Sell Like A Leader – Episode 35
David Kreiger sits down with Aaron Ross, author of the bestselling Predictable Revenue, to revisit the principles that reshaped how the SaaS world thinks about sales, and examine what those principles mean in today’s high-noise environment.
Aaron brings two decades of perspective on outbound, specialization, and pipeline building, and he challenges revenue leaders to stop chasing the playbook and start developing the instincts the current climate demands.
In this episode, he breaks down:
- Why the tactics from Predictable Revenue may have changed, but the core principles are more relevant than ever
- How AI is accelerating buyer attention fragmentation, and why ICP focus is now a non-negotiable
- The case for even deeper sales specialization as AI agents take on more of the SDR and AE workload
- Why the corporate world’s hunger for stability is colliding head-on with a fundamentally non-linear era
- How emotional agility, intuition, and creativity are becoming the true competitive differentiators in sales leadership
Aaron’s outside-in perspective will challenge how you think about building predictable revenue in 2026.
About Aaron Ross
Aaron is a bestselling author, sales advisor, and keynote speaker, known for co-creating the modern outbound sales playbook. He authored and co‑authored influential business books, including Predictable Revenue and From Impossible to Inevitable, helping leaders build repeatable sales systems.
He has advised CEOs and high-growth B2B companies worldwide, sharing frameworks to restart and scale revenue predictably.
Podcast Key Takeaways
- The tactics died, but the principles didn’t. The core ideas from Predictable Revenue are not just still valid, they’re more critical than ever in a world flooded with AI-generated noise.
- As AI makes it cheaper and easier to launch campaigns and spin up competitors, the only sustainable edge is going narrower. Companies that win will be the ones that know exactly who they’re for and go impossibly deep on that niche.
- Emotional agility is the new competitive differentiator. As AI handles more of the left-brain, analytical work, the skills that will set sales leaders apart are creativity, intuition, and the ability to navigate uncertainty without freezing.
- Sales specialization still holds and needs to go deeper. Dividing roles between prospecting, closing, and customer success was a game-changer before.
Connects
Connect with Aaron Ross: https://www.linkedin.com/in/aaronross/
Connect with David Kreiger: https://www.linkedin.com/in/davidkreiger
Subscribe to the podcast and follow our Podcast LinkedIn page so you don’t miss any episodes!
Transcript
David: Welcome back to another episode of the Sell Like a Leader podcast, the podcast for revenue leaders who are on a mission to cultivate a high-performing sales team within their organization. I'm your host, David Krieger, founder of SalesRoads, America's most trusted lead generation and appointment setting company, and today we have a very special guest: Aaron Ross.
You probably know him from his bestselling book, Predictable Revenue, which really set the SaaS community—and I think really sales in general—on a different trajectory on how they look at sales and creating predictable revenue. And I'm excited to have him on at this juncture in our sales history to talk about what predictable revenue means today and how things have changed over the past few decades. So Aaron, thank you so much for [00:01:00] being on the show.
Aaron: Yeah, David. Interesting time in history, honestly, right now.
David: Yeah, not, not just in sales, in general, right? Everything is, is kind of interesting as, as we live through these, these times. But let's talk about sales first. In one of your, your LinkedIn posts about a year ago, you had talked about how traditional sales strategies are falling short and everyone is looking for new ways to get results. I think there's a lot—and we'll talk about—there's a lot of reasons potentially for this. Obviously, a lot of people point to AI, but there's a lot of other things I think.
And so I'd love to really unpack that with you today and how sales is changing. How sales leaders need to maneuver through this time, what to expect. Let's start with just the basics. When you say traditional strategies aren't working the way that they used to, what are you currently seeing breakdown?
Aaron: I think [that] captures a lot of the mood for a lot—not only revenue executives, but just a lot of people. And there's a lot of people who are excited and terrified. You could [00:02:00] either be, you know, more on one side or more on the other—kind of 50/50—and you know, for good reason, because, you know, it's what's interesting.
I worked at Salesforce.com, um, and some startups, and then... but I've also, for the last 15 years, like, had a family of 10—10 kids—and working on new books, new ideas. And so while I still work with some companies, I'm on boards or sometimes do sales advisory, and I work on new sales books. And so I, I talk to people in the, in the tech world and the sales world and the revenue world. I'm not in it myself, which is, it's good and bad.
It's challenging 'cause I don't know the details and, honestly, I don't really—I'm not interested in those. But it's good because of the outside perspective. I'm [not] caught in the echo chamber. And you know, I think everybody, I think generally people feel like, "Wow, the stuff that used to work doesn't work anymore." Some [stuff] does work, but not necessarily the copy-paste from what you did two years ago, or five years ago, 10 years ago.
