A 2025 AI Reality Check for Sales Leaders, Reps, and RevOps

What happens when you stop predicting the future and actually audit the past?

In this episode of AI Powered Seller, Jake Dunlap revisits his 2025 AI predictions and gives them an honest scorecard. No hype. No backpedaling. Just real lessons from the front lines of revenue teams adopting AI.

Co-hosted by Skaled’s Head of Marketing Kara Burd, this conversation breaks down how AI really impacted sales teams over the last year and why some widely held assumptions completely missed the mark.

You will learn:
 • Why reps adopted AI quietly while leadership debated policy
 • How AI created performance gaps instead of replacing jobs
 • Why most copilots became distractions instead of deal support
 • Why personalization is now table stakes, not a nice-to-have
 • What surprised Jake most about high performers resisting AI
 • What sales teams must operationalize in 2026 to win

This episode is for sales reps, sales leaders, RevOps, and founders who want a grounded, experience-based view of AI in revenue, not theory or trend-chasing.

If you are trying to figure out how AI actually fits into your sales motion, this episode will save you months of mistakes.

Listen now and start 2026 as a truly AI Powered Seller.

Transcript

Cold Open: Right Or Wrong

SPEAKER_01 0:00

You were wrong. I don't think that happened.

SPEAKER_00 0:01

I nailed that.

SPEAKER_01 0:02

By next year, most revenue teams will have AI agents running real workflows, right or wrong?

Setting The Stage For 2025 Recap

Kara Joins To Keep Score

SPEAKER_00 0:08

I nailed that. I know number four and five in particular were some horrendous uh guesses by me. And a little pop-up comes up and it's like, Jake, you didn't mention the competition. How many of you out there are like, oh, thank you, Copilot? If you're gonna use AI to generate it and then have a human hit send, why uh AI powered seller. Welcome everybody to another episode of the AI Powered Cellar, episode number 34. Really excited for 2026, but today's episode is all about 2025 predictions. No, you are in the right place. This is still 2026, but today's episode, I'm going to recap last year. And if you listen to the podcast, you follow me on LinkedIn, you know I talked a lot about AI. Maybe even saw my uh AI remix that Riverside just did me dirty on, where it pulled out this clip of me just saying AI five like 5,000 different ways. So today's episode, I'm gonna break down all the predictions that I made in 2025: the right, the wrong, the somewhere in between, the really wrong, etc. And I'm really excited for today's episode in particular because I have our head of marketing, Kara Bird, joining me to help keep me accountable, call it like she sees it, and make sure that we really cover. I think she's more excited about the wrongs, let's be honest here, right? As a part of it. So, Kara, excited to have you join me. And, you know, who knows? Maybe we'll maybe we'll make this a regular thing.

SPEAKER_01 1:35

Yeah. No, I'm excited for this one. We have talked about a lot of AI. And I even went through the files and pulled up some quotes. So I'm ready to hold you together.

SPEAKER_00 1:45

Yeah, there we go. All right, love it. That's great. And yeah, as we get into this, I know number four and five in particular were some horrendous uh guesses by me. So you'll make sure to want to tune in for those. So, all right, well, look, there's no point in in wasting time. So we've got my 2025 predictions. I think I've already made some of my 2026 predictions. So we'll make sure to link to those uh as a part of this. So uh let's kick it off. Let's start with prediction number one.

Prediction 1: Reps Beat Leadership To AI

SPEAKER_01 2:11

All right, let's get into it. What Jake got right or wrong. Um, so like I said, you're going to grade yourself. Basically, was it a hit or a miss? So, number one, reps adopted AI faster than leadership. So I actually went digging and found that in January of 2025, you said, here, I'm paraphrasing a bit, but not by much. AI won't be a leadership-led transformation. Reps will adopt it quietly, daily, and without permission, and leadership will still be debating policy, right or wrong?

SPEAKER_00 2:41

That facts.

