AI-Powered Seller

How Top SaaS Reps Use AI Digital Teammates to Win More Deals in 2026

• Jake Dunlap

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In this episode of The AI-Powered Seller, Jake Dunlap sits down with Ryan Staley (Founder & CEO of Whale Boss) to break down the 2026 AI mindset shift every CRO, VP Sales, and frontline rep needs right now.

If you’re being asked to do more with less, increase personalization, and keep pipeline moving in a noisy market, this is your tactical playbook. Ryan and Jake go beyond basic “prompting tips” and show how to train AI like a digital teammate — not a tool you poke for answers — so it can take on multi-step work across research, deal strategy, enablement, and leadership workflows.

In this conversation, you’ll learn:
✅ The difference between a prompted assistant vs. a true digital teammate
✅ The top AI teammates to build first (account research, next-best-action, deal strategy)
✅ Why AI “liberates intelligence” and how to avoid the AI pit of despair
✅ What’s really holding sales orgs back from adoption (overwhelm + no top-down sponsorship)
✅ How to talk ROI in a way CFOs actually buy
✅ What’s coming next: agent orchestration, Cursor 2–style multi-agent management, and everyone becoming an “AI manager”

Whether you’re a rep trying to level up fast or a leader redesigning roles for the AI era, this episode will help you move from AI curiosity to AI execution.

👉 Subscribe for weekly episodes with real GenAI sales use cases.
⭐ If you got value, drop a comment: what digital teammate would save you the most time this week?
📩 Share this with one sales leader or rep who needs a 2-year edge.

Connect with us:
Jake Dunlap on LinkedIn: https://www.linkedin.com/in/jakedunlap/
Ryan Staley on LinkedIn: https://www.linkedin.com/in/ryan-staley/

Skaled: https://skaled.com/
Whale Boss: https://ryanstaley.io/


#AIPoweredSeller #SalesAI #GenerativeAI #SalesLeadership #DigitalTeammates

Speaker 2:

I think what we're seeing is digital teammates can kind of step in and take over four or five different things and really sit as like a part like a little sidekick, a little buddies. A lot of reps are kind of sitting there and just saying, like, uh, isn't my boss supposed to build this shit for me? Or like it, like, who's gonna help save me and implement Gen AI for me? Because the my boss isn't doing it and I'm just still prompting.

Speaker:

Like, it's funny, I had an invest a group of investors tell a C-suite that like ROI with AI is really, really hard and like it's it's not easy at all. And you you, you know, like, okay, you've probably never tried to implement anything with AI in your life, investor.

Speaker 2:

We are in an era right now where it is our job to completely rework the way that our people work. And if you as a leader are not staying on top of this, your ability to continue to earn hundreds of thousands of dollars is gonna quickly diminish. Welcome to another episode of the AI Powered Seller. If you are a CRO or a sales leader who's like, hey, you just got to figure this out and do more with less. Your quota is getting ready to go up, et cetera. You know, you're grinding 60 hours a week, and now it's, you know, more pipeline, more personalization, or more, more, more than ever before, more volume, et cetera. I'm telling you right now, today's episode's for you. We're gonna talk through some very, very, very tactical ways that sales reps and sales leaders are leveraging Gen AI to cut through the noise. Not just your prompting, not just, oh, here's a quick tip, but some tactical assistance, some tactical ways that you'll be able to deploy it, whether it's from prep, whether setting more meetings, closing more deals, et cetera. And I'm super pumped for today's guest, Ryan Staley. Ryan is the founder and CEO of Whale Boss. I've known Ryan for, I don't know, 10 plus years probably. He's helped 2,500 go-to-market leaders multiply output without adding headcount. He's taken divisions of companies from zero to 30 million with just four reps, no SDRs, no marketing. That's what I'm talking about. And what's this guy's secret? Why did I think he would be a good person for you to hear from? Is it's not treating AI like a helper that you prompt, it's training it like a teammate. And so if you're somebody that's stuck in prompt mode, or maybe you're trying to figure out why AI, this episode, the 2026 AI Mindset Shift episode, is for you.

Speaker 1:

AI-powered seller.

Speaker 2:

All right, Ryan, excited for today's conversation. As usual, we're gonna talk a little bit about AI and about its impact. You know, today's episode's all about mindset in 2026. So help me to understand for you. When did you realize that AI was not another technology? Like, where was there a moment where you started to realize yeah, this is like different, different?

