From Referrals to Sales Success with Ryan Staley, Whale Boss

Hello and welcome to the Fuel Growth Podcast. I'm Clint Oram.

And I'm Lizzy Overlund.

And today we have with us Ryan Staley, CEO and Founder of Whale Boss, a sales and marketing consulting company based in Chicago. Welcome, Ryan, great to have you here today.

Yeah, pumped to be here.

Excellent. Right on. Well, we're excited to have you here as well. I had the opportunity to meet you in the last couple of months and have become very impressed with everything that you've been doing at Whale Boss and want to have the opportunity to get to know a little bit better today. Let's talk a little bit more about you, Ryan. So tell me about your your superhero origin story, as you referred to it, where, where did you come from? And why are you doing what you're doing today?

Basically, it all started, I've been in sales my entire career, or a capacity related to it—started off all the way from being a paperboy to yellow page advertising to inside sales in a boiler room did a lot of those what you would call character-building jobs. And from there, I shifted into outside sales for an unknown brand, did really well and then eventually transition into a leadership role where I had to revive an underperforming market made it into one of the top-performing markets in the country. And then also then got tasked to start an enterprise group where I grew from zero to 30 million in ARR, was another 30 million capital with only four salespeople and no marketing, like five and a half years. So I left that corporate environment and right now I'm helping companies apply the same principles that I did to leverage that in a resource constrained environment, specifically for tech startups and other startup type companies. And then on top of it, I have my own podcast called The Scale Up Show, and I am an instructor for the Chief Revenue Officer school for Pavilion as well. So teaching Chief Revenue officers and VPs of Sales, how to execute enterprise sales.

You know, you went back and you started off your origin story as as throwing newspapers, I did the same, right. My first job at at 11 years old was throwing newspapers, my first sales job, my first job, overall, what about you, Lizzy, what was your first sales job?

Well, interestingly enough, it was working at the carnival from a very, very young age. In fact, there's a carnival that happens did happen every year in Malibu, California, where by a lot of celebrities happened to go by and I'm going to comment on the picture behind you, Ryan, because I happen to meet David Spade doing that. And typically, you wouldn't consider it a sales job. But me on my periods had me selling everything I could at the joints, we call them the joints at the carnival to bring people in three darts for five bucks to pop balloons and whatnot. So I learned very quickly, how to bring in leads.

Lizzy, I think we could go down a whole path for a half an hour asking you about all the tricks of the trade at the carnivals? That's awesome. That's something I didn't know learn something new every day. So Ryan, back to you here. You know, we talk about fueling growth here on this podcast. And we talk about how companies can can really think about that next stage of growth and what they need to do to get there. As you're working with companies, where do you focus the discussion? What's what's the what's the core of a growth story as you talk to your clients about how they can take their business to the next level?

Yeah, so there's a couple areas that I focus on, I always start with, like, what do they think is their biggest problem? First, because sometimes what they think is their biggest problem might not be what the numbers telling me their biggest problem is. So those are kind of two areas. I start as like, what do they think their biggest problem is? And then, you know, like, for example, if someone's like, you know, we just need more at bats. We just need more medians, right? But then you look at it, and they're trying to get 6x their pipe in terms of the amount of deals they need to close, then more often than they're not, there's, there's something wrong in the sales process, if you need six times the amount of pipeline to target it, like if you're really good, you could, you could be 2x, two and a half x, 3x in there. So but there so that that might be that would be shifted to the sales process side. Or, if you're looking at the frontend, there is pipeline problems that companies have, where they just can't create enough pipe. A lot of these VC-backed companies or invested in companies like even PE companies to get all this money dumped into them. And then they'll hire, hire hire, but then they'll do it based on capacity planning like bodies, versus looking at a combination of capacity and demand. So then then it'd be more of a pipeline problem if you got salespeople with not a lot of consistent meetings. So that's kind of how I look at it through a framework Because like, do they have a pipeline problem? Or did they have a sales problem, and then from there, prescribe a recommended program to facilitate that. And there's like six or seven different levers you can pull, when it goes to creating really fast growth. And the beautiful thing is a lot of people think you got to throw people at it, and 9 and a half times out of 10, you don't need to add a single person, you can just adjust what you're doing and make really big jumps in growth.

