine getting that with all the kit and all the stuff you need, but no directions, right? And you know, we've all tried to put together a key of stuff and imagine like, you know, the one piece is missing or the, whatever the directions aren't very clear. You put it all together, you gotta take it back apart because you're like, I did it wrong. Sales is the same way. And I think in a lot of cases,

Organizations show up, hire people, like, you're talented, you've got all the attributes to be a seller, but they give you no instructions. They give you no framework. And that was my example. I used to call it welcome to the jungle. I feel like I got a Buck knife and a flint and kicked into the jungle. Like, hey, if you survive as a 22-year-old, awesome, you're going to be a great salesperson. If you don't, well, we're just going to go hire another 22-year-old and figure it out. That was really what my experience was starting at a big corporation right out of college for sales. And I think that's

Digital Rebels Consulting (22:31.936)
You

James Santy (22:47.696)
That's the problem in a lot of companies too. They don't have the step-by-step directions. They don't have the playbook. They don't have the ability to give you frameworks on how to sell. They give you product knowledge. They give you, here's what our company does. Here's our value prop. And left with nothing else, you know what happens is a kid shows up and goes, guess what? Let me tell you all about my product. And the customer's going, are you kidding me? Like, nope.

Digital Rebels Consulting (23:09.695)
Hahaha

James Santy (23:10.836)
I don't want any of that. So I went on a tangent there, sorry about that. But like I do think what else is missing in a lot of organizations is the fact they don't have sales process, they don't have sales frameworks. So again, I'm hiring talented people, putting them in the jungle and hope they survive. And if they do, awesome. But if they don't, well, I'm just going to go fire them and hire another person. And it's just we got to do better.

Digital Rebels Consulting (23:33.841)
Yeah, certainly. and lot of organizations you mentioned, there's probably a playbook for everything else in the organization, whether it's operations, R and D, plant level stuff, logistics, supply chain, procurement for, you can never find the playbook on sales for some reason. It's just a non existent or if it, or if it does exist, it hasn't been updated probably in a decade. so, but you know, and, and in your tool, also is it, you said industry agnostic, but can you, can I,

James Santy (23:55.704)
Yeah. Yeah.

Digital Rebels Consulting (24:03.807)
Can I tailor it or tune it to a specific industry? If I'm selling into pharmaceuticals, if I'm selling into construction, can I tailor it to those, whatever I want it to do?

James Santy (24:13.166)
Yeah, one unique thing about our tool is you can grab a persona down from anything, right? Basically, all I have to do is put in a name role in company. And we're doing deep research on the backside. So then it's basically tuning up the agent to deal with you. So I could be like, all right, I'm calling a transportation company, shipping company to move transport for them. I'm calling a pharmaceutical company. I'm calling an insurance company, whatever it is, and whatever my customer would be, we tune the tool back to

that that decision maker, their role, the company they're in and what they likely care about. And it's up to the seller then to be able to sell into that, right? And say, well, here's what you care about. Here's all my solution can solve that. And so that's really kind of the simulations that we've built. So absolutely industry agnostic. And then the cool part is as you tune up, whatever decision maker you pull in, depending on what you're selling, who you're selling to, the conversations will change every conversation based on the decision maker you pull in.

Digital Rebels Consulting (25:08.83)
Yeah, that's a good strategy. think especially potentially changing personas as you're preparing for like a meeting or something like that. Cause I don't know most of the other means I go to, I'm not necessarily just, it's not a one-on-one. I might be meeting with a CFO and maybe a technical director and maybe a, sales rep or something like that. It's a mix of people in the room. And so I think you have to at least tailor your preparation and your due diligence ahead of time to be able to field questions from all these different types of people. So do you recommend, I guess, as far as like, you know, either multi-threading.

I'm ahead of time with like this tool or in preparation for a live meeting to go through, guess those different types of personas. Is that sort of the, I guess a process that you would recommend?

