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Using AI to Scale Successfully

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[0:00] It's an amazing tool to be like a strategic advisor to you because like that's what you get paid on is creating results and solving the hard problems.
So now you could leverage the best minds in the world to help co-author and solve those biggest problems that you have.
Welcome to the Full Funnel Freedom podcast. If you are listening to this,

[0:23] you are likely leading a team responsible for generating revenue.
Purpose of Full Funnel Freedom is to support people like yourself and keep your funnels consistently, reliably full.

[0:36] Welcome to the Full Funnel Freedom Podcast. I'm your host, Hamish Knox.
Today, I am really excited to have Ryan Staley from WhaleBoss as my guest to talk about AI and sales leadership.
So, Ryan is the founder and CEO of WhaleBoss, where he helps technology founders grow from $1 million to $30 million through the principles he used to achieve

[0:56] the same results personally.
Ryan has He has taught over 800 CROs, VPs, or leaders his proprietary enterprise sales frameworks for startups and companies like Google, Amazon Web Services, Stripe, Salesforce, Uber, and other companies you might have heard of. Ryan, welcome to Full Funnel Freedom.

[1:14] Thanks, man. Happy to be on here. This will be a lot of fun, dude. I love to nerd out on AI and sales leadership.
It's some of the funnest topics to talk about.
Amazing. Well, before we get to that, I've given the audience the 30,000-foot

[1:27] view, a little bit of a teaser about who Ryan is.
Tell us your story. How did you get from where you were to where you are today?
Yeah, it's not a problem.
Probably similar path to a lot of people listening in the sales leadership role. Maybe, maybe not.
I started off as I had a couple of shit sandwich jobs, if you will, to start, right?
Where effectively I did the door to door when I was in college.
And then I was, well, I guess the predecessor to predictable revenue SDR, where I would make $250 a day, try and one call close people, right?
That was foundational for me, did mid-market and then enterprise sales, and then moved into leadership, turned around an underperforming office, and then was tasked to say, to grow a enterprise group. And they're like, hey, we want to move up market. I'm like, awesome.
Like, what's my team? They're like, you don't have one. I'm like, okay, cool. What's the go-to-market playbook or strategy? Like, we don't have one. Go figure it out, right?
So always work for companies that were resource constrained.
And it was always like a go figure it out type approach. And so grew that from zero to 30 million in ARR in about five and a half years with only four salespeople.

[2:31] Had no SDRs or marketing really effectively. So did some really unique things to make that happen.
And so for about three and a half years, maybe two and a half years, I was really focused on applying those principles and helping tech startups

[2:45] apply those to their business.
And so what happened, though, about 14 months, no, it was about 15 months ago now, I guest on my podcast called The Scale-Up Show.

[2:55] Basically, the founder of Wistia, a guy named Chris Savage, is like, Hey, Ryan. He's like, have you tried Dali yet?
And I'm like, no, I haven't tried Dali. And this is like when Dali first came out.
You tried it. And I was like, OK, this is kind of cool. You know, it's got potential. But I wasn't blown away. Right.
And then what happened was Chachi Beauty got released and I was on the early, early list for that.
And so I started using it almost instantly. And one of the things that was kind of a trend on social was people are like, hey, let's see how good this is and

[3:21] test it off things that I know to be true or my job.
So I did that. And I was both scared and like like petrified and excited at the same time because I asked it a couple of questions.
Questions and it basically gave me 95%. It got me 95% of the way there, 90, 95% of the way there with just a couple of questions.
And so I'm like, this is going to change everything. And when I was in sales leadership, I spent so much time just trying to hit my number and support my team.

[3:51] So I didn't have any time to focus on outside areas like AI.
And so I'm like, hey, this is going to be a big gap. If I could bring this to the community and then combine my background and in sales and sales leadership and then integrate AI into it, people will be able to carve out 10, 20 hours a week while just doing things that they never thought were possible.
And so that's really what I'm focused on now, my big core mission to help the revenue community, if that makes sense. I love it. Very, very cool story.
And I appreciate you sharing that when you first dug in the chat GPT, you're like, hey, wait a second.