SPEAKER_01 2:41

It is. You're right.

SPEAKER_00 2:43

I think so. What do you think? I mean, you see this, you see a lot of our clients and what they're doing. What are you seeing?

SPEAKER_01 2:49

Yeah, no, I think I think this one is spot on.

Evidence From Client Workshops

SPEAKER_00 2:53

Yeah, we're seeing this across our clients, you know, where clients are coming to us and it's, you know, we go and we'll meet with the reps, and you know, we're doing kind of intake with different clients. And okay, what are you guys doing? We're using Chat GPT. Then you ask, then you ask like the sales leadership or RevOps, oh no, we use Gemini. It's like, no, you don't. Like, you think you use Gemini. And some people do. We have a lot of clients that use Gemini, so it's a good tool. But yeah, I think if anything, I think it even exacerbated it. I think whenever I made this prediction, we had just done this kind of workshop with uh a client of ours at their kickoff, and you know, we had all the reps raise their hand. I think it was like a a rumor, like three or four hundred, and probably ninety percent of the hands went up. And then we talked to the sales, we did a big session with their leadership team, and leadership was like, yeah, maybe I'm using it, etc. So I still think the reps, yeah, salespeople were resourceful. If there is a if there's a faster way to do BS time, you know, we're gonna find it. So I'm glad that that one, hopefully this year, you know, my prediction is sales leaders will start to catch up, but still I think it's gonna be rep led for sure.

SPEAKER_01 3:57

Totally agree. It's like you can't control whether your team uses AI, they're going to use it, but you can control whether they use it well or not.

SPEAKER_00 4:04

That's right.

Prediction 2: Leverage Gaps Not Layoffs

SPEAKER_01 4:06

All right, let's move on. We've got number two. AI created leverage gaps, not job losses, at least not yet. And I've got a quote from here, from you here. AI won't replace sellers first. It'll replace average output. One rep will start doing the work of two or right or wrong.

SPEAKER_00 4:23

I think like in between. I think I got that right. I think that, you know, I don't think we're seeing mass layoffs right now. You know, I don't think we're seeing mass layoffs. I think we are seeing, you know, as we go into the new year, sales leaders and marketing leaders with numbers that don't maybe have the same headcount for a growth standpoint. You know, if there's companies trying to go to, you know, a few hundred million, maybe you used to get X number of headcount and now it's like figure it out. So I I think that's right. I don't think we saw this kind of big job loss versus you know productivity gains.

SPEAKER_01 4:54

Yeah, you're right. You're right. I'm gonna do that.

The Coming Divide Between Reps

SPEAKER_00 4:56

Two in a row. There we go. There we go. Two in a row. That's right. You all still have jobs. That's great. I do, I will say, I think 2026, um, I think you're gonna start to see called like the have and have nots. That uh, you know, my prediction for this year is you're gonna start to see a divide. You're gonna start to see a divide between reps that are consistently using it, they're they're AI curious, you know, they're doing certifications, they're doing um, you know, building their own custom GPTs or gyms or uh agents and co-pilot, and and the other reps that are like, oh man, what's what's Carolyn doing over there? Why is she doing that? And then Carolyn's crushing quota by 130% and they're they're missing numbers. So I think I think you'll start to see a pretty big divide this year. That would be my my prediction.

SPEAKER_01 5:38

Yeah, I agree. And you've you've talked about from a hiring standpoint as well. A ten-year rep comes in and does it by the books and does it this way compared to a younger, newer rep who's super efficient in AI. I think we'll start to see it there too.

Use AI Smartly, Not Sloppily

SPEAKER_00 5:52

Yeah, the key, the key though, is that you can't just copy and paste AI. Like, let me, I'm just gonna get this as a pro tip, everybody. Do not send me a document that has a line in between every section that has double spacing between every bullet. Okay. And that at the end of whatever bullet is, there's another space. Okay. Like I know that that's AI. Like make sure you take the time, you put your, you know, two cents on it, you make it your own. Um, you know, but uh, you know, at this point, like I even though I know it's AI, uh, you know, what I do when I meet with people now is I just test it. I'm like, great. Well, over here you talked about this, this, and this. So, you know, what was your thought process here? And so, you know, you gotta make sure as you're using it, you're using it smart.

