AI-Powered Seller

Top 5 AI Predictions That Will Separate Top Sales Teams in 2026

• Jake Dunlap

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2026 is the year AI stops being optional in sales.

In this episode of AI Powered Seller, Jake Dunlap walks through his five biggest AI predictions for 2026 — and why sellers and leaders who don’t act now will be forced to catch up later.

This conversation goes beyond tools and trends. Jake explains how AI becomes a true go-to-market teammate, why generic personalization is dead, and how signal-based selling will redefine outbound, deal cycles, and account growth.

You’ll learn:

  • What digital teammates actually look like in modern sales workflows
  • Why AI-generated personalization alone won’t cut through
  • How coaching shifts from post-call to real-time execution
  • Why signal-based selling becomes mandatory, not optional
  • Why AI fluency becomes table stakes in 2026

If you want to win in sales next year, this episode is required listening.

Learn more about Skaled: https://www.skaled.com

Connect with Jake on LinkedIn: https://www.linkedin.com/in/jakedunlap/

Check out Journey AI: http://meetjourney.ai/

AI Certification for Reps:  https://bit.ly/ai-sales-certification-rep

AI Certification for Managers: ​​https://bit.ly/ai-sales-certification-manager 



SPEAKER_00:

Welcome everybody to another episode of the AI Powered Seller. Today's episode is one of my favorite of the year. This is my 2026 predictions episode. And the fun part will be we're going to drop an episode here in a couple of weeks, which is all the stuff that I got wrong in 2025. And trust me, I got a lot wrong. I'm feeling pretty good. I'm feeling pretty good about these predictions. Now, where we're at on the adoption curve with these predictions by mid-year, end of year, TBD on that. So look, whether you are a CEO or rep, today's episode is going to hit home. I want all of you by the end of the episode, I want you to go back and maybe listen to two or three minutes, and I want you to pick one of these trends to do something about in January. To me, this is non-negotiable. 2026 will see the gap really start to widen. And if you don't start your journey now, you're going to have to start it at some point. I don't know what to tell you. So without further ado, let's jump in to my top five AI predictions for 2026. AI powered seller. Today, my friends, I'm going to break down the top five 2026 trends for AI. Now, look, 2025, a billion different things happened. So anything I'm going to talk about now, I'm probably going to have to do again in like three months and say, oh yeah, now, like here's my new 2026 uh trends predictions. But based on what I've seen and based on where I see organizations that we work with going, here are my top five trends. And I have to tell you, trend number four is probably the one I'm most excited for. So definitely make sure you tune in to listen to trend number four. So trend number one, AI stops becoming a tool and starts becoming a teammate. I still think 2025 was the year where leaders, no offense, you're still really behind, but reps at scale, consistently, whenever I would go into rooms or we would work with clients, I would say, how many of you are using Gemini co-pilot ChatGPT every day or at least four or five times a week? And in 2024, maybe 50, 60% of the hands went up. This year, probably 80, 90% of the hands went up. So what I see consistently is reps are continuing to use the tools. But also consistently, there's no centralized best practices. I have to tell you, maybe 5% of our clients, maybe five. I think I'm maybe being generous, actually have a centralized best practices, even like a prompt library. So the issue is it's still kind of a tool that's being used a bunch of different random ways. In 2026, the difference is going to be this. The difference will be yes, reps will still be chatting, but the way that it's going to be a teammate is through automations. There are ways today to automate a vast majority of the let's call it BS, no value add parts of a sales job, logging to Salesforce, listening to, you know, did I do this in a call, et cetera? To where for me, when Genai becomes a teammate, it listens to my call, automatically rips my call transcript, automatically logs the activity to Salesforce for me. It then uh sends me a Slack message and says, Hey Jake, here's kind of the trends that I saw. Do you want me to log those notes to Salesforce for you, key up an email for you, and put together version one of a proposal for you? Well, yes. Digital teammate Sam, I would love for you to do that. Guess what, my friends? AI can do that today. And I think what we're gonna see in 2026 is more and more and more of those types of use cases where AI sees your meeting, automatically does your prep, does everything that I said. Then it maybe even reminds you, hey, hey, don't make sure to follow up with Ricky or whoever it is. So 2026, AI's teammates start to be a part of your go-to-market team. It is possible to do this today, but I think we're gonna actually start to see it, maybe not at scale scale, but maybe each organization introducing one or two of these digital teammates is what I like to call them. Because I feel like digital teammates