Software Sales Tips by Matt Wolach

Scale Your SaaS

Can AI Boost Sales – with Ryan Staley



In this week’s episode of Scale Your SaaS, host and B2B SaaS Sales Coach Matt Wolach sat down with Ryan Staley, Founder and CEO of Whale Boss, a cutting-edge consultancy at the forefront of integrating AI for revenue teams. In this insightful discussion, Ryan shares his journey, from achieving success in sales to harnessing the power of AI to drive unprecedented growth.


Podcast: Scale Your SaaS with Matt Wolach

Episode: Episode No. 306, “Can AI Boost Sales – with Ryan Staley”

Guest: Ryan Stanley, Founder & CEO at Whale Boss

Host: Matt Wolach, a B2B SaaS Sales Coach, Entrepreneur, and Investor

Sponsored by: Leadfeeder


Embracing AI for Sales Success

The conversation began delving into AI and its potential impact on scaling SaaS businesses. Ryan reflects on his introduction to AI and how it instantly resonated with his extensive sales experience. He emphasizes the transformative power of AI, citing instances where it delivered remarkable results in terms of quality, quantity, and speed.

Promoting Professional Growth

Drawing from his climb up the corporate ladder, Ryan shares valuable advice for professionals aiming for promotions. He stresses the importance of owning your numbers, proactively seeking improvement, and understanding your boss’s evaluation criteria. Building a personal connection with superiors beyond the workplace is also critical to career advancement.

Getting Started with AI

Ryan urges SaaS leaders to embrace AI from day one in the era of exponential technological growth. He recommends starting small, incorporating AI into daily routines, and documenting use cases and ideas for future applications. By consistently experimenting and learning, businesses can unlock the immense potential that AI brings to the table.


The Dangers of Overreliance

While AI offers incredible efficiency and effectiveness, Ryan warns against overreliance without understanding the fundamentals. He highlights the risk of people neglecting core skills and becoming dependent on AI as a crutch. Ryan’s advice is to strike a balance – leverage AI for its strengths but ensure a continued focus on personal growth and skill development.

Strategic Focus on High-Value Clients

Ryan encourages SaaS leaders to gain a deep understanding of their top clients’ Annual Contract Value (ACV). Software businesses can significantly boost revenue and deal size by focusing attention and resources on the top 20% of clients.

Final Advice on the Use of AI

As the conversation ends, it’s evident that AI is not just a tool but a catalyst for unprecedented growth and transformation. Ryan’s journey serves as an inspiration for SaaS professionals looking to leverage AI, ensuring they not only survive but thrive in the rapidly evolving landscape. 


Ryan Staley

[17:37] “The more people that I can help avoid that and be able to spend more time with their family and their community and their friends… that’s a huge win for me”

[21:35] “AI is not just a tool; it’s a catalyst for unprecedented growth and transformation.”

Matt Wolach

[15:39] “Consistency over time is huge.”

[09:36] “You have an opportunity to either be victimized by that or become superhuman in the process.


To learn more about Whale Boss, visit: 

You can also find Ryan Staley on LinkedIn: 

For more about how Matt Wolach helps software companies achieve maximum growth, visit

Head over to and sign up for a 14-day (no strings attached) free trial: 


Check out the whole transcript of the episode here:

Matt Wolach  00:07

And welcome to Scale Your SaaS, thank you very much for being here. So glad that you’ve joined us. By the way, if you’re looking to do that, if you’re looking to scale your SaaS, meaning generate a bunch of leads, grow your team, close a bunch of deals, whatever it is that you want to do. That’s what we focus on on the show. So make sure that you’re subscribed. You don’t want to miss any of the amazing people that we bring on to show you how to grow your company. And one of those amazing people that can show you that that’s our guest today. His name’s Ryan Staley. Ryan, how you doing today?

Ryan Staley  00:35

Good man. Love the energy, love the flow excited to get pumped in. As I mentioned before the show, it’s good to talk to you in real life, man.