James Santy (25:48.362)
Absolutely. mean, here's the deal. A couple of things are happening today in sales and I've talked about this a lot on LinkedIn, but sales reps are getting less and less at bats, right? Like it's harder to break through, it's harder to get meetings, it's harder to get people on the phone. So I need to make sure I've got a practice tool now for my team that allows them to have those conversations. So again, if I haven't had a CUFO in the room in a while, I had sure better practice with like what that CFO is probably going to be asking me, what their train of thought is going to be, how it's going

work. If I've got a procurement person, you know, maybe an operational person, like those questions are all going to be different. And if I'm not ready and prepared, I'm going to be caught off guard. And we all know this. We've been in those meetings. I've been in those meetings where you get that question and you're like, why does it go? Because you're like, I have no idea how to answer this. Right. And the number one thing you can do and lose that credibility pretty quickly in a sales call that you spend a lot of time to get to. And, you know, it's like they're not growing on trees these days. So you got to, you know, prep and get ready for every single one.

the thing you can do is just not be ready, right? Like, I wasn't expecting that line of question, I don't know how to answer that. You know, the whole, I'll get back to you, okay, but you know, if you got three different people you weren't prepared for in that room with you, and all of a sudden you're like, I'll get back to you, get back to you, I'll get back to you, you're gonna lose credibility pretty quickly, so I do think preparation and getting ready for that based on role and persona would be huge.

Digital Rebels Consulting (27:09.489)
Yeah, certainly. My cheat code, at least from years past, is just bringing somebody else that can answer those questions just in case.

James Santy (27:15.298)
Yeah, that's totally fair. And it's not a bad strategy.

Digital Rebels Consulting (27:21.595)
you know, sometimes that works. Sometimes it doesn't because then you got to, you know, prep the people that you bring to the meeting too, but they could also use AI as a tool to prep their side too. It could be a team prep activity. What are you hearing from like your clients as far as just, there's been a lot of turmoil over the last couple of years as far as just the company layoffs and downturns and it's been, it's been a tough market for a lot of people globally and businesses. Are you hearing as far as like a wait and see strategy?

I guess companies hunkering down or, know, Hey James, we're not going to invest right now because, know, we're trying to wait and see like what happens with like tariffs or, you know, other labor shortages and things like that. What should people be doing instead of, you know, maybe hunkering down or waiting and seeing in these markets.

James Santy (28:04.194)
Yeah, mean, look, I think the pervasive strategy is one of two things, right? I either need to grow revenue or I need to cut costs. Right? So if I think about that, I think almost every company out there today has been pulling the cost lever as hard as they can, as much as they can, suspending travel, cutting people, you know, whatever. It doesn't take long to go on the news and you look at the job market today and the, you know, the number of jobs that are out there and the loss and decline we're seeing there. So I think, I think the market is really challenging for sure. I think most people have been pulling that cost lever.

managing costs as effectively they can, weathering the storm. But for me, I look at it like, if I'm going into a storm, I want to hit it head on. And I think the hard part is, if you're not focusing and investing in the right stuff in your business, how are you going to come out better? And if you're rudderless in a storm, on the sea, it's a pretty dangerous place to be. Whereas if you're attacking it and you can push your direction and go, I think it's a much better spot to be in. Look, the number one thing I would tell any organization, and I'm

I'll say this probably a couple of times in the podcast. There are two things I'd be focusing on. I'd be focused on training, getting my salespeople trained up, getting better training, better equipped. Buyers are more intelligent than they ever have been. Reps are getting less and less reps and at-bats than they ever have been. We've got this dichotomy. Our rep skills are shrinking and buyer influence and understanding is growing. That's a dangerous spot to be in with your organization that's investing in a growth strategy with your sales organization. So I think we've got a training.

opportunity inside every organization right now. The second thing I'd be doing is I'd be implementing a culture of practice.

And look, know it's like taboo in the sales world to be like, oh, you know, we should practice. I know that sounds funny, but the number one, number two thing I do after I trained everybody, be like, look, keep this live, keep it going because you're not getting as many intro calls and as the many discovery meetings, as many proposals and final negotiations. I need you to have those skills sharp so that when you are called upon to be in front of that customer, you can absolutely crush it versus be like, Ooh, that wasn't a very good rep because

James Santy (30:10.478)
I'm really rusty, right? So I think about it that way. If I were a company, I'd be looking to say, how do I invest in those things as quickly as I could to make sure that I can maximize my investment I'm making in my sales organization in 2026.