makes it sound less boring than we're gonna automate this, this. It's like, well, Sam, Sam does these five things digital teammates, trend numero uno. What is trend number two? Trend number two, ooh, I love this. Personalization becomes the minimum, not the differentiator. Ooh, I want you all to think about that. With Gen AI, I can literally in 20 seconds create a customized white paper just for you. It will analyze the industry trends that are happening, how that relates specifically to your job title and how we solve for that, and use 25 outside sources to where I can literally send a personalized white paper to you and from email creation to email a three or four minutes. So, what does that mean for you? That if you aren't in the trenches, in the nuances of it, if you aren't able to take it from it's just it's not that, it's actually this, you know, and and make those, I'm gonna call them like the 10 to 15% tweaks, outbound is most likely never gonna work for you. I wanna be that blunt. That if you aren't leveraging AI to get to a level of personalization that your peers can already do, and you have human beings that are able to take what AI does and do those slight tweaks, it's actually not quite that. They actually care more about this. You know, AI isn't perfect by any stretch of the imagination. And so generic outreach won't just underperform, it will tank your credibility. If you are doing bulk send, non-customize, I saw you went to Arizona State, I went to Arizona State, I saw you posted these this LinkedIn article. I really enjoyed your insights. If that's the crap your team is sending, you are done. Done. And to me, what I'm most excited about is the cream is going to rise to the top. The interesting part is we're actually kind of going back in time. Before all these tools came out 10 plus years ago, every single email that a rep sent or call they made was customized. It had to be. I didn't have the ability to send all. So I had to customize every single interaction. And so for me, 2026, what all of you should be excited about is not only is the quality of what I can do higher, I can do it faster, but then I get to turn my own unique perspective into the differentiator and crush the competition. So generic is dead, AI-generated personalization won't cut through the noise. The only thing you'll have left is you. You as the human to do the small tweaks, make sure you're doing everything in a customized, personalized manner, and you can still win an outbound in 2026, but you have to do it the way that I just said. That, my friends, is trend number two. So before we jump into trend three, I want to do a quick shout-out. We will be launching V2 of our AI certification this February. So if you're an organization that is trying to get up to speed on Gen AI, Jake, I hear you. We need to do some of this stuff. We need to know how to build these digital teammates. Sign up. It's like a few hundred bucks. This is really just to help organizations and leaders get up to speed. So make sure to sign up. Additionally, as usual, if you're getting value out of the episode, please make sure to subscribe on your favorite podcast channel. If you're watching on YouTube, make sure to hit the like button, subscribe to the channel. And as always, what I really love is share something in your Slack channel. If there's something that resonated, share something in your own teams and say, hey guys, I think that we can all you know benefit from this. So without further ado, what is trend number three? Trum roll. All right, coaching moved to the moment. This one's a little controversial, and I'm a little torn on this because let me tell you a little story. I very specifically, this is old school. Let me take you back a little bit. What we used to do is imagine if I'm a rep, I'm on a call. You used to have, and your leader is next to you, used to have what we called a Y chord. Okay, and so here's how it would work. Uh, like, you know, you're like on the phone, right? And it's, you know, it's not a phone, it's like a headset. And then your boss can kind of cord in as well, too. And they can't talk, it's just they can listen in. So your boss is kind of right here, you're here. I didn't have really ever have a problem with it. Like, you know, I I don't know, it didn't really ever bother me. But long story short, what your boss would then do, and then I was the boss doing this as well, too, would just kind of, you know, maybe push the mute button, say, hey, look, slow down, think about this, etc. And you're like, okay, you're right, I'm getting ahead of myself, etc. And and candidly, it kind of worked. The issue of I've seen with a lot of, you know, I'm gonna call it tools, is they're not focused on that. They're focused on, oh, they said they said gong, and I work for outreach. Oh, they said gong. Oh my god, oh my god, uh uh, say this thing. And and it's annoying. It's like jump. I I haven't seen a single one of these, I'm gonna call them co-pilot tools that reps are actually able to you know use at scale. And where I feel like co-pilots in 2026, friend three will move to is to help the reps to have a better conversation, right? Sure, I think what it'll potentially do is maybe again, maybe it could it could say, hey, let's slow down. They