Episode 45: The Best Way to Embrace AI for Your Sales Team with Ryan Staley

Hi, everyone, I'm Ben Wright, successful entrepreneur, corporate leader, and expert sales coach to some of the most talented people our amazing planet has to offer. You're listening to the Stronger Sales Team podcast where we bring together and simplify the complex world of B2B sales management to help the millions of sales managers worldwide build, motivate and keep together highly effective sales teams. Teams who grow revenue and make their businesses actual profits. Along the journey, we also provide great insights and actionable steps to managing your personal health. A happy and productive year is not only better for your teams, but everyone around you. So if you're an ambitious sales leader who wants to build the highest performing and engaged teams, stronger sales teams is right where you need to be.

Welcome back to Stronger Sales Teams, the place where we provide real world and practical advice to help you develop superpowered B2B sales teams. So today we have Ryan Staley with us and we've been having a great chat before we jumped in today around AI and what he's done. And I really like some of the cool things he's done, but certainly this epic background around building teams that succeed. So Ryan, now he's the founder and CEO of WhaleBoss. Cool name, Ryan, by the way, where he helps technology founders grow anywhere from kind of that one to $30 million ARR and beyond. And that's all through the principles he used to achieve the same thing personally. Right. So we've got someone who's actually taking what he learned and he developed himself and then applying that out to teams now around the world. So Ryan's taught over 800. 800 is a good number. CROs, VPs or leaders. And that's all around his proprietary enterprise sales framework for companies and startups such as Google, Amazon, web Services, Stripe Salesforce, and Uber. So some terrific experience, what we have in here with Ryan today. And but before we get into that, Ryan, first of all, thank you for jumping on board. Great to have you here.

Yeah, man, looking forward to it. I love working with folks, I don't want to say on the other side of the pond because that kind of shortens, like that 24 hour flight we were talking about before we jumped on. But yeah, man, I love folks from New Zealand and Australia, you know, just really great people down to earth. So happy to be on the show, man.

Thank you and we're very grateful to have you here. So tell us more about whaleboss. What do you do in Whaleboss? Why do you do it and why is it successful?

Yeah, no problem. So what happened Was it was kind of born out of, I don't know, an intrapreneur itch, if you will. So before I started the company, I was at the same organization for nine and a half years, had multiple roles where I had to grow, grow things from nothing. I started off turning around a group or an office that was very underperforming. They were only interviewed me at Starbucks and didn't interview me in the office because it was so bad, which was something that I didn't know during the interview process, but it was a really good experience. Eventually then grew a group from 0 to 30 like you mentioned in the intro, in only five and a half years with four salespeople and had to do some really original things from that. So what happened was in the pandemic they furloughed, I don't know, this was, I think March 31st of 2020, March 30th, I started to work on my own personal brand and the company that I worked for was fine with it. And then everything kind of went south with the pandemic, things starting to get shut down. They decided to furlough 75% of the company and effectively said, hey man, like you can't do that, that stuff outside of work if you wanted to still work here. And so this was what 29 March 30 brought in a deal with, I don't know, over a million dollars in profit in it. My team did and they said, okay, well we had a board meeting last night, you can't work here anymore. And so that was after nine and a half years, right. So it was a good learning experience. But I wanted to leave probably for a couple years and do my own thing and help other organizations out. So that kind of kickstarted things very aggressively, shall we put it that way? Right. And so what happened was I started working with effectively CEOs of tech companies and startups and CROs, right, or sales leaders as a byproduct and help them implement what I did to grow from that 0 to 30 million in a unique way through enterprise sales. And so that's mostly what I've been focused on. Fast forward, I don't know, about ten and a half. No, it's probably about a year ago as of right now when we're recording this, ChatGPT was introduced. I got introduced to it from a CEO of a $50 million company. Suggested I play with it or try it out with my daughter. Used the dolly with my 10 year old daughter. We're like impressed with how Easy and simple it was. Then ChatGPT came out and I used it and I tested it with one single question that took me 10 years to learn, and it got it close to 95% accurate from that one question. And so once I saw that, I was both terrified and excited at the same time. And I decided I'm going to run towards it, understand it the best I can, and help educate, you know, know my peers and people in the revenue community about it as much as possible so they don't get run over by it. So that's been my core focus over the last, I don't know, close to 10 months. Completely pivoted my business to focus exclusively on that. And so, yeah, so that's what I've been up to, man.

