AI-Powered Seller

AI Maturity Part 1: Getting Out of the Wild West

• Jake Dunlap

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Most teams say they “use AI,” yet few can prove ROI. We dig into why that gap exists and lay out a practical roadmap any sales org can follow to move from ad hoc prompts to automated, connected workflows that save serious time and lift performance.

We start by reframing generative AI as a foundational shift, not another tool in the stack. Then we map stages 0–3 of AI maturity. Stage zero is AI curious: lots of interest, little action. Stage one is the Wild West: tools without guardrails, inconsistent results, and off-brand outputs. Stage two introduces emerging assistants—specialized AI that handles repeatable jobs like account research, messaging co-pilots, call reviews, and deal strategy. Finally, stage three connects those assistants into end-to-end workflows that trigger on real events: calendar invites that auto-generate dossiers, transcripts that draft proposals, and notes that update the CRM with zero manual effort.

Along the way, we share concrete examples and time-saved math that translate to real headcount efficiency—think sixty-plus hours reclaimed per month on a 20-rep team. You’ll hear how to pick the first bottleneck, standardize use cases, build or adopt assistants, and stitch them together with no-code and low-code tools in weeks, not quarters. We also include a quick checklist to self-assess your current stage and define the next step, whether you’re a frontline seller, a manager, or a VP building the roadmap.

Ready to trade copy-paste chaos for measurable impact? Subscribe, share this with your team, and leave a review to tell us which assistant or workflow you’ll build first. Your feedback helps us shape part two, where we explore the next levels of AI maturity and scale.

SPEAKER_00:

The reality today is 53% of sales reps admit they don't know how to get value from Gen AI. 70% of marketers say their employers don't provide AI training. I'm surprised the number's not higher. Honestly, usually when I go into an organization, I'll ask him, I'll say, how many of you are using Gen AI every day? Hands shoot up. I say, how many of you have had any formal training other than like AI best practices from compliance? That's the most formal training that most people have had is AI compliance saying, don't upload this document. I consistently have sales leaders tell me, I know my team is using AI, I just have no idea what they're doing. And the truth is, and you've heard this a million times, is AI won't replace you. It's the sellers who know how to use AI that will replace the sellers that don't. Because even if they're a C plus, B minus, but they're able to be 3, 4, 5X productive, they're gonna outmaneuver someone who's a B plus and is 1x productive. AI Powered Seller. Welcome everybody to another episode of the AI Powered Seller. This is Jake Dunlap, your host. Uh, you just got me this week, uh, and I am very excited about what we're going to jump into. Our team for the last you know really year and a half has really been leading the way in terms of how organizations are implementing generative AI for their company. And I've done some previous podcast episodes about how individuals can uh you know up their own proficiency, but I also want to talk a little bit today about organization level. And whether you're on the front lines or you're a frontline leader and you're trying to lead the way, this episode, my friends, is for you. Uh what sparked this episode, I heard this stat. 81% of sales team say that they're using AI, but only 26% are seeing ROI. Uh, I think what I see in a lot of these organizations is there's a very clear reason why. When I'm talking to a VP of sales, what I consistently hear is yeah, I know this is some technology that we need to look at. And we still haven't realized that, as my friend Larry Sweeney said uh at Nerdio, shout out to Larry. He said, This is like the wheel. He goes, This is that big. And I agree, this is a foundational shift that is going to disrupt the way that everybody works. This isn't another technology, this isn't another like cool tech or you know, some version of some sales engagement platform. This is a foundational shift in how we solve problems as humans. And so in today's episode, my friends, I'm going to get very tactical with you for you and your organizations. Uh, and I'm gonna talk you through this article that we put out, and I'm gonna focus today on just zero through three. Today is gonna be this is gonna be a two-part episode. I think most of you, this episode is gonna be the one you want to listen to. The next one is kind of the 2.0, 3.0. Today I'm gonna cover stages kind of zero through three in AI maturity. And I think for many of you, this is where you're at. And the things we're gonna talk through today, maybe you'll go back and listen to this episode two or three times as you're kind of on your journey here. But you know, today's episode to me is one of the more critical episodes. If you're somebody who is on the front lines, if you're a leader looking to make a difference and really want to be able to drive impact, I'm gonna try to lay out steps, you know, one, two, three, four here, zero, one, two, three that are gonna help to get you from point A to point B. So without further ado, let's jump into it. So the reality today is 53% of sales reps admit they don't know how to get value from Gen AI. 70% of marketers say their employers don't provide AI training. I'm surprised the number's not higher. Honestly, usually when I go into an organization, I'll I'll ask him, I'll say, How many of you are using Gen AI every day? Hands shoot up. I say, How many of you have had any formal training other than like AI best practices from compliance? That I feel like that's the most formal training that most people have had is AI compliance saying, Don't upload this document, don't do A by ABC as a part of it. And so, you know, again, I consistently have sales leaders tell me, I know my team is using AI, I just have no idea what they're doing. And the truth is, and you've heard this a million times, is AI won't replace you. It's the sellers who know how to use AI that will replace the sellers that don't. Because even if they're a C plus, B minus, but they're able to be 3, 4, 5X productive, they're gonna outmaneuver someone who's a B plus and you know is 1x productive. So I'm gonna jump in and we're gonna talk about these three various stages here. Um, if you're new to the podcast, make sure to sign up for downloads in your favorite uh podcast platform. If you're watching this on YouTube, make sure to subscribe uh to the channel. Uh we drop episodes every single week. And without further ado, I'm going to get into it. So stage zero is what I like to call AI Curious. So let's brand this the AI Curious stage, all right? Is you know AI matters, but you are paralyzed by options, right? You're waiting for your company to roll out the perfect strategy. Meanwhile, months go by and you're sitting there going, guys, what is going on? Like, why do I keep just using this on my own? When is when are we gonna do anything? And the competition isn't isn't waiting. I'll give you a very real story here. I was talking to a pre-sales VP, somebody who runs uh like solution engineering, things like that. And we're talking through, it's like, yeah, we're evaluating this tool and this tool, and yeah, we've got to you know start to deploy Gemini, and we we know we need to do things. I'm like, you need to stop. This is what I have to do, I feel like, in almost every single conversation is the reason people never get out of stage zero is they just make it too much, right? They try to say, We need this. I'm like, guys, let's start with the bottlenecks we're having today. What's the first one? It's X. That's what we're gonna do. And so, you know, in that conversation, I think he had an epiphany where he goes, You're right. I think as a third party, sometimes it's easier for me to say that to people, and for easier for me to say, like, hey, stop. Like, I'm not in the day-to-day, I'm not in the weeds with you, so I have that luxury. But, you know, in that conversation, I think he had the epiphany, which is I know I've got a lot of bunch of people randomly using this, and they're all AI curious. I'm AI curious, and I hear about this tool and that tool and this tool. Uh, and you know, I'm like, we gotta keep thinking through it. So the number one barrier from moving from stage zero to stage one is you have to stop being curious, and you've got to do one or two things. That's it. And so, as you're thinking about how do I help my organization move from step one to step two, that is how you have to do it. Say, guy, I get it, I get it, I know, yeah, yeah. And then you're gonna hear, well, we could do this, Jake, we could do this, we could do this, we could do this. And somebody in the organization, it could be you as a rep, guys. I totally get that. I'm just gonna do this one thing, which is a big pain