mentioned this, let's think through how we can position that later. I'll tease something up for you then. So, so listen to the behavior. It's less about just surfacing a random thing and it's more about being a coach in the moment. It's being a coach, it's not just saying, here's the battle card, here's whatever it is. And so for me, in the moment, you know, reps that are gonna rely on managers to catch their mistakes are gonna fall behind reps who get coached during execution and post-execution. Because what also AI is getting better and better at is taking that call transcript, taking what's happening, and then turning that into actional insights for you to continue to get better as a rep. So my prediction around this kind of co-pilot motion is that AI stops becoming an interruption machine that refs just are like, God, go away. Because I've seen these tools sometimes that'll be like, okay, they said this, now do this, and then there's another thing, and you're like, I'm trying to talk to this human. Why the Y chord worked is I'm trying to talk to them. They're talking. The boss hits mute and says, Hey, let's just slow down, let's do this, let's make sure it asks this follow-up. Unmute. You know, I'm distracted for maybe two or three seconds. In this new world, there's like clicks, I gotta X out of things, I gotta move a thing because it's now in the way of the person's face, etc. So trend three, coaching moved into the moment. It becomes true coaching, not stupid advice that reps ignore every single time. Okay, here it is. As promised, trend number four. This one for me is probably the one that if you are a sales leader, a VP, a CEO, a PE, a rep, I don't care what level you're at, this one for me is the one that is going to separate the reps that are crushing it from the teams that are not. And it is signal-based selling. And I'm not just talking about prospecting, I will talk about prospecting and signal-based insights during the deal will be required. That if you are not able to analyze trends that are happening, and that's what I see, most of these tools that are doing signaling intent. The the first set of tools are tools that say somebody from IBM's marketing department was on a piece of content. Just so you guys know, this is how Bombara, Sixth Sense, a lot of these tools your companies are spending hundreds of thousands of dollars a year for. Like the third-party intent is they've got their cookies. Let me just pull the veil back here for you. Okay, they've got third-party cookies on hundreds of thousands of websites that they've negotiated deals with. They also have a list of IP addresses for companies. It is very easy to kind of understand companies' IP addresses all follow this, and then specifically departmental IP addresses follow bump, bump, bump, boom. A lot of you may not know that this is how this actually works. And so, what third party intent is like somebody that we think from IBM's marketing department looked at a piece of content on xyz.io.x, you know, wire.com on you know, sales engagement, you know, like what are people doing for modern outbound? And then you as a rep get this little notification like, uh oh, IBM's marketing department showing intent. Guys, it could have been an intern. No offense to my interns out there. We've got interns, they're they're fantastic. My friends, third-party intent is okay. Directionally, I'm fine with it. But what I would care more about is hey, here's an alert that IBM just released their quarterly report or is about to release their quarterly report. Uh, here's what the street is saying about their business growth metrics for this division in 2026 and what they need to hit based on what the street is saying. Let's wait to the annual report comes out, and then I'm going to craft a perfect email to reach out to the VP of Marketing. This is doable today. So on Outbound, we're using signal-based reasons to engage because we're not just looking at third-party intent. We're not just looking at ways that people looked at our website. We're also looking at what's happening in the world, and we're making a tight, tight, super hyper personalized hypothesis on how we can help. Let's fast forward to the sales cycle, right? The sales cycle says, okay, I've got these people, these people, this person is closed lost, these people are engaged, these people are in funnel. Imagine I'm doing a very similar activity on all my active opportunities and all my closed lost opportunities over the last six months. I want you to think about how this is going to impact your pipeline. Every single sales leader I talk to talks about multi-threading, right? We got a multi-thread. We got a multi-thread. We got a multi-thread, right? And the reason that you don't ever very rarely do you get what you want is you don't have a business reason for it. You say, I'd love to talk to Kara. It would be great to talk to Kara and maybe walk her through it. And the, you know, director's like, well, just send me some information. I'll talk to her about it and come back to you in a couple of weeks. You didn't tell them why. Whereas what's signal-based, you know, kind of pulling from publicly available information, first party, third-party data, it can craft a narrative. Say, hey, John, I know