First thing I want to do is ask you what that one single question was, but let's do that later on because otherwise we'll get distracted. But I love that saying around running towards it, right? We can run away from the storm or we can run into it and embrace it with both hands. So for me, I look at you now and I think you are at the cutting edge of. Of AI application, right? So that is right at the front of the peloton where you are driving change and the application of AI into real world and leaders and sales jobs, right? So how did you get to that point now where you're actually one of those people driving that change of adoption?

No, it's a great question, Ben. And it was one of those situations where, like, how I got to that point is I remember, like we went to. I went on vacation earlier this year with my family. We went to Turks and Caicos, which is absolutely amazing. And I'm like, I started using it prior to that, probably in like January is when I really started, or December of 2022, started using it. And I kept seeing all these posts on social media or in the news and it was just like, this is gonna sound weird, but it's like AI porn, right? Where it was like, look at all these cool things it could do, but it had nothing to do with business, right? Like. Like this is missing something, right? Like there's like real use cases that folks can leverage in business that I've seen. And so I just started creating a lot of content around it. And in order to be able to create the content, I had to use it. So I just started using it and testing it, things that I knew to be true. And then what happened was I got to the point where I'm like, I'm Gonna commit and just spend at least an hour every day in a large language model or ChatGPT using it, right? So this was all the way back at the beginning of the year. And what started to happen was I'm like, I didn't want to get discouraged because it can get like, if you're not totally into it, there's times just like, I don't feel like doing it. You know, it's like prospecting, right? Like, I don't feel like doing it. I'm not going to deal with it. And so what happened was I started to create an AI log of, like, what I did that day or what I learned differently, and then what new ideas came as a result of it. So what started to happen is I started to stack results for myself, track the progress, and then on top of it, it helped me innovate on top of it. And so I started to do that and then started to create content to share it with other people with different use cases, and just got me deeper and deeper into it. So that's kind of how it all happened, man.

Yeah. Cool. An hour a day. It's easy to say, but it's impressive to be able to devote that amount of time to something. We all struggle, right? To find that time to exercise, to do something just for ourselves for a small period of time. So to hit an hour a day, well done. And I think you deserve to be at the front of the peloton for doing that. But today, unsurprisingly, we're actually going to talk about AI. And for me, it is absolutely still a buzzword. It's the buzzword, right? Everyone's talking about it. What does it mean for you, though, when we look at it from an opportunity lens, and particularly for sales leaders? So what's the opportunity you see out there now for sales leaders around AI?

Love that question, man. And love the focus on sales leaders, because sales leaders have one of these single hardest jobs in the world, like, if you look at it. And so, like, that's where the lens of part of where I was coming from. This as like, okay, if I'm a founder or if I'm a sales leader, how can I leverage this? It was interesting when I was doing some research, just like, on messaging, one of the things that kept popping up is I'm like. I'm like remembering as a sales leader, like, how many different types of jobs I had to do, right? And like, if you look at it, I think I mapped it out. There's close to, like, 22 different jobs you had to do as a sales leader, that would be from, like, reviewing data and understanding data at a deep level. That would be motivating your team. That would be leadership. That would be, you know, actually tangibly be able to execute to help your team, right? So all those differences, and I'm like, all right, for shits and giggles, I'm going to look it up. I'm going to see how many people have the unique skill set to do all those really, really well. And it was so funny, I actually asked AI this. I'm like, how many people have the skillset to do all these really, really well? And they're like, well, basically nobody. Because there's so many different, like, unique personalities required to do that. And so, like, I kind of look at it through that lens of like, all right, there's still gonna be three to five things that you're amazing at. Lean into that leverage AI for all the other stuff that either takes you a really long time to do it and you're just mediocre at, or you wanna bounce other ideas off of. So you could look at it from strategic thinking. You could look at it as creating a management operating system. You can create, like, for deep work. And so I created this acronym around it called Teams that I think is very simple. So it'd be time, execution, acumen, money, or skills. Those are like the five buckets you look at to kind of codify it. And what that'll do is, like, that'll walk you through, like, use cases or categories in your brain and how you can leverage it. And I could give you specific examples too, if you want me to go through that. But as a starting point, that's kind of how I look at it in terms of helping leaders with that. That makes sense.