in the butt that we're all trying to solve for, and then let's just then go do the next thing, right? So that's my my big feedback for everyone who's trying to move from AI curious to you know, stage one, which is the wild, wild west, uh, which we'll jump into. And if you're an organization that where this resonates, obviously, you know, our folks at scaled, we can help you with that. Um, I think that's one of the reasons I also created Meet Journey, is you can immediately have a group of assistants that kind of puts you in stage two or stage three. Um, and so you don't have to think about the next thing because we've already thought about it for you, which is you know, automating account research and messaging and social media posts, etc. So, you know, we're trying to do a lot uh around that. Like I said, today's episode, we'll drop a link to the article that inspired it, but it's definitely worth a read, whether you're on the front lines or a leader, uh, to really understand kind of where you're at in this continuum. So stage two, or edit that. Okay, so stage number one. So we were at stage zero, now we're in stage one. I don't know if there's technically a stage zero. I don't know if you can have actually stage zero, but we're calling it stage zero. Stage one is what I like to call the Wild Wild West. And the Wild Wild West doesn't sound like a step forward from AI Curious, but it is. And I'll give you a real example here. Is a VP of sales showed me an SDR-generated email by AI. It was completely off-brand. It referenced a competitor's product by mistake, and it factually uh gave out information about a product spec that wasn't real. Uh, and it went out to an actual prospect. And look, at the end of the day, the prop person on the other end probably didn't know. They were probably like, ah, this is fine. But the Wild West is, you know, I've got my teams. We've actually maybe invested in a tool for everybody, but there's no standards, there's no tracking. The outputs are Wild West. We don't know what people are doing. You know, people shared some slack. One rep is crushing it, like doing their own thing. Four of the other reps are like, yeah, this AI thing's a fad, etc. So you've got all these other, you know, people that are using it and you've realized like we need to use it just in a chat format. It's usually just chat only, right? And what I encourage every leader to do is in your next meeting, ask your team who's using AI? What are they using it for? Um, and I think you're gonna hear a lot of like, yeah, we're using it. And then you're gonna hear John uses it this way, Rachel uses it this way, Susan uses it this way. Um, and so I think for a lot of people, you have to start to kind of understand where your org's at. And most companies, I would say, what would I guesstimate? Set 60, 70% of companies are either maybe 70 to 80 percent are either in stage zero or stage one. Um, but you need to start to provide structure. And how you move from Wild West to you know the next phase, which is like emerging assistance, is you you one, you know, you've kind of moved from stage zero to stage one because you've said, okay, we're gonna deploy this tool, we've got one or two key use cases. Great. Now you're in stage one, the wild, wild west, and you may have these use cases, but it's inconsistent in how people are are doing it, right? And the move to stage two is is really the understanding of okay, we can't continue to operate this way. It's good that we've gotten people a tool, but we know it's not where it needs to be. I did a podcast, if you did not tune in to my episode with the head of enterprise sales from ChatGPT OpenAI, Connor. Go check out that episode. And he called this out. He said, Jay, I asked him, I said, What are some of the big myths? And Connor very specifically said, one of the big myths is you have to have this big strategy. That was one piece, right? That's your stage zero folks. His second myth is you can give people the tool and it will all work out and they'll figure it out. And so if you go back and listen to that episode, I think you'll hear him in particular call through, you know, exactly those uh details. And I think actually two and three will be the other one that he called out. So we'll we'll jump into that here in a second. So stage two. Okay, so now here's what we've done. We've said, all right, I get it. We got to do something here. We need to provide some type of structured platform meet journey for my sales team or Chat GBT or Jim and I. Now we're in stage one. We're wild, wild west in it. People are using it. There's no real guardrails around it. We don't have, you know, maybe maybe at this stage you've started to build some prompt libraries, right? If you want to know if you're in stage one or getting ready to go to stage two, stage one is like we're starting to share some best practices, not some other best practices. It's still a little like, you know, people are doing this, people are doing that. But maybe you've started, you're kind of like, if you're creeping towards stage two, you've probably already built like a prompt library, kind of realizing like, oh man, this is there's a lot of mistakes and mess happening we need to fix. So stage two, my friends, emerging assistance. Okay. And let's talk about the concept of assistance, um, agents, gyms if you're a Gemini user, agents if you're a co-pilot user. Um, think of assistance are things that we interact with that don't require us to be the prompt driver or vehicle. And what I mean by that is a good assistant, an agent, a gym, it prompts you. It knows that it has very specific use cases. So it knows its job is outreach messaging co-pilot. That's one that we have. And it knows that its job is to research sub-industry trends for a very specific company or persona, triangulate that with what you do, and say, hey, here are the three things that you should talk to them about. Right? You all you all it will tell you, give me a link to the website. And it knows to go and look for the company and the sub-industry that it's in. It's not in you know, uh retail, it's not in health and beauty, it's in cosmetics, like for example, right? And these assistants, we start to say, okay, you know, we move from step zero to step one because we knew we had an issue. Now what we're gonna do is take it a step further. What are the top three things that our team is doing? And we're going to now build custom GPTs around it. So, real life example here. Organization says, Jake, look, I know that we could be getting more out of our call transcripts. You know, we're using Gong and we're, you know, we're listening for MedPIC and it's cool and it's helpful. But you know, then we still have to kind of listen to see like, was it a good call? What did they say? And I just don't have time anymore. And so a company that's kind of ready for an assistant says, okay, we're gonna build a custom GPT or an assistant. We have one in journey called call call review, and it already knows its job is to do call review. So on the back end, I tell it here's our criteria for what goes into a good call, uh, discovery, demo, proposal, et cetera. And you just upload the transcript.