uh, you know, we're focused on this. With a lot of the CROs I'm talking to, a big trend for them is this. And I want to make sure in our next conversation, maybe we don't loop Kara in then. I want to at least walk you through what we're seeing in more of an executive brief. I'll bring our VP of sales. And so maybe what we can do on the next call is let me take you through it. If you think it's something that she's gonna find value in, let's set up a call and then they can kind of talk about trends that we're seeing unrelated to what we're talking about and go from there. Boom. Right? That's a mix of multi-threading internally using publicly available information. And then imagine the signals are coming to you daily, daily and weekly. It just says, hey, these deals you're in. If you want to get to the CTO, this thing just popped. If you want to get to the CFO, this thing just popped. So signal-based selling, signal-based multi-threading, and this goes for current account growth and upsell. My friends, that's the future. No doubt about it. Trend number four, if you are not doing this, you're gonna get smoked by sales teams that are just so precise and add so much value in the process that your like static value-based messaging pitch is gonna just look like clown shoes. You're gonna look, it's gonna look like, oh, well, here's how we help you. Like you're not making anybody smarter, right? You're not making it relevant to what's happening in the economy right now, which is what these people care about. Executives only take meetings with people that make them smarter, period. And so if you're not using signal-based selling, you're gonna get smoked. And maybe even referred to as clown shoes as a part of that. So last but not least is trend number five. And what I'm excited about with trend number five is how we think about the roles that we hire for and how we work in our roles. And before I get to that, I want to shout out Journey AI. If you have not signed up for Journey, I don't know what you're waiting for. If you are in sales, Journey has out of the box every go-to-market assistant that you could want. And, you know, they've got company deep research. It says, just give me a link, it does the best prep you've ever seen. Then you can at mention outbound co-pilot, and it says, Hey, I've pulled in Johnny's LinkedIn profile, which you can't do in Chat GBT, is pulling LinkedIn profiles. And do you want me to craft like three or four value props for Johnny based on industry trends and what he's going for? Yeah, absolutely. And then do you want me to push that to Salesforce or it pulls into your sales engagement platform? Absolutely. And so with Journey today, you're able to do research, craft messaging, push it to sales engagement platform in minutes. And that is the future, my friends. Like all of your workflows, you shouldn't be prompting anymore. Agents and assistants should be prompting you. So go check out you know, meetjourney.ai and you can sign up for a free trial. But it's absolute no-brainer. If you're one of those reps, you're out there prompting, you're like, what's next? Go sign up and you will quickly see, you know, this is what's next for you. So last but not least, trend new. I don't know how to say trend in Spanish. Uh, so I'll just say trend numero cinco. Uh, is AI fluency becomes assumed? So to me, most orgs are still 2025, is this? Jennifer likes AI. And so she built a Jennifer built a custom GPT and it does this. And people are like, oh my gosh. And no offense to Jennifer. I mean, my wife's name's Jenny. Well, I can't count her Jennifer, she'll get very mad. My wife, I she goes by Jenny. So it's J-E-N-N-I. I know I say it like it sounds with a G. No offense. Like, I appreciate appreciate Jennifer's putting in the work, but my friends, this is this is the future. Everybody has to be Jennifer. If your whole team is not working smarter, you're all working like we did three to four to five to 10 years ago, or maybe even further. A lot of what we could do 10 years ago is just the same that we can do today. If your teams are going to Google the research, if they're manually reviewing things, like you're just, you know, you're just gonna be left behind. And and I'll I have to tell you, the people I am most scared about is the high earners in sales today. The 40, you know, again, and I'm just gonna all use, I won't use ages, I'll use years of experience. Uh, let's say the people who are 10, 15, 20, 25 plus years in the game, they built a playbook for how they work that has made them millions of dollars. And now Jennifer comes along. Jennifer's got five years of experience. She is so much more effective and efficient and can sound like an industry vet in the matter of seconds that it took, you know, 10, 15 years to sound like. And and it's and it trust me, as somebody who's been in the game for 20 plus years, it's a very humbling thing to think, man, is that the 20 years of experience obviously has value. But the reality is, this person can sound as smart as me. Now, hopefully, if we go toe-to-toe in a call in a sales deal, I can beat them because I've got more of like the crevices of nuances of how things work. But AI fluency is going to be required. And that's why, again, I called out our certification