Prediction 3: Operationalizing AI Was Slow

SPEAKER_01 6:29

Moving right along, I like this one. Number three.

SPEAKER_00 6:32

I'm not gonna look at my notes.

SPEAKER_01 6:33

Yeah. Number three. How slow companies would operationalize AI. I pulled a quote you said last year. By next year, most revenue teams will have AI agents running real workflows, right or wrong.

Workflow Example: Hot Points To CRM

Why Adoption Still Lags

SPEAKER_00 6:47

Oh no, I missed that bad. No, it's uh I remember back in 2023 or 24, you know, as we started to, you know, kind of start our AI journey of, you know, even myself, like mid-23, I guess it would have been. Um, you know, really seeing the future and looking ahead. You know, back when my you know, my my good friend KD and I used to talk about this stuff back in 23, 24, and early last year, like what's possible is just amazing. And I think I just assume that sales leadership and revenue leadership would care about productivity more. And it's not that that leadership obviously doesn't not care about productivity. So to be very clear, I'm not sitting here saying they don't, but I do feel like if I go to you, like let me, I'll give you a practical example here, Kara. Okay, we got a client right now. Here's what the client does today. Their reps finish a call, they finish a demo. They then have to go to the CRM and some of the data pushes. They got to go log their notes, then they go to Gmail and they write their email, maybe they copy and paste some stuff from a summary, et cetera. As opposed to the workflow we're building, which is as soon as the call recording finishes, it immediately rips the transcripts, ports the relevant, we're calling it the hot points. Hot points go straight into a CRM field. I think it's just one field, maybe it's multiple, right? So then if they're going to their next call, they're like, what did I talk to Sandy about? I don't remember. It's like the notes are there, I don't have to go pouring through them, and then automatically address an email draft in their Gmail. It's like you cannot listen to this and say, that obviously seems better and faster. But for some reason, we're still slow. I don't know.

SPEAKER_01 8:20

Yeah.

SPEAKER_00 8:21

I don't understand the logic, but I don't know. I think we're still waiting. Why? Exactly. If I was a rep, I'd go, oh, please, God, please, I never want to write another follow-up email. Or let's be honest, you don't write the follow-up email, right? Uh, as a part of it, too.

Prediction 4: Most Copilots Disappoint

SPEAKER_01 8:35

Couldn't agree more there. Moving on to number four, and I like this one because you thought co-pilots would be a big win here. Number four, how bad most co-pilots would be, right? Or wrong?

SPEAKER_00 8:46

Okay, I said they were bad, right?

SPEAKER_01 8:48

Yeah, yeah.

