AI-Powered Seller

AI Proficiency in Sales: Stop Dabbling, Start Deploying Digital Teammates

• Jake Dunlap

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Most sellers say they “use AI,” but the real question is: is AI actually running your sales workflow? We pull back the curtain on what true AI proficiency looks like, why dabbling won’t keep you competitive, and how to jump from basic prompts to digital teammates that own the work. This isn’t a tool tour—it’s a working blueprint for transforming prospecting, research, coaching, and follow-through so you win more deals with less manual drag.

We map the five levels of AI proficiency, from ad hoc user to multiplier, with crisp examples you can copy today. You’ll hear how a “New Account Research” teammate can scrape signals and context before you even open your CRM, how a pricing-objection specialist can produce competitor-aware responses in seconds, and how manager-trained GPTs can review call transcripts and give targeted coaching using your actual playbook. Then we zoom out and show what happens at the agent level: calendar-triggered prep, Slack clarifications, automated recaps, and draft SOWs that land in your docs without you lifting a finger. The numbers are real—a 47% productivity lift, roughly 12 hours a week back—translating into more selling time, better personalization, and cleaner pipelines.

If you’re at level one, we lay out a fast track to level three: convert your best prompts into assistants, feed them product and persona context, and standardize outputs so quality is consistent. Leaders get a roadmap to become multipliers by setting a GenAI backlog, prioritizing high-impact workflows, and rolling out shared assistants across the team. Hiring is already shifting; candidates who can show live AI workflows will outrun those who “know ChatGPT.”

If this guide helps, subscribe, share it with a teammate, and leave a review so more sellers find it. Want to level up faster? Explore the AI certification for sellers and frontline leaders, and test-drive the MeetJourney assistants tailored for sales teams.

SPEAKER_00:

A lot of people, when they think about AI permission, they're like, oh, I use it to like help me do some research and write an email. And my friends, that's the lazy version of AI. That's the beginning of the beginning of the beginning. Building a system in place is where sales represent is it's prioritizing the call list, it's allowing you to compete with insights. It's pulling out, let's say you sell something that helps a company with their website load speed. It's scraping the site for you in advance, it's putting together white papers and case studies even before you even log into Salesforce for you. AI Powered Seller. All right, what's going on, everyone? Welcome to another episode of the AI Powered Seller. I am your host, Jake Dunlap. Uh, hopefully, if you're joining us on YouTube, welcome to the channel. If you are listening uh on Spotify or your favorite podcast, welcome as well. This is the show where every single week I break down the latest and greatest uh details that every single seller needs to know around AI and sales and how to supercharge your career in 2025, 26, and beyond. So today's episode should be an amazing one. I think I hear this all the time. We need to be AI proficient. We've got to be more AI forward. And I think the interesting part is what does that mean? Like, what does it mean if I'm a sales rep and my boss is asking me, you know, Jake, you need to be AI proficient, or if you're a CEO and you're bored saying you guys need to be AI proficient. What does that mean? And really the uncomfortable truth in 25 is if you aren't proficient, you are going to fall behind. And yes, most sellers today are using AI. I think it's like 80% is a stat that I've seen, but they're just dabbling with it, just barely, barely scratching the surface. Only, I think less than 13% actually know how to build assistants or agents, et cetera. And so in today's episode, I'm gonna break down for you a few key areas. One, what the heck is AI proficiency and what does that mean for you as a seller? Uh, two, what are the five levels of AI proficiency that we've developed that we have seen lead teams from just walking around the gym, you know, uh wearing their Lululemon to actually like hitting the weights and seeing the outcomes? And then I'm gonna talk about why leveling up isn't some type of productivity hat, it is a complete change in the way that you work. And so without further ado, let's jump into what proficiency actually means. Oh, and a quick heads up for those of you, make sure to check out the show links. Uh, we have built the first AI certification for sellers and a whole separate track for frontline leaders. So those are live. They are gonna kick off here in the next three weeks. There's no theory, no fluff. If you are serious about getting you know ahead and not being left behind, this is your 2025 checkbox. So make sure to go sign up for that as well, too. So, first, uh I'm gonna talk you through the definition of proficiency, right? And and I think where I am qualified to talk about this is over the last year, I have easily talked to hundreds of VPs of sales, CEOs, CIOs around this. And I have seen the complete gamut, right? I would say most people are gonna be in some of the earlier stages. So I'll talk about what non-proficient looks like. But I have also seen organizations out there that are literally like little human cyborgs where all their people have digital teammates, they're cranking, et cetera. So let me try to make this very tactical, right? So to me, AI isn't about having tools, it's about transforming the way you work. So think about it that way. If you want to be proficient, it's not I know this technology. It's oh, I work completely different now. That's how you know it's integrated. It's a part of every single thing that you do. So for example, try to give you a very real world one. Let's say you're prospecting. I think a lot of people, when they think about AI proficient, they're like, oh, I use it to like help me do some research and write an email. And my friends, that is that's the lazy version of AI. That's the beginning of the beginning of the beginning, right? Building a system in place is where sales reps and teams is it's prioritizing the call list, it's allowing you to compete with insights, it's pulling out, let's say you sell something that helps a company with their website load speed, it's scraping the site for you in advance, it's putting together white papers and case studies, even before you even log into Salesforce for you. And so if you think about writing an email as step zero, the future for Outbound is insight-driven one-to-one communication. For managers, if you're saying, hey, am I proficient? It isn't about asking Chat GPT, you know, how do I be a better coach? It's really creating a GPT trained on your specific playbook. I think everyone, you know, I've got a little Jake version of a playbook that can review the call transcript, surface insights, and automatically give that rep feedback and insights. And that's really the difference between the people I see that are that are dabbling and the people that are proficient. The dabblers are the people that are saying, Oh, yeah, I do some prompting every day. I do like some basic prompting. It's very, you know, high level, you know, one or two sentences, etc., for the people that are actually building systems for themselves. So if you want to think about where you are on the spectrum, take a second. Am I somebody who has built out multiple systems for myself, for my team, that is running behind the scenes or that we interact with every day, or am I still dabbling? And let me just tell you the reality of the art of possible here. The last stat that I saw is a 47% increase in productivity when sales teams actually have AI into all their workflows. That is almost 12 hours per week. Let's be honest, selling time. Maybe you're doing six hours a week. That's two days a week, right? This is not incremental. It is literally career altering. And that's what gets me so excited about a lot of this is this is the future. This is where I see, you know, this ability for you as an individual, whether you're