Matt Wolach  00:44

I know Ryan and I, He’s all over. you guys have probably seen him on Twitter or LinkedIn. This guy’s everywhere because he’s super smart, sharing great ideas. And we’ve communicated a lot online and kind of such as the world today. You don’t really get to chat very much. But here we are getting a chance to chat some I’m excited about it, Ryan. 

Ryan Staley  01:00

Yeah, me too, Matt. This will be a lot of fun. I know you love to nerd out on sales like myself and making businesses grow or I should say enabling businesses grow, not making them grow right that’s that sounds a little negative. But yeah, man pumped, pumped to get into a mass. Let’s get rolling. 

Matt Wolach  01:17

Super cool. Let me tell everybody who you are and what you can do. So Ryan, he’s the founder and CEO at Whale Boss and basically this guy I love his story. Ryan had his first success in business as an inside sales representative selling cutting edge technology and training to CIOs, CTOs and VPs of the largest investment banks and brokerages in the world. He finished number one nationally and was promoted to manager and then to senior manager it’s such a cool story. Whale Boss is a new cutting edge consultancy designed around providing fast results versus billable hours. Revenue Sprint’s are the new way for companies to implement scalable sales success systems fast without sacrificing ownership or control of your organization to investors. Now, he’s also the podcast hosts at The Scale Up show. So definitely go check him out there. But Ryan, thanks for coming on. So glad to have you here. 

Ryan Staley  02:07

yeah, it’ll be it’ll be fun, man. This is this will be good. So looking forward to it.

Matt Wolach  02:12

Me too. So tell me what’s been going on with you lately? 

Ryan Staley  02:15

Yeah, man. Well, I’ve been focused on AI for the last year. So it’s been like eight years of my life effectively crammed into one year, right. So here’s how it all kind of came down, Matt. When I was on when I was interviewing Chris Savage from Wistia. So he introduced me to Dolly in October of 2022. And so dolly is the image generation created by open AI, where you type in text and go to to pictures. Where if you haven’t, aren’t familiar with it. And then from there, I got introduced into really chatGPT, basically, as soon as it came out, almost in that beta mode. One of the things that like, kind of rocked me to my core, but also excited to me at the same time was I’m like, Alright, I’ve been through close to 10,000 hours and customer meetings, right, in terms of dealing with C level executives, understanding how they operate, what are the biggest challenges? How do they emotionally interact? And then how does that influence what they do on a day to day basis, how they make decisions. And so I’m like, Alright, I’m going to ask this frickin AI tool, something about that I know to be true from actually doing the damn work, right. And so when I did that, it got close to like, 95% of the way there within a couple of questions. And so that did two things, it like I said, it scared the hell out of me, because I’m like, this is going to change everything. And I even talked to my wife about it, because I’m like, this is just kind of unsettling, like how good this is. And on the other side of it, is there’s massive opportunity. So I’m like, okay, I can either run away from it, or run towards it, and help people so they don’t get blindsided like this, like I would have when I was a revenue leader. And so that’s the path I chose. And that’s what I’ve been really deeply focused on in terms of integrating AI for revenue teams, and then helping companies deploy that as well. 

Matt Wolach  04:16

I love it. So when you talk about revenue teams, and if they’re thinking, Yeah, I need to use AI, I need to make this happen. Obviously, everybody’s talking about it. What are some of the mistakes they make when they don’t have professional help like yourself? What are they doing wrong? That’s putting them in a bad situation?