Speaker:

Yeah. Uh great question, Matt. So I think like, and by the way, thanks for having me on. Love, love being on the show and everything like that. So I'm excited. I guess like to answer that question, there's kind of two really core things, or maybe three things that happen. One was like I had a guest on my podcast called the Scale Up Show, where about three years ago, uh Chris Savage, who is the founder and CEO of Wistia, had me on. And afterwards, he's like, Hey Ryan, he's like, Have you heard of the tool Dolly? And I'm like, What the hell is Dolly? This is like like the image generation version one, where it was like, it was terrible, man. It was absolutely brutal. But because of that, I got on early access to ChatGPT. So that was like kind of my epiphany moment, right? When I started using it, I guess what really internalized it for me was that remember when they had on LinkedIn, like, hey, let's see if AI could replace me with my job. And there was like people testing it out. This was like GPT 3.5, and it was like all over the place. And people are like, Yeah, meh, it only does like 60% of what I could do. I'm fine, right? Like, that was people's attitude, right? Well, what I saw there was like, I'm like, I'm gonna stress test this against like what took me, something that took me 10 years to learn in enterprise sales. And that was really how buyers were like evaluated and stated, what was specific to their vertical niche. Um, and then what really drove the business all the way from like an executive perspective down to like an individual department, all the way up to the board and investors, right? And it got 95% of the way there in three questions. And so that was one of the things that, like, absolutely I'm like, holy shit, this is gonna be completely different than everything else I've ever seen. So I would say those were kind of like the key moments in time.

Speaker 2:

Yeah, I had one very similar. I remember afterwards, and now I've I've kind of coined this, I call it like the AI pit of despair, where you're like, you're really excited about it and you're like, wow, we can do this and this and this, and then you test it and it does things. You go, oh my gosh, like what does this mean? And then you fall into the pit, and then you kind of come out the other side where it was like it was it was actually, I think, maybe the exact same, like a deal evaluation thing where it's like, all right, well, can AI actually break down and help to give advice with really no context on like what are the steps in a good like mid-market enterprise deal? And it gives the advice. I'm like, pretty good. Like, that's like 80, 90% there, like and it has always like one or two good ideas. You're like, oh yeah, that's probably smart. Right. And then it goes and finds the stakeholders in real time for you and everything. So I think a lot of people have had that moment. And and for those of you listening, don't be scared of that moment. Like, it is what it is. That's what I try to tell a lot of sales leaders, Ryan, is like, look, you have to know what this thing is capable of so you can harness it, right? And and I think that kind of segues into this next uh question I've got. One of the things you said is AI isn't just about productivity, it's about liberating intelligence. So if I'm not answering deal questions, what can I do? How is this liberating my intelligence if my job isn't as a sales leader to answer the exact same question 500 times in a year?

Speaker:

Good question, man. Okay. So we could hit this on a lot of different areas. I think like I've seen it with a wide range and I've used it, and I'm gonna use some like non-work examples and then lead into work examples, if that makes sense. So I think, you know, one of them actually was a guest I had on my show. He he basically journaled electronically, put all his journals into general entries into a GPT, and he had lots of stuff about how he worked with his son. And his son, I think, had like extreme ADHD and some other like challenges that made it hard from a parenting perspective to really like understand like how to work. And so he would actually rely on and kept updating the instructions on how to work, and it helped him like kind of co-parent in like a non-objective way. And he said it's worked out really, really well for his and his son's relationship. So, like that's one example where it's like you're tapping into a mind of someone else to do that um from a health perspective. So that's like yeah, parenting, right? From a health perspective, one of the things I did is um basically I have um I had like a chronic condition um that was happening. I'm not gonna really get into it, but it was something that I went to multiple doctors on and I asked them, you know, questions. They're like, try this, Ryan, try that. Um didn't work. Nobody could uh diagnose what it was. I took all my blood hormone tests, created a really killer like prompt around being like a pattern recognition expert in terms of like health and chronic illnesses, and it basically identified it for me in a snap, and it's pretty much gone now. So, like that's on the health side, right? So I'm not a doctor by any means, and I'm I'm you know, don't have that skill set. And then last but not least is like I've seen executive teams do top-down and bottom-up planning for the entire year and with like KPIs and very specific, like 45 minutes, right? That process used to take days. So those are three like core examples that come to mind.

Speaker 2:

Yeah, and I think the key is like what you're getting at. I mean, it it was able to sift through like data. It wasn't and it was able to kind of pull through and pull out it to get to like first version of insights quickly. And I think for a lot of people, that's how we have to think about this because then you still had to turn your brain on, right? Then you still have to say, hey, as an exec team, how can we actually manage this? Is this possible? You know, even going back to like your health piece. It's like, okay, this has gotten me to hear. Now let's go validate. Let me go inspect, and it's a little bit more of this or a little bit more of that. That's whenever I hear, you know, what you said around call it creating, you know, space for more, you know, uh, I call it like creativity, you know, resourcefulness, et cetera. That's what I love about it, right? Is like I can get now to V in the same amount of time it took me to get to a rough draft. And that to me is where I feel like the unlock is I'll I'll give you a really practical example. One of our clients, they're getting ready to plan for SKO. And she surveyed the entire org, 50 plus people responded. And then she's like, okay, let's summarize this and put it in. I was like, okay, there's two different ways I could say they're summarized. You can go read every single one. And look, let's be honest. Some AI, if it's reading 50 different rows and nine and 80 columns, it's gonna mess up. Like it's still not perfect in terms of those sense. Or I could just summarize it with Chat GPT Pro and it'll take 10, 15 minutes and it'll be pretty good. And it's like, it's that's that to me is a good example. It's like, I probably don't need to pour over all of this. I now can actually trust but verify, I can get a really good like outcome, spend another hour just kind of combing through for the nuances instead of taking five hours. And I think that's where when I think about liberating intelligence, it just allows you to save time and also do a more thorough job, you know? Yeah. When people are already, you know. Okay, look, if you are somebody who can feel what we're talking about, these different AI use cases, you're like, Jake, how do I possibly make the time? We have got you covered. Okay. So if you're getting value from this episode, make sure to subscribe to the AI Powered Seller Podcast. We do episodes every week where I'm interviewing somebody or talking about what I'm seeing in the market. And make sure to pick up a copy of the innovative seller, USA Today bestseller that I wrote around what you need to know about sales in the future and the sales around AI, sales with technology, the human interaction, etc. Subscribe to the podcast and make sure to go to Amazon, pick up your copy of the book as well.

Speaker:

I was kind of like you where I was naturally born through the the uh the the the child raising of sales, right? Like there's a lot of other go-to-market activities, and like I didn't grow up being a marketer. I didn't grow up being in a bunch of different areas. Now, granted, I touched all them with the roles I did, but like if I just apply certain concepts and frameworks, I could operate at a level of a peer that's been doing the job for 25 years. So, like that's another example, man, where it's just like like ancillary skill sets that are close but not dead on with what your experience level is. That's where there's huge opportunity.

Speaker 2:

I think that that's the that where a lot of, especially if you're a younger seller and you're listening, that it can just help you get up to speed. You know, for example, you know, when I was getting up to speed at a company, I got a binder that had a bunch of industry insights in it. And it was like, you know, here's what's going on in manufacturing and this and this and this and and all these things. And so I, you know, it took me, you know, nine to 12 months worth of con. And I was a good, I was really good. It took me nine to 12 months to get up to the speed where I could have an intelligent conversation with a business owner in manufacturing and then switch gears and talk to someone in pest control and then switch gears and talk to someone in tech sale. It took a long time. Whereas now I can get the insights. And I think one of the things I'm curious to hear your thought on a lot of what we're talking to our clients about right now is there's two different levels to think about AI productivity. There's one, which is getting them access to information and insights faster. But number two is retention, retaining the information. And so, how do you think about these two? Because a lot of like, I'll give you a good example. We built an account research assistant for one of our clients, and she goes, I want you to at the end of every single one of these as prompt them with a five question trivia game to make sure they actually remember. And I was like, that's a really good idea. Like, we need because then they actually remember it. So, how do you think about you know I've seen conflicting studies? MIT says it's making us you know dumber. Other people have said actually it's gonna unlock the intelligence. How do you think about the balance of like speed to getting the information and parroting it versus actually retaining it so you actually can become a true professional?

Speaker:

It's a really good question, man. I think I don't say it's making us dumber. I think it makes us smarter and different. Or right, it can make you dumber if you if you go down that path, just like any social media tool can make you dumber, right? Just by by using it. So, in terms of like retention, I think like, and this is what I see with my clients too, with like large-scale AI rollouts, is like the only path to retention, in terms of my opinion, is like doing right, like because like you could have a deep research before it spit 50 pages out, but you're not gonna remember all that shit, right? So if you however, if you start to implement it, and that's where it gets it gets really exciting. I'll give you an example. This is like another kind of like apple flying on my head. I was like, I remember one morning and it was right after voice came out, and this was like GPT 4, not even 4.0. And I'm like, I was shaving, I'm like, hey, you know what? Like, there's this book I've always wanted to read, but I don't have time to. And so I'm just like, screw it, I'm gonna put on voice. So I threw it on voice. I'm like, apply, you know, the 8020 principle and deconstruct this book into two pages, give me all the high points and quotes with exact examples, right? Something along those lines. And boom, it busted it out, but it verbally talked to me while I was shaving. I was like, all right, that's cool. I'm like, this is my business, this is what I'm doing, this is what I'm focused on. Customize this book so I can implement this tomorrow, right? And it gave me an exact like implementation plan. I go now make checklists and sheets in a daily routine that I could use to do that, right? So, like, that's a quick path because it goes all the way from like idea to execution in like minutes. So that's what I think helps with retention as well.