Digital Rebels Consulting (30:27.484)
Certainly. think everything you're talking about, I think like you mentioned, it all goes back to the culture and kind what is the culture of your teams? What is the culture of your business? Kind of everything you talked about as far as just seas and storms and training kind of just makes me recollect. I was in, you know, like the Marine Corps for many years and, you know, saw how different teams train, especially during down times, because there's a lot of downtime. If you're familiar with the military, whether you're

you know, on a aircraft carrier steaming across the Pacific Ocean, you have 30 days. Well, guess what? For 30 days, you're not just sitting in your bunk, you know, waiting for the war to come to you or till you hit the shore. You know, you're still training, you're still putting other reps, you're still doing, you know, work on the deck as far as just like with your weapons or talking to your teams or communicate. There's always an opportunity to, to, to optimize something that way when you do hit the shore, so to speak, or you do have that sales call or you meet with that company that,

has been ghosting you for a couple years, you're ready to go and you're ready to go full steam ahead. Because these days, most people don't even want to talk to a sales rep. that journey that your buyers are on, once they get to you, you better be sharp and ready to go because you might only have one call or you might only have like 10, 5 % left in their decision making process to be able to strike bullseye as far as just your value proposition and what it means to them, the problems that you're solving.

It means everything. I think as far as like, you know, waiting and seeing that's a, probably a terrible strategy, um, you know, in any business, well, I guess it depends on the business. I'm sure there's arguments on both sides.

James Santy (31:59.502)
I couldn't agree with you more. think you're spot on in that analogy.

Digital Rebels Consulting (32:04.09)
where do you see sales training heading in the next three years? Obviously the previous three years have been, you know, quite, exciting, know with AI and just everything else coming out of COVID and, all the advancements and everything's progressing pretty quick. so what is from your perspective, like, what does the next three years look like either for like your AI tool or sales in general, or are we all just going to be using agents to do the work for us?

James Santy (32:28.216)
I think, I mean, for me, I think, you know, the human is going to be in the middle of all the sales stuff still. So like, think, you know, making them as, as quality and high, you know, high efficiencies we possibly can is going to be the name of the game. You know, for me, I hope in three years, we've kind of democratized the whole sales training thing where it's like every company has it, every sales rep has it. Like today, I will tell you, like I've got an 18 year old and if he were going to go into sales, the one number one thing I'd ask him to talk to the company would be like, all right, what's my onboarding

process look like, what's my training, what's my development, like how am going to get coached, all of those things because without that infrastructure, I don't think you could be successful coming in. Now, you know, again, maybe you're going to be the best ever and you can figure it out and, you know, grind through it, but you got to have an ecosystem around you that's going to be successful. And so the number one thing I'd love to see in three years is like, you know, there's just a great ecosystem of training for most corporations. And it doesn't matter if you're, you know, coming into a two person sales team or a two thousand

in person sales team, you feel like there's tools available to you to help build your craft, get you experience. Look, I learned this way, I'm sure you did. I learned by failure. I learned by trial by fire. And I don't think the next three years, that's gonna be the way that people are gonna do it. You just can't afford it. If I were hiring sales team right now, I wouldn't be like, all right, hey, jump in and learn as you go because they call that customer that's ready to buy something and they suck.

Well, it's like, I'd miss out on a rep. you know, again, I think three years from now, what I'm hoping for is like, it's much more universal. This isn't like a casual thing. It's not a, hey, yeah, come to this class or seminar. It's deeply rooted in sales organizations to go, yeah, we have a sales training methodology. We've got a plan. You know, you've got access to it on a kind of whenever you want to access it perspective. And it's really a tool.

Maybe that's the best analogy I could use. Training today is not a tool in most sales organizations toolbox. And if I could say three years from now, I'd love to say that that's a tool in every organization's And you know what? The sales rep then, it's about them using the tool. Just like anything else, if I never pick it up, I'm never gonna get good with it. So, you know, that's probably incumbent on the user. But I think in most cases today, it wouldn't be a tool in the toolbox that a sales rep's gonna get access to.

