Episode 217: Ryan Staley – The Intersection of Sales and AI: Supercharging Success in the Digital Era

Ryan Staley  00:03

Because we’re in the tech space, or a lot of the folks that I work with are in the tech space. They focus so much on the product which is necessary and they focus so much on the process. But they forget to really focus on authentically connecting with people at a human level, multiplying that times the amount of people involved in the process, so that it’s scalable. So I would say that that’s what I think of when I get asked, like making sales social is really connecting out with them, what’s important to them, that drives them to work and what’s important for them outside of work.

Intro  00:34

Welcome to the Making Sales Social Podcast featuring the Top Voices in Sales, Marketing, and Business join Brynne Tillman and me, Bob Woods. As we each bring you the best tips and strategies. Our guests are teaching their clients so you can leverage them for your own virtual and social selling. Enjoy the show! 

Bob Woods  00:57

My guest for this episode of Making Sales Social is Ryan Staley, founder and CEO of Whale Boss, which helps Software as a Service founders and revenue leaders unlock, unleash and unify their efforts regarding their annual contract values of a very admirable goal, I think for any company. He’s also a podcaster. So be sure to catch his scale-up show series. It’s very popular lately, though, he’s been concentrating on using AI to grow businesses. And as you all may know, using AI in social selling and on LinkedIn is one of my favorite topics. 

And one of our favorite topics here at social sales like nowadays, to say that AI is starting that game-changing process and sales is the very definition of an understatement. AI is quickly becoming a game changer in the sales industry, enabling sales pros to do so many different things, but definitely including automating mundane tasks, and allowing them to really delve deep into the needs of their customers. I’m really looking forward to this conversation and exploring generative AI in my conversation today with Ryan. With that, Ryan, welcome to Making Sales Social.

Ryan Staley  02:11

What’s up, Bob? How are we doing? Hump Day, if you will.

Bob Woods  02:15

Yeah, Doing, doing good, weird, weird hump day. We’re actually recording this the day after July 4. And it’s just as it’s going to be a strange week, I think we just need to embrace that and go forward. So with that, our first traditional question on the show always is, What does Making Sales Social Mean to you, Ryan?

Ryan Staley  02:34

Yeah, no problem, I can hit that. So essentially, what that is, I think this happens, I say it all the time, with the companies that I work with, the CROs I work with. And because we’re in the tech space, or a lot of the folks that I work with, they’re in the tech space, they focus so much on the product, which is necessary, and they focus so much on the process. 

But they forget to really focus on authentically connecting with people at a human level multiplying that times the amount of people involved in the process so that it’s scalable. So I would say that’s what I think of when we get asked like Making Sales Social is really connecting out with them, what’s important to them, that drives them to work, and what’s important for them outside of work.  

Bob Woods  03:17

Yeah, Definitely a spoiler alert for everybody out there, we’re actually going to be getting into making sure that AI is social and personal. Because trust me, if you do something in AI, and you just copy and paste, or whatever it is you’re doing without putting your voice in it, everyone’s gonna know about it, but we’re gonna get into that a little bit. So let’s back up a little bit, Ryan, and just tell us a bit about your background and the journey that led you to establish Whale Boss.

Ryan Staley  03:45

Yeah, So I mean, like, I had every I don’t wanna say every but I started off and in my sales career, I started off door to door, like in college, then I did the inside sales, which is effectively an SDR grew into leadership there then went into complex sales, then went into building an organization and then eventually, kind of what led to whale boss was like, when I was starting a, what happened was I actually was a business leader grew, the manager started in office, and really was brought into upgraded because it was failing. 

And so new geographic territory got that up and running. But what happened was, I was so focused on working hard and long hours, and hitting the result that I forgot about the people. And so what happened was like, even though I was having results with my team, nobody on my team wanted to work for me, because I wasn’t really fun to work for that time, right? I’m just getting suppressed by the CEO and then at the same time, I was pressing myself and because I didn’t have the experience and I didn’t look at my life holistically led me to be just a very crappy person. 

So what happened was I got demoted and basically, they’re like, “Hey, your team doesn’t want to work for you right now, so it was a failure in leadership, if you will, from my perspective, but we want you to start this new group, and basically effectively build out our enterprise sales team.” Now, that’s not what they called it at the time. But they said, “We want you to move up market,” Right? And so long, thin, you know, that actually became a blessing because you end up growing that from zero to 30 million in ARR. 

