AI-Powered Seller

AI Maturity Part 2: The Road to AI-First Selling

• Jake Dunlap

Share episode

Imagine logging in and your day is already in motion: target accounts analyzed, buyer signals surfaced, follow-ups drafted, and deal risks flagged—while you slept. That’s the reality we dive into as we map the jump from connected workflows to automated insights and, ultimately, an AI-first go-to-market hub where digital teammates handle the grind and you double down on the human edge.

We start by grounding the maturity model: most teams sit in the Wild West or early assistant stages, with scattered tools and no roadmap. Then we show how stage four flips the script. Instead of waiting for prompts, your AI scouts LinkedIn updates from key buyers, ingests annual reports, compares year-over-year changes, and suggests targeted actions with one-click approvals. For managers, we go beyond checkbox scorecards to true deal intelligence: auto-scored calls, focused coaching on executive presence or financial acumen, and Slack nudges that cut through the noise so you can coach where it counts.

From there, we pull back the curtain on stage five: AI as the operating system for revenue. Reps log into the AI hub before the CRM. Overnight, a network of digital teammates researches accounts, composes context-rich outreach, syncs notes, and builds a morning brief. Marketing adjusts campaigns based on live pipeline signals. Leaders stop asking the same 20 questions and start acting on precise recommendations with clear guardrails. We outline how to get unstuck—assign owners, ship small wins weekly, codify what “good” looks like, and train reps and managers to build lightweight agents—so adoption grows from the front lines and compounds.

If you’re ready to trade busywork for real conversations and build a moat your competitors can’t buy off the shelf, this guide lays out the path. Subscribe, share with your team, and leave a review telling us which task you’ll hand off to your first digital teammate.

SPEAKER_00:

The top reps, I really believe this might be true. A rep might be able to execute more high-value activities before 9 a.m. than their competition. That the rep who is in when the organizations get to AI first go to market platform stage five, their reps are working because they got digital teammates working for them. Digital teammates are out there busting their hump, doing all this stuff for the rep. And then the rep is turning their brain on and doing a great, great job of being able to go out and do the human value ad. They're having more calls, they're having more conversations with customers. AI powered seller. What's going on, everyone? Welcome to another episode of the AI Powered Seller. I'm your host, Jake Dunlap. Very excited to announce founder of Journey AI. If you have not checked out Journey yet, it is a love passion project, um, really focused on all of you, on sales and sales leaders. Uh, it's really the first ever set of go-to-market assistants. Uh, and I'm so pumped it's live. So go check it out. It's meetjourney.ai. Um, also CEO of scale consulting, author of Innovative Seller, USA Today Bestseller, and you know, payroll manager and about 55 other jobs uh whenever you run a company. So uh excited for today's part two episode. I hope all of you are as well too. Today we are going to talk about the later stages of AI maturity. And I did part one a few weeks ago. So make sure if you did not check out part one, go back and check it out, where I really started to get tactical where most companies are today. And I wanted to do this part two to help organizations understand what the next like, what is like really good look like? You know, and and I would say this is top five percent type stuff. And I think most sales leaders, revenue leaders, they want to get there, right? But they're like, I have no clue. So if you have not listened to the episode a few weeks ago, I highly recommend you go check it out. Um, it was a very popular episode in terms of people, you know, commenting, getting a lot of value out of it. So definitely go check it out if you have not. And we're gonna jump into it. Today is gonna be an action-packed episode, lots of tactical advice, but also hopefully some things that will get you thinking to say, you know what? It's time. Like for me, what I love is when I meet with a sales leader and they finally get out of their own way and say, We gotta do something. Like, we just can't sit here and keep talking about Gen AI or, you know, oh, we bought it for everybody. It's like, yeah, but and like just because you bought it doesn't mean it's gonna actually work correctly. And so uh just a quick recap, okay? So definitely go back and listen to the full episode, but let me just give you a quick foundation check on the last episode. In the the first AI maturity episode, I just talked about the kind of fit stage one, two, and three. You know, the first is what I call wild, wild west, which is you got everybody doing their own thing. Maybe that maybe you have a license for like a company-wide thing, maybe you don't. Um, a few people have it, or maybe this leadership has it. You have no idea who's using what, but you know, look, hey, I would rather my team use Gen AI and you know get value out of it than not use it, which, hey, kudos to you. There's like a stage zero, which is command and control, probably, which is like, hey, we've shut down access that we didn't get into. But um, stage two, I call this kind of a merging assistant, you know, kind of prompt library assistant land. And this is usually whenever you you've really defined two, three, four core use cases for some teams. You've either built out maybe one assistant, um, or you have some prompt libraries, things like that. But you're starting to get more structured. Um, you know, you still don't have maybe a roadmap for each group, you know, where sales, here's the things we're gonna be building this quarter, you know, CS, here's the things we're building, marketing, et cetera. You know, you're kind of sharing in pockets, uh, but you're starting to get a little bit more serious. That's my kind of emerging assistant, kind of initial team adoption level. And then stage three is what I call connected workflows. And this is, you know, where I left off on the last episode. And this means AI is starting to get integrated into your tools and systems. You know, it's not just a standalone tool. Maybe it's pulling in data from your CRM or from Slack or from Teams or from Zoom or from something like that. Um, but you're really starting those first phases of data integration. Um, that there are guardrails in place, and not guardrails in a bad way, it's more so like you've already built out even more assistance, you know, for them. Um, you know, I was just on with a uh VP of engineering right before I'm recording this. And you know, we were talking about this idea, and he's like, look, I'm getting ready to do a training with our organization around you know, prompting, etc. And then, you know, we're as we go through, and I'm like, or you could just build them, you know, assistance or custom GPTs. He's like, I know. He's like, I know we're training on some of this stuff that we could be doing more of. So um, I think most people I would say are one, two, that's fine. You know, stage three is is to me the foundation. Stage three is you know, we've got a program at scale, we call it our AI jumpstart program. And in that program, we build out a handful of assistants for one group, we build out one automation, and then we build out Kanban boards for different groups. And by the way, please rip that off. You know, you don't have to work. I don't really, so many companies, I'm like, just do this. Like, I promise you will come back to me, whether you pay me a dollar or not. So if you are ready to move forward, let's say maybe your company is like, they're not ready yet. I highly suggest we have the first ever sales and revenue leadership AI certifications on the market today. These are not BS Zoom webinars. Use they are six weeks. It is not too late to sign up. You can watch the first few and we can assign you to a pod as a part of it. Um, the rep certification is going to show you how to create your own assistance, how to build automations. The manager certification will do that and teach you how to use it in your day-to-day interacting with your reps. So if you are serious about not getting left behind, this is how you get ahead before 2026 while everyone else is still waiting around for the company to give them permission. And so, you know, that concept of department by department, Kanban board for each one is really the right way to do this. Um, but really, every single one of you listening, your goal should be to get to stage three. Hmm, Q1. Yeah, Q1. I'd say if you're not there yet, if you don't have assistance that each team's using for their own specific workflows, you haven't built out some automations, whether that's to automatically log data in Salesforce, whether that's to log, uh you know, check on some notes in Slack or something like that. Um, that is to me the new foundation. Also a great show on Apple TV if you're into uh like sci-fi type stuff. So shout out to the foundation