Digital Rebels Consulting (34:50.649)
Yeah, it's a great, great question. think for anybody entering any company, no matter if you're, think 18 or much older, as far as just asking those questions about what does the onboarding process look like? What does the training program look like? Because if they can't give you like an articulate, a well-defined answer of what that looks like, and how they're going to onboard you effectively, then it's kind of like, on a red flag canary in the coal mine. It's not going to get any better as far as we want you to get involved and start dealing with other people. And they just talk.

about, you know, KPIs and that's all it really matters without giving you any, any training whatsoever. so yeah, good question for anybody to, as they entered the job force, let's pivot to our next segment called a burn it or build it. Everybody's favorites. we go through a rapid fire questions, top 10, some hot takes in here. You just give me a reason as to why we should either burn one of these ideas down or build it for the future. And then maybe an answer why. so we'll start with number one.

standardizing the sales training for every single rep, matter what their experience level.

James Santy (35:53.004)
I'm probably a build it. I think most companies don't have common language, common vernacular, common perspective. I think you get so much for having a standard approach and process, utilization of your technology and tools, your CRM, all sorts of stuff. I'm a build it on that one.

Digital Rebels Consulting (36:14.7)
Love that, standardizing it. Number two, let your top performers operate independently from the rest of the team.

James Santy (36:23.05)
I'm gonna burn that one. Not to be long-winded, but I had a rep, turned out to be the best sales rep in the company for several years running. I hired him, brought him into the company. I legit had to take him to lunch one time and tell him like, hey, by the way, dude, if you wanna operate like a lone wolf.

your career's gonna flame out. And you've gotta figure out how to embrace teams, work with other people, do this other stuff, and become not a lone wolf, but somebody that's gonna work with the pack. And turns out to be a best salesperson ever. I would be like, those people are more detrimental to your culture than they are helpful to your organization from a revenue generation. So I'm a burn it on that one.

Digital Rebels Consulting (37:05.303)
I agree. 100%. Number three, prospecting at scale, even if the conversion rate is low, you hear a lot of this, I think in different industries, it's more of a spray and pray mentality, but you know, but you know, they're still getting responses. So a prospecting at scale.

James Santy (37:20.722)
I'm a build it. I'm a gotta get on the phone, gotta cold call. You you gotta grind it. You gotta own your destiny as a salesperson. If you're not willing to do that, I don't know how you're gonna sell. today's world's harder than ever to get ahold of buyers. The attention economy's real. People are inundated. I don't see how you're trying to, if you're not trying to break through the noise and do it well, you're, I don't know how you're gonna get customers.

Digital Rebels Consulting (37:45.281)
Gotcha. You still need to differentiate, I think, your approach or else it'll just kind of sound like noise like everybody else, but I do agree with you. Number four, doubling down on proven markets instead of experimenting with new ones.

James Santy (38:02.83)
I'm probably a build that one as well. I mean the hard part is you can chase and if you're chasing you're probably away from your core and your core is probably driving money. have methodologies and experience there so I would say build it.

Digital Rebels Consulting (38:20.439)
Managers focusing on metrics instead of hands-on coaching. So there's probably just those dashboard jockeys out there just looking at your KPIs instead of actually going back to training, which we talked about for the last 30 minutes or so. Focusing on metrics or hands-on coaching. Or both.

James Santy (38:39.47)
I would burn the metrics, focus on coaching. If your sales manager's not coaching, who else is? And I would say the number one job of every sales manager out there, in the unpopular opinion, it's to make sure every one of those assets are the highest performing assets they can be. And so I think those people that are like, okay, I'm out of the desk now, I've earned it, now I'm gonna watch you all do it and just keep an eye on you all.

Burn that thing to the ground. Give me the person that's like rolling up the sleeves, shadowing reps, helping them out. They should be servant leaders on the best way possible. And I don't think that's pervasive in sales management culture.

Digital Rebels Consulting (39:23.872)
Love that. It's Trusting your gut over messy CRM data. CRM data is typically a mess anyway, but should you just trust your gut or just, I don't know, burn it or build it.

James Santy (39:36.526)
I'm probably a burn the gut, build the tools. I do think we need to rethink the way we're doing tools in general. CRMs are brutal.

in their 19th century perspective. Like, let's be honest, we're dealing with a database. So I think we have to reimagine, rethink CRMs for sure too. Sales reps want to do one thing. They want to sell, right? They don't want to be administrators. So I think we've to be careful in striking that right balance. So it's a little bit of burn and build. If your team has 27 fields to enter for an opportunity, burn that. Okay? If they've got two or three core ones, build

it, keep them fluid, keep them moving, automate it as much as you can.