Ryan Staley  04:32

They try it once or twice, get mediocre results, and then kind of write it off and don’t do it again. Right? That’s one mistake that I see. That’s very commonly Yeah, I tried it and it was okay. Nothing special. And, you know, I think it outcomes a lot because I’m a high D personality profile, right and the DISC profile. And so that I think maybe that’s why it came very easy to me because I was very prescriptive on the outcomes I wanted from it. And so it’s formulated that so that’s step one. Then step two, I think is leveraging it only for very, very limited use cases. And like writing emails or transcribing notes, like that’s the most common where people look at it. And those are a great use cases don’t get me wrong, but there’s probably 15 to 20 different levels beyond that. And like, I’ll give you a real quick example. And this is what I haven’t even shared, because like, literally, I just did this yesterday, I. So I listened to a podcast called Market against the grain. So it’s got the CMO of HubSpot and the CMO of Zapier on it right. And they were talking so like very credible people, they’re talking about their framework in terms of creating basically content that converts, right, so high converting content that HubSpot has been amazing at. And so they broke down this framework. So what I did is I’m like, Alright, I took my notes about the framework of basically creating like your product, I should say your features of all your products, or product that you have, and then creating a content strategy and a content plan around it based on each feature. So then anything you create helps the conversion rate of basically converting that. So I took their framework, applied AI with my feature set, and then basically created an entire content plan within this probably took like an hour and 45 minutes to do, if I would have done that manually. First of all, I couldn’t have done it manually, I didn’t have the skill set to do that, right. Second, if I tried to do it manually, I probably would take me like three days to do it. And I got that done in like an hour and a half. And it was. So there’s two things from it. One is the time and the speed. Number two is like the quality of giving me skills that I don’t even have yet. And taking someone’s expertise, and then personalize it for me and then giving an output that I can immediately use. So that’s like one example of how I think people kind of missed the mark on it, and just use it for very trivial use cases, if that makes sense. 

Matt Wolach  06:57

Yeah, it does. And I think that that actually resonates across all different channels that we try to use in terms of lead generation or anywhere within our sales process. Because a lot of times we start something and then we stop it too soon, a lot of times you’ll see a company or a founder or leader put something in place, and they think that it’s going to work and then they do it a couple times, just like you said and they stop. And that’s really, really bad, whether it’s cold lead generation, you do a few emails and you stop, whether it’s posting on socials, you do a few posts, nothing happens. You stop was posting on YouTube, okay, nobody’s I have no subscribers. Anything that we should be doing. A lot of times people just stopped too soon. Sounds like it’s the same with AI.

Ryan Staley  07:38

Totally agree, man. I totally agree. So let me ask you this, like, from your perspective, not to not to flip the question on the host, right? Like, what do you see is the number one thing most because like you work with a lot of SaaS founders and revenue leaders like, what what’s the number one thing, Do you think they stopped too soon? Like, when it comes to the sales process? Or sales in general? What would you what would you think is the number one thing that people stopped too soon? 

Matt Wolach  08:01

I mean, I feel like they stop SEO too soon. If you’re just saying, what’s that thing that you think there’s gonna be good that you stop, SEO. Like, oh, we’re gonna be awesome at SEO, we’re gonna create content, and it’s gonna be amazing. And then you do a few articles, and you look at your analytics and like three people visited your site, you’re like, Okay, I guess isn’t gonna work. I mean, that’s one strategy. In particular, that is definitely a long term strategy. Like, I’ve had people who are SEO experts say, don’t stop before a year, right? And that’s a big commitment. So a lot of people don’t even do it. Because they think, well, if it’s going to be a whole year, I don’t have the time, I’m going to focus on more quick lead generation strategies like outbound or something. But I would say of all of them, because I think there’s a lot of them, that would be the one I would point to. What about you? 

Ryan Staley  08:44

Yeah, that’s a good example, man. Um, you know what, like, I think there’s so many, if I had to pick the most common one, like, I’ve seen, like, technical founders, do that just with sales as a whole, right? They’re just like, oh, well, you know, we were trying to sell this customer and it’s just not working. But it’s like, they don’t understand there’s like, five things of the seven that they’re not doing, right? Like there’s, there’s such a gap. So I like what you mentioned, because that’s more of like, a grit consistency factor. More what I’m talking about, I see is just not knowing, you know, just like, that’s how valuable that knowing is right. So I think I see that. But the SEO thing definitely makes sense as well.

Matt Wolach  09:37

Yeah. And I mean, another one, I think a ton of time actually was just giving a talk to a group this morning. It’s funny that you bring this up, and they were they were asking something different, but it brought me to the same point. And I mentioned to them that most people give up on their cold outreach to soon. You know, and I said, How many touch points are in your sequence? He’s like three, like I do a couple emails on a call and if I don’t hear from him, I turned it off. I say Make it 12, 12 minimum on a touchpoint on cold, outbound and post talking to them. So post demo, I recommend 20 touch points. And it doesn’t matter if they haven’t gotten back to you at all. But I just had a client last week, tell me, holy cow, I can’t believe it. I believed you. So I followed it. And they didn’t talk to me for 18 touch points. And on the 19th one, they responded and they’re closing. And I hear that all the time. We just have to be persistent. We can’t give up. And that’s something I drive home with my clients big time.