And, you know, big picture is what a lot of people in the corporate world... they're inherently drawn—we're inherently drawn to the fact that it offers a lot of stability. You kind of know what you're... you can build a career, [00:03:00] you'll be able to make money, you'll be able to get a job. I mean, there's always some uncertainty, but compared to a lot of other areas, whether it's music or art—I mean, there's so many—science. So people are drawn there generally for opportunity and kind of like "safe" opportunity.
Now, let's leave aside the natural entrepreneurs. Talk about the bulk of people in corporate America: it's stable, relatively predictable, safe, and people are generally relatively risk-averse. Even in tech companies. There's a lot of founders who go into tech because it's a safe way to start a company.
Now it's like tech entrepreneurship is the well-paved road accounting, dentists, and doctors were in, like, the seventies, eighties. There's this veneer of, "Yeah, it's risky, da-da-da-da." Okay. But generally, it's like if you're gonna start a tech company, you feel like...
AI, for most people who are older... you know, there, there's some younger people that hasn't hit them. But if you've been in the tech world, corporate world, for for more than a few years, or in obviously decades AI and the other changes in the world, but primarily AI is really accelerating. It's like pulling the rug out from under your feet. [00:04:00] And that shows up in the tactical things, like you're SDRs, SDR manager, VP of sales, or the marketing side. The same things, like the stuff that used to work doesn't. Now it's not to say—
In other words, like you used to... you know, when I was at Salesforce and it was early days, or even a few years ago, you could create a technique and, you know, a marketing technique, a sales technique, and you could probably rely on that working for years without having to really change it too much. And that's, that's changing now. You can't rely on it anymore.
So again, it's kind of this... a lot of people who by default want to have something predictable, some sort of safe path. Now it feels unsafe. And so I think there's an extra level of anxiety in the corporate world because of the nature of the general psychology of people who go into it. There's a lot of other things, but generally, it's for most people, it's a safe bet. Again, like the old worlds of other SaaS—it's just the new version of the safe jobs of, you know, prior eras.
David: Yeah. So, so let's, let's dig into what is changing. Do you think it is primarily this inflection point of [00:05:00] AI or generative AI that we've seen, seen come on the, the scene? Or is there other things that are, are deeper at root here?
Aaron: You know, when I left... so I worked at Salesforce 2002 to 2006, and before that I had a—I started a company that failed. But, um, in 2007 ish, I worked with a VC fund for a bit and I studied the lead gen space. And I remember I did a presentation and even at that point, it was kind of clear to me that just the general... because I'd been doing outbound prospecting at Salesforce and other things, but it's just clear that just the march of technology ever since then, when there's always more technology and easier to create apps, easier to create tech, uh, new channels to send more messages. Like, that was just an upward trend and any new technology was just gonna continue.
And so what that means is people's buyer's attention, anyone's attention, is gonna be a bit more fragmented, a bit—you know, it's gonna be more noise, more overwhelm.
AI is just now accelerating that. So I think ultimately there are... I'm sure there's other things at play, but the core of it is that when you've got a certain [00:06:00] number of buyers and they've got a certain number—not just an amount of attention, but also certain, certain number of priorities—and you've got explosion of not only messages and content whether that content's coming over email or LinkedIn or newsletters. There's so many types. So there's this explosion of content and this explosion of opportunities, right? You could do so many things now.
So ultimately what's happening is that, um, it's kind of like this root level... people—and again, it's kind of called corporate worlds or executives, managers, but even individuals—there's, it's harder to to say like, "What do I actually do with my time, energy, and prime priorities?" Or, "Okay, I want to grow something, what do I grow and how?" And then like, "What tools?" And there's just a lot more opportunity.
And to be fair, AI's helping people think through that. So it's a bit like a hamster wheel where, you know, as much as things change, they stay the same. So ultimately, like for at least a few years—and I'm ignoring kind of robots and quantum stuff—AI for [00:07:00] the most part, I believe, is going to keep the general, you know, the people who are working hard will just work harder and be more anxious and probably make more money.
You know, it's like the corporate, the hamster wheel. It is gonna spin faster for most people unless you consciously step off that hamster wheel.
Whether, again, you're in an SDR role, choosing to work differently; whether you're in an entrepreneurial role, choosing to work differently; and kind of like, uh, taking a step back, which is rather than getting caught up in all the FOMO, right, the Fear Of Missing Out, and the fear of, or FU for Fear of Fucking Up. Like, what do I actually really wanna do with my life, with my business, with my team?
And I can't do it all. So how can I kind of come up with a system to figure out, like, where my approach is, and kind of to maintain my sanity with the swimming and swimming and stuff? Mental noise, and opportunity.
David: Yeah. So I think, I think there's, there's, there's a few things I wanna, I wanna unpack there. So, so first of all, I, I, I think AI, like you're saying, is, is an accelerant to, to, to the [00:08:00] idea that people are getting inundated, and they were getting inundated before, before AI. Right?