[4:24] This is kind of scary. And I also like how you said it got you 95% of the way there, because that's one of the things that I've I've discovered in my use of AI is it's great for getting us 80 to 95% of the way there.
And there's whatever is left over, 5 to 20%, that's the human stuff.
That's where we have to apply our knowledge and our background.
So, Ryan, for the sales leaders who are listening out there who, let's make it stupid simple at first.
No, we'll get to accelerate into the cool stuff. Mm-hmm.
Where would you recommend a sales leader who's probably like you, like you said, trying to hit their number, trying to support their team, don't have a heck of a lot of time, but they're like, hey, this is kind of cool.
I can't hire Ryan yet. I'd like to, but I'd really like to get at least started

[5:08] so I don't waste a bunch of his time with the beginning stuff.
Where would you recommend they at least get their feet wet so when they do engage with you, they at least have a baseline knowledge so you don't have to start from zero?

[5:19] Yeah, that's a great question. And so probably of the new SaaS products or AI products that are created, probably 90 to 95% of them are all created on top of the large language models, right?
Or as a byproduct or they're integrated, right?
So my core belief is that if you understand how to use the large language models, then you could arbitrage the need to buy thousands of dollars a month in solutions while at the same time, usually having better outputs than some of the solutions.
Now, Grant, don't get me wrong.
There's a lot of really good niche solutions out there that are just easier than using the app alone as a standalone.
But as a core basis, that's how I would use it. And so what I would do is I would pick one tool, either ChatGPT, Microsoft Copilot, or Google Gemini.
If you have Workspace, I would use Gemini.
If you have basically Office 365, I would use ChatGPT or Copilot because Copilot would be integrated right in there.
And this just happened, right? So that'll make everything easier.
So that's step one is pick a tool. Step two is what I would say is if you are basically using Google, which everybody basically is on a day-to-day basis.

[6:37] Take instead of using Google, try and use one of those tools for what you would use Google for, right?
Now, that's really, really simple. And anybody can do it. They do it every day anyways.
And just basically see what happens from there.
Now, here's a little hack for you, too. Outside of those tools I mentioned, there's one tool that has the potential to replace Google, in my opinion.
It's called Perplexity AI.
It's so good and so fast at research. If you're looking at just core real-time research, that's a tool that I would recommend for that.
So basically pick a tool.

[7:12] Then basically replace a job to be done that you would do with Google with the tool.
And then step three, here's the part that nobody does. does, but like I've gotten the biggest gains from it, which blows my mind is.

[7:28] I like to journal. I'm into personal development and biohacking and all that stuff, right?
Well, I don't even know what they call biohacking anymore, but basically caring for myself as I get older. So my body doesn't give a shit and I can still perform.
So effectively, the real, real simple thing you could do is write, like have, I have a basically like a AI log.
So what I'll do is I'll write down what I use AI for, what are new ideas I have from it, and then I'll just keep rinsing and repeating.
And what happens is it becomes a flywheel of how you can continue to integrate this into everything that you do. Very simply, it costs nothing.
And just by like taking literally two minutes to say, hey, I used it for this today. What can I use it for tomorrow? And then the ideas will just flow.
Super simple. I like that. Now you're doing that in like a journal or something.
You're not doing that in an AI tool.

[8:16] No, I'm actually just using Google Sheets for that. Oh, cool. Right? Right.
And I'll, what I'll do is that you can post the link of what you did in the AI chat. So if you want to go reference it later, you can go back in there. Right.
And then if it's good, then I'll record a prompt and I have a prompt library so that I could stay organized with the good workflows that I use.
And I mean, truth be told, that's why I created like a membership so that go-to-market professionals could leverage it.
It's like literally less than a hundred bucks a a month, super simple, has all these details.
So you can go from zero to like top 1% just by spending, you know, four hours in it.
So it's like an hour a week and you will be way faster and way better than everybody else.
That is, that is incredible. And we'll certainly make sure to put a link or something like that in the show notes. So everyone could take advantage of that, that group.
So, all right, so we've got the baseline, got it, pick a tool, you know, use it, you know, use what you would use a search engine for is,

