How to Stay Human in Sales Enablement’s AI Era | TFOS 24

In this episode of The Future of Selling, host Rick Smith continues his conversation with Roderick Jefferson—bestselling author of Sales Enablement 3.0—to explore how AI, coaching, and culture are reshaping modern sales.

Roderick lays out the evolution of enablement, the rise of “Sales 3.0,” and why the best leaders today combine IQ, EQ, and AI. He shares six practical ways AI is transforming sales teams and makes the case for using technology to make reps more human, not less.

He also shares what most managers get wrong about coaching, how to build a sales process around the buyer’s journey, and how to design sales kickoffs that actually drive change.

📘 Learn more at roderickjefferson.com
🔗 Connect with Roderick: https://www.linkedin.com/in/roderickjefferson
🔗 Connect with Rick: https://www.linkedin.com/in/rick-smith-094b29b
🔗 Learn more about Conquer: https://conquer.io/

Creators and Guests

Host

Rick Smith

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

What is The Future of Selling?

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

Roderick Jefferson (24:45.531)
Yeah, yeah, so phase one was the traveling salesman. Whether it was snake oil or if, like I said, it was knives, it was encyclopedias, these are folks that were essentially doing hand-to-hand combat out there. And one of the hardest definitions of selling, if you will, and that's what they were doing. They were selling, right? As we move forward into that Y2K space,

Future Of Selling (24:50.415)
Okay.

Future Of Selling (25:13.617)
Remember it.

Roderick Jefferson (25:13.765)
That actually shifted where, yeah, easy for you to say, Rick. That's where we moved into a phase where we were all about automation. That's when Salesforce Automation started, we're moving into CRM and we were really burgeoning on where we sit today with AI, right? And how do we leverage tools and processes and programs and platforms to really be bigger, faster and stronger, but also to be more productive and work smarter now.

Future Of Selling (25:16.805)
assessment.

Roderick Jefferson (25:44.198)
That next phase is all about how do we wrap our arms around a new way of doing it. And I don't call this the new, the next, this is the new. Because next infers that it's something we can lean on and we've seen before. AI has proven this is new. This is like something we've never seen before. And the analogy I always give is, and I asked the question, Rick, do we still have horses?

Future Of Selling (26:14.693)
Yes

Roderick Jefferson (26:14.865)
Okay, now think about, and it's not a trick question, everyone goes, what do you mean? Like, yeah, okay, where's this going? So I always ask that question because you think back to where we went from our motor transportation being horses to this new motor carriage. And I always say, well, we still have horses, we just utilize them differently now. They're not the primary mode of agriculture and or.

Future Of Selling (26:18.898)
I feel like I'm getting pulled in, like, alright, I'm just doing it.

Roderick Jefferson (26:43.963)
transportation. Well, the same thing's happening right now with AI. I believe that AI is no different than Word, Excel, and PowerPoint. And what I mean is it's a productivity tool, but the output is only as good as the input. So I believe that AI is going to kill all jobs. No, I don't. I think in actuality, it's actually creating some jobs as well. And I don't think it's going to take everyone's job.

Future Of Selling (26:52.773)
Okay.

Future Of Selling (26:59.504)
Yeah.

Future Of Selling (27:09.423)
Okay.

Roderick Jefferson (27:12.097)
I think that the people that don't know how to leverage AI will lose their job.

Future Of Selling (27:17.179)
Yeah, okay, okay. So you would see AI then as a, mean, it's certainly a tool, but also a disruptor, probably both, okay? So what are, so, and I know you spend a lot of time speaking about this from a keynote standpoint as well. So what I, as I was kind of thinking about our interview today and our discussion, was like, okay, what are three things that every sales leader

Roderick Jefferson (27:26.349)
no doubt. No doubt.

Future Of Selling (27:43.011)
should be doing right now with AI. And if they're not doing that, they're like, man, they're absolutely in the dust getting left behind. what are those? And you can give me five if you want, but three is a great number for me.

Roderick Jefferson (27:53.479)
Yeah, yeah. Yeah. One is if you are not utilizing and leveraging AI every day, you're already behind the curve. You are one step towards becoming a dinosaur and we know what happened to them. Secondly, you need to be able to incorporate AI into every single conversation you have with your teams and you need to be able to spot check it. That's the reason you need to be using it, right? And thirdly,

Future Of Selling (28:07.375)
Yes, sir. Yep.