Real-Time Coaching vs Real Distraction

Where Copilots Actually Help: Digital SE

SPEAKER_00 8:49

I said that they were gonna be bad of you. That's a huge W. Like, nobody tell me one rep. Please, okay, please. If you are a rep right now, please, please, please, please. I want you to DM me one of two things. One, if you're a rep that loves, hey, you're on a you're on a demo, I'm talking to Kara. I'm like, I'm uh I'm in the mode, I'm doing my thing, I'm like connecting the dots, talking ROI, I'm all into it. And a little pop-up comes up and is like, Jake, you didn't mention the competition. How many of you out there are like, oh, thank you, Copilot buddy? I'm gonna now, oh, by the way, Kara, do you know that we actually have two times more integrations than ABC.io? No, nobody is gonna do that. Now, and and I if you're a rep that loves it, please, please, I want you to DM me, or if you're watching this on YouTube, drop it in the comments as well. Too tell me the tool you love. I would love to be proven wrong. I love the idea of having real-time feedback. I love that, right? And I think back to back in the day, day, whenever I was growing up in sales, we used to have these things called Y chords. So here's what would happen you'd have your phone and your manager would like why, like, like you, like this thing was like a why, if this makes sense, if you can visualize it. So, like there's one, it plugs into the phone, and then it goes to you and it goes to your manager. And like I remember very Amy, Amy was her name. She was listening here. And I'm doing the you know, I'm doing the the conversation. She hits mute, she goes, Jake, you're talking over them. Like you need to pause, but you need to hit mute before you do this. I'm like, what? And sure enough, I started doing it. So she like corrected me in real time. And it was fine because it wasn't like too much. It was like a subtle this. It was like a subtle, like that as a part of it. Now, the interesting part is I that's really tough to do in the video world, right? Like, you know, I don't know how do you get how do you get virtual Amy whenever, you know, Jake's on that. I guess you could just turn off your video for one second. Nobody would really know as a part of it. So I I feel like these things where they all where they do work, Kara, where we're seeing this with our clients is digital product essay. So Kara asked me a question about hey, Jake, tell me, is this SOC 2 compliant with a blah, blah, blah integration? And the rep's like, option one is rep goes, hey, that's a great question. Let me answer it there. Option two is they pull up a co-pilot and it knows all your product information, et cetera. And it goes, yeah, it's real. Yeah, actually, hold on one second. Let me take a look. Okay, next question. Uh yeah, actually, we do integrate with Blue Jeans and it does it this way and blah, blah, blah, blah, blah. So uh, yeah, the co-pilot thing, I would love to hear from you people, from anybody who loves it. Um, I'd also love to hear if anybody feels like I do that your company either has it or makes you use it. And you're like, this is a complete waste of time because I am still very much in the waste of time camp.

SPEAKER_01 11:28

I feel like there's so much curiosity around using them.

SPEAKER_00 11:31

I get the vibe. I mean, I real-time feedback is a good thing. I just wonder if there's a better way to do it. And I do think maybe it's so tactical too, Kara. It's like it, you know, these things don't have a lot of context. And so they're kind of bringing up things based on like keyword or a thing or this. It's not, and my guess is it's probably overcorrecting too. You know, if you think about if you're a sales rep, maybe I can remember one or two things to improve after a call. But if you give me 55 pieces of feedback, I'm not gonna remember any of it. So yeah, you know, that would be my take on it, is you know, I think there probably is a path forward where these could be helpful. Product, no-brainer. Every company should have a digital SE that rides copilot. And we're trying to figure out a way to build this with one of our clients into the recording software, like into Zoom's AI companion, for example. I don't know if we'll be able to do it. I'll report back to everybody in the next like month on if we can do it or not. Yeah.

Postcall Scoring And Adoption Reality

SPEAKER_01 12:22

I mean, when you sit down with a client, are they are they knowing like, hey, I need a copilot, or do they know that? Yeah, I'm sure they are.

SPEAKER_00 12:30

Yeah, no. I think what you get is you get leaders that say, how do we get our people to adhere to our best practices more? And it like I like I said, on paper, it doesn't seem like a stupid idea. On paper, it seems it's like, oh yeah, like that would be helpful, but it's the execution of it. So yeah, uh, I think you're seeing it, or you're seeing a lot of it postcall, right? Postcall grading, scoring, that type of stuff. But yeah, definitely more and more people, I think, are curious about it. But again, like, are your reps going to use it? That's the question you got to ask yourself. Right.

Prediction 5: Personalization Or Bust

SPEAKER_01 13:01

All right. On to number five. We've got personalization became table stakes. Early 2025. You said generic outbound won't just stop working, it'll damage trust. And you also declared very, very boldly, I will say, uh, that battle cards were basically dead. Still standing by there. There you go.