Aaron: And they will after AI too. Yeah.
David: Exactly. And at a time where I think everyone has decreasing attention spans, maybe just because of our devices, or society or, or whatever, right? So, and then also what I think you're, you're driving at too, it kind of makes it harder for everybody in some ways to, to execute.
And I think one of the beauties of your book and, and why it resonated so deeply was it was a roadmap for people in a very simple way, um, to think about revenue and to think about how to make it predictable. Right. And you broke it down in a way that people could understand. And that's why it stood, you know, the test of time. And it's still—people still are executing based upon that playbook.
Aaron: Yeah. And the principles are still true. And even more true. And for example, if you haven't read it, or it gets really associated with just outbound prospecting, but really there was like a few key ideas. So one was that [00:09:00] you need to separate the, the closing of deals from lead generation. And you know, for older people, for the most part, that... you know, the old days, that was the same thing. You hired more salespeople to get more business. They would do their own lead gen and closing.
Okay, so breaking out the different jobs to be done: sales specialization. That's more important than ever. Even if some of those jobs are done by AI—whether they're AI or humans—like important than ever, the more overwhelmed and busy the world gets, the more you need different ways to focus more thoughtful about it.
So that's one. The other was different seeds, nets, and spears. Different types of leads need to be treated differently. And then of course, just predictable lead generation, breaking it down into funnels and things, which now everybody does to some extent. But those are... and there, there's one other topic, I think a key idea, which didn't get as much airtime. A lot of the book was really about kind of sales management and really like collaborating with your team. You know, there's, there's one example where, you know, uh, in changing the comp plans, I, you know, had the team review 'em and gave their suggestions and kind of involved the team to collaborate in creating new comp plans.
So those are some of the key ideas. Now, the tactics died—nothing ever really dies, it, it just goes away for a while then it comes back. Like direct mail still works today. Knocking on doors can actually can work. Knocking on doors can work, cold calls can work. All these things can work, um, including the referral techniques. But, um, so the tactics are all different, but the principles are the same.
And actually even more important in my mind—and sorry, the last one was the Ideal Customer Profile, which is just like really knowing who your ideal customer is. And those are still true, even more important than... the busier the world gets. I don't care, you know, the whole AI thing, I, you know, super interesting. It's gonna change a lot, but some things that really aren't gonna change that much.
David: Yeah.
Aaron: And ultimately you still have to have humans in some loop someplace. A lot of AI agents will take over lots of things, but there's... we have lots of humans. There's gonna be new [things]. So a lot of stuff will change, like the way it works and the math, technology and jobs and... but a lot of stuff won't, which: you'll still have humans who need to work with [others], who still want to work with humans and sell to humans and get help from humans. [00:11:00] That's still gonna be there.
So again, there's um, more variety, kind of like the old channels that used to be just, you know, direct mail. Then it was like phone calls and direct mail. Then phone calls, direct mail, and email, then added LinkedIn, then added WhatsApp. So we used to have humans, then we'll just add AI to this, but we still have humans there.
So it'll just be, you know, a more—not complex, but it'll just be more ways that people work together and more ways that humans and AIs, you know, work together and buy and sell. But for the most part, the way that we work is still not gonna change that much.
David: Yeah, so I think that there's a few principles I wanna dive in there because I think that they are so relevant today and in some ways more [so], and people just need to go deeper on 'em.
So, yeah, my, my feeling with with AI is we're gonna see a lot more either specialized companies really going after very specific niches because you don't need to raise a whole bunch of money necessarily to go after a very specific niche. You have, you know, one or two coders doing what a team of 50 maybe [00:12:00] did back, back in the day—well—
Aaron: Sorry, but... and that's now... one second. So that's true. But the flip side is now you've got 50 more companies. So the noise goes up. So that's why everyone who's like, "Oh, I'm using an agency." Like, okay, yeah. But pretty soon, anything that works well is gonna get swamped by copycats. So again, running in place, running in place.
David: Absolutely. And so I think that, so, so I really think that it's easier to create, obviously competition is gonna go up. So that's why being very focused on an ICP and maybe even a very specific... like, ICPs are gonna become even much more narrow. Right? Because you can really dedicate yourself to a niche of an ICP because, all of a sudden, it doesn't cost as much to—at least from a tech side—to create something that is really meaningful for that niche.
And because there's so much competition, you've got to niche down. So the principle that you have of really defining your ICP in this world, it's almost gotta be even more [00:13:00] defined for a specific startup. Yeah, exactly.