Roderick Jefferson (28:22.17)
you need to understand what works at the maturation cycle of one, your company and third, your prospects and your clients because it can become shiny syndrome, right? Where, ooh, this is cool. Boom, squirrel, squirrel, what happened? No, just because your peers or someone you know is utilizing a specific tool or platform does not mean it's going to work at your company or

that it is the right agent stage of your company to be able to service your company, your clients. And the final, I'll give you the bonus one. And that is you need to learn how to leverage AI to make both you and your sales folks more human. And that's why I say it's about IQ plus EQ plus AI. And what this does is it will teach you and your...

Future Of Selling (28:54.32)
Right.

Okay.

Roderick Jefferson (29:18.192)
I'll say your go to market folks, not just sales folks, but your go to market sales, excuse me, go to market people on one thing, how to have conversations instead of giving presentations.

Future Of Selling (29:30.031)
Got it. AI comes up often on the podcast, right? And they've had some great answers around AI and how it's impacting the future of sales and things like that. But your answers actually are very specific in my point of view, right? Which I like that. And I think that's great. Now, the first one, you utilize and leverage it every day. Okay, I agree with you. And I think most people would go, yeah, that's got to be number one, right?

Roderick Jefferson (29:50.278)
Thank you.

Roderick Jefferson (29:58.419)
Yeah, but there's more than just chat GPT folks. You've really got to broaden your spectrum beyond just Claude, perplexity and chat GPT.

Future Of Selling (30:06.671)
Yeah. Yeah. Okay. So break it, break these down if you will. And, maybe you want to start there with kind of that statement, right? There's more than just chat GPT, but I also want to break down, incorporate AI into every conversation with your team. That sounds awesome. Practically though, what does that look like?

Roderick Jefferson (30:25.976)
thanks for asking about that. To me, I think there are six ways to incorporate AI to increase efficiency and productivity. And where they are is first and foremost, it's about streamlining lead scoring. How do you use AI to do your research upfront? Because I think we both agree.

Future Of Selling (30:37.435)
Okay.

Roderick Jefferson (30:53.19)
that prospects are not asking us to inform them anymore. There's so much information out there. That's the last thing. Matter of fact, I read the other day that prospects are 80 % down the road before they even talk to a salesperson. So it's really about doing all of that upfront, the 10K, the 10Q, and then looking at where they are and understanding how to articulate your differentiation.

Future Of Selling (30:57.329)
through that.

Roderick Jefferson (31:20.868)
around your competitive advantage, your business value and why you bring that's different. The next piece is the thing that we're doing now, which is automating task management, right? Taking all the data entry and appointments and scheduling and all that, and finding a way to create an agent that will do that for you or leverage an agent. The next piece is like we talked about, real-time analytics. Right now, you can't make a statement right.

today that cannot be checked in a matter of going to one of the GPTs or even going to Google. So you don't get to make things up anymore because that will kill your credibility right away. The next piece is, and I'm talking to my leaders now, personalized coaching. And that means understanding your reps, individual strengths and weaknesses from analyzing data again and no longer being able to peanut butter.

And the problem I have there is, and I say this with all humility and from the bottom of my heart, because I've been there before. Most managers don't know how to coach. They really know how to either A, make you a mini me of them, right? And they may have sold 30 years ago. Keep that in mind. And the second piece is how do you now share something that is intrinsic to you? And I always use

and NBA analogy, best players ever, Jordan, Bird, Magic, Isaiah, et cetera. Worst coaches, Bird, Magic, Isaiah, because they could not teach what they did because it was innate and intrinsic to them. Go find a way that works for the individual and then coach them that way. And there's a difference between managing and leading as well. And we can get into that in a whole other conversation.

Future Of Selling (33:03.505)
Yeah.

Roderick Jefferson (33:16.551)
The next piece is around how do you leverage AI to effectively make your sales process more efficient? And what I mean by that is finding a way to go back to the baseline of the buyer's journey and then flipping all of your sales processes, sales motions, let's call it selling motions so that it now ties back to their buying journey. Do they have buying seasons? Do they have buying committees?

How do they buy? When do they buy? Why do they buy? And when are they at a point where they're at a use it or lose it, where they have to spend that money, right? Of course, I'm talking about different segments here. And the final piece is all about automating, and we forget this part, automating customer communications, right? And that's for your account managers and for your CSMs, your customer support or success managers, excuse me, because they don't need to learn how to sell.

Future Of Selling (33:53.073)
Yeah.

Future Of Selling (34:11.173)
Right. Yep.

Roderick Jefferson (34:14.259)
They need to learn how and leverage AI so that they can help and they can now make recommendations so that they don't do the one thing that we all as humans hate. I don't ever hear from you 90 days before my renewal. You're my best friend all of a sudden. Now gives you an opportunity. You can create the communications that are now really narrowly and laser focused to a given customer as opposed to copy and paste, copy and paste, copy and paste, and you just change the name.