What kind of metrics when you said just a moment ago, that you start off by looking at the metrics? What are the metrics that you look at first, and by the way, I want to absolutely come back to that six or seven steps that you just referred to unlocking growth. That seems like the magic right there. But before we get to that, tell me about the metrics that you look at to help orient yourself to a business when you come in to give him some help.

So yeah, so it's the quantity of leads the average deal size, each single step in the pipeline, in the conversion process, and then also the speed of the sales cycle. So I would say that roughly amounts about seven, and that's just on the frontend. I mean, there's also areas in the backend, where you're talking about expansion, cross sell, upsell, and then one of my favorites is systemising customer-to-prospect referrals, because pipeline will close in half the amount of time with twice the conversion rate, and 90-95% of companies aren't doing it. So it's like literally like bags of money sitting on the floor, and people are jumping over it to pick up a penny. It's crazy.

You talked about volume, talked about value. You talked about conversions, you talked about velocity. Is your is your whole sales program that you talk about come back to just tuning those different metrics? Or are there other elements that come into play as well? I've got to imagine sales skills and coverage. And that sort of thing kind of fits into the discussion as well.

Well, that's what I was talking to you about is those are more like symptoms of focus, right? So a company at 10 million, or a company at 100 million, there's probably 100 different things you could fix. But what's the one that you have to put the least amount of effort in, that's gonna get 90% the results? And so that's what that's typically telling us. So those are symptoms of problems. And then kind of the way I look at it, and I focus, there's a lot of different areas you could focus on, you can focus on leadership development, you can focus on a lot of different areas. But if I had to break it into two core focus areas, what I help people with is the mid-market and enterprise. So any kind of deals that are $30,000+ in average deal size. And within that, there's basically the sales process, which a lot of companies try to focus on. But it's crazy. There's 100 companies that are hundreds of millions of dollars that have no sales process, and it was just mind blowing to me. There's this strategy. So how do you systemize strategy? And what that is, is that's orchestrating the relationships in those accounts, but then also aligning to the buyer need in terms of outcomes deliver. And then last, is the execution. So that's like, what every person what you say, when you say, who you say to it, at what step in the process. So that's more like the tactical hand-to hand-combat. So for the frontend, that's how I would look at it. And those same principles apply for the backend. So that's kind of what I look at when we're doing that. But that should give you a high-level understanding of it.

I have a question for you. I sounded like I think I heard you say mid-market and enterprise customers that you've worked with, you've found that they don't invest or don't have a process for their sales team. Why do you think that is?

I think that so there's, there's it's really interesting, there's two kind of camps that I've seen. And this isn't intentional, this is usually the organization emulates the leadership function. So if the CEO is more of a relationship-based selling person, then that's the way the entire org will be created, they'll have like no processes in place. Then the other thing is, which is really interesting, some of the technical founders, they'll be awesome at processes and they'll be awesome at setting up systems, but then they won't focus as much on the relationship side. And so there'll be massive gaps in terms of customer relationships that don't allow them to hit that backend that NRR, that reoccurring revenue or that expansion revenue or the referrals because they haven't done things along the way. So usually, you'll find the organization whether it's operationally driven or sales driven legacy slanted to one of those two sides. And so that's how we're you see kind of those situations.

And if I had to take against the magic lies in somehow blending both of those and that's where you probably come in because you're able to identify the gaps in that and raise that to your customers.

Here's the thing: the market's been lied to for so long. And like, the number one biggest lie that I see, maybe it's not the number one, but it's up there. It's top five, let's just say it's top five, is that a sales methodology is gonna fix everything. Did you realize the sales methodology that most people use as a default, is MEDDPICC for enterprise deals? And there's some really good things about MEDDPICC. But MEDDPICC was created