Activity Metrics vs Outcome Thinking

SPEAKER_00 13:20

I am definitely I am standing by. I look, maybe I should have said like static battle battle cards are dead if I want to walk back it a little bit. I think that was right. I think I think outbound in particular, I don't see I don't see the trend in outbound going up right now. You know, I don't see the trend. And I also, I'll tell you the other thing, care, that's maybe another leading indicator. I also don't see more companies focusing the way they manage outbound, both for AEs and SDRs, to outcomes versus activity still. I still see most people activity is king, and it's like more and more. And by the way, there is a certain level of output that a human being should be doing in a workday. I want to be very clear. You know, I'm not, you know, saying oh, John should just be able to do five assassin type emails and he can book meetings. I mean, if he can, sure, great, go for it. But, you know, so I feel like that was probably right, and I think it's just getting worse. I feel like if you're not doing personalization now and you know, doing remember what Tanner, Tanner's doing like white pay personalized white papers and things that were cutting through the noise and booking meetings, and it took, you know, 10 minutes to generate one and 10, 15 to fix it, but it worked. So yeah, I think that's right. I think outbound is just gonna get harder.

SPEAKER_01 14:34

The fact you can now generate an entire ROI presentation, but people are still doing your general emails that take three seconds to do. It's not gonna cut it.

Tools, Journey, And Practical Shortcuts

SPEAKER_00 14:42

That's right. And also just think about the the mindset. Why are you again going back to like you, you know, we talked about operationalizing it before? Why would you pay a human to hit send all? Why if you're gonna use AI to generate it and then have a human hit send, why uh why? Yeah, and so that's for all my my people doing outbound. That's account executives, strategic account executives, enterprise account executives, SDRs. You have to learn how to turn your brain on. Kind of like I gave you that cheat code on like don't copy and paste, you know, fix the formatting, et cetera. Um, you know, you're gonna have to do that. So, okay. Look, and I think that that's another reason why, you know, we created Journey too. So if you guys haven't checked out, it's meetjourney.ai. And, you know, meet journey is your suite. You know, we've got a digital SE. We just kind of custom built in for a client, like I mentioned before. You know, people and reps don't have time to build custom GPTs and they don't have time to go and build agents or learn prompting best practices. And that's why I think Journey is saving companies so much time is, you know, they don't have time to go and teach everyone how to prompt, teach everyone how to go and build these things. You know, I can just go, I can create different accounts, I can have each assistant, you know, focused on that account for me. I can go and do the research for me. Coming up, it's going to be integrated with Salesforce, so it can write the notes back. And so for any company that's looking for like how do I move from, yeah, this is interesting to crawl walk in a month versus nine months. I think Journey is like a, or if not the only way to do that, you know, right now. So make sure everyone go check out Meat Journey. Put a lot of time, a lot of effort. It's pretty badass. But I'm not gonna lie. I'm obviously biased, but it it works. I use it every day.

SPEAKER_01 16:21

I also use it every day. Total game changer.

SPEAKER_00 16:23

Boom. Shout out.

Prediction 6: High Performers Resisted Change

SPEAKER_01 16:24

All right, moving on to number six, and I like this one. I feel like it's come up in conversation a lot recently. How uncomfortable this shift would be for high performers? I think this one really surprised a lot of people.

SPEAKER_00 16:34

Yeah, I think I probably I don't remember exactly what I said. I'm gonna guess I thought high performers would recognize it and that high performers would realize that, oh yeah, this is a cheat code and it can help me get ahead, or more seasoned reps would realize, like, hey, I need to do something. I don't know if that's what happened, but did I get it right or wrong?

SPEAKER_01 16:56

You were wrong. I don't think that happened.