And five and a half years was only for salespeople, we didn’t really have any marketing or any STRS. And so that led me to creating Whale Boss, because after going through that experience, I looked at my boss’s job and the CEOs job and I didn’t want to be at the company I was working for anymore. It was in the middle of COVID started my own business. And then that’s kind of how things began.

Bob Woods  05:43

Yeah, wow, that’s something, especially during COVID. I mean, you hear so many stories about companies either, either starting up like yours or like in our case a lot of our offerings really, really exploded during COVID. So it’s just, it’s just, it’s weird yet, you know, good how that type of thing happens out of adversity. So let’s branch into something that I think some people see as adversity as well. But I think that people like you and I are only seeing opportunities out of it, which I think is how it should be. 

And I believe that you would agree with that and that’s generative AI, which is shaking up the sales industry with all kinds of AI-based applications I get, I get emails and everything about it all the time, it seems like there’s at least three launching every day. So what I’d like to know is what sparked your interest specifically in AI, particularly the generative ends of things? And how are you incorporating that into what you offer your clients in terms of services? And also you’re probably seeing, you’re probably using it internally too. So that as well.

Ryan Staley  06:51

Yeah, exactly. So I think it kind of sparked my interest because this was in November of last year. So in November of 2022, I had a founder on my show, and he’s like, “Hey, have you ever heard of this program called Dolly?” And I’m like, “No, I haven’t that idea.” Which is open eyes, text to picture platform, right. And so I tried it out, like, “Wow, this is amazing.” You just type in a couple of words, and I get pictures out of it while playing with my kids. Then from there, I got switched on. I think that’s oops, shortly thereafter, Chat GPT got released. And so I started using it like right when it was released over that timeframe. 

And so that’s where that’s where the initial spark came from. And then when I used it, there were really three unique applications that I saw for it that really just blew me away. One was there are Tasks that used to take me eight hours to create that I could get done in minutes. So that was step one. Step two, whereas like if you look at long term productivity, like acumen that acquires a lot of cycles to happen, like, for example, there was there was trying to really deeply understand how C level executives were evaluated and compensated took years and years of work to truly, truly understand from business meetings, Right?

And so just by typing in the right question, I can press a decade of different meetings into a couple of minutes. That’s the second one. And then last, but not least, was really looking at the capability to automate and identify outcomes for things that I want, and then have it all done for me, right. So I would say those three layers are where I see the biggest opportunity. And so you know, that’s where I decided to start creating content heavily focused on the intersection of sales and AI. This year, this is probably back in February of 23. 

I’ve had millions of views on my post as a result of it. And then you know, what I’ve decided to do as a byproduct of that, instead of just trying to teach people how to use AI is to put it in their hands without them taking the time to learn it. And so I’m actually in the process. And I have a MVP of a tool that’s leveraged to enable those three things that I mentioned for sales and sales leadership.

Bob Woods  09:07

Yeah, That’s really cool. Because I think that when it comes to the base, not upsells, I think that that’s what you want things to do. When then, as we were talking a little bit before the call, when you bring in the social selling part, that’s when you start talking about more with it helping generating content and, parsing out and piecing up content so that people aren’t freaked out about content, especially salespeople, because salespeople are expected to sell and they’re not expected to generate content all day long. And if a tool like this can really help them get back to selling, I think that that’s huge. 

Ryan Staley  09:46

Oh, yeah. And you nailed it, Bob. I mean, the fact that like I was looking at this, this is kind of what inspired me to try and create something special for the sales community is because like, I looked it up, there’s probably like 18 different skills that you need to be successful in selling the range and all the way from persuasion, questioning organization, data analysis, copywriting, like what you just mentioned, for content, storytelling. 

I mean, there’s so many different skills. And like, We don’t have Renaissance men and women running around. And I think that’s why there’s almost, it’s probably going to be higher this year, but a 70% failure rate in terms of people hitting their annual goals in the sales community, right, because of that alone, like, nobody’s a master of 18 different skills. So I don’t know what your thoughts are on that. But that’s kind of my viewpoint on it. 