[9:12] you know, as you said, most people are are using Google.
So something else that I have, I have heard about from lots of people I know who use AI, like, you know, as an assistant, right, is their, their second hand is about questions and asking really good questions.
So from your experience, what are some of those questions that sales leaders might not even think to ask an AI tool to get them a bit further ahead, that, that the listeners might appreciate knowing about?

[9:41] Yeah, it's a great question. And so here's, I was thinking about this the other day.
And I'm like, one of the core things is because this is such a change to anything that's ever happened to us in our lifetime, because of the infinite amount of capabilities that it has.
It's like, I've been thinking about it and trying to create frameworks around people wrapping their mind around it, because that's the biggest barrier right now.
It's not the cost, like you can use it for free, right? Or $20 a month or so, like, kind of how I look at it is there's three stages to it.
There's there's basically assimilation and that's kind of just starting to use it like what i mentioned right there with just core elements it can even be with like writing emails or condensing transcriptions in a follow-up email like people are starting to use that um so assimilation is phase one phase two is integration and that's really connecting different like processes or tactical tools that you use it's stringing them together with ai so that basically you're doing batches of work that's done, that starts to get more like the Jarvis level, obviously from Ironman, but not at that level of sophistication.
And then the third one is like innovation, right? So that's like how you can innovate and be an entrepreneur, an entrepreneur within your organization and create basically new AI workflows, reverse engineer prompts and frameworks and things like that and do really amazing things with it. So those are kind of like the three stages.

[11:05] What I think most sales leaders are not using it for, to circle back to your question, it's really, I think most of them are stuck at phase one, right? That first level.

[11:15] And they're like, yeah, I help it write emails. I help it do this.
Whereas it's an amazing tool to be a strategic advisor to you because that's what you get paid on is creating results and solving the hard problems.
So now you could leverage the best minds in the world to help co-author and solve those biggest problems that you have.
I'll give you an example. I did this the other day. So let's say example, I wanted to create a tech startup right now. I wanted to create it.
I could literally say, I want you to act like Gary Tan, who is the president of Y Combinator.
And I want you to give me the top 10 most successful go-to-market strategies that leaders have used that have created unicorns over the last five years.

[11:56] Rank them in terms of the most successful, the least successful, right? Boom. It'll do that and give you examples.
Then you could say, okay, my personality is I'm a high D profile personality, right? right? Like most sales leaders are.
And this is my background. I've been in sales leadership for five years. I've done X, Y, Z.
Now recustomize that list on which best work with my strengths.
So if I want to create a business, I know what I am like built to create as of right now. And then it'll do that, right?
And then, so basically you can keep going deeper on that. And that's something

[12:29] like, you know how much like time and research you would need to do that.
And then it wouldn't even be customized to you. It would just be general shit, right? Right.

[12:37] So that's one one example another example is if if you're doing a process uh let's say internally you're building a new team or you want to do customer segmentation or customer segmentation you could you could if you have a team's account uh which is protected like it doesn't train on your data for chat gbt you can literally drop a customer csv in there have it analyze it trend it and look at hidden in opportunities that you're not seeing to go after to increase your deal size. Right. Like that's one example.
Another example is, you know, if I wanted to create a whole another team, you could go in there and create go from start to finish of like, this is the outcome I want. This is the comp plan.
I want you to help build. I want you to help build a management API structure.
I want you to build a meeting structure. I want you to build a job description.
And I want you to build the tech stack for under a thousand dollars.
And it can do all that in like 15, 20 minutes. Wow.

[13:35] So those are examples where people are not really using it. And that's more level two.
Level three is probably better for another day because that's really advanced.
But that's kind of where I would say is level two that most people are not using it at yet.