Future Of Selling (34:26.885)
Yeah.

Future Of Selling (34:44.059)
Yeah, got it. Yeah, no, those are great. Those are great. I love all of them. I wrote each one of them down. So streamlined lead scoring, automate task management, real time analytics, personalized coaching. There's such a thread we could go on there if we had time.

Roderick Jefferson (34:45.011)
Doesn't that help, Rick?

Roderick Jefferson (35:00.499)
That's a whole other episode by itself right there.

Future Of Selling (35:03.621)
Maybe that's, you just committed to a second interview. So that's a great thread. then really leveraging it to make your sales process more efficient. And finally, automating for customers, right? Customer success and count. And so those are incredible. The other thing you said was what works at the maturation of your company and your customers?

Roderick Jefferson (35:08.227)
Absolutely, I got no problem with that at all.

Roderick Jefferson (35:20.113)
Absolutely.

Roderick Jefferson (35:32.125)
Yes.

Future Of Selling (35:32.921)
Unpack that just a little bit for me. I like the but I couldn't... I don't know if I can tell you. yeah, that's what he meant.

Roderick Jefferson (35:34.788)
Yeah, we-

When you start thinking about the maturation of a company, when you are in growth phase, what matters to you? It's all about onboarding because you're bringing in headcount, right? So now I'm focused on how do I get messaging and positioning correct? How do I make sure it's consistent? How do we put in, know, guide rails and also things like, you know, certifications and accreditations to make sure everybody is speaking from the same book, if you will, right? As your company grows, now,

Future Of Selling (35:42.438)
Yeah.

Roderick Jefferson (36:08.763)
you're looking at, we're moving towards a big ticket sale. So now you need a different seller. So we always talk about ICP, right? The ideal current profile. I wanna talk something different right now. I wanna talk about IEP, the ideal employee profile, because the type of go-to-market person you bring as your company matures more is a completely different person. You can bring in a less seasoned early on because it's small, it's quick turnaround.

Now these are people that have to really have those stories and those case studies down pat to go, you know what? I can't walk into Bank of America with the same case study that I walked into, you know, to AT &T and then I turn around and I walk into a GM. Doesn't work. These are folks that have been to a couple of picnics and rodeos, right? They can really tell those stories. And then the final piece is when you grow and you become an enterprise level, because now the

Future Of Selling (37:00.494)
Right.

Roderick Jefferson (37:07.739)
sales cycle has extended, you need someone that can squarely focus on what really matters and that is relationship building. Because they're not gonna buy right now. You've got to continually nurture these folks and touch them with something that they can't just get by going to GPT or going and Googling. Does that help Rick?

Future Of Selling (37:27.214)
Yeah, yeah, no, that helps a ton. That's a great, great description. And then the last thing you said was learn how to use, I maybe liked it because I know we don't have a ton of time left, but maybe this is where we get in drill in a bit. Learn how to leverage AI to be more human, because I think that's what everybody worries about, right? It's just like you said, everybody's people are fearful that it's going to take.

all the jobs and there's going be nothing left. And even heard a sales leader the other day say something to the effect of, can see where the future is going and I've got to find, basically I've got to find another path, right? At some point. And I'm like, okay, okay. Well, I see how it gets there, but I like what you're saying. Learn how to leverage AI to be more human. So talk about how that's going to happen. One, how do you teach people to do that?

But also, where's it going?

Roderick Jefferson (38:25.437)
Yeah, I think where it's going is, and I will play that same broken record, IQ plus EQ plus AI. And what I mean by that is, and my definition is,

It requires the human touch to add in what AI can't give. And where I'm really trying to go here is AI can give us content, God, for the next 9,000 years after we're all gone. It requires a human to still give you context. People still buy from humans, right? And I always give an analogy, not even an analogy, but an example of my book.

Future Of Selling (38:55.182)
Yeah

Future Of Selling (38:59.706)
Right.

Roderick Jefferson (39:08.699)
I wrote the whole book. I wrote it from my soul. And then once I was done, I dropped it into Claude.ai and I said, please tell me what I've missed. I don't want it to write my book. I want it to augment. And do you realize that, remember that resource piece that I was talking about? I didn't have it in my book before I asked Claude that question. It was...

Future Of Selling (39:28.911)
Mm-hmm.

Future Of Selling (39:32.56)
Okay, got it.

Roderick Jefferson (39:34.291)
And it said, right, you've given them all of the opportunities to learn and to grow and to move forward. Now it's time to give them resources that can help them, whether it be something from, you know, American Stroke Society or American Heart Society, or even if you're a caregiver, there's a piece in there as well.