I think the piece for me that really jumped out at me was, know what you're good at 22 jobs, more or less. I mean, you can debate the number, but if you know what you're good at, lean into that hard, right? Lean into those three to five to. If it's more. More things that you're really good at and use AI to then support the rest, right? Use it as an addendum to your skills. Does that mean that there are challenges in reverse around leaning too heavily into those areas where you're not so strong at? Or are you seeing something else from a challenge point of view for sales leaders and AI at the moment?

Harvard published a report on this. Like a paper on it. It's like there's a jagged edge to it. Right. So there's nuances of each large language model. And I look at AI through the large language model lens because that's what like 98% of AI apps are built on. So I'm like, hey, if I just understand the large language models that all these are built on the foundation, then I could basically have tens of thousands of dollars of tools for free. Right. Or for $20 a month. Right. And so that's kind of the way I look at it. So if we're going through that, and here's what I would say is, yeah, use it to support you all the things that you don't. Like. For example, I wasn't naturally born an amazing copywriter.

Right.

But now I can unlock AI to do that. For me, I was not good or proficient at creating graphics. I could do that amazing now. And that would have taken me years to learn. Right. Um, so those are examples of like, skill acquisition where you could leverage it for things you're not good at. That includes like presentation creation. The other thing, though, I do like, Ben, that is a little different than what you mentioned is I like leveraging also to multiply your strengths as well. So, for example, if you're a strategic thinker, like, that's one of my strengths. Like, if you look at like the strengths finder test, I don't know if you've done that at all, but one of mine was like, we've all done.

One of them in some form. Yeah.

All right. Is that your top five strategic thinking as well?

Like, yeah, yeah, yeah, mine's absolutely in the strategic thinking. It's one of my big ones in getting things done. One of my huge ones is. Yeah, yeah.

Okay, good. Yeah, that's really good, man. So put that up there, you know. So like, for example, one of the things I identified is like, for example, creating a go to market strategy. Right. Like, you could leverage that to accelerate and have your own personal board of directors specific with their functionality and then have it customize answer questions or problems that you're experiencing. So that's like how you could leverage it to augment strategic thinking as well, right?

Yeah, yeah, absolutely. Well, let's talk about that team's word acronym that you've developed, because I think that might expand really well on particularly around leveraging your strengths. So if you've got a moment, we'll run through what the teams.

Yeah.

What the letters mean there for you, and I'd love to know how you can apply each one.

Yeah, sure. So if we look at time, there's a lot that fall in there. But what I would look at are like, that's more the area of like, okay, an example would be like if you're a consultant, you can create a statement of work within 20 minutes. That's all the way there. That would have taken you a couple hours to before. So that's when we look at the time aspect of it, right? Execution, which is the second one that could be, or actually another one with time and execution too, is like a deep work project. So for example, I created an entire sales org in 20 minutes. And the way that I did that was through leveraging the time and the execution principle. So what I did is identified exactly like the situation, the revenue number to hit, the number of reps, the average deal size, like all the key characteristics. And then from there what I did is created a compensation plan, a management operating structure, how to evaluate people by KPI's job description, and then a tool stack for under a thousand dollars, all within less than 20 minutes. And that's something that would have taken hours and hours to do. So that's like the time and the execution piece, right? So leveraging it to do that deep work at a hyperspeed. Hey, hey. A is acumen man. So that was the one question that scared the hell out of me and then excited me at the same time that we talked about in the beginning. And effectively what I did is, you know, there's a certain level of in depth, like deep depth of understanding when you've been on 10,000 hours of anything, right? So I started testing out 10,000 hours of meetings that I've been on and how C level executives were evaluated, compensated, the challenges they had in hitting those KPIs and the emotional response. So I asked it those questions and it basically got 90, 95% of the way there with one single question. So that was the acumen. So for folks that are newer, whether you're a leader or whether you're a rep, this could give you instant acumen by asking the right questions around who you're trying to sell to or who you're trying to lead and manage and develop.