[13:49] And just as you're talking about that, I'm thinking about like the leaders that we support and how the things that they come to us and ask for.
And I know I've used other tools, like when leaders have come and said like, hey, what should we pay this role?
We're looking to hire an account manager or whatever. And there's tools out there that I leverage and I may sound really smart and I tell them what I'm

[14:10] using so they don't think that I'm some kind of genius because I don't want that pressure.
And also as you're sharing this it's like what is our ultimate mountaintop our ultimate mountaintops hit the number fair and so what can we do to accelerate getting to that mountaintop well all the things that you just laid out and especially if you're at that beginning stages and you're looking to start and scale then you've got this great tool to actually get you 95 percent of the way and then the five percent is your implementation so ryan as we are building these things up so let's say that we get a sales leader uh who's listening to this and goes absolutely i'm all in let's do this and they start building out these processes things like that i don't want to go to level three because that's advanced we'll have you back sometime in the future to talk about the advanced stuff so how do they actually put this into the real world because it's all great when it's on a piece of paper or on a chat GPT screen.

[15:06] What's the human side? What's that implementation side that actually makes all this awesome, cool process and data run and scale?
So there's a couple of different ways to do it. So I think step one is like the leader has to understand what's possible and how to use it because they can't lead their team on having them do it if they're in the dark, right?

[15:29] It's like the equivalent of like, Like, and I don't know how many of you have had this happen, but you have a leader in your business that has never done what your job is, doesn't understand your job, what you're expected to do.
Let's say you're a rep and you have a sales leader who's never done what you've done, has no idea how to sell.
And then they'll be like, you should do this, right? Like, it's the same thing.
And there's a lot missing. So you've got a one lead by example.
Two, once you're done with that, I think you need to create an environment where you're your team can thrive and have the space to use this.
So how I would do that is there's a couple of ways. One, you've got to give them the capability to create a prompt library.
And so right now, a prompt library is the foundational AI workflows with how companies operate.
That could be a notion. Some people do that. I have other tools that I use, which are basically you type in one word and it could build out like a 50-word prompt.

[16:22] So there's capabilities like that. And then what you do is you start off and you give your team some examples of prompts that they could use, have this in the meeting, show them what's possible, and then expect them to go over the next week, spend a couple hours, and identify the three best ways that they can make their job better by using AI, right?
Whether it's shortening the time, giving them a higher quality result, or doing it faster, right?
And then what you do in your next team meeting, the following week, is you have each of them present what they found, what they learned, what was hard, what was good, all that kind of stuff, right?
Then you upvote the top workflow use cases and make that a standard for your team to leverage moving forward, right?
You keep doing that process, you can keep iterating on top of it.
And before you know it, you have a self-scaling organization that's working two to three acts faster than every other company in the space.

[17:16] And it'll just get you amazing results as well.
Phenomenal. As you were sharing that, that word was iterate that was coming

[17:22] to my mind is like, if we start this and we build and build and build and build on it.
So Ryan, I'm not interested in the whole, like, is AI going to replace us?
Because quite frankly, that doesn't interest me. And I don't believe it's going to happen that we've been having that conversation since we invented the weaving loom way back when.
What I am curious about is linear thinking, because, you know, we have these, you know, the stories of people driving off cliffs, because they're just following their gps and all that stuff so when you have a sales leader who gets really into this but then they just say well the ai says that i should blah blah blah how do you coach your clients to think about you know it's not the whole answer it's most of the answer so how do you encourage leaders to not just copy paste repeat whatever the ai spits out but to actually critically think on it and make adjustments before they go rule it out.