for everybody too. So without further ado, let me jump into stage four. And stage four is a land I don't know how many people will get there by mid to end of next year, probably not as many as I expect. Um, but it's a land that we should all be striving for. You know, the cool part is like if you're a sales rep and you're listening to this, getting into stage three is something you could do on your own. Um, there's enough tools out there. You know, most of you actually have the ability to build assistance for agents and you don't even know about it. You know, I can't tell you how many of our clients they use Copilot, and it's like, you see where it says agents right here? Like, we're gonna do that. We've got actually one of our clients, uh, Portland Trailblazers. Shout out to the Trailblazers. We're doing a workshop with them on Friday around this. Um, but you can do the same thing in Gym and I with gyms, you know, Chat GPT, you can build custom GPT. So, you know, user rep can certainly uh do a lot of that. Um, if you're interested, I'll also put a link. We did a whole article on this. We got some great visuals in there. It's called the five stages of AI maturity. Um, I'll also link to another article, which are the five stages of like individual competency. So if you're kind of thinking, hey, what is this, you know, what does this mean for me? What should I do? Go check out the full articles, forward them to your team. I think you'll get a ton of value from them just in terms of you know, a more tactical roadmap. That's really why we put together all of this content is I think it's really hard to know, gosh, what does good look like? Because we're still so early in this process and so many people are still trying to figure out how to get started. And so our goal here is to try to you know find different ways to get you to, you know, let's get you to the foundation, right? Okay, so stage four is what we call automated insights. This is really the step in your journey where AI stops being something you use and AI starts doing things for you proactively. By the way, Jen AI gave me that statement. I was like, that is really good. It's like I was like, how do you describe this? It's like this is how you describe it. It's like that's exactly right. So what shifts is look, it's able to look at patterns. It's able to say, I think I know what we're trying to do here. Um you know, think of things like external signals. This is this is to me is one of the easiest ones. What it does is it understands who your top 50 accounts are, and every single day it is going out. Oh, oh, oh hey, Jake, here's something that they talked about. It's then looking at the people that you're reaching out to. Oh, Johnny Smith um posted on LinkedIn. Here, do you want me to go ahead and uh write up a quick little comment back for his post? Yes, I would like you to do that for me. Great, here you go. And you know, think of this as you know, it's going ahead and automating, ripping in an annual report. It's you know, comparing that annual report to last year's annual report and saying, hey, here's some things you might want to talk to their head of marketing about. Uh it then says, you know, okay, Jake, based on that, do you want me to go ahead and send this email? So again, it's a more intuitive system. And by the way, all of this is doable right now. I am not talking about the foundation, you know, science fiction. I'm talking about the foundation reality land. And reality land is you can do this in real time. Now, when you're ready. And, you know, just imagine this new seller, their morning starts with look, forget these crazy third-party intent signals. The marketing department of some random company visited a page on this article. Give me a break. Come on. You know what I care about? Like their CTO or whoever posted this exact topic, which is something I solve for. That's a little more valuable, in my opinion, right? And every morning you come in and you go, Jake, go take these five actions. You know, or or you know, and it's assisted, but they'd say, Hey, do you want me to go ahead and do these two and then you take this one? Yeah, I got you. Okay, great, let's do that. So think of it like that. Like these are automated insights. It's telling you what the insights are. It's in the not only automating the insights, it's an automating part of the action as well, too. For my managers out there, automatic deal risk flagging, right? This is this is maybe a three to four, uh, you know, call it like potential of where this one falls. But this is where every single, and this is we're doing this for companies now, where we're ripping the call the conversational intelligence, you know, pulling out the API, working with the sales organization, and it's not just medpic. There's a million tools that can say Jake didn't ask for the champion or whatever. That's not what we're talking about. We're talking about real deal review. We're talking about real, like diving in and saying, this is what I know a good, great call looks like, not did Jake check a bunch of boxes. And then I'm auto-scoring that, I'm automatically slacking that to the rep. And then from that, even as a manager, you know, maybe I'm only listening for two or three things on that call. Maybe I'm working with Jake Dunlap on Jake's executive presence. Jake needs to do a better job of communicating to his CFO, which could be true. And instead of it looking at all the different parts of my scorecard call scorecard, what I'm actually looking at is I'm looking at the ability to just look at Jake's executive presence in that call. And so instead of it going through and it's analyzing all the call, maybe it's just working with me on the top two or three areas that I need to get into. Um, but that is automated insights, right? Automated insights is it stops becoming something that you prompt it to do, or even as an agent or assistant, it prompts you, it starts just doing all these things behind the scenes. All right, so that is stage four. Okay, that's my automated insights stage. Stage five. Uh make sure if you are getting value out of this video though, first, always, make sure to like, subscribe to the channel. I do my best, commented what would be helpful. You know, I love it. You know, each video we get multiple comments. People say, Jay, can you go deeper on this? Love this clarifying question. So make sure to like, subscribe, comment. Um, if you're watching this on YouTube, if you're listening in your car, or maybe on your run, make sure to, you know, you get back when you get to a safe place. Make sure you sign up uh to get downloads uh when the new episodes come out, for sure. Uh, stage five. AI first go to market platform. AI is not a tool anymore, AI is the operating system. One of the sales leaders who I really admire, shout out to a friend of mine, Larry Sweeney. Larry said, I I really think we probably will be using these AI systems more than CRM. So, like, absolutely we will be. That's exactly right. You know, and instead you're gonna have your AI go-to-market hub. The AE logs in before Salesforce. Overnight, you've got five, six, seven, eight, nine, ten, forty-one digital teammates going out and doing a bunch of