listening to this and you're on the front lines, whether you're listening to this and you're in the frontline leadership, or maybe you're an executive or you know, private equity. Um this is the opportunity. And I think what we have to realize is we've all been programmed to solve different problems or to do our jobs a very, very certain way. And so we've become proficient in the old way of doing it, right? We've come proficient, right, in um, you know, how I use Google and how I use LinkedIn and how I use a sales engagement tool and how I use CRM. But there is a new proficiency game in town. And I'm gonna break down the very tactical five ways. I'm really gonna spend my time in today's episode. Maybe in a few months, I'll spend more time on number four and five. I'm gonna spend most of today's episode talking about one, two, and three. Because I think most of you are probably in one, two land. And I wanna try to get really tactical over the next 10, 15 minutes and really help you to get into, you know, kind of two, three, maybe, maybe like peak, peak at four land. Um, so before we dive in, I want to make sure, make sure to hit the subscribe button. Uh, make sure you you sign up for downloads if this is your favorite uh podcast platform. Make sure to hit the like button for this video. Uh share this video with your teammates. You know, again, I think everybody's trying to figure out this AI proficiency piece. Uh, and definitely check out meetjourney.ai. Meetjourney.ai is literally the only set of assistants built only for sales teams. There are workspaces in there for all of your accounts. There's a whole bunch of assistance that will help you do research, uh book meetings, scenario plan, role play, et cetera. So make sure as you're starting to think about your proficiency journey, if you want to skip ahead to step two or three, just sign up for Meet Journey. They've already done a lot of the work for you. They built out the assistance. You can program it with your org, uh, et cetera, and it's free. So make sure to go check that out. So, my friends, let's get into the five levels of AI proficiency. Uh, as a part of this, I want us to think what we call level one is well, let me just clean that up a little bit. Let's get into the five levels of AI proficiency. I'm gonna spend about the next seven, eight, nine minutes just talking about these five levels and really, really honing in on the ones where I feel like most people are, you know, today, which is one, two, and three. So let's talk first about level one as the ad hoc user, the basic experimenter. This is where, again, I want you to look yourself in the mirror. There's no shame. We're still early, so don't worry about it. If you are here, don't feel, you know, like you're uh like you're you're too late to the game or still very early in the game. The mindset, I think, is what can be your litmus test, which is AI feels optional. I want you to think about that. Does AI feel optional? Does it feel like, yeah, I should be, uh, yeah, I'm dabbling, I'm using it a little bit here. Um, it's, you know, relatively generic ways that we're using it, inconsistent outcomes. We're constantly like not happy with the outcomes, heavy editing required. You know, we're saying, hey, help me write a prospecting email for here's my company, and you know, here's the company that I'm trying to book a meeting with. And I'd call this still like AI is a novelty, it's another tech stack. It's not something that I really view as has to be infused in everything that I do. Right. And to me, if you stay here, you are going to be dead weight to companies compared to your peers in six to 12 months. The good news is I don't have the actual like specific stats. My gut tells me 70 to 80 percent of people are right here. From working with thousands of reps over the last year, I'm gonna say a vast majority, you know, call it three three-fourths, are in this ad hoc user, basic experimenter level one. Okay. Where again, we're there's a couple of key factors I think about when I think about this level. Number one is we don't talk to it like a person, we still talk to it like Google. We can't fathom that we should be giving it everything and more context and more context and more context. Number two is we have very specific use cases like research, like messaging that we've latched onto, and that's how we that that's how we do it. So if you want to know if you're in level one, those are my two key criteria. You know, think about again, are you using it in just a couple of you know key use cases, right? Are you also you know thinking about it again, giving it very basic prompting, one or two words or sentences, and that is how you know if you're in level one. Okay. Number two, now I'm gonna call this the skilled prompter. This is somebody who's starting to get, I'd call it, a little bit consistent around some of these things. So, what are the behaviors of somebody who's in my level two, the skilled prompter bucket? Uh, these are the types of people that are doing some next level. They have saved prompts. They've realized, like, why do I keep typing in this exact same thing over and over again? And I use it for multiple use cases. That kind of is a very clear way for you to say, hey, Jake, I think I'm here. I've got some go-to prompts. I've got two or three areas in the sales process that I use it. And I'll toss in a third here. I I'm starting to get good at adding context. I'm saying, hey, oh, I'm feeling a little bit like this. Um, you know, my role is a little this, or this industry is nuanced this way. So again, they're starting to make the shift from like, okay, I can feed it a couple of things, it'll give me some answers to say, okay, I definitely see value in in more than just one or two areas here. I'm saving the prompts because that saves me, you know, time as a part of it. And I'm starting to be able to understand, I need to give it more. I need to give it more context. My answers are more rich, they're better. Right. So again, it's like it's not writing an email to this. It's saying, hey, I need to do a three-line opener to this director of marketing. Here's what happened on the