Future Of Selling (39:52.56)
Yeah. Yeah. Got it. Got it. Well, I like that. And IQ plus EQ plus AI, right? It's what's needed to make sure that we keep this thing human. Cause I do a lot, I do a lot of posting and videos and stuff like that on LinkedIn. And, and, and, know, just like you, mean, there's times where I, you know, I'll drop it in and say, Hey, what do you think? But if I rely on it too much, I don't feel like it's me. And so I've, I've got,

Roderick Jefferson (40:18.526)
No, no, no. That's why you need the IQ and the EQ to be able to direct the AI tool.

Future Of Selling (40:22.084)
Yeah.

Yeah, yeah, completely, completely agree. Okay. Good deal. Thank you for that, by the way. So, you've, you've led, you've led enablement at companies like again, Salesforce and Oracle, you're a consultant now, you get your own, you know, your own business where you're basically going in as a fractional enablement, kind of chief enablement officer or enablement leader.

Roderick Jefferson (40:31.7)
Absolutely.

Future Of Selling (40:53.168)
What lessons have you learned from some of those really large scale environments that may be translated to smaller scaling, you know, sales organizations?

Roderick Jefferson (41:02.004)
Absolutely, because I treat them both the same. Make sure that you're going to get a consult neurofractional that can give you experience and also case studies and to give you video testimonials because especially in today's world, I can get anybody to write anything or I can go write in chat, GPT and put your name on it, right? Instead, have asked them for video testimonials. And what that says is

Future Of Selling (41:06.53)
Okay. Yeah.

Roderick Jefferson (41:31.826)
That's someone that's willing to put their name and their brand on the line to now validate this person. The other piece that I would say is make sure that before you move forward, understand what their framework looks like. What are the steps they're going to take you through? But more importantly, what does success look like? What are the outcomes? And then that way you can both work co-jointly and collaboratively to reverse engineer that piece.

Future Of Selling (41:35.695)
Yeah.

Future Of Selling (41:54.33)
Yeah.

Future Of Selling (41:58.117)
Got it. Well, you've got, so we're coming up on, you know, for a lot of companies anyway, not all companies, but for a lot of companies, we're kind of approaching this sales kickoff season, right? So if you were in, and you know, I'm sure you've got a ton of them lined up. As you, you know, what is...

Roderick Jefferson (42:10.677)
yeah.

Roderick Jefferson (42:16.596)
I still got time on the calendar though right come on now don't put me in a box

Future Of Selling (42:23.535)
If anybody is looking for somebody, here you go. If you were designing the perfect sales kickoff for 2026, what would that look like?

Roderick Jefferson (42:25.78)
That's right, you're looking for a keynote speaker. I know a guy.

Roderick Jefferson (42:35.188)
Mm-hmm.

It would be kind of three components. It would be one, I call it edutaining, A mix of education and entertainment because you've got short attention span, especially with go-to-market folks. So make sure that it's structured, but make sure that there's enough time for networking. And I mean, for people to get to know each other. Because if you're going to pull everybody together, especially globally,

Future Of Selling (42:40.303)
Okay.

Roderick Jefferson (43:04.212)
They know each other by social media. may have been on, give them a chance to get to know each other. Swap stories, right? I'm working on this. Oh yeah, I know someone, so let me introduce you to them. Cause they did X, Y, and Z. That's one piece. The other piece is to make sure that it is what I call knowledge bites. And that is things that can be tackled and taken in right now and go put into practical application. Don't hold people for eight hours and over the hostage over.

PowerPoint Fest, nobody has time for that. Make it engaging, it entertaining and make sure that it's impactful. And then the third piece, and I think which is more important than the event itself, is to always make sure that you have a reinforcement plan. I always look at SKOs or RKOs, however you guys call it, right? As the foundation, it is the floor, it's not the ceiling. It is what you build upon.

for the remainder of that year. So roll out anything new or anything foundational in that SKO that one cannot be tracked, cannot be measured, and also cannot be reinforced. Most importantly, as you are building this SKO or ROK, RKO, make sure that enablement is the center point of the owner of and the architect. Bring sales, marketing, product marketing, HRs, and sales together.

excuse me, and marketing to the same table to make sure that it's communication, collaboration, and organization.

Future Of Selling (44:33.988)
Yeah.

Future Of Selling (44:39.45)
Yeah. Yeah. Got it. Got it. Okay. Yeah. Yeah. Okay. Got it. You've been on 250 podcasts plus what's the best question you've ever been asked? Because I want to ask that question.

Roderick Jefferson (44:42.377)
We are the orchestra master. Let us conduct.