program. You have to do again, hit me up, we'll figure something out. But I just really want sellers to win and leaders to win. And we've got a sales rep track and a sales leader track. I'll figure out a way to get you in because I just want to make I really want as many people as possible in 2026 to get to that level of like, I know what assistants are, I know what agents are, so I'll make something work for you just because this is so important, right? Reps today that are not using AI consistently or still just maybe, oh, I use it here or there, I use it to correct my emails. Again, the people that figure out, you know, they're using Journey, they're using a digital teammates, they're gonna perform, and and I know we've been talking about this, but but my friends, it's a reality. They're gonna perform like two or three B player reps. And I'm gonna tell you right now, two or three B and B pluses are gonna beat an A minus. And so if you as a rep are like, well, hey, I'm good, I'm better than most people, cool. You now need to become more AI fluent and know what's possible. Possible to get to the next level. And AI fluency, you know, might not get you promoted in 2026, but it certainly can get you passed over. If I've got two candidates in front of me for a director of sales or VP of sales, let's even say, John walks me through his experience at sales for. And then, oh, and then John went to Snowflake. And then John went to this startup that did really well. And John walks me through the 2020 14 playbook that he learned about oh, I hire people, this is what we do, command of the message, blah, blah, blah. Okay, you know, again, if we've got to get 20% more revenue, how are we going to do it? Well, you know, I bring in this sales tech and he doesn't talk about AI. No chance. No chance that person gets hired. Maybe not, maybe not the first part of this year, but by the end of next year, VCs, PEs, CEOs, we're all going to be hiring for AI fluency. And so number two candidate comes in, and Rachel is maybe didn't work at all of the biggest companies or has the pedigree, but has, you know, a good track record. She says, Look, let me tell you how you scale the team of 2026. Here's what my outbound team does. They do this, this, this, and this. This is what we do. This is how they use AI. And we do less volume, but we book three times more meetings. Boom. Here's how we run our sales cycle. We think customer first, right? She read the innovative seller, obviously, right? We think customer first, we reverse engineer the process. We don't we do away with these silly like stage gates. We better triage people when they have high intent to get them through the process faster. We treat, we treat each buyer differently. And then for current customer growth, I build a proactive team that is focused on solving business challenges for clients and not answering tickets. I'm hiring Rachel every day of the week. Of course I'm hiring Rachel, right? So, my friends, AI fluency will become the bar. And so if you are not thinking that way, if you're not thinking about how to become AI fluent, my friends, this is your wake up call. This is your like, okay, I hear you. And I don't want you to look back in March and April and say, too busy. I had to hit the number, Jake. I had to hit the number. My friends, pretty soon that short-term only mindset is gonna end you up underemployed. You used to make 250, 350, 400 as a leader. Now you're making two as a rep. You were riding high when the economy was high, making a buck fifty two. Now you're making 90. And I'm just telling you, this is coming. It is happening. And so AI fluency, trend number five. Don't be scared, embrace it. So let me wrap this bad boy up. Let me bring it home for you. Okay. Is 2026? We're not gonna see mass role casualties. I don't think. Maybe later in the year. I feel like 2026 is not going to reward. We're gonna start to move away from the concept of effort to the the concept of leverage. That Kara is so good at creating leverage that she performs like a bunch of people. Jack is a really great guy, but you know, he's still doing things the old school way. And therefore, Kara's moving up, up, up. You know, Jack's kicking it. Shout out to uh K-pop demon hunters there, uh, for all of my uh folks with kids as well, with the up, up, up reference. Oh, 2026 is gonna be fun, right? And I don't want anybody to be, you know, nervous because this is exciting, this is the future. So it's gonna, I mean, to me, I I've used it multiple, multiple times every day. And it's like, man, it hasn't made me more, it makes me even more insightful, more creative. And so these five trends, I want you to go back and pick one of these. Pick one trend. I'm good with that, right? Pick one trend that you think is gonna move the needle for yourself. Uh, make sure if you haven't already, subscribe to the channel, like the video. I hope you got a ridiculous amount out of it. I hope you had uh an amazing 2025 and get excited for 2026. So there you have it, my friends. My 2026 AI predictions. I hope you got a ton of value out of it, and I will see you in the new year. See you on the next one.

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Jake Dunlap

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