[18:14] Yeah that's a good question i think um like i think you just give real world examples of where things have gone terribly wrong right where people have done that like you saw that where i don't know maybe you've heard of it maybe you didn't but it happened in legal where someone did that, with uh the research for their use cases and then it got called out that it was like completely fictitious right because these systems are not perfect and

[18:38] they're not built to be right they're built to follow a pattern of words.
And so by that nature, it's not always going to be correct. And so you have to go with that assumption.
And so I think, and this is what like, so my kids, I've been educating my kids on how to use it. My son did a science project on it.
Awesome. One of the things I said to him was like, I'm like, Hey man, this is a great tool to use.
However, like it's not always perfect. And you, you could look terrible if you don't just double check this and basically refine it and you will sound like a robot.
And so that definitely helps, but you gotta set the expectation with the team that that's gonna happen.
And like you said, that it's not gonna do everything for you in this situation.
It's only gonna get you 90% of the way there.
Fair enough. I'm now hearing my former math teachers yelling at me to check my work as you were sharing that.
So thank you for that triggering event, Ryan. Appreciate that.

[19:33] So I could nerd out about this stuff all day with you and clearly you can't because i've i've seen some of your stuff on online and by the way if you're not following ryan go follow ryan because his stuff is really really cool um and i learn a ton from it every time i check it out i have a few questions uh to wrap up today and certainly would love to have you back and dive deeper into this topic in the future because it is evolving all the time the first question, If you could go back and coach younger Ryan, right? Go back as far as you like, and you can say, hey, younger Ryan, in the future, you're going to have this amazing company, WhaleBoss.
You're going to be cutting edge AI, helping sales leaders.
You're also going to have a bunch of scar tissue and bumps and bruises.
What would you coach younger Ryan to say or do differently to get to the same spot, but with fewer bumps and bruises and maybe a little less scar tissue?
And it's funny because I was thinking about this the other day, right? So I'm three and a half years into having my own company,

[20:24] and there's some stuff I've done great.
There's some stuff I've done wrong. on. I think what I would say is that the number one thing, if you want to build a company or a team or an org is really focused on creating systems every week.

[20:39] And it's either, it's a combination of creation and optimization every single time.
Right. And so like that could be for something as simple as the core outreach messaging that you have and the enablement material design behind it and like all those details right or like with ai systems and i'm this is why i've been so focused on it is like i'll give you an example of why this is important, literally there's a process that i was saying i need to do this you know uh there's a lot of speaking i'm doing to create content as a byproduct of it right and i would go in i would adjust it and do this so the other day i'm like you know what i'm not going to quit half-assing it I spent two hours, built out a system with prompts and everything.
And now, like, literally, I've invested two hours, and I probably gave myself back 40 to 50 hours over the next three months because of that, right?
And so if you do that, the only way to create a sustainable business or org is to have that compounding effect of systems that are repeatable that work well.
Love it. Great advice. Huge fan of systems myself.
And, yeah, iterate on them. Don't just say, set it and forget it.
Like we always got to be building on them.

[21:53] Ryan, curious what you might have read, watched, listened to in your career, whether recently or in the past that you would recommend that the audience check out aside from your own content to further their own growth and development

[22:06] in this area of AI. Yeah. Yeah.
Well, I got, I got two, I got two for you. One is called the gap in the game.
It's like the achievers formula for success and happiness.
Right. So that's one of my favorite books. And one of the most gifted books that I give people just because it's, it helps you with how fast things are changing, focus on progress, not the destination.
And so that's one. And then the second one, and literally here's the way you could leverage this for free.
I use the chat GPT app while I was shaving the other day.
And i wanted i was looking more into systems so i asked it to give me use pareto's principle give me a two-page summary of the e-myth revisited basically the e-myth revisited is heavily focused on systems system design it created that then i said okay this is my business this is what i do and who i serve i want you to now customize it based on that right then it customized it then i said okay i would now want you to create an execution cheat sheet for me on these two items systems so that I could execute what you just recommended.
Please create these now. And by the time I was done shaving, I had all that built out.
It was all in written form. And all I did is talk to it. Right.
So that's something really simple that you could do if you're looking at system design or any other book.