Right?

So that's another one. Money, an example of that. That's the M. So with the money, that is an example of like let's say you want to repurpose content from this podcast episode, right? In the past you used to have to take and send this out to a freelancer, have them edit all the video, put that together. Right now there's like simply that would have cost. I'M sorry, it would've cost $600 to do for whatever, eight episodes a month, but it's taken 48 hours each episode to have. Now, what you could do is you could leverage that specific function with a tool that costs $30 a month, not $600 a month. You can get it in 15 minutes versus 48 hours, and you can get a higher quality output. So that's the money aspect. And then skills. I mentioned skills earlier, and that was where, you know, I became a copywriter, a graphic designer. You can even create music now and you can create videos like. So you're hitting on all these different modalities of skills that would have taken you years to learn. And if you just leverage the right tool or the right sequence and kind of baseline tools, those walls are destroyed and you now have the ability to hyperscale your skill level. Combine that in addition, with, you have the ability now to get summarization of books within a page or two to determine even if you want to do that, but then have a conversation with that book about specific subjects that they mentioned. Do the same thing with YouTube videos. So those are a couple of different examples of how that applies to that acronym.

Yeah. And I've used that summary technique myself. Don't have time to get through a significant piece of literature, but I'm keen to really understand the major points and where I use an AI tool and you can get a great summary. So there's a couple of areas you've spoken about. Right. Leveraging your strengths, supporting your weaknesses, but also quite a broad spectrum right around how you can use AI to really drive your skills. Right. But also for those in your team. So, as leaders, how do you avoid that? I call it the doom loop. How do you avoid that doom loop of time and time and time going into learning AI and seeing what's out there? How can you short circuit that and say, right, here are some of the key things that I need to leverage with AI now without taking too much time to actually get up to speed with it.

Yeah. So it all depends on kind of your starting point, but let's assume that you haven't really leveraged it that much at all. And you've heard the hype. You've tried it once or twice, and it hasn't quite worked out. Right. I think there's a couple key elements to it. One is, like, there's ways where you can get massive jumps or starting points on it if you just know the right places to look. I publish content all the time. That's free on this just to help people. Like, you could look at any of my content on LinkedIn. There's other folks that are in the business space that have content. So what that'll do is enable you to understand what's possible first because it could be overwhelming. You feel like you're boiling the ocean. So I would say understand what's possible. Right? That's step one and step two. Just start like. And you could take, you don't have to take an hour a day like I do or did, I should say. You could literally just have like what you use Google for and try and leverage ChatGPT for. Right? Just start to like integrate it into what you're doing very simply and small. You'll start to find as you're like, wow, this is like a better, more customized version that I don't have to weed through all the ads and crap and blue links that Google has. And it's customized to what I need within leveraging an AI model that'll start to get the wheels going of what else is possible for you to do. And as long as you just keep iterating and trying it a little bit more or trying to help you in different areas, you're going to start to see a snowball effect that'll really accelerate over time.

I really like that piece of advice there. So essentially what you're saying is start somewhere, right? And that starting point is to substitute in ChatGPT from hearing this, right? Is to substitute in ChatGPT instead of Google and start to actually comprehend some of the opportunities you have with a tool like CHAT GPT. That's a great one. In fact, I'm going to do that out of this podcast today. It's something that I'm going to follow through. So if I take an alternate opinion for a moment, I heard a quote or a sentence a few weeks ago and it went something along the lines of all the information available through AI tools is a summary of everything out on the Internet. Right. It's an average of what's come out from the Internet. Which means if you're taking too much from AI, you are relying on the average content that's out there, which makes you average in what you're putting out. Right. It was an interesting thought. Whether I agree or disagree is irrelevant to it, but what I'm keen to hear is what you think about a comment like that.