The large companies need to have divisions or groups that are focused on each of those niches because they can satisfy them. And so I think niching down and being very focused on that ICP, I think is gonna be critical to sales success. Because then, going to your point that you just said, the competition for any given niche—or if it's slightly broader—it's gonna be harder to compete in. So the more niche you are, the easier it will be to compete in a very competitive world.
Aaron: Yep. And you know, something might change: you might have a niche of AI agents who are the buyers, right? There's no relationship. You know, you might have the shapes of jobs and shapes of companies and things are gonna change. The principles will not.
You know, ultimately, like, there's... probably a friend of mine told me a story. I don't think it's true. It may or may not be true, but it was a good story and I was like, it makes sense. And I said, "They unearthed—someone unearthed a Roman [00:14:00] Army manual from 2,000 years ago." Or, and basically the, the issues that they were describing with their people—like in terms of management—were the same as basically today. You know, people are people. Now, that could change at some point with
Neuralink and the... you know, there's all kinds of weird stuff coming down the pipe here the next several years, 10 years, who knows.
But, um, a lot of the, you know, again, making money through like tech, business, work, all this stuff—there will be a ton that does change while a lot that won't. Now, I will say that something, I think one of the biggest changes that I'm seeing and predicting is that the way that we work in the corporate world—and by "corporate world," it's like kind of the linear side of things—which is: "Hey, if I do X, I get Y. I'm gonna build a company and I'll do these steps and then I'll get, you know, X and Y." And kind of create spreadsheets.
And spreadsheets usually don't come true, but it's some... you can, you feel like you can kind of predict something.
And I'm working on a new book with my partner in Brazil. And so we call—let's call that [00:15:00] "linear mode." Because you can kind of spreadsheet it out: a lead gen campaign, a company plan, some sort of financials, and you know, alright, it feels like that could work. Again, a lot of times the feeling is an illusion, but as, you know, we've learned with COVID and AI... like you could have all the projections you want as detailed as you want. They may or may not mean anything.
But there's this "non-linear mode," and I wish I had a better name. I really don't. But it's like where you can't—
David: You just—
Aaron: You kind of... maybe you need to know that you can't make predictions; they are gonna be useless. You can kind of predict at a high level, which is... okay, maybe my family even: I want to continue to have better relationships with my family. I'm gonna work towards that. Do I know what that really looks like? I really don't. I kind of know.
Or with a business in some areas. You know, I experienced this in consulting, which is, I kind of did, you know, I created content, right? I wrote a book, wrote another book. I would do newsletters, and I kind of felt like if I just put good ideas out there, stuff will happen. And stuff did happen.
Like, I would get business. I made a lot of money. It was really never, though, something... ironic for the [00:16:00] outbound guy. Anytime I tried to do something in a regular like outbound way or methodical way, just it never worked—didn't get anything. But when I just kind of trusted doing things almost like emotional navigation...
Like, "I wanna write a book, I wanna do this newsletter." Like, I'm inspired by this, or I have to do this: get married, have 10 kids. You know, again, I can't explain how the things, a lot of things I did, led to making money. But they did.
So again, it's this world of, I would call, you know, EQ, Emotional Intelligence, non-linear. You can't always really predict. You kind of have to trust. You have to trust in yourself. You have to trust in your agility, which is: I don't know what's gonna happen. First of all, we don't know, like this year we know there's gonna be more surprises—unhappy surprises, probably some happy ones too. But there'll be more world shocks of some sort. Tech shocks, world shocks, right? We just had this Iran thing. A hundred percent that's gonna happen in next year.
We're in the world where the chaos temperature's going up because the more connected the world is, the more that one [00:17:00] aspect in one world, you know, ripples through and hits another. So we're not gonna have a more calmer world, I don't think, ever. It's probably just be more drama. We [call it] drama not as like "good" or "bad," but just like stuff happening, you know, things changing.
So what does that mean? I can't predict what's happening this year and I can't get ready, really. I just have to be... but for me, it's not about being prepared. It's being like kind of "ready." It's like being attuned to what's happening and being ready to kind of change in a moment's notice to do what, I don't know.
And so again, our team in Brazil, it's: "Okay, we have, you know, we have projections, we have thoughts," but a lot of times it's like we're just using that as loose guardrails for generally where do we want to go. And, you know, we wanna be profitable, we wanna have the team be, you know... I'm just using a word here... "strong," good relationships and um... but there's so many changes that it's really more about... you know, it's almost like just like emotional agility.
'Cause you know, we don't really know what's coming next week by week and whatever comes, we're like ready to [00:18:00] meet it. 'Cause we're not locked into this: "Oh, we have this projection. We need to hit these projections and this is the way it has to do. We do A, B, C, D, E," like kind of some fixed spreadsheet.
It's like constant iteration and almost like an evolution of... I think like a slime mold, right? You have this like culture and it's like strong and there's like some nutrients. You don't really know where it's gonna go. You just, it's just gonna expand. You just kind of see where it goes.