Speaker 2:

Yeah, okay. And I think this is a good transition. So a lot of what we're talking about is using AI to do stuff we already know, right? Or or some some flavor of that, right? It's like, hey, I've got an assistant. Hey, AI, can you do ABC? I want to talk about the concept of a teammate. And we're talking a lot about this. We're kind of coining this term, this idea of like a digital teammate, right? Which is somebody who has, you know, it really is just a series of automations that are just kind of orchestrated together. I mean, at the end, if you kind of look at its insides, like its skeleton and its its organs, maybe just explain what that means to you. Like, what's the difference between an assistant and a digital teammate? And and where do you see the impact? Let's start with like for sales reps, and then also let's go for for leaders as well.

Speaker:

Yeah, I think um like everybody kind of like defines it differently, right? So I think like the best probably, and this is a great question, Jake. You're asking me. So, like if I was if I were to use a teammate, it's usually like like a like a co-pilot could just be for like a single function, right? Like, like you're talking about that research assistant, like boom, bust out enterprise account research, do this, customize it to my company, all that stuff, right? Spits it out. A teammate, I think, would be something that could do a string of different activities when you either link them together, right? So you have multiple kind of assistants linked together to do that, or you have someone that that does autonomous or semi-autonomous work for you. So, for example, if I'm using a tool called GenSpark, right? I could take a recording like this that I'm doing with an explainer and then infuse the transcription and then have it totally put together my entire newsletter as well as thumbnails for the YouTube design, and it does all that in like a couple minutes, right? That's like a multi-step process. And then if we're looking at it from a leadership perspective, and I think there's still a lot of work to be done, and that that's why I would say more from an individual contributor, right? We're talking from a leadership perspective, it's the same thing. It's like, all right, I'm about to have a deal review with my rep, a deal strategy. Here's the transcripts, analyze all these, give me ideal nest best actions and holes, right? That's an example. Or if I was like a leader where it would be a little bit different, I would look at more of like an orchestrated teammate structure. That would be like where you're taking like transcripts, you're taking support calls, you're taking um, you know, details from your chat bot, integrating all those together, creating a customer brain, and then spitting that out, right?

Speaker 2:

Okay, if you are somebody who just heard what Ryan laid down and you are saying, My gosh, where am I gonna find the time for this? The AI certification course is it, right? Shout out. We are wrapping up our very first cohort, which is really exciting. We've we've got the rep track, we've got the manager track, you'll see the AI certification badges all over LinkedIn. And DM me, shoot me a note on LinkedIn, we'll put a link there if you're interested in signing up for the next cohort, or check out the link, the pages that I'll link to below for the landing pages, you could just sign up yourself. But DM me, happy to give you more insight into what other people are doing to carve out that so, so precious time and get up to speed in just 12 to 24 hours on what's the latest and greatest with AI. I'll tell you how we're thinking about this is that when you go to a client or an organization and you're like, okay, so here's how this works. We take the Zoom API, we pull it in, we run it to three or four assistants. That's like your call grading's great, you know, framework, skills, whatever. Then we're gonna, you know, ship that to Slack, ask for a little bit of feedback, and then put the output into a Google Doc for the rep to be able to review. I'm just making something up, or push it to Salesforce or push it to, you know, whatever template. We find that that's difficult for people to comprehend. If instead, and and not comprehend, but more of just like really get a picture of, instead, if you say, hey, Ava, Ava is our digital teammate that does your call scoring. And what Ava does is Ava takes your call, runs it through our four or five step rubrics, and then comes back to you with a personal development plan that feeds off of the previous conversations. We find that that is more palatable, you know, and it's like, oh, cool. Like, and it's also like, I think, less threatening, maybe, and understanding of like, hey, what is an agent, what is an assistant do, et cetera. So for us, the concept of digital teammates, and even for us, we're we're thinking now about like we're adding digital teammates into our accountability chart. Like we're building in like a consulting ops digital teammate. And what they do is they, you know, running a consulting business, they analyze hours, they analyze project milestones, and on a daily, weekly basis, they're like, hey, what's going on? Like this one's behind. Do you need a new template? All those types of things they're able to do. And so I think I think of a digital teammate as something that is orchestrating, usually I'm gonna call it more operational or or consistent tasks, because even call scoring, right? Like if you go to a leader, he or she, you know, if you put the same call in front of them, different reps, they're gonna give probably similar advice. And so I think what we're seeing is digital teammates can kind of step in and take over four or five different things and really sit as like a part, like a little sidekick, a little buddy, right? Ryan, that's like sitting there helping you to do things throughout the day. So those are just like a couple of examples.