Roderick Jefferson (44:56.945)
Ooh, man, see that's a secret one, right? If I tell you that, then now I have broken trust of the other person. Cause I told them all, this is the first ever and they're like, don't tell anybody, Cause now we've got, well, you know how you guys are as podcasts. You'll want that exclusive. I'd love to give it to you, but then I broken trust.

Future Of Selling (45:01.712)
Is

Future Of Selling (45:10.896)
Alright

Future Of Selling (45:16.354)
Okay. Okay. No, I don't, I don't want you to do that. I don't want you to do that. Let me, let me ask it a different way. Is there anything that we, so it's been a great conversation. love everything we talked about. You've given some incredible kind of information for folks to walk away with and apply. Is there, is there anything that I haven't asked you about that you go, Hey, Rick, there's this one point you, we didn't really talk about it, but I want to make sure that people walk away with this. Anything. Okay.

Roderick Jefferson (45:43.486)
One thing and one thing only. For folks that wanna move forward, how do they contact me? I think that for them, right? And that is if you wanna find my company, you can find me at Roderick Jefferson on LinkedIn. You can also find me at my website, roderickjefferson.com. On Instagram, Roderick underscore J underscore associates. And I will give you show notes for all of this.

Future Of Selling (45:49.678)
Okay. Yeah.

Roderick Jefferson (46:11.773)
to make it easier for your listeners as well. And if you are looking at the need for an offsite or you've got a conference or you've got an SKL coming up, and I've said something today that resonated with you, please reach out. I would love to be able to connect with you and see if we can do something together.

Future Of Selling (46:30.106)
Beautiful. Love that. Love that. Yeah. We'll make sure we post all of that in the show notes. And I found you easily on LinkedIn. So if anybody's looking for you, might absolutely easy to find. So, okay. I've been let you go in just a second. Let's say this, I'm a sales leader, right? I'm looking to kind of, you know, improve my results and upscale my team. From your experience as a sales enablement leader, what are three key takeaways from today's conversation?

Roderick Jefferson (46:40.917)
Thank you so much.

Future Of Selling (46:59.162)
that you would say, think about this, think about that, think about the other.

Roderick Jefferson (46:59.219)
Yeah.

I think as I said earlier, I've used the two brain cells already that I have left, but I do have one thing for all leaders. And it is a three-part question that I started using years ago. I use it with my team, with other executives, et cetera. And that is as you're having these one-on-ones, irrespective of who you're having with, other than your spouse, don't use this with your spouse. I'm going to warn you right now, it doesn't go over for a while.

Future Of Selling (47:29.264)
So now, my wife. Okay, thank you for coming in.

Roderick Jefferson (47:33.482)
It's a three-part question. Do you want me to listen? Do you want me to coach? Or do you want me to fix? Let me say it again. Do you want me to listen, coach, or fix? And there are two reasons that that I believe is one of the best questions that anyone has ever asked me in my entire professional career. And it's because one, as leaders, we're natural fixers. That's how we got to where we are.

But most of the time I've realized your people, that's not what they need. Sometimes they need to just be able to bounce. Does it sound crazy outside of my head? And I've thought this through. Is there another way to better message and position this? When I ask them if I want them to coach, it's because it's like, hey, you've done this before. You've got an extended network, whatever it may be. Help me on this. And then the third one is, look, I've tried everything I know, almighty one, right? Just tell me.

Future Of Selling (48:27.802)
Right.

Roderick Jefferson (48:28.895)
How can I do it? Or give me another set of lenses. And the second reason this is so important is because you are telling those people to tell me as the leader what set of ears I need to listen with. And this is all about you and your time. So do you want me to listen? Do you want me to coach? Or do you want me to fix?

Future Of Selling (48:46.959)
Yeah.

Future Of Selling (48:50.66)
Yeah. Yeah. That's I love that question because it positions you to bring value to the, to the team member who trusts you as their leader. That's power.

Roderick Jefferson (49:03.633)
Absolutely. And it yields an enormous amount of credibility for both the leader and for the team.

Future Of Selling (49:10.83)
Yeah. Love that. Love that. Okay. Roderick, thank you, sir, for the time. Thanks for the conversation. I will continue to follow you. hope you and I can stay connected and looking forward to the book. So thanks, man. Appreciate you being here today.

Roderick Jefferson (49:21.422)
we definitely were. Come on now. We're two Dallas guys. We've got to stay together.

Roderick Jefferson (49:28.701)
Looking forward to it. Thanks for the opportunity.

Future Of Selling (49:30.928)
All right, thanks a lot. Bye-bye.

Roderick Jefferson (49:32.778)
Bye now.