unknown:

Boom.

SPEAKER_00:

And just like a manager would break down the deal, it'd be like, here's what's the issues are, here's our stakeholder map, great job here, et cetera. So, so what that organization did and what every organization is starting to do is say, what are the bottlenecks? What's causing my leaders a lot of time? What's doing this? And we're gonna stop the prompt madness. We're gonna stop our team from trying to guess what the right prompt is, or how long does the prompt need to be, or how much context, or we're gonna just say, forget that. We're gonna solve it for them and put all that prompt context and knowledge documents on the back end. And then you're done. You're done, right? And then you don't have to have people prompting, you don't have to have 20, 30, 40 reps copying and pasting a prompt. My friend, just do some quick math there, right? If you do some quick math, you're like, okay, let's say copying and pasting prompts, tweaking them, you're spending 10 minutes on 10 minutes. Let's say let's say in five minutes, and you're doing that a couple times a day. So 10 to 15 minutes. Let's just call it 10 so the math's easier for me, let's be honest. Uh, you've got 20 reps on your team, that's 200 minutes a uh day, right? You've got 20 reps spending 10 minutes copying and pasting, that's 200 minutes a day. Um over a month, let's say there's 21 days in a month. Uh that's like 4,000. Is that right? Yeah, 4,000 and change minutes? Alexa. Oh, she's unplugged. Hey, Siri. What is what is 4,000 divided by 60? They both heard me. So that's 67 hours. Hours you saved your sales team by having them not just prompt. You know, my folks that are still having people Google and LinkedIn, I mean, just think how much time you're saving. Your people that are um already that are still in the wild wild west, they're just having your people make up your own prompts. You're not even in the prompt library world. Those people are spending four to five X. That's like, you know, a team of 20, that's like having one to two extra sellers a month if you are going from Wild Wild West, you know, just prompting to this emerging assistant world. You know, but 60 hours a month is real sales leaders, you know, and that's again, like I said, if you're doing the Google, you know, LinkedIn game, still shoot, that number's probably, yeah, at least the equivalent of two reps. That's 10% extra headcount you get without having to actually add any headcount. So just think about that, right? Emerging assistance is stage two, right? This is where we're starting to build these GPTs. We're building some very specific use cases. Um, you know, so for me, account research is a big one. The messaging one I mentioned, deal strategy is another really big one. In Journey, you know, we've got strategic account plan, we've got uh outreach co-pilot, we've got rep GPT, which is like a general assistant. And so we've got 15, like I think 10 or 12 of these out of the box. So if you want to jump to stage two, uh meet Journey to me is the only tool that has all of these pre-built. So if you want to skip ahead and automatically with an uploaded document, it programs itself with everything it needs to know about your org. It's a really, really strong uh tool. The other thing that I will highly recommend before we go into stage three is if you are somebody who's like Jake, I am ready, make sure they we just launched the course, you're only one behind, and they're all recorded. Sign up for our AI sales certification program. This is an opportunity for you. We've got a rep track, we've got a leader track to learn how to build assistance, how to build automations, the different use cases in the RevOrg. So if you're ready, if you need a little bit more hands-on support, other than just this pod, but obviously, hopefully this gave you a lot of stuff here too. That's what you need to go and sign up for, everyone. Um, links are in the description there. Okay, stage three. And then, like I said, we're gonna do a part two to this. I don't want to overwhelm you all, is connected workflows. So this is where we start to say, okay, you know what? That that example, Jake, can we actually automate that instead? Uh so again, I'll give you a really good example. So lot real life example here that I think is is exciting. Um, man, it is our our our SOW process is really manual. And we've got a, you know, we we do a call, the person grabs their notes, they're copying and pasting in the notes, um, you know, they're reformatting them inside of a statement of work. And that's how most people are doing it.

unknown:

Right?

SPEAKER_00:

Let's be honest. How many of you out there, raise your virtual hands, um, are creating statements of work by manually having a template that you fill out, right? Probably a lot of you. Um and so step one is how, you know, okay, maybe I build that assistant I talked about that could potentially say, okay, hey, from the transcript, uh, here's a couple of sections copy and paste. Well, a connected workflow takes it to the next level, right? It's a connected workflow, and this is a pretty awesome one, uh, does this, and this is a very real, we have built this uh application. And what it does is it says, okay, zoom API, pull in the call and call transcript. Then look at the key elements of the statement of work, send a Slack message to the rep asking for three to five clarification questions. The rep answer those, and then as soon as they do that within five to ten minutes, it then spits out a Google Doc with a completely finished proposal. This is you can do this today. There's a million flavors of it. That that to me is like what's so exciting. Like, I'll give you another one around CRM updates. Who do who likes CRM updates? Right? We've got a client. Uh the reps love to take notes in the email. Don't get me started, it's a whole thing, right? I'd love a call transcript instead. And then what we did is we created a a shared inbox. The rep emails the inbox, all the notes. The note that the agent then goes and verifies the accounts that it thinks it's referencing, confirms that with the reps, confirms the setup of the notes. The rep sends an email back, and again, you could do this in Slack or Teams. The rep sends a note back, says, ah, actually make this annotation to the notes. It automatically puts the notes in the right fields and logs the activity. So, my friends, when you think about connected workflows, that's how you know you're starting to get into like the early middle stages, right? Is you know, a calendar invite hits your calendar, and then what happens? It looks at the domain, it goes, runs it through account research, it then sends you a Slack note with that account, and it says, here's your dossier for your meeting tomorrow, Jake. Hope you're ready. So, you know, connected workflows is where all of you should be. If I'm just being blunt, I look, I think a lot of us are still in wild, wild west, but I want you to think about the efficiencies I just talked about. Rep1 books a meeting, then goes to Google, then goes to LinkedIn, researches the person, jots down some notes, copies and pastes some things, and then has their meeting. Then after the meeting, that rep has to guess, uh, okay, yeah, let me go send it. Or maybe, you know, they use like a there's a lot of these email summary tools. They use the email summary, they send it out, etc. Well, then the next level rep, the rep who's using GPT, says, uh, I can do a little bit better. They have an assignment one called account research GPT, uh, automatically copy and paste in the domain, boom, does a research for them, etc. Rep three, meeting gets booked through an automatic calendar link, runs through the GPT, automatically slacks in the dossier, sends them a reminder the night before, uh, scans for the news the morning of of any relevant topics to bring up from the blog post in the last week, and then completes a dossier and sends it to them. And then automatically pulls in the call transcript from what the rep wrote, automates, you know, writes the email, sends it to the rep in Slack, says, Do you want to send this? Yes, and then automatically sends the email and logs all the activities to Salesforce. That is what a connected workflow stage three organization looks like. Right. And I think for a lot of people, you don't need to be the expert at understanding AI. You need to be an expert at understanding what the art of possible. And so for me, that's where I get so excited about this, right? And I think for a lot of you, I'll get you know kind of tactical as we we wrap up here, is if you want to kind of think where you're at, here's a quick checklist for you. Is most AI usage ad hoc and untracked copying and pasting into Chat GBT, stage one? Okay. Are you piloting uh you know different use cases, but they vary manager by manager? Uh are trainings happening but not the kind of cross-functional strategies, you're probably stage one moving to stage two. Okay. Um, do you have one to two assistants that your team uses every day? You cannot be in stage two if you do not have that. Qualified assistants, agents, gyms, whatever they are in your org, uh, digital teammates uh as a part of that. If you want to move to stage three, it's are you can are you consistently automating the day-to-day tasks that are not customer facing or value add? If you do not have one or two workflows, you cannot be in stage three. Uh, the beautiful part, there is an amazing silver lining I want to call out, my friends, is to move from stage one to stage three can happen in like four to six weeks. That the ability to build these assistants is literally 10 to 20 hours. To build an automation or workflow, 30 to 40 hours. This is not, you know, old school web development, right? This is nimble, no code, low code, secure systems that can move at like literally the speed of light. And so that's my you know, my challenge to you is audit where you're at. Take a look at the article, forward this over to your uh you know, senior sales leadership, your CEO. Here's where we're at. This is what I want to do to get from point A to point B. If you're a rep, go forward this to your leader. Go listen to this podcast from Jake, go look at this article. This is what we have to do. I am as a rep, right now, many of you as frontline sellers and frontline leaders, you are wasting this next year coming up, you're going to waste hundreds of hours of your life. And I want you to really think about that. If you don't start to move, you are gonna waste hundreds of hours of your life doing the exact doing things the way you did them to where in this new world, not only is the quality higher, but you could be doing a lot less of the boring BS and spend a lot more time interacting with customers. And that is today's moral of the story. So this is episode number one of part two that will come out here in a couple weeks, uh, of your AI maturity gut check. And and I think the cool part is hopefully you're gonna walk away from this and say, Jake, I get it. Like, here's where I'm at. Maybe I'm a little like, ah, dang, like we're missing out. But if you follow my path here, and trust me, we work with hundreds of companies on this. This is everybody's path. This is just what has to happen. So if you're out there, you need some support or help, obviously hit me up. I'm happy. DM me on LinkedIn, always happy to help there. Make sure if this video was helpful, please make sure to subscribe to the channel. Uh, really appreciate the views that have just been going up every single week. Uh, if you're listening on the podcast, make sure to sign up for downloads so they always get you there. Um, and in that next week's episode, I'm gonna go through how you get into this kind of next level four and five stuff. Make sure to read the full article, uh, check out our AI certifications, uh, and you know, pick one workflow for this week. That's what I want you to do. Pick one assistant or one workflow and shoot me a note. You're like, hey, Jake, how do I do this? I'm happy. I'll help you out. That's what I'm here for, y'all. So, again, in the future, AI is not replacing you. It is the sellers who know how to use AI and the organizations that are able to move through this maturity faster that will outpace the competition. So that's what I got, everybody. Thank you for another episode of the AI Powered Seller. Thank you for tuning in, and I appreciate you, and we will see you all on the next one.

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Jake Dunlap

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