Speaker:

Yeah, I mean, everybody gets freaked out about getting replaced to some aspect of it, right? Or these AI tools becoming Skynet, taking over everything. So the other thing, too, and I'm sure you've seen this, is like the branding of what an agent can do versus the actual execution of what an agent can do is massively different for a lot of companies, right? It's like night and day difference. Um, that's something always to consider too, right? If you're looking through it. So I do like the teammates concept and I use that as well on a continuous basis.

Speaker 2:

Well, what do you okay? So what I mean, for you, I mean, you've it says, you know, you've run 500 plus AI use cases. Like, what would you say if somebody's out there, whether it's a digital teammate or series of assistants, do you have, I don't know, maybe like top few where you're like, hey, if you're a and let's start with the rep, right? Because I think here's what happens. A lot of reps are kind of sitting there and just saying, like, uh, isn't my boss supposed to build this shit for me? Or like, it, like, who's gonna help save me and implement Gen AI for me? Because the my boss isn't doing it and I'm just still prompting. If if I was a rep today, okay, and let's say I had I had the ability to build out an assistant, my team had paid for ChatGPT, my team had paid for Microsoft Copilot, my team had paid for Jim and I can build a gym. What would you what would be the top one or two things you would tell them to build in you know the first you know month or two?

Speaker:

I would say, like, I don't think it's the same across the board because you have like high velocity SMB reps that are churning and going through demos left and right versus mid-market versus enterprise, like on the sales side, right? And then you know, existing accounts. So the way I kind of look at it is like either there's kind of like three ways to attack it. One is like, what's the number one blocker to you hitting your KPI or goal, right? So that's more like outcome driven. Two is like, what do you waste a ton of time on as a rep? And then three is like, what do you hate doing? Right. Like you could look at it through any lens just to start to facilitate adoption and do it that way. And so, for example, let's say you're you're on the enterprise side and you're doing massive account research, then like map out all your ideas and what you're doing, and then create it once and ask for like, you know, open AI to create, or I'm sure to say Chat GPT to create custom GPT instructions for that exact process. And then what it'll do is it'll take that process that took 45 minutes to do and turn it into like a 30-second process, and then you just kind of iterate on it, right? Like the time that that it would take you to do one research process with that would basically it would finance from a time perspective the cost to make one to infinitely get you know 35 minutes every time moving forward. So I think that's super easy.

Speaker 2:

Research would be research would be one that you would peg then, like again, like basically building something out.

Speaker:

Yeah, and that's like I hate saying that because that's that's common, right? But like another one is next best action. Like, I think next best action with like integrating your sales methodologies into that with transcripts is so freaking easy. It used to take me 45 minutes or an hour to do that. Now I could do it in 30 seconds, and it's probably better than what I would do if I did it all manually looking through my notes. So that's another example, is what I would say. How about you, man? What do you think are your top top couple that come to mind?

Speaker 2:

I think look, to me, research is a no-brainer that and again to because to your point, you're like, yeah, everybody says it, but most people are just prompting. And by the way, prompting is like not bad, right? If you're like, hey, I'm doing research, blah, blah, blah. The problem is most reps are still, and most people I think are still using very basic prompting. They're not layering things in. So it's like, I want to do this and this and this and this and this and this. And that's where, you know, you don't want necessarily copy and paste anymore. It would be easier for an assistant to just ask you those questions. And so I think there's like, you know, if you're somebody who's consistently doing enterprise deal, what is your enterprise research process? Well, great. Just put that all into custom instructions inside of a gym or an agent or a custom GPT. And then it says, great, what's the account we're working on today, Jake? And it's like, uh, we're working on this one. And you could even upload a document of like three or four of your best account, you know, research plans you've ever done. So I think research is an absolute no-brainer. The other big one, with more, again, maybe not less on the rep side, but I think digital C S slash digital S E, like, I don't need any more. Like, I'd say those are probably some of the more common ones, Ryan, that we're building out out of the gate. Is I don't need to loop in a human to say, does this integrate with Azure or not? Or what are the five things that I need to think about around A, B, C, or D? And so for me, I think I'm looking at these use cases where where is there information that isn't really value add in the customer lifecycle and really isn't even value add between the two people that are interacting, right? Like product data. Hey, I'm a customer, I have a question, hey, I'm an inbound lead, I want to book a meeting. Like, I think that there are certain use cases at the exec level, customer success, digital SE, inbound, that are kind of those to me for the the executive level are no-brainer. And then I'll call it like research and prospect insights. We've got kind of a uh a message framework we call the triangle, which is it basically says, okay, for this persona in this sub-industry, what are the trends that that that persona is facing in that sub-industry that we actually help to solve for? And that's where Gen AI is really good. It's like trends for industrial manufacturing, especially it's like specifically heavy equipment machine manufacturing for a VP of operations, here are the top three headwinds this person's facing. And you you have a product that does X, here are the three things you should talk to them about. And that's where you know that used to take someone 15 years in an industry. So I think building an assistant that knows, you know, your version of good messaging, an assistant that knows your version of great research, that's going to get you a long way. And then I like the one you said, that's probably the other, if I had to pick a third, which we'd call that deal strategy evaluation, where it knows, and what we have it do is it looks at competitive threats, it looks at stakeholder map threats, right? Hey, you're only talking to these two people. Typically, your deal has a CFO. I by the way, I found it. It's Lisa Henderson. Here's her LinkedIn, here's five things that she just talked about. So being able to build an assistant that can, I don't need to go ask my boss. I call it 100% deal coverage. Yeah, I'm gonna talk to my boss about the top 15%, 20% of deals, but I can actually run 100% of my deals through some type of evaluation framework that should help to increase my close rate by five, 10%. You know, so those are yeah, those are some of my, I don't know, like go-to go-to's as a part of it. Tell me a little bit right now, what's holding people back? So we're talking about these use cases, right? Of like implementing these tools, the time savings is very obvious. What do you feel like is holding people back right now? Why do you feel like more people aren't leaning in? I know, look, we're all busy, everyone's busy, but why do you feel like more most people aren't leaning in further?