Like, that's kind of like more how I think. And again, we're still shaping how we're gonna describe these in the book and like what this even means. But you know, that's kind of how I think—more of an emergent approach versus um, something that's really planned and executed and reliable over a David: periods of time.
David: Yeah. And, and so I think a lot of these principles have been important and we've definitely hired on EQ before, but in some ways these types of things are more important first. Just velocity of ideas. You gotta, you gotta lean in, you gotta be you.
All of a sudden you can create a lot more things. You can spin up new ideas for sales ideas or spin up a lot of new [00:19:00] ideas so much faster. And so now there's no excuse to just getting it out there, trying to figure out what works, iterating on it. And you gotta lean into the chaos and almost be a chaos agent yourself, uh, to be able to try more things while at the same time—and I'll use the word again 'cause I do really like it—you know, the "emotional agility."
Aaron: Yeah.
David: And as sales leaders, as executives, as people in society... those that have the emotional agility are gonna be able to deal with this chaos, this fog of society.
Aaron: Yeah. Emotional agility, you know, or words like, um, "taste." I think that's been thrown around a lot. Like, yes: taste. You know, I think three things a lot are like creativity, relationships, and intuition. And these are a lot of, almost by definition, a lot of the EQ stuff—the Emotional Intelligence stuff—because in my mind, like right-brain... AI will take over a lot of left-brain things.
So, you know, we were very left-brain dependent in the corporate world for a long time. Now, maybe it's more of how we balance IQ, EQ—or AI and EQ. [00:20:00] It's not [that] EQ is like "the" important thing, it's more like an integration. But you have strong IQ with AI.
And I get the frustration. A lot of people are like, "Well, how do I develop my intuition, my taste, my emotion?" These are difficult things to explain until you have enough life experience. It's almost like it's just hard to even describe it. It is hard to describe it. So I feel for that.
And I feel like I've developed a lot of mine, again, through having a very intense life for the last, especially, 15 years with so many kids. And not just supporting them and growing the family and making money, [but] supporting them physically, emotionally. Um, it's like going through a sausage grinder and coming out to the other side and [people ask], "How'd you survive the sausage grinder?" I'm like, "You know, I don't know actually. I just [did]."
So it is tricky. I'm sure there are some things that, again—whether through this book or AI—can [help]. "How do you develop EQ?" but yeah, it's a feel for it. But again, by definition, this area is not easily built into a copy-paste. [00:21:00] "How do I become higher EQ? Do these three things." It just doesn't work that way. So it's, almost by definition, a frustrating exercise where you kind of know these words and [say], "Yeah, that makes sense. But like, what do I do?" Okay.
David: Yeah. And sort of coming back to what you were saying at the beginning, if people go into the corporate world wanting stability, wanting less chaos... in some ways, at least with certain parts of emotional intelligence, that's one of the harder ways to go through the sausage grinder and build some of those types of things.
And so it seems like if there are ways to challenge both our kids, people coming out of school, to try to... and again, it's a little cliché, but maybe it's even more important now to take more of those risks, to build that EQ and to try different things because those skills are in some ways more important as they go through life.
Aaron: Yeah, no, I'm thinking like... you actually go [into] doing some specifics. Like the things that we encourage—or at least I'll say I encourage—the kids to do or, if I was giving [00:22:00] advice, or what do I do for myself?
So I've kind of been focused, having to reinvent myself the last five years and how I work and how I make money. So with the kids, you know, I feel like we... they go to regular schools and there's so many different kids—like five are adopted and they're different ages. Some are working, some in college, some are younger. And so there's never really been like one school, one system that works for everybody, but they do go to regular schools. We looked at homeschooling things; it just never worked out for us.
And, but I think given that, still, if they have interests... supporting their interests, encouraging them, but not pushing. You know, sometimes pushing them, sometimes not. It's kind of like a "taste" thing. It's like: how often do you push and how often do you give them space?
I think you only develop that through practice unless you have some inherent instinct. Uh, so that's one area I think is really important because, you know, by the time they're in the workforce, a lot of the regular school skills may or may not be relevant. It's more like: "Okay, can they keep themselves organized? Do they..." I don't know. I don't even know.
But the [00:23:00] [other part] is really important as well as being confronting and difficult things and just doing them. So whether that's chores or conversations, uh, my wife's really good about that. So I think those are two things, right? So if you notice when you're avoiding something, you just do it if it needs to be done.
And the other is like: what do you wanna do? What are you interested in or excited by? And I feel like that question can be really tricky for people in their... you know, once you're out of college, twenties, thirties, forties, fifties. Uh, and so that is something I've been working on the last five years. It took me like... you know, I got out of a business divorce with a prior business partner in business.