stuff for you. It's automatically logging all the activities you did from the day to day. It automatically goes out and makes your morning brief for you. I don't, they can't make your coffee yet, but maybe it will get there. You could probably order it, it could definitely order it. It could like door dash the coffee for you. Um, marketing immediately gets an email, sees which campaigns to pause based on the pipeline data, which ones to flag, which ones to optimize, right? And for me, you know, the top reps, I really believe this might be true. That a rep might be able to execute more high-value activities before 9 a.m. than their competition. That the rep who is in when the organizations get to AI first go to market platform, stage five, their reps are working because they got digital teammates working for them. The digital teammates are out there busting their hump, doing all this stuff for the rep. And then the rep is turning their brain on and doing a great, great job of being able to go out and do the human value add. They're having more calls, they're having more conversations with customers, right? And all this nonsense, the logging of data, the calendaring, the follow-up emails, the stuff that's really not that value add. And that's what you have to realize is we're talking about orchestrating motions and redefining the job to where if it is not interacting and adding value to people, we do not have people doing it. It automatically sends, it's see, it sees that John Smith asked for a reference for a client on ABC. It sends an email, it looks at your current client database, it looks at, you know, maybe people have a health score over 80, and then it slacks you. Hey, you got this email from John. I think you should introduce him to these two. What do you think? My friends, all this is doable today. Everything we are talking about now, you can be doing in your organization right now. And so we're going past, you know, this stage four, which is hey, it's doing a few things for us here. Uh, it's going, you know, it's going past it's surfacing a few insights to where it's taking actions on our behalf. And that's okay because you can put guardrails around it. This is not 2023, everybody. This isn't this hallucination era. Well, Jake, what if it hallucinates, guys? We're not talking about automating, you know, a customer interaction at a key point in a deal. And in fact, I can tell it never to do that. You know, and again, it's not always perfect, but it's pretty dang perfect. Right? And and like we always say, is AI will never be worse than it is right now. So if you are somebody who is struggling to comprehend why you would do this, I'm actually trying to empower salespeople to only focus on the customer conversations, which I think almost anybody would want to do. I want my sales leaders out there, instead of focusing on asking and answering the same stupid 20 questions every week, stop the madness. Automate yourself, create the digital John or Susan or Rachel or whatever, and then you can go and add value, hop on a call, do a really great one-to-one coaching session, etc. Right. And to me, you know, I want you to think about what this can do for your organization, the strategic moat that this can help your organization form over the course of the next six to twelve months, right? They're not gonna be able to buy any of these new tools to outperform you. They won't. If you focus instead of on buying the latest and greatest technology, you just focus on implementing generative AI and getting to stage three first, then stage four, then stage five, your competition will not be able to keep up. In six to twelve months, everything I'm talking about, I promise is going to be table stakes. Every single thing I'm bringing up about the ability to automate this or do this or check in with you or pull this data in, all of that is going to be table stakes over the next two years. And so even if your company isn't there yet, you as an individual need to start to build your competitive mode. I truly believe that you as a seller or you as a frontline leader or as a VP, a CEO, whoever's listening to this, you can truly future-proof your career and your you know, uh performance in your organization by even just doing part of what we're we're talking about here. And I think, look, if you start today, your company is gonna be ready when the next big shift comes. Because a lot of this is about change management. A lot of this is about change management in terms of the way that organizations uh think about their people, uh their people's day-to-day. It's really a shift in how people work. And so your people can either start shifting the way they work now, or they can do it in six to eighteen months. And then you and the competition's already been shifting. And so the brutal truth, I have to tell you, just from the data we've looked at, is 90% of companies are stuck in stages one to two. Only 10% again from the clients we work with, we would even remotely consider in stage three, and maybe only one we would consider in stage four. And so the organizations that think this is something cool or a new tech, or yeah, yeah, yeah, I know we need to get started. Now is the time to get started. And again, I cannot stress this enough. You know, the whole reason I'm doing this show, the AI Powered Seller, is to make sure we bring what's up next and what's doable now that you should know about so you have something to strive for. So that's what I got for today's episode. That is stages four and five of our AI maturity. You can check out the full links in the show notes for sure. And again, if you enjoyed the video, you got value, please like, uh, subscribe to the channel, make sure to share, share it in your Slack. You know, it's a hopefully this is a pretty quick hitter little episode. Someone can listen to my voice. I know me at 1.5 speed is a lot. So, you know, maybe put it at 1.15, and uh you'll you should still be able to follow along. So again, if you didn't listen to the first episode, go back and check it out. Make sure you go back, uh, you listen to that. I think my homework on that episode was for you to kind of gut check where you're at, put together a plan to get to the next phase for sure. Um, make sure, check out the full articles. If you're ready to get to stage three immediately, just sign up your whole team for Meet Journey AI. Meet Journey AI automatically gets you to stage three. It has all these pre-built-out engines, it allows you to sync um all of your accounts so you have new workspaces for all of your accounts. Um, all the assistants then know that they're working for you on that account. So if you're trying to get ahead, you don't want to go through it all, just sign up for Meet Journey AI. Um, the team will take care of you for sure. So that's what I got, everyone. Hope you have a great rest of your day. Keep making sure you are staying on top of this. There is no bigger shift or change in sales today. Uh, people still buy from people, people will continue to buy from people, but the AI powered seller will be the one that they want to talk to. Have a great rest of your day, everybody. I'll see you on the next episode.

Head Shot

Jake Dunlap

Co-host