Bob Woods  10:39

Yeah. I mean, I couldn’t agree more. I do think that people are getting into and then out of sales all the time, just because they don’t have everything there. But if, but if AI can help people with some of the areas that they’re not as strong and it just, it helps them not only stay in the industry but make money for themselves and for their companies. And just helps them become better, more well-rounded people overall. 

Ryan Staley  11:07

Yeah, I totally agree. 

Bob Woods  11:08

Yeah, So why are you in the SAS sector? Do you think that not only SAS but just a sales professional in general are attracted to AI, like, I would say, “Cancer and laser pointers” So you know, they’re obsessed with them, and they’re ready to pounce at a moment’s notice? I think that a lot of people, probably higher up people in sales, but still, a lot of them are a lot of people are going this is really neat. I wonder how we can use it. Why do you think that is? 

Ryan Staley  11:39

Well, I think it’s because 55% of their job, or maybe even 65% is on non-selling activities that they don’t enjoy doing. So two-thirds of every day is on crap that they’re either not good at or don’t want to do.

Bob Woods  11:49

Right.

Ryan Staley  11:50

So if they could point something and quarterback a solution to handle that forum, I think that’s a nirvana for salespeople, because that’s one aspect too. It’s a really hard market right now. And what I’m seeing is based on data that’s coming back, and this isn’t just like subjective data, this is like tactical data. There’s probably going to be massive lows in terms of quota productivity, as well as, basically, sales executives like CROs or VPs of sales.

Staying at companies because they’re not meeting goals. Right. And so I think you mix those two in a blender, you know, 65% of things they don’t want to do aren’t good at. Plus, it’s one of the toughest markets right now with the lowest production that people are having. Those are, that’s ripe for disruption. So I think that’s why people are looking for a different solution.

Bob Woods  12:40

Yeah, definitely. And that actually flows right into my next question. So you know, putting stuff in that blender, can you share some best practices or advice for the salespeople sales team? And I would, and since you mentioned it, I would like a lump in sales leadership as well on effectively and efficiently leveraging AI for their benefits.

Ryan Staley  13:04

Yeah, definitely. So I think step one is, I have a useful cheat sheet that came out recently. It’s at AI for revenue revenue forward slash, I’m sorry, “AI for revenue.com forward slash cc.” So it’s cheat codes, right. And so basically, you just click on that, pop in your email, and you’ll get the Cheat Codes of AI for revenue and how you can leverage it and I’ll give you exact prompts on what to do and how to do it. So it’s something that’s super simple that I created to get started. So I think that a leverage tool like that doesn’t have to be mine. 

It could be anybody’s, but just get acclimated. I think that’s step one. Step two that I would look at too is literally, if you haven’t, and you’re at the beginning of a learning curve, whether you are a CRO or a sales rep or even a Customer Success account manager, whatever your role is, take an hour of your time and block an hour. And think of how you would use Google or how would you do any kind of tasks that you want to do and just try it out? In Chat GPT or being right, or barred? Right, see how it comes back? Right, Bart is better for, like real-time research and data. And then because Chat GPT just disabled their browser function.

Bob Woods  14:28

Yeah, I saw that. Yeah.

Ryan Staley  14:32

And so and then Chat GPT is better for creative writing and other areas. So just think of something that you want done in your job, take the time and try it. And then what’ll happen is your mind will continue to expand based on what’s possible for what you’re doing just from that little moment or action doesn’t mean it’ll be an hour, it could be a half hour, but that’ll get you started. So that’s what I would recommend to get started and move in. And then you know, there’s a lot of people creating content out there. I dropped a lot on LinkedIn with that.

So like workflows, like eight-hour workflows, and 20 minutes, there’s also people on other people on there or Twitter. What I would focus on though, is because there’s a lot of prompt bombing, where it’s like, leverage these 10,000 prompts, and you’ll get everything you want, right? But if you look at their background, they have no domain expertise or business expertise. So really, really try to filter through who you follow and listen to based on their, their experience and the area that you want to get better at.

Bob Woods  15:26

So yeah, absolutely. And, I think that when it comes to the prompting, and you mentioned that, I mean if you have a cheat sheet that has 10,000 prompts on it isn’t really a cheat sheet at that point.

Ryan Staley  15:39

It’s so overwhelming man. Like, yeah, by the way, so like, I looked at, I’ve gotten, I got tons of those. I’m like, Alright, I’m gonna look at this. And then I test like, I’ve probably spent over 150 hours in Chat GPT. And like, the results suck from a lot of the free prop templates. So you can tell somebody just like spammed it together, so.