And for a while I was like, "I know I need to do something that really fulfills me, like something I want to do, like something I enjoy doing." The activity that I enjoy—and then to make money from it.
And I had no idea what that was and it probably took me like a year or two to kind of have some different glimmers, clicks, and sparkles around. "Oh, okay. I just love books, so I want to do new books and help people do books." And you know, I [00:24:00] always like public speaking, right? So kind of like books of different types, not just sales books. Uh, I got like half a dozen I'm kind of working on—some myself, some with other people.
And then like speaking. And I'm realizing, you know, partnerships really work for me. So I have different business partnerships and not [where] we're 50/50—like someone needs to be kind of the operating person and I'm more of an amplifier. That works really well.
And then the fourth thing is crafting, and I just kind of realized this recently, but, you know, I was having fun—like actual fun—using AI to develop like custom coffee brands and like these funny—I call 'em "Banana Peel Wisdom" cards—but these like funny tarot cards almost. And um, got a typewriter here.
These physical artifacts and crafts that I'm planning on... you know, this year would be like executive gifts. Whether I send them out just for fun to friends or people I know—like my handwritten letters with wax stamps—or actual like corporate marketing.
So I got some friends, I'm doing these card decks that are funny. It's like Dilbert, but making fun of like tech. And they'll send out these decks of cards to [00:25:00] people, customers, or people they wanna have meetings with. And, you know, we say like a sense of humor is a good indicator. If they don't think it's funny, they're probably not gonna be very good to work with anyway.
So anyway, these different areas are ones that I'm really drawn to. Like I want to do these things anyway. Um, I'd fit "vibe coding" into the crafting part, but I don't really... I haven't found something I really wanna make. It's kind of fun, but I would like to do it, but I haven't found like a project I really want to do.
And so, you know, again, if you're in there, it's like really trying to, um, disassociate the ROI in your head between: "Oh, I wanna do something, but is it gonna make me money, or how's it gonna help me?" No, no, no. It's like: how can you just tune in? Like, what do you actually want to do? And take away the "if-then," right? "If I do this, then I'll get that." It's like: I just want to create books. I just want to do cards. If I didn't make money, I'd still do it in some way.
So that's, I think, a really helpful place to tune into. And again, it took me like a year or two. I was pretty burned out at that point, so it might [00:26:00] happen sooner. You might even know what they are. There's a lot in, you know... I'd be doing lists of stuff I want to do and it just, over time, it just kind of like going for walks and sleeping and just, and exercising.
So for me it was like trying to sleep, and the kids are getting a bit older at that point, so sleep is a bit better. Getting into regular exercise-ish. And then continuing to kind of think about what are these things, and that helped trigger new ideas in a bunch of areas that I'm really excited about.
And I think AI's really gonna help the stuff I'm doing. And it's not really, you know... it's like new books and speaking and into partnership stuff and these kind of cool crafts. I think it's really gonna help and I don't feel like there's a threat in my world right now because it's kind of like these things are like extensions of me and my interests.
And the way that I do them will be... even when [someone] copies them—'cause they will, they've already done that—it doesn't really bother me. It gets kind of annoying. But like, this is all stuff I have fun creating: new stuff, new book ideas. And uh, if I have good partners, so I'm not too worried.
It's led me to interesting places I could not have predicted when I just kind of let go and said, "What do I wanna do?" over and over again in five [00:27:00] years. But now I'm at the point where I kind of have these new projects and I'll make money from the new stuff this year.
And at some point, I'll make more money from these types of things I really enjoy doing—and things that I love doing—than I ever did doing sales consulting. And I made a lot of money doing sales consulting and speaking.
David: Well, I think what you're talking about is the exciting part of AI, especially for folks like you, for folks who are more entrepreneurial. It's gonna be a creativity enhancer. You know, what folks have been able to do on TikTok for content over the past five years.
People who are just creative and want to create businesses and new ideas and put things out into the world—all of a sudden you don't need all these different people to be able to just try something, play with it, do it. It's a passion project and maybe it'll turn into something, but you get to just—
Aaron: Yeah, it's fun just an idea to a mockup.
David: Yeah, and [00:28:00] so the explosion of ideas. And it's gonna unlock, I think, for people who want to be able to go on that creative journey; it's gonna be a beautiful thing. Where it will be challenging—going back to what we talked about—is those folks who do want that security, those folks who do want that structure.
Aaron: Yeah. And so the question... someone's gonna create something to... you know, there's gonna be like jobs and people. There's gonna be enough of a demand that new things will be created to create that type of—
You know, structure. It may not be as profitable for... I don't know. There's just too much demand. There'll be too much talent.