Digital Rebels Consulting (40:25.684)
Yeah, CRM just needs to be a topic for a whole nother episode because there's a lot to unpack there. Number eight, revenue's down. Let's just push the reps to work harder instead of slowing down to figure out how we need to fix it.

James Santy (40:30.914)
Yeah.

James Santy (40:39.458)
Alright, so I'm gonna use an analogy here. I think there are two things. It's a battle cry, right? Or a battle plan. And most organizations show up with a battle cry. Sell more! Win more! Grow more! That's okay as a rep, I'm going, yeah, got it. But how the heck do I do that?

I would say burn the battle cry, build the battle plan. So tell a rep what they need to do, show them how to do it, walk with them, understand what's gonna take to achieve success. That's the number one thing I'd be doing.

Digital Rebels Consulting (41:13.962)
Number nine, this kind of ties into one of the previous questions, but using AI to scripture prospecting emails.

James Santy (41:23.614)
Script, bad, email automation, good. mean, yeah, there's a lot to unpack there. I would say be cautious right now. The tools out there are okay at best.

from what I've seen. I think they're pretty transparent. I think they're pretty scripted. So be careful. If you can figure out how to get that more customized, I'd be a little bit more on that. I love the automation concept. think moving it faster further, yes, automate, take some of the junk out off your plate. The problem is what's the output? If the output's bad, ooh, don't, like here's what I would talk about. If you have a bad, if the music sucks, don't play it louder, okay?

If the music's sweet, sweet music and everybody's gonna love it, amplify the crap out of it. So I think you gotta be careful on how you're thinking through that. It's really back to the core message. If your core message is great, amplify it as best you possibly can. If it's resonating with your customers, go put it on 11, right? But if it's spotty at best and maybe kind of crappy noise, turn that thing down as low as you can, because it's only gonna create more noise in the marketplace.

Digital Rebels Consulting (42:35.507)
Agreed. And finally, number 10, tracking rep activity as a KPI.

James Santy (42:41.838)
build it 100 % of the time. I don't think people really understand effort is the leading indicator here. And I'm a huge effort guy. Like I want to know that you're putting the effort in because I can coach you around the ways of everything else. If you're sitting back and not giving me the effort, then what are you doing? So I'd be building that one.

Digital Rebels Consulting (43:02.899)
agree. Awesome. That was, that was really good. final takeaway for our listeners. We'd like to end the pod with a one mindset shift that sales leaders need to make right now. What would you recommend?

James Santy (43:14.766)
Train and practice.

I mean, that would be the two things. Think about it this way. How much money, energy, tools, stuff have I done or built for my team, right? And again, back to the amplification kind of theory. All right, I got them an outreach tool, great. But if they suck, you're just amplifying the suck, okay? So like, I need to be thinking about the core basis of my skills, capabilities, and competencies of my team. If I can focus in and get those as great as I can, if I can move it from six out of 10 to eight,

or nine out 10, now I'm ready to amplify. Now I'm ready to really get to market. The number one thing I'd be thinking about for next year is getting my talent.

to a spot where I'm really comfortable with them being in any room that they can be and practicing that so that when they're in those rooms, they're crushing it. I mean, I know I probably sound a little bit like a broken record, but I'd be hunkering down right now, investing into my team, getting their skillset and their practice regiments great. And then letting that turn into awesome outputs for my 2026 year.

Digital Rebels Consulting (44:19.204)
I Now is the time to invest, not necessarily to hunker down and do absolutely nothing, but if you want to crush your 2026 goals, probably reach out to James and the sales stream and he'll put you on track. Where can people follow your work?

James Santy (44:32.78)
Yeah, so you can follow me. I'm on LinkedIn. You can look at the Sales Dream or James Santee LinkedIn profile website, thesalesdream.com. You can go out take a free trial for the tool if you're like, hey, this is kind of curious. I want to see what this is all about. Go out there. You can sign up for free. Get 24 hours and test it, like give it a ride. You can kind of see what we're building and how it works and looks. Yeah, those are probably the two main places.

Digital Rebels Consulting (45:02.43)
Awesome. Well, thank you for your time today. It's been a real pleasure.

James Santy (45:05.259)
Awesome. Appreciate it.

Digital Rebels Consulting (45:06.9)
All right, thanks.