Bob Woods  16:00

Do they use Chat GPT to develop? Yeah.

Ryan Staley  16:02

Yeah. They got to come up with 500 prompts, Right? Yeah.

Bob Woods  16:05

Yeah, exactly. Yeah, I mean, that’s why, one of the things, one of the things that we’re promoting, and at least as of the recording of this, it’s not quite done. I think that by the time this drops, it will be done. But you know, definitely thinking of using prompts is more of a framework. And we’ve actually developed kind of a framework with a cute acronym crisp, but really constructing each prompt and then remembering that just because you do one prompt, you’re not done, you could keep on going.

And the way I like it is that because I’m a sci-fi fan, every single time you start a chat, it’s like you’re developing a new universe. And everything gets folded into that one universe. And you can keep building and building and building from that, and then developing the story and air quotes more and more about that. And it’s just, I think that especially for salespeople, when you really start drilling down, and when it comes to discovering what a particular customer may need, what a particular company may need, what a particular title may need. All of that really comes down to how you write the prompts and how exact that those prompts are.

Ryan Staley  17:19

Yep, exactly.

Bob Woods  17:21

Yeah, definitely. Let’s go to the flip side now, with skeptics. So just like anything else in the world, there are skeptics out there. The skeptics I’m talking about specifically right now, as the ones who worry about AI’s impact on sales jobs, I see it as potentially more of an opportunity for differences, sales jobs that may not even exist right now. Or if nothing else, maybe more support for salespeople with people who have specific, especially what we were just talking about, prompt writing experience to help their salespeople out? What are your thoughts on that?

Ryan Staley  17:59

Yeah, I think there’s gonna be new jobs that are created in that aspect. I do think at the same time, though, I can see companies because I hear this, I literally just heard this from a founder. And I’m like, What’s your biggest challenge in sales and like finding the right people or executives, he’s like, all the other founders I talked to, you have the same thing. And so like, I think, what companies are going to start to do is they’re going to try and enable superhuman sellers, which is, like, kind of my vision of what’s possible. 

But at the same time, there’s gonna be a lot of people that are half and that are gonna get cut. Right? So I see new opportunities popping up that are not fully materialized yet. Right, instead of Rev ops, and might be like aI ops, Right? With enablement from that perspective. But I do see people at the bottom that are refusing to adapt, not making it right. So I could see a big trimming of folks with that, like, I’ll give you an example. Like, I see this with agencies, like for example, I was looking at how I can repurpose video content, Right? 

On this agency, they’re like, “Hey, to do all your clips from all your episodes for the month, at least 600 hours a month, Right?” Then talking to other entrepreneurs that I know and founders and are like, I came across a school called Video AI, right? So video AI isn’t really cool. That took 600 hours and 48 hours for the video clips I got. I could spend $50 a month, put this in, and get the videos back in 15 minutes, Right? 

So like that. So why I’m bringing up that example is because if there’s companies that are in Let’s even say an agency that are using that tech versus others that are still manually doing everything by hand, they’re gonna get blown out of the water and so I see the same kind of analysis or not same kind of analysis same kind of situation happening with the sales world as well for those that aren’t like leaning in and leverage it they’re gonna get left behind. Yeah,

Bob Woods  19:59

Yeah, yeah. exactly what is superhuman sales? Rep. I mean, you, you had mentioned that and I kind of went. Ooh, What is that? What is that? Exactly? Because it sounds like something that a sales rep should actually be aspiring to be like.

Ryan Staley  20:13

Well, So I’m basically my newsletter, I’ve, I have been focusing on creating, like, giving folks the ability to become superhuman by doing those things that I mentioned to be in the episode, you know, tasks that take hours and minutes, or compress decades into days or short periods of time, as well as having automation. So if you have someone like that, and that’s what my newsletters focus on, it’s called superhuman revenue, which I Oh, I love, I love the idea. 

I just like how it just rolls off the tongue, you know what I mean? So I’m superhuman. And so I’m sharing how to do that. And so think of it this way, like, what’ll happen is like, you’ll have sea-level players start to become a minus player, just because of the fact that they’ve really leaned into this. And if that happens, that means they’re going to pass the B players that aren’t, right, or B players turned into a players, a players turn a plus ramp time instead of being nine months or six months, and might be six days, Right? So it’s like, how do we really just deconstruct.