Ryan Staley  10:29

Love that man. No, that’s very sage advice. And that’s true. Because that’s, I mean, attention is more and more valuable than ever. And so there’s less of it. And I think that consistency over time is huge. 

Matt Wolach  10:44

Yeah, I agree. So tell me with Whale Boss, how are you helping people, especially around AI? How are you helping companies? What are some of the strategies? What are some of the tactics that you’re able to help them put in place so that they can get to their goals?

Ryan Staley  10:59

Yeah, so I kind of look at it from two ways. One, I have a membership site where it’s effectively a sales AI accelerator. And iit’s turning into a go to market AI accelerator, because it’s encompassing marketing did analysis and sales and revenue areas, right. And so, effectively, what that is, is it goes from like A to Z. So literally, and if you take it and you go through the Success Path, within two hours, you can be better than 99% of people, I believe in the revenue space at it at the same time, you can prompt 95% faster. So I provide a whole prop library to do that and walk them through step by step in terms of like, how to set it up so that the AI can be customized to you like a large language model like ChatGPT, what models to use at the best time how to prompt and then how to use it and integrate it and everything that you’re doing. Right. So like, that’s one aspect. And then what I’m starting to do is also work with companies and deploy this to their teams. So if you look at Have you seen the study by it was by Ethan Moloch. Who is the professor over at Wharton. Have you ever heard of him at all?

Matt Wolach  12:04

No, I haven’t seen that. No. 

Ryan Staley  12:06

Ok, so he did a study in conjunction with BCG consulting, where they basically took 800 consultants and they had, you know, 400 leverage ChatGPT and 400 of them not right. Didn’t give many training, just they got to use a tool on one did not. So what they did is they tracked it given the same exact jobs to be done right across a consultancy project. And what they did is they found out that effectively, there’s there’s three metrics that they graded on. One was quality, one was quantity, and one was speed. Right? So if you had to guess, like, what would you what do you think the improvement in quality was? From a percentage perspective? You have any idea?

Matt Wolach  12:43

I don’t know. Maybe. I mean, I would think that a lot of people preconceived would think that AI is not quite as quality as maybe a person who put some effort into it. So but since you asked the question, I’ll say 20%. But I would think most people, if you were to guess, is AI produced content, better quality than a human actually doing it. I think most people would lean towards human right now. 

Ryan Staley  13:08

Yeah, And so it was actually a 40% improvement. Right. So then if you look at the speed to completion, it got done in 75% of the time, the people that got to use AI, and then on top of it, they got 12.2% more tasks done, right. So if you’re here, like some people are like, oh, yeah, 40% quality, yeah, that’s not bad. But if you do the math on it, just like you would like conversion metrics for like a pipeline, like that’s a 200% improvement when you stack all three of those. So this is even without training, this is without even people that that like, truly deeply understand how to use it. And that’s just surface level. So imagine what’s possible, if someone has that highly integrated and into what they’re doing. And so I’m starting to help companies deploy that, like CROs or founders deploy that to their teams. So they could basically 2-3x the output of their entire team while also shaving out, you know, it could be 10 hours a week, right? per person. So that’s, that’s like my mission, because like, one of the things I think there’s two things one is I’ve lost my job before, right? I’ve gotten either demoted or fired, right. I’ve had amazing success after that. It was like, the best success happened after like my biggest downfall, I guess, you know, so it’s kind of like a storybook approach. But one of the biggest stressors is if you don’t have a job, and you don’t have income, and you get blindsided like that. So like, I believe that this is going to happen to a lot of folks in the revenue community, in the business community, and they have an opportunity to either, you know, be victimized by that or become superhuman in the process. And so the more people that I can help avoid that and be able to spend more time with their family and their community and their friends and like, that’s a huge win for me, while also really truly spending time on the things that they love doing with their job, as opposed to the things that they have to do. 