first call. I'm a little nervous about this. They work at this type of industry where we do okay here, and I want to focus on this use case around time savings and their recent funding around and ABC, insert something else, right? So you're just getting good at giving it context, right? At this layer, I'm telling you, if you when you move from layer one, level one to level two, you move from the ad hoc to the skilled consistent, at least a 2x game. You're not having to write things out anymore. You're starting to see those gains in productivity. Um, you're faster than the manual drafters, but my friends, you're still tactical. You're still stuck a little bit, a little bit in prompting land. That is level two. Okay, and I would say my top 10, 15 percenters in AI for frontline leaders, most execs, honestly, I would say most execs I talk to, maybe 10 to 20 percent are in level two. I think most leader executive leaders I talk to are pretty level one. Um, sales reps, I'd say maybe 20% or so are kind of in this. They're starting to flirt with this level, right? 15, you know, 20 or percent. Whereas I think it's a very low percent of execs uh that get there. Um, again, if this is helping you, make sure to like the video. Uh, if you're listening on your podcast, make sure to sign up to get the latest. Uh, and I'm gonna walk through the next three. But again, my goal here with AI Powered Seller is to always bring you the tactical advice. How do I get better at this? How do I get better at this? How do I get better at this? So appreciate you tuning in. And let's jump into the last couple here. Number three is the assistant builder, the task specialists. These are my friends who are starting to create either gyms and Gemini, agents and co-pilot. Uh, in Meet Journey, they're using the Meet Journey agents, their uh custom GPTs. They have realized why do I have to copy and paste when I can just take some time, put my best prompt into this, and now it's my competitive deal winner, digital teammate. And that's a new word I'm starting to use more and more, and even instead of the word assistant, because it truly is that powerful. I think Journey now is up to like nine digital teammates. You can build, you know, more and Chat GPT, you know, you can build obviously as many as you need to. But think of these things, you know, like competitive deal winner. This is like a digital teammate. This is like a person that I have on call 24-7, ready to help me win every single deal. It knows all my products. It knows, you know, what what my industry is that I sell into in the sub-industry. It knows my personas, it knows who we compete against. And therefore, I'm not having to give it all the context all the time because I've taken the time to put the context behind the scenes. So these are my my level threes are the assistant builders, the digital teammate builders, right? They're training um assistants on playbooks, battle cards. They use these things for they help them to do. I have, you know, my favorite one that I use probably three times a day. I is called new account research. It says, I say, I'm ready to go. It says, give me a link to the company, and it goes. It's that you know, I can go deeper if I want to say, oh, you know, help me to understand a few nuances, but it's gonna pull mission values, it's gonna pull, you know, uh how they make money, who the exec team is, you know, found rounds of funding, uh, competitive landscape, who they sell to. I mean, it can pull everything for me. And I don't have to prompt it, you know, et cetera. So, you know, this is somebody who's, you know, maybe runs into pricing objections. So they've created a pricing objective GPT, right? That outputs kind of a company aligned, competitor aware, and immediately usable, you know, proposal battle card uh to be able to help them to win more, you know, deals. So again, you know, I I think that the mindset here, oh, this is a really good, this is a I don't know if I've put it this way before. The mindset is a shift from AI helps me to AI owns this task. Think about that mindset shift. AI is a helper, yeah, it's helpful. Oh no, no, no. My digital teammates got this. I don't do that anymore. My competitive deal intelligence teammate does it. And that to me is a big, big shift. And so that's why I wanted to spend time on these first three. I'm gonna talk you through really quick level four and level five, but I want you to think, just hit a quick pause right now for yourself. Where am I if I'm being honest with myself? Am I level one? I'm in the ad hoc world. Am I kind of making that move to level two? And a lot of you could just go from one to three, right? You could just say, hey, instead of me writing these prompts and copying and pasting them, let me just write these prompts inside of a digital teammate or an assistant, and it'll do it for me. Again, like I said, that's why, you know, obviously I'm a big fan of, you know, Meet Journey here because, you know, it already has the assistance built out. But you can do this in any tool, okay? Uh level four and level five, I'm gonna talk about this very briefly. Level four is when people, you start to learn how to build agents. And this is another reason why I truly believe everyone should sign up for our AI certification program. It's literally a few hundred dollars, and you are going to learn everything. You're gonna learn how to build assistance. You're gonna be, we're gonna take you all the way up to like the beginning of level four. That you're actually going to build an agent in like an hour, and you're gonna start to see how easy this stuff is. So, agent builder, I'm gonna call it process engineer, is someone who doesn't just say AI does this task for me. It's I've got AI teammates working together and they're doing much more complex things for me. Right. So this could be things like you know, you leveraging the Zoom API, you know, in and pulling that into innate in or make or zapier or agent force or you know, insert uh you know, layer. And then it automatically, you know, creates a Slack that asks clarifying questions. And then once you integrate Slack and answer the questions, it automatically