Or I should say, change and tear down and build a new opportunity of what’s possible, versus the old model that was built on a paradigm and technology decades ago? So that’s kind of what I mean by that, where, you know, it’s not just from an education, it’s from a productivity perspective, Right? Like, if you have the ability to do something, and it cuts out, two hours a day, five days a week, that’s, I mean, 10 hours is a lot. Right. And so there’s capabilities to do that. And Marc Andreessen even talked about that as about, like, where are all the super productive people because of what’s available now tools versus, when we’re kind of growing up to the sales ranks? 

Bob Woods  21:59

Yeah, definitely. So let’s kind of back away from the tech just a little bit here, and talk a little bit about the balance between all this AI stuff, which is cool. And both you and I love it, I can tell, but you still need to maintain human touch. And that’s actually one of the things that we train on here at social sales, like making sure that every, every bit of copy that gets spit out, I train on this, I do this all the time, I think it helps read it out loud. If it sounds like it’s coming from a computer, it’s going to read like it’s coming from a computer. So make sure that it’s as human as possible. So I guess just talking about in general, the balance between automation and maintaining that human touch and sales.

Ryan Staley  22:50

Yes, I think that’s really, really important. And, like, I agree with you. So it’s funny, you say that to read it out loud. That’s what my mother used to tell me all the time. When I was in grammar school, my mom was a former teacher. And so, but it works. I mean, it really, truly works. Like if you actually read it out loud, I will tell you, whether it’s fake or not. So I think you do have to be careful with automation. And I’ll give you an example of it. Like I had, so there was someone’s like, yeah, it was like a technology and it’s like automatic books, 10 appointments a day or whatever, Right? 

One of those like, “I’m gonna check this out,” see when you see what this you know what this is, right? What’s this? snake oil. And so I just signed up for a case study, Right? So within 24 hours, I got hammered with calls, texts, email, and I’m like, don’t ever I’ve liked, put them on do not just unsubscribe, do not call it like everything because it was so freaking annoying. One, so that’s what I caution people not to do. Because you’re gonna lose a customer for life. If you try to over-automate and spam the shit out of people.

So where I was kind of coming from on it is like, “Hey, there’s a lot of opportunity to if you if you offload the mundane, the things that you aren’t good at Ray for 90% of the way there and then you do the 10%, like you’re saying, then that’s going to enable you to to be exceptionally well or exponentially better than a lot of other people.” However, what you should use, this is my advice, the time and the space for is to because you’ve automated the mass pieces that you can that aren’t like spam ish, like I mentioned, it’ll give you freedom and space to be a real human with the people you’re actually selling to and connecting with them at a deep level. So that’s my two cents. You’re nodding your head. So I assume you agree on that, But that’s. 

Bob Woods  24:51

Oh, yeah. Yeah, you know, that’s actually something that I’ve I’ve kind of always felt but I’ve never really been able to like Voice it in such a succinct way. So I’m going to be going to the transcript and like writing it down. Like right next to my monitors, I’m like that because, because that’s actually perfect that, you know, using AI can help you be more human, which most people don’t really think of it like that. 

But as long as you’re going through the thought process that you just went through, it actually can help you be more human. So with that in mind, talk about social selling and LinkedIn, how do you see that kind of plus? How do you see AI Chat GPT? Whatever. Plugging into social selling and LinkedIn, just I obviously have my perspective. I’m curious about your perspective.

Ryan Staley  25:37

Well, there’s a lot of ways to leverage it. Like do you tap Leo at all? Or have you heard of tap Leo?

Bob Woods  25:42

No, that’s a new one. There’s, there’s.

Ryan Staley  25:45

So many. Yeah, it’s like a LinkedIn tool for creating LinkedIn content or helping with LinkedIn content, okay. So there’s ways to leverage tools like that or Chat GPT with it where you could for social selling, I should say, “You could customize the information or the content based on who you’re selling, or not selling, but who you’re trying to be dialed in with at a social level on social sign,” Right. So you can leverage it based on their profile, you can leverage it based on their experience. 