Why Playbooks Are Hard To Abandon

SPEAKER_00 16:58

Come thinking, yeah, you're probably right. Like, if I'm being honest with myself, I don't think it happened either. Yeah, I I I guess if I had to kind of I think it's really hard to tell somebody, hey, you were wildly successful. And I think that's why I, you know, honestly care why a lot of sales leaders are struggling with adopting this or changing their mindset. You know, hey, look, I worked at Salesforce and I've got my playbook, and this company hired me because of my Salesforce playbook, you know, and now you want me to do something different, you know, like, but this has made me successful. Why would I do something different? So, you know, I just think change is hard, and most likely a lot of reps just kind of were maybe still able to be pretty successful because the bar, you know, you're not seeing like that, like it's talking about that divide yet, maybe, you know, where it's really like the have and have not. So, you know, we're definitely seeing some top performers for sure. I was on site with a client last week and it was actually pretty fun, you know, some of the reps, but you could tell some of the other reps were like, eh, maybe I use it, but it's real basic stuff. You know, they're not even thinking about how they can feed it, their transcripts, and it can come up with trends and write their, you know, even the manual version where it can write the email for me or those types of things. Yeah, come on, top performers, let's do this. Come on, let's get on. Now's the year, 2026. Let's get on that. Am I gonna now? The key is am I gonna live? I'm gonna, I'm gonna retract that. I'm gonna retract for 2026. I now that I know what I know, I don't think I think it'll be probably about the same. Maybe some more top performers will figure it out, but still, you know, more will not have it figured out.

SPEAKER_01 18:26

Yeah. No, I I agree. And I'm that's all I got. So what three right, three wrong, you get a 50%.

SPEAKER_00 18:32

That's not bad. 50%. I mean, I feel like in in AI predictions land, like that's not terrible, right?

Final Scorecard And Reflections

SPEAKER_01 18:39

It was a it was a long year. A lot happened.

SPEAKER_00 18:42

I feel like that's right. It was a long, it was like a very short year too, though. I feel like it's like, wait, it's 2026 already?

SPEAKER_01 18:48

Yeah.

SPEAKER_00 18:48

You know, I do I do feel like that like came about very quickly. So look, that's awesome. I I think look hopefully people listening out there, you're you're taking all of this in. You're kind of reflecting on yourself, maybe as well, too, and your own usage of AI as a leader or a PE firm or a rep. And Kara, I think you did a great job co-hosting. You know, I think we're gonna bring I think you gotta come back. You know, I think you gotta come back. It's good because then you know, people don't want to just hear me like go on and on and on about stuff.

Wrap Up And Share Request

SPEAKER_01 19:18

I'm always down to hop on and hold you accountable.

SPEAKER_00 19:21

There you well, yeah. Well that yeah, I think that's probably why you wanted to do it, right? You're like, this is a chance for me to just show Jake how off how often he is wrong and be like, hey Jake, remember that 50%? Remember this decision I'm trying to make now in marketing? Like, hey, 50%, Jake. Yeah, 50%. Well, that was awesome, Kara. I really appreciate you joining. Um, definitely, uh, you know, I think, yeah, definitely, especially these these episodes, non-interview ones. It's always fun to have someone to bounce ideas off of. And, you know, you are definitely for the work we're doing at scale, doing a great job of leading the effort. So thank you for joining. I appreciate episodes.

SPEAKER_01 19:54

Yeah, this was great. And uh we've got a lot of good things going on, so I'm excited to keep things going on. Going and I'm always happy to step in and be a guest or a co-host.

SPEAKER_00 20:04

Co-host. Co-host. I think co-host. We'll see. Um, and thank you everybody uh for tuning in. Uh, really appreciate you joining us. Make sure to, I always tell people look, you can like, you can subscribe, but what I think would be even better is share this with your coworker, share this with your sales leader, share it with in your Slack channel, etc. You know, maybe there's something in these trends that stood out to you, right or wrong. And, you know, I really just appreciate you taking the time to join us today and to listen and hopefully continue to improve as an AI powered seller. That's all I got. Excited for 2026. I hope all of you are excited as well, too. And we will see you all on the next one. Take care. Bye, guys.