Matt Wolach  14:58

I love that. So where does AI kind of go bad? Are there things that people are doing that make it less helpful? Are they missing the point? Are they doing something wrong around it? What do you think? 

Ryan Staley  15:14

I think it’s a good question. It’s good to always look at the, the yin and the yang, right. Everything isn’t puppy dogs and ice cream is I think Vince Vaughn said in Swingers, right.

Matt Wolach  15:23

Was one of my favorite movies, by the way. Amazing. You just called that.

Matt Wolach  15:55

things that we might do wrong, that might make us not as strong.

Ryan Staley  15:59

So here’s what I would say is like, and you know, I’ll give a real world example of it. And I think this is a danger that many people can run into, like, it’s so easy to use. And once you understand it, it’s like bringing a like a gun to a knife fight, right? Like, you could just plow through things really easy and quickly. And but what I what I see happening, it’s funny, somebody brought this up in a post, I saw this, my son did his science project on AI, right. But there’s the risk that because people see it so easy. They don’t take the time to think about basic things. And they just delegate it to the AI and what’s going to happen is like, they’re not going to learn fundamental skills to grow and develop, because they don’t understand the core concepts, right. So that’s one of the things I think you’ve got to be careful of, especially with, with younger kids, or younger people in their career of just like going the whole AI route, and not truly taking the time to really understand what needs to be understood to be an expert in a field.

Matt Wolach  17:02

I love that. I think that makes a lot of sense. Because if you don’t want it to become a crutch, such that you just you have to have that you don’t have a way, like you said to grow and learn and become an expert. I think that’s amazing advice. And speaking of grow, I want to talk about your career, because you came in sales job, you’re you know, entry level, and then you just crush it and you rose up the ranks, you got better, you rose, you got better you rose, you kept getting promoted. I love that story, it obviously was probably a lot of work for you, but also a lot of fun looking back, what advice can you give to others who are looking to learn to grow to improve and and be promoted through an organization? What can you share with them?

Ryan Staley  17:46

Yeah, no, it’s a really good question. Because I had a guest on my podcast, David Ferrell, whose was like an RVP at namely, and I’m friends with them. And we talked about this exact subject. And at the same time, I presented for sales assembly for a group of folks for their certification on how to do this. So it’s something that I haven’t thought about in a long time, but for some reason, it’s come up like this is the third time it’s come up in the last 30 days. Yeah, it’s awesome. It’s awesome to talk about. So here’s what I would say is like, the the thing to get promoted is number one is like, find a way to create results. Like that’s the simplest way in revenue orgs. Now, what I would say, though, outside of that is there’s a really unique opportunity. I’ll give you an example of a use case, I broke this down for, like, 30 people in the training I did it for and basically, you know, most companies have like a pipeline review meeting, right? So if they’re in a sales role, they have a pipeline review meeting. And that’s usually like an hour with your manager, where you go through your pipeline, what’s coming down, you know, what’s next? What’s happening, how you’re gonna make those deals happen. You talk about strategy, usually talking about personal development. So here’s, here’s kind of the framework that I gave is one, like, own your numbers, and be proactive with the opportunities for improvement you need to take to get the results you want, whether they’re, if you’re hitting your results, getting to the next level or two levels beyond that. That’s step one. So that alone will separate you versus 99% of people because most of the time, from what I’ve seen, they don’t show up prepared. Sales Reps don’t show up, always prepared and they don’t truly own their numbers and know what they need to do. That’s step one. Step two, then is asking that revenue leader that you worked for, of like, where are your blind spots, you know, like, this is what I’m doing, just call me out, like help me understand in terms of developing where my blind spots so I would say that’s number two. And then number three, and this is very basic, but most people miss it is truly understand the pressures and how your boss is evaluated. So you could support that and then also connect with them as a real human on what’s important outside their life. So then they become, you know, you become one of their favorites, right? And here’s what I would say is like, this isn’t about being a teacher’s pet or anything like that. However, I can’t tell you how many times Matt, you’ve probably seen this as well, where, you know, basically a CRO or a VP or someone that you report two, you know, gets promoted, and then they get promoted out of the company. And then they bring people in, that used to work for him for really sweet opportunities that, you know, I just thought with somebody at openAI, right, like I was talking to go to market lead there. And he basically said, Hey, I worked for this woman before, she was awesome. She loved me. And she brought me on at open AI and he he left Gartner and wouldn’t have the opportunity to do that. So that’s not just a job, you just show up and get right. So like stuff like that happens as a byproduct. So those are the three steps that I would take for getting promoted. 