spits out a statement of work at a Google Doc. This is here today. My friends, we're doing this right now. This is how we do statements of work at my company. And so this is where, again, you know, it pulls from a Calendly, it pulls the data from the CRM who you're meeting with, it automatically runs the account research and auto slacks it to the AAE. So by the time that thing hits your calendar, the prep is done. The automatic email is sent to the prospect that says, hey, I'm looking forward to a conversation. Here's the basics around us, here's what you know, and it automates it out. At this level, AI starts to become invisible because it's running your systems while you sell. I truly believe if you are not thinking like this as a seller, by the end of next year, you're gonna be surpassed. Right? I think again, if you can't get to that assistant builder, that teammate, digital teammate partner in the next six months, man, people are gonna be running laps around you. Um, last but not least, I'm gonna call this like force multiplier, right? AI multiplier, fluent across pomp uh prompting, fluent across building teammates and libraries, coaches, peers, says, how do I raise the bar for my team? Right. It takes it from personal productivity to organizational or department uplift, right? So this is where you know a leader or a group of people are working together on a true Gen AI roadmap for their department, right? And this is a lot of work we do with our clients as we're kind of going out, we're having different conversations, we're helping them to put together kind of their Kanban boards, and then we're kind of building out these different work streams on a consistent basis, whether it's a new digital teammate for this, whether it's a new, you know, behind the scenes for this, a workflow. You are a leader when it comes to AI proficiency, right? Multipliers, you know, the people in this group, the AI multipliers, they don't just win deals, they change the way their organization sells. And so for a lot of you, one through three, okay. One through three is where I want you to focus. Okay, right. And again, like I mentioned before, if you want to make that move from kind of a skilled prompter to teammate, go to check out meetjourneydata.ai, and that's a good starting place. If you're leading a team or you're a frontline piece, that's why I keep pushing these certifications, get involved there as well. So to wrap things up, I want you to think about this journey. And we're all on this journey together, right? Myself included. Somebody asked me. I was at a workshop with one of our clients in the NBA. Shout out to the Portland Trailblazers. Um, and uh one of the women in the uh the the session, she said, Jake, how long did it take you to get to uh you know the level of proficiency you're at? And I go, you know what? I don't even think I'm there. I'm like, I think I'm like a four, like three, four, maybe somewhere in there. And you know, my organization, I think we're a four. I think we're a solid four moving to five. Um, but you know, the the ability to be proficient, it might not be a skill that your company is gonna teach you because they don't know. They're still at step one in the maturity curve, they're still at wild, wild west, right? And again, I want you to think of the the future here is you know, the reps that are are gonna win in the future, you know, they're gonna spend more time selling, less time doing the BS work. They prep faster, they coach better, they ramp faster, right? Uh hiring managers are gonna be screening for this, right? And I'm telling, I was talking to somebody, he's like, um, how do I screen for AI? Like, if in the future will be if they can't show me their AI workflows, they don't make the cut. What am I gonna work with somebody who's like asking me these dumb manual questions? Like, absolutely not, right? So, again, I want you to think about this. In two years from now, if you are still level one, I really maybe there's certain industries I think it's gonna be tough to compete. Because somebody, you know, you might think I've got all this years of industry experience. But again, if I know how to build an assistant and a teammate that has all those years of experience already, well, that person can help me there. And then I'm gonna be spending more time with customers than you can possibly do. Right. And I think this isn't about more efficiency, it's about becoming more effective and surviving. Right. So for everyone out there, you know, this episode, you know, for me is hopefully a little bit of a wake-up call and also maybe a little bit of a tactical, you know, okay, cool. All right, I got me a little roadmap here. What we will do for you to make this even better, I'm gonna put a link in the show notes that's got like a little AI proficiency, a little roadmap for you. So do not worry. I got you covered. Make sure if you have not already signed up for Journey, do it. Um, it's assistance out of the box. It gets you literally to almost a level three, like out of the gate. Um, and for sure, make sure if you're somebody who wants to get serious about this, sign up for the certifications. They're kind of a no-brainer. I really feel like this is something that everybody should do who's trying to get really, really serious about their AI game. And so that's what I've got for today's episode. Again, if this helped you, I'm I'm so glad to hear that. I love to hear it. Make sure to like and subscribe to the channel if you're watching on YouTube or if you're listening on the podcast, make sure to sign up to get the download every time I've got a new episode dropping. And that's what I got for you, folks. That's my AI proficiency roadmap. That if you follow it, I promise you will be from, you know, what do they say, zero to hero in literally no time. So thanks again for tuning in, everyone. Thank you so much for you know taking the time to invest in yourself to realize how important this is. And we will see you next week on the next episode of the AI Powered Seller.

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Jake Dunlap

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