And so I think there’s a lot of opportunities for that. I know folks, like we talked about before the show, are leveraging comments and other areas. However, one of the things is like growing up, when I first started publishing on LinkedIn, I never knew the copywriting frameworks, right, I didn’t know when they were, they’re just like, “Ohh, just create content, do this tell a story, blah, blah,” Right. And so there’s a lot of technical components like that would take a really long time to learn and understand. 

And if you just have the core frameworks understood, you could integrate that into your content, writing, profile, all those areas. So that’s kind of where I see the opportunity with that, as of right now on day one, and then also expanding and contextualizing the content, from LinkedIn to Twitter to across the other platforms so that you can get much more reach for the same content. So that’s more like distribution systems and growth is what I was sure of.

Bob Woods  27:13

Absolutely so. So we always kind of wrap up the show with one of those one thing you can do right now, Types of things. So what is one thing that salespeople sales pros can do right now with AI that will immediately help them? I don’t know if immediate is probably the right phrase, but something that will make a big difference in how they do things when it comes to their jobs? 

Ryan Staley  27:40

Yeah. It’s a great question. And there’s, there’s a lot of different areas, you could go down for this. So I think the way I would look at it, because there’s basically every step in the sales process, there’s content, there’s so many different areas. So I think, and I’ve never really had anybody ask that question this way. But I think this is probably a good answer. Look at what you really love doing in your job, Right? Like I took a Strengths Finder test, and found out what I was really good at. And usually if you’re doing what you’re really good at, you really enjoy what you’re doing. 

Which is a flywheel that creates asymmetrical results. So look at what you really love doing, and then look at what you really hate doing and are not good at doing. Okay. And then try to leverage AI for the things you hate doing or not good at doing. Because then that’s when you get the stuff that I’ll go from like two hours to a couple of minutes. That’s probably better than the way you do it. If you spend the two hours on it, then your whole world will change because they start compounding use cases of that. But just that one spark, I can think will make a really, really big difference in terms of your overall job satisfaction and your results too.

Bob Woods  28:48

Wow. So because of all those things that you hate people tend to just probably push those off or never do them so AI could end procrastination.

Ryan Staley  28:58

Hey, good. I mean, like, I’m telling you, man, there’s a way where like one tool that you could literally create a website in like 15 minutes. Yeah, like a WordPress website. And like, that’s something that would cost five 8000 hours to do or $3000 or $2,000. To do right. So yeah, that’s amazing.

Bob Woods  29:19

That’s just amazing. So before we go, tell us a little bit about your podcast, the scale-up show and what people who listened to it can expect to gain from it.

Ryan Staley  29:30

Yeah, So I’ve been interviewing AI founders a lot lately, and where companies are, like exceptionally good, and have like, just ridiculous results and deconstructing like, how they did it, why they did it and what they’re doing to make that a reality. So I think that’s the biggest gain you’re gonna see from the show. At the same time, I mean, I’ve had I’ve had like the founder of Travelocity on I bet people that have access to LinkedIn. 

So some amazing folks to learn from. I’m Going to start incorporating more content myself because I’ve seen so much. Aggregated views in such a short period of time that I want to start sharing with the world. So I need help with those superhuman aspects, I’m gonna start doing more solo episodes as well. So that’s what you could expect from it. 

Bob Woods  30:17

Cool,  very nice. Looking forward to hearing that. So if people want to learn more about you and your offerings, just in general, including an equipment newsletter, because I think I’m going to sign up for that myself, where can they go?

Ryan Staley  30:28

Yeah, so you go to my website, www.ryanstaley.io There’s a link to click on the newsletter there. And then daily content for LinkedIn is in you know, I distribute that almost daily, I have all these cheat sheets. But if you’ll see a link in there also to subscribe for my newsletter. So you can do it on LinkedIn and my profile or on my website, www.ryanstaley.io.

Bob Woods  30:54

Very, very good. So Ryan, Staley founder, CEO of Whale Boss, and host of the scale up Show podcast and and just doing a whole bunch of things and newsletters and LinkedIn. Thanks so much for joining us today. We really appreciate your time.

Ryan Staley  31:08

Yeah, that was a blast being on the show, man. Thanks for having me on. 

Bob Woods  31:12

Oh, you’re very welcome. And thank you for streaming this episode of making sales social. So remember, when you’re out and about this week, be sure to make your sales social. 

Outro  31:18

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