Speaker:

So, and it's a great question, man. I think like there's there it like I think there's naturally people who are hungry to learn and others that aren't. And like, you know, obviously your brain rationalizes to save energy and avoid pain, right? So, like those are the two core things it tries to do every day. And so, like, there's a couple things that it influence. I think what's holding people back is like things are moving faster and faster every day in terms of the number of releases, the quantity of releases, the number of SaaS tools that are released. And so it's just so overwhelming that people decide to do nothing, right? Like, I think that's number one. Number two is I would say, and like, it's why your business is doing well and my business doing well right now, is like um if companies aren't like sponsoring this and saying this is a priority, then most people don't come to that conclusion on their own. There's a fraction of power users that do, right? And those are the power users. And then if that doesn't happen though, innovation happens in the dark and you lose all that insane tribal knowledge integrated with AI for those power users. If you if you like bring it all together through like a corporate-led approach with a top-down and bottom-up, then that's when you start to really see things take off. So that's what I would say, man. Top of brain. What do you feel like?

Speaker 2:

What do you feel like at the top? What's stopping people at the top from diving in? Why do you feel like leaders are, and again, maybe they're not reticent, but they're not doing it. Why do you feel like from the top down there's struggle points to kind of really get started on this AI journey?

Speaker:

Yeah, I think a couple points. I think, you know, one is a lot of it's fear-driven, to be honest with you. And so now that we're reaching more of a level of maturity, like it's funny. I had an invest a group of investors tell a C-suite that like ROI with AI is really, really hard and like it's it's not easy at all. And you you, you know, like, okay, you've probably never tried to implement anything with AI in your life, investor. Um so that's one aspect of it. I think the other thing at the top of like why someone wouldn't is like the median tenure of a CRO is 15 months, right? So it's like their their time to execute is so freaking tight. Um if they don't do that and they just look at this as like another barrier sometimes of just focusing on just doing the work of like hitting the number, right? So I think that's the other thing, man. That's super, super critical. What do you think on that side?

Speaker 2:

Are you saying the same thing? I mean, time is certainly a part of it. ROI, here's what I would tell you. Just in general, and all my sellers know this time savings is the worst sales argument. We as humans struggle struggle struggle to properly credit certain initiatives as like the correlation or direct impact on a productivity gain metric, right? We love revenue gains. We love uh, you know, whether that's you know dollars or whether that's volume um base, but I'll just in general, productivity gains are difficult. Now, the good news is how you know how we're doing it with AI is we're mapping how long a job takes to be done today. Okay, this is what is happening. We're gonna build an assistant around X. And here is the actual impact. Here are the user logs. The user logs say this job used to take 19 minutes. They're now doing it in five. And let's say I only get credit for 40% of that gain, another 40%, they're just using it to mess around and not to sell. That's real money. That's that's a lot of money. And so that's how we're trying to quantify it. And then the other thing that I try to uh this is my favorite one for a CFO when they ask that. I go, okay, what's the ROI on Net Suite? And they go, What do you mean? I go, what's the ROI on Net Suite? How did you quantify the ROI? Well, it's obviously better than the way that we Exactly. What's the what's the ROI of Google search? Well, it's better than going to the library. There are what's the ROI of Salesforce? All of these are about making our people more effective and more efficient. And so I think you really have to think of AI in that bucket. That AI CFO is net suite. It is obviously better than Excel docs and version control and people not adhering to processes, as opposed to, you know, yeah, I'm gonna manually go to Google search and LinkedIn and do this and go to a website and think and blah, blah, blah. Like it's obviously better and faster. But I think, look, if you can tell the ROI story, all the better. But I feel like there's a there's a gap at the the CFO level. I agree with you 100% on the time at the leadership level. And I think the reps are just, I think reps actually are just way outpacing leaders. I think reps are coming to your point, the bottoms up play. I think reps are coming up with all kinds of smart, innovative ways to do things. And if they even had the opportunity to learn how to build assistants or agents, it would be even more effective as a part of it.

Speaker:

So there's definitely something that gravitates towards a I think yeah, I I think there's definitely elements of truth to that with at the rep level. I have seen though, I will tell you this I've seen a ton of reps just using basically these AI tools. Get an enhanced version of Google and that's it, right? Like, that's the other thing that I think a lot of people are lying to themselves or about their AI competency because it's like I use AI every day multiple times a day. It's like, how do you do it? I use it to look up stuff, like like Google. I'm like, well, that's that's you're missing you're getting like one percent of it, right? So it's like that's an opportunity too.

Speaker 2:

I think, but that goes back to, I mean, it it's changed a little bit, but you know, we'll go and we'll we'll meet with a client and we'll be doing something with their revenue org. And you say, How many of you use Genai every day? Probably 90% or more hands go up. How many of you have had any training from your organization on how to use it other than compliance training? All the hands go down, right? And and I think it, but this is we're kind of in a cycle where sales leaders, you cannot afford to not master this. It is our job as leaders over the next two to three years to completely rework the way that people do their job. Like that, this is not a new technology. I'm shifting. Hey, you used to do this this way, now you do it this way. You used to do it this way, now you do it this way. And and that's the journey that we're all signing up for if you're gonna be in leadership over the next two to three years, is you are signing up to it's the same way, like, look, we didn't get a pick this point in time, right? It's like if you were a sales leader, I wasn't, or a revenue leader or CEO back in 1995 or six, you didn't get a pick that the internet happened. Somebody had instead, someone had to retrain Brenda on how to send an email. Hey, Brenda, we're not doing that anymore. Hey, and uh, we're not gonna print our emails out anymore, Rachel. We're gonna do this. Like, hey, Frank, we're not gonna send the facts anymore. Remember the email thing. Like, that's a real thing that happened. And and I think we have to realize that that's where we're at right now. That we are in an era right now where it is our job to completely rework the way that our people work. And if you as a leader are not staying on top of this, your ability to continue to earn hundreds of thousands of dollars is gonna quickly diminish because I'm gonna be able to bring someone much smarter, more effective, and more efficient, and where you're just used to being the deals guy who just comes, the parachutes in, gives deal advice, parachutes out. Guess what? Like to your point, how how Ryan and I both found out about the power of AI was seeing how good it is at deal evaluation. And if you think you're better than me and Ryan, maybe you are, but I want you to go and run your deal evaluation criteria through it too. And it will be definitely a uh an awakening for you, potentially. Yeah.

Speaker:

I don't know. I mean, dude, I don't know. I I agree with you, like in terms of reimagining what's possible with work because like there's a couple things you got to look at is like, all right, how are roles gonna change or how how do they need to change? Not just like um how they're gonna organically change, but if you're intentional about it and then you're aligned with like updates as they happen, that's when you can get like a two-year head start on your competition. And that's something that you know I'm starting to work with is like with clients on is like redesigning roles and and creating outcome charts more as opposed to you know org charts, right? And um, it's really pushing people forward. And even if they're not at the bleeding edge of like executing that, the fact that they're already starting to do it now, they're ahead of 99.9% of people, is what I would say.

Speaker 2:

All right. So what's next? All right. So as we start to kind of like wind down, wrap things up here, great conversation. I hope everybody out there had a ton of tactical takeaways in terms of, ooh, I like that thing Ryan said. Like, I think I can do that. And again, the funniest part is I was at a conference last week, Ryan. Um, content marketing person, she was doing a presentation and she was talking about this cut how they turned this kind of product-based asset into a custom GBT and it took off an adoption. And somebody, you know, an older gentleman asked her a question and said, you know, how long did that take you to build? She has a few hours. And it's just like, that's that's all it takes. It's a few hours, and like it's yeah, if she spent another few hours, it'd probably be like, you know, even better. But but where do you think this thing's going, man? If you had to predict in maybe next six to twelve months, you know, what are some of the exciting use cases? And what are some things that people need to be thinking about today?

Speaker:

Well, that's a great question, man. I think everybody is gonna get promoted to be a manager, and what I mean by that is like you're gonna have the capability for folks to take advantage. Actually, have you used like cursor two at all? Have you looked at that or used that at all?

Speaker 2:

Yeah, yeah, yeah. Cursor lovable.

Speaker:

But no, have you seen Cursor Two, like the newest version they just released weeks ago? Okay. So basically, they almost have like an agent interface window, so you could have multiple agents running at the same time, and you could see what they're all doing. So, what I think is like, and I'll do that sometimes with Claude Code or other areas, I'll fire up one on the side and have it do law inform while I'm doing other more tactical things, and then every now and then I'll need to respond. But basically, I'll kind of hybrid and use those like law-inform agents to do that while I'm doing my main job, and I think that's gonna be a big change because the reasoning models are getting so freaking good. With, I mean, I don't know if you saw Humanity's last exam. I think GPT-5 is now at 47%, which is better than most world-class humans. So the intelligence layer is getting so freaking smart, and it grew 8x in seven months in terms of like from the the quality. So that's the other thing. Outside of that, man, I think like so. Everybody is now gonna have the capability, especially over the next 12 months, to have these agents almost like sitting in a window that you could manage and orchestrate that aren't like these complex like N8N diagrams that you see from like the automation bros on X or LinkedIn, right? So that's what I think is gonna continue to go down and they're gonna make it easier and easier for normal Joe's and Bob's and Susie's and whatever and Ryan's to use it. And so that's what I think is gonna change over the next 12 months.

Speaker 2:

I love that. Yeah, I I agree. I think the and and the other thing that I'll say is that you have to start to take time to learn this. And the other thing that I again for a lot of you, um I really want a lot of you to think about is this is that you have to invest in yourself, which which by the way, it might mean that you got to do this stuff after hours. You might need to take five hours, 10 hours on a weekend to learn this stuff because the alternative is what Ryan said. I want you to picture, picture this world, Ryan said. You got, you know, Jenny over here, and Ginny has four or five automation. She's figured this out. She took the extra 60 hours over the last three months to go and mess around with Cursor 2, etc., to go build her own assistant. And you're over here being like, but yeah, I had to go to Costa Rica for a two weeks. And I had like, my friend, like, this is happening. And I'm not that, you know, I'm not trying to, you know, don't get me started with like the hustle culture and all this. This is not about hustle hard, out work, kill your quota. This is about being super, super employable in three to five years because this is a very real use case that Ryan just gave. He is doing this right now. Ryan, are you a programmer? Are you like a a never sales guy? I mean, like, and again, like you know, we're we're a couple of you know, sales leaders, you know, who have who have kind of woken up and realized that this is where we're at. So I just really hope everyone, again, you really start to think about your own professional development. I don't care what level, if you're 25 or 55, unless you're planning to retire in a few years, then maybe you're good. But but we are entering a world where not understanding what is possible today will put you behind the eight ball significantly in, I don't know, two years, three years.

Speaker:

I mean, I think it's gonna be shorter than that, man, with how faster things moving. I think it's gonna be a year. And yeah, it's crazy, it's going fast, amazing opportunities. And like on a parting note, man, because I know we're just about up on time, like the one thing, and you were talking about work on the weekends. Like, if I want to use clawed code and understand it, I might watch like a half hour YouTube video, and I might only get 15 minutes of the way through it because I'm pausing and implementing it, and it might take me two two hours or three hours to do, right? But the next time I do it, it's 10 times easier. So, like, here's the way that I approach it, and I was funny, I've gotten asked this question a lot is like, Ryan, do you approach it where like you have very specific outcomes you want, or do you just free flow it? And the answer is both. There's some times where I'm like, I gotta get this shit done, I got a super tight time frame, just go, go, go, go, and I'm laser focused. And then I have other more like exploratory time where I'm like, all right, this is what I think. Let's see where this takes me. And that's where I see like helping me really advance development in terms of uh AI usage.

Speaker 2:

Yeah, I love that. Again, it's it's not about being perfect, right? It's in and it's about finding a system that works for you. So, Ryan, I appreciate you, man. It was good to good to chat, man. It's been too long. We got to set us some time separately to just kind of go deep and kind of find out what the latest and greatest is. So thank you so much. I really appreciate you joining in. Yeah, man, it was awesome. Thanks for having me on the show. That is another episode, everybody. Thank you so much. Make sure to hit that subscribe button. Make sure to share this with one person, one person, one peer, one leader, somebody who's like, man, I've talked to this person about AI all the time. I know they will, they'll get something out of this. And make sure to leave a review if you enjoyed the episode on your favorite podcast, Apple, Spotify, et cetera. I always really appreciate the reviews and I take the time to read those as well. So until next time, everyone, go build these AI teammates we were talking about.

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Jake Dunlap

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