[23:22] Not all the newest ones are probably on there, but really, really good trick to do it. And you could just talk verbally, which most people are really good at.
Very true. Awesome. Thank you for those recommendations. So Ryan, last question for you.
You've given us great ideas and insight on how sales leaders can implement AI, not only for themselves, but for their teams to successfully scale.
What else do you have as a final bit of wisdom, a closing thought,

[23:46] or maybe even something to plug? The floor is yours.
Here's what I would say. There's kind of two things. One is like.

[23:53] I missed on opportunities as a leader because I was always saying like, it's not a priority. I would get to them later. I'm too busy, whatever. This is like one of the few life-changing priorities that I stopped everything in my business and pivoted.
Um, because it's, it's, there's going to be winners and losers in my opinion, uh, big time.
And so you can be on the winner's side if you jump on it now.
And you know, if you want to hear more or see what I'm doing, um, my website is
You could, you could check things out there. I have a lot of content on there and things like that. In addition, just email me if you're a sales leader and you're looking to do this for yourself or for your team.
It's Ryan at
And just reach out to me. Tell them, mention that you heard me on this podcast with Amish, and then we'll take it from there, man.
Awesome. Thank you, Ryan. And we will certainly link to your website in the show notes. We will not, for spam-related reasons, link to your email address.
But I hope all of you made note of it. or if you didn't, rewind a couple of seconds and get that email address from Ryan. Mentioned you heard him on Full Funnel Freedom.

[25:01] Ryan, I've had a blast chatting with you today in our previous conversations.
Thank you for being a guest on Full Funnel Freedom. Thanks for having me on, man. This is a lot of fun.

[25:11] Sales leaders, I learned a ton from Ryan on the podcast today.
I am really excited about this whole world of AI. And also, you know my passion is that more effective human-to-human interactions and.

[25:25] We can use AI as an accelerant to have more time to have those more effective human-to-human interactions and more time to support our team, whether it's in the field or in role play or whatever that might be, because we have these technology tools available that are getting us that 80 to 95% of the way with the stuff that used to take us hours and hours.
And as Ryan shared, he managed to get an entire summary of a really amazing book customized to his business while he was shaving.
And I love the fact that he did it while he was talking because that's my brain hasn't got there quite yet.
I still like to type things, although I can totally see how speaking out your

[26:09] commands to an AI would work really, really well.
A few things that I took away that I wanted to highlight for you.
I'm really excited to hear what your takeaways were in the comments on our social media. So, number one, this idea of just pick a tool.
Like, there are tons of tools out there, and just pick one.
Now, I use a tool called Poe, which actually combines all of the major ones.
So, it's got GPT-4, it's got Dally, it's got all these cool things in there.
I don't know if it's just because I like to have all the toys or not.

[26:40] And so, that's my one that I use is Poe. I love Ryan's suggestion, like, pick a tool, whatever you might use.
And that insight of use AI, replace your Googling with AI-ing, for lack of a better term, and see how that can develop out for you.
The next thing I took away from Ryan was really leveraging this idea of systems.

[27:05] Really, really helping getting AI to help you build systems, implement systems with your team and then iterate on those systems using your team's own data.

[27:15] Right. Make them the heroes in the story. And they're much more likely to leverage whatever you have implemented.

[27:21] And the last thing and it came right at the end.
And it's this idea of check your work. You know, AI is great and we've got plenty of stories out there about how things were fictitious or things were, names were replaced or images that were created did not represent the historical accuracy of what the user was looking for.
So for both us and for our sellers, when we are using AI.

[27:53] We definitely want to be checking our work and not just going copy, paste, implement that linear thinking that ends up being really, really damaging for us.
Thanks for listening. Again, let us know what your big takeaways were on our social media.
Until we connect on the next episode, go create full funnel freedom.
Thanks for listening to today's episode of the Full Funnel Freedom Podcast.
You can continue to support us by leaving us a review and a rating, sharing this episode with a couple of sales leaders in your network who you care about.
I'd love to connect with you. I'm easy to find, Hamish Knox on LinkedIn.
Also, if you'd like a free 15-minute call with me, go to forward slash howtosandler. Until we connect on the next episode, go create full funnel freedom.

[28:47] Music.