Matt Wolach  20:52

I love it. Amazing. And as I look back on my career, as I look at other friends who have gone through similar processes, or or, I guess, achievements like you have, I’ve seen a similar story. So I think that’s amazing advice. And as we wrap up here, Ryan, what other advice can you share? If you’re a software leader, you’re saying, Okay, I want to grow, I want to scale I want to be able to use AI, what advice can you give to those leaders? 

Ryan Staley  21:17

Yeah, so one of my favorite things, and I wrote a post about this that did really well, I was speaking at a SaaS Event for SaaS executives, it was lakas event last year. And I asked the question, I said, there’s probably about, I don’t know, 45-47 people in the room. And I asked the question of how many people here know what the ACV, or the annual contract value average is of the top 20% of their clients? Right? And literally only two out of the 47 people knew the answer that question. And the opportunity there is if you truly understand that, what you will be able to do is you can basically have like a separate ICP, and then a PCP, I call it the perfect customer profile, right. And basically, just like you would investments, you allocate a certain amount of attention, resources, and focus on that top 20%. So that you can multiply those clients because typically the top 20% equals 80% of your revenue, you will do that we did that and two extra deal size every single year for five years straight. Also, like basically 100x, our largest deal size, right without any people without any resources, anything just literally that like level of determination of focus. So that’s one and then when it comes to AI, what I would say is like, the simplest way is this is the most transformative technology that we’ve ever had. And reason being is because t’s on an exponential curve, that’s changing so fast, that there’s going to be massive opportunity as a byproduct of that. And so what I would say is, if you haven’t started using it, start day one, literally, instead of using Google for a question, go to ChatGPT start using that even if it’s only 15 minutes a day. And here’s the other part that nobody does. But it’s like the most amazing thing that that happened to me is write down what use case you used it for and what idea you have for another use case, just do it on an Excel spreadsheet, Google Sheet, whatever. Like I have ideas and ideas that were created off of that, that created mind shattering results just by like trying it and documenting, trying and documenting. And so if you do those two things, before you know it, you will be amazing. Obviously, I have lots of information and content on it too. But that’s one way where you can you know, your own self operating system and do it. So those are those are two recommendations. 

Matt Wolach  23:41

I love it. Great recommendations, very actionable as well. This has been fantastic. Ryan, I really appreciate you coming on and sharing all of your wisdom with us. How can people learn more about you and Whale Boss? 

Ryan Staley  23:51

Yeah man. Thanks, Matt. It’s been a blast having me on. So I would say there’s there’s two things. You know, one is literally if you want to get in touch with me, on my website, there’s I even have my email on the website where you can connect me it’s At the same time, too. I have a I should say, on LinkedIn, I post tons of content, you know, DM me on there with a connection request. If you haven’t say you heard me on, Matt show and you know, just engage with me there. That’s super easy, because I post tons of content daily, just like Matt does. 

Matt Wolach  24:26

Perfect. And we’ll link to all that in the show notes. So if you’re listening, if you’re watching, go ahead and grab those there. But Ryan, thanks so much for coming on the show. This has been fantastic.

Ryan Staley  24:34

Yeah, it was a blast. Thanks for having me on. I really appreciate it.

Matt Wolach  24:37

Absolutely. And thank you all for being here. Really appreciate it. Make sure that if you like this, if you thought Ryan was really helpful, submit us a review. I want to see those reviews because it’s helping us understand how we can craft more great content for you. And then also other people will see that this is something that can help them so I really appreciate when you do that. And thank you for being here and we’ll see you next time. Take care.