Yeah, I think it's partially true. The training data is taken from scraping a large scale amount of content. I think that person who gave that quote probably didn't really know how to use it effectively. Because if you understand the unlock of asking specifically not just in terms of like, who is looking up, but the outcome you want to create, you're not going to get that generalized answer. You're not going to get an average of everything on the Internet. Right? So I think I know who you're talking about. It's like an Internet marketer, right, that said that.

Yeah, we don't say names in this podcast, but certainly, yes, a well known Internet marketer. Yeah, okay.

Yeah, yeah, I know who you're talking about. So anyways, that was positioned to sell what he was selling. So here's an example. This will get you started whether you've used it or not. But like to get like a tactical takeaway, a way to avoid that is to specifically say, like, for example, if you wanted to create a startup, right, Or a go to market, let's say a go to market function. I said act like you're Gary tan, who's the CEO of Y Combinator, right? And identify the top 10 go to market strategies for a tech startup to use and give me specific examples of companies that have implemented each one of those. Right. So like that was an example of a post I did, right. And. Or I should say a thread I did in ChatGPT. So what happened was it gave me a listing, right? It gave me those 10 listings. Might have been eight I asked for, not 10. Right. So it gave me those listings and then from there what I said is, okay, now identify. This is my disc profile, right? Like my disc profile is a high D and I have a relatively high I, which is what a lot of sales leaders are. So if you're listening, that's probably falling that bucket. You might not. I mean, just when I've looked at sheer volumes, if you don't know your disc profile, go take it. It'll take literally five minutes online, but you could leverage it, right? So then you do that and it'll say, okay, for this disc profile that I have, what's the optimal go to market strategy that I would be best to execute against with my personality? And then it'll rank from like best to worst. Which ones? Like, that's not an average of the Internet. That's like custom to you based on it, as long as you just know how to use it the right way. And so that would be my kind of response to that, if that makes sense.

Yeah. And I think what else is coming out there is it's a supporter to what you're doing rather than a driver to what you're doing. Well, one of the things we ask, I love to ask, is a really chunky piece of practical advice for sales leaders. I think you've given that already. Right. That to get out onto ChatGPT and use it instead of Google. So instead of doing that now, before we finish up, I'd love to know what was the question that you asked back when you were really forming your understanding around AI?

Well, that was the one I mentioned in the acumen aspect. So I said, okay, identify the top five KPIs that a CIO is evaluated at a company between 10 and $30 million in revenue in this vertical. Right. So once again, I was asking specifically so that I could get in the head and walk around, you know, the person that I was trying to sell to or that I would have tried to sell to. Right. So that was step one. Step two was, what are the top five challenges they have when trying to hit those KPIs? And then step three is, how did they emotionally feel when they had those challenges? And that was what was really interesting because it hit all three of those question layers really accurately because I knew those to be true from, like I said, over 10,000 hours of, like, in meeting experience. And so that's what kind of blew me away. Excited and scared me at the same time.

Yeah, yeah. So the side note there is, regardless of what questions you're asking, what a great way to do preparation as a salesperson or a sales leader that when you're going to meet with particularly prospects where you don't have that experience level or know as in depth as you might. Fantastic. Okay, well, thank you, Ryan. Very grateful to have you on board today. Absolutely. People should be checking out whaleboss so they can get to know a little bit more about you and follow you. Ryan Staley, where can they do that? Where can they follow you? Where can people get in touch with you?

Yeah, yeah, no problem, Ben. So I have a podcast called the Scale up show, if you want to listen to episodes where I share content like this. And then also, like, maybe if it's cool, we could put it in the link. But, like, I have a site where basically you get nine free AI resources and, like, cheat sheets and all those details. So that could exponentially shortcut it. And all you have to do is just trial my sales AI accelerator. Right. So basically you can get those resources for free. So we can do something like that?

Absolutely. We'll try that in the link. We need to be able to support each other in this big bad world that we live in, so we'll be more than happy to do that. Thank you, Ryan. It's been fantastic. A couple of chunky takeouts for me myself that I'm going to go and apply so I know it's a good episode when we get to that point. So thank you again. We'll check you out anywhere we can. But for everyone listening, keep living in a world of possibility and you'll be amazed by what you can achieve.

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