David: Yeah. Uh, yeah, I I think there's definitely something to that. I think when you increase the number of businesses that are being created, if they need a fraction of the people, that's still gonna need people. So there's more opportunities. I do think even those jobs, though, will be... I mean, if you think about our parents' jobs, or at least [00:29:00] especially our grandparents' jobs, I mean, the stability was much, much higher—at least in the corporate world—back then.
And then [it] has gone down and we're gonna see it even being probably less so, where there's more churn in different companies you work for and things like that. But you're right.
Aaron: Well, the good news the stress has gone up at least, right?
Well, that's the thing is everyone... it's like, AI lets you work [faster]. People aren't gonna work less. Most of the corporate world... it's like, you know, what was Elon—I don't know, some of the AI people—like, "Oh, you know, people aren't gonna have anything to do." I'm like, "Have you ever met a technology that didn't just create more work at the same time?" No. People will create more, there'll be more stuff created, more slop to navigate.
So I don't know how it's gonna shape up, but it's not gonna be some clean... I don't know. It'll be a lot of good stuff, a lot of bad stuff. Change and bad actors and good actors. But, um, I think there'll still be a chance, again, in the corporate style of working hard. People will still be able to do that and make money and get [00:30:00] really overwhelmed and anxious.
And to get off that, I think it's gonna take more of that conscious choice, which is: there'll be more opportunities to make money on your own terms. But to do that in a way which really feels like you and you're differentiated. I mean, I think there's gonna be a lot of opportunity to do that. One of my books later this year, I hope, is called The Grind Must Die, which would be kind of that career reinvention.
So, I don't know, it's gonna be interesting, whatever happens. And it's not... I don't see the world getting any less... um, you know, I don't see it getting more boring, which you could take that for however you wanna take that.
David: Yeah. Or both. Yeah. They say the old Chinese curse, I think—it may not be real, but it may [be]—"May you live David: in interesting times." It's true. I think that the time... I am super scared and excited for the future. At the same time, I'm super fascinated by what's gonna happen. In many ways, if I could push a button, I might stop what's gonna happen at the same time.
So it's, it is [00:31:00] it's a bizarre world that we live in.
And I look at going back to the kids. My kids look at like the eighties when I grew up [and say], "Oh, that was so different. You didn't even have phones and things like that." Their kids are gonna look at the times they grew up and be like, "That was so weird. That's so different. Like, you didn't have robots, you didn't have [whatever AI they] come up with. You had to drive your own car? What was that?" Right.
Aaron: But by the way, I will say like... it does feel like this moment for people who are kind of, let's say, our age, maybe even thirties... like, we get to experience the magic of not having AI, then having it. Because it does feel like magic. And people who grow up with it, they won't know that. They might now—they might go through the not having the Matrix and having the Matrix, their version, because you know, I feel like the technology changes will probably keep accelerating.
But it's pretty amazing to go from... if you stop and don't let yourself get caught up in the habituation. 'Cause that's what thing, that's the whole... humans habituate to whatever we get. That's why people are like, "Oh, we'll have all this free time and Universal Basic Income."
And I mean, yeah, but we're [00:32:00] still gonna be frustrated and unhappy if you... unless you work on your mindset. But it's pretty amazing. Like, it's just like magic if you stop and just really think about it and remember what it was like a couple years ago.
David: Pretty, I mean, yeah. Yeah. Um, we are... I get mad at my AI [if it] is taking too long to think now, and it's like spitting out RFPs and things like that for me, and I'm getting mad that it's taking too long. It's kind of crazy.
But um, going back, so I do wanna end with something that you talked about from your book that I think is really interesting in how we look at sales today and how sales leaders look at it, and look at the principles you espoused in your book that I actually think are more relevant today. And that's the concept of job specialization, right?
You had come up with—or at least popularized and really explained [00:33:00] very clearly to people—how specialization in sales from the SDR to the AE to Customer Success... all those things are so much more efficient when you can have specialization. And what you said at the beginning of this podcast, I think is interesting: that, all of a sudden, we can now maybe break that down even further where AI has certain jobs that it does for an SDR or an AE and whatnot, and you need to maybe further define it.
So all of a sudden you go from three or multiple [roles]. So I guess, what are your thoughts on that and how do we look at job specialization in the age of AI?
Aaron: Yeah, I mean, pretty simple. Like, and again, in Predictable Revenue and even the From Impossible to Inevitable books, the example was in the B2B world: four core roles, right? Outbound prospecting, inbound lead response, signing new customers, and account renew, uh, [00:34:00] account management or customer success. That's just more of a generalization of the idea that specialization as a principle... you might have different jobs.
I mean, if you have a soccer team (or European football), you know, you say like you've got a goalie, you've got midfield, attack, and defense, and a coach. It's the same thing. So it's not about doing the jobs "outbound, inbound, close, and renew." It's about: what are the jobs that you need to be done? You know, for your business or your function. You do it in coding (or at least used to) with backend, frontend, UI, QA, and so on. In marketing, you know.
So what are those jobs that need to be done and divide and conquer so people can do fewer things better. I think that's gonna be the same thing with AI and agents. Uh, I'm... look, I'm not a researcher professional, but I'm thinking it happens in the natural world, like with bees and ants, and there's probably some exceptions—I don't know, slime mold, maybe not.
You know, in nature there's a lot of, you know, specialization. So it conserves energy. There's that... I'm sure there's some principles in nature around specialization that would apply when people study [00:35:00] AI and when AI develops its own stuff. They'll use parallels in how AI decides to better allocate resources and specialize, but I think that's just a fundamental kind of building block.
Now, you might decide to specialize if you have, like in these days, enterprise huge customers and this and that. So one salesperson might specialize in doing everything in one company, right? So again, you have to think about [it]. It's not just the copy-paste [of] these types of jobs and you divide the jobs up. It's: what needs to happen here and how can people do fewer things better, or people and agents do fewer things better.
And I saw someone's post online yesterday: "Oh, AI's gonna kill the SDR, BDR, the junior salespeople." Like, nah, I don't know. Maybe. There's always a need for humans in the loop someplace. And I saw—I don't know if it's true—but I saw that OpenAI was hiring a Head of Sales Development. Uh, you know, so there's always gonna be companies and people that want a human touch. That's not gonna change.
David: There'll be some people that don't care, some people that want a human touch. So I [00:36:00] think there's some people who never wanna talk to a human when they buy. And there's some that'll wanna talk to a human sometimes. And there's some that wanna talk to a human a lot. That's gonna be the same in the future. I can't tell you the proportions, but so humans can be around.
Aaron: There's no job that will die, although they will evolve.
David: Well, let's end on that optimistic note. Yeah. And what I would love to do as we wrap up here, Aaron, is hit you with a few rapid-fire questions.
Aaron: Um, okay.
David: Alright. I'm gonna shoot a few questions at you and would love to get your perspective on each one. Sound okay?
Aaron: Yeah.
David: Alright. What is one thing people don't give enough value or attention to in leadership?
Aaron: You know, I talked with my Brazilian partner about this. We call it "good vibes," right? It's kind of like tuning into... whether you call it intuition or your emotional navigation for what may feel right. Uh, and not being too dependent on [00:37:00] data.
David: Not being dependent only on that. Uh, so vibe predictions or—
Aaron: Yeah. Internal emotional navigation. You know, kind of... yeah. Feeling that what's right.
David: What's one skill you advise everyone in sales to master—leaders or non-leaders?
Aaron: I think really taking off your sales hat and putting on your Sherlock Holmes slash Columbo hat. There's not enough curiosity, inquiry, discovery and it could be whether you're coaching someone you're in a deal, sales cycle.
David: Favorite business, leadership, or sales book?
Aaron: I would say, you know, probably Wooden. I read this in my early days at Salesforce.com and it was incredibly influential on my kind of management style and even my very first book. Um, but yeah, it's called Wooden, about—
David: Wooden, the UCLA basketball coach. Yeah, he's a legend. It's amazing. And [if] people have not checked that out, I definitely recommend it too. Favorite quote, mantra, or saying that inspires you as a sales leader?
Aaron: Um, you know, it's something to the effect of like, "We'll figure it out." You know, again, I know a lot of people want to [00:38:00] have clarity of the future, but a lot of times the future will be clear by figuring out step-by-step, day-by-day. So we'll just, we'll figure it out.
David: "How are we gonna do that?" "I don't know. We'll figure it out." That's a good core value. What is the most important goal or project you're working on right now?
Aaron: You know, a lot of it is taking these projects that I've done. Again, there's like books, talks, these crafts, these executive gifts, and um, it's two parts. Like finding... there'll be customers who, you know, they'll make money this year, so kind of going to market with them. But at the same time, it's still maintaining: "How can I, um, keep up my enjoyment and the fun and the excitement about working with these projects and my partners?"
David: Hmm. That's nice. Awesome. Well, Aaron, really appreciate you taking the time and chatting with us. If people wanna connect with you, learn about what you're doing, how do they find you these days?
Aaron: Probably the best place would be my Substack. You know, I'm on LinkedIn of course, um, but Substack is freshair.substack.com. [00:39:00] You know, but I'll... I'm sure I'll put stuff out on there. I'm not a regular writer, but that's, you know, or freshair.substack.com.
David: Aaron, appreciate the time. Thank you all for listening to the Sell Like a Leader podcast. Please hit me up anytime on LinkedIn too with ideas, questions, guests you want to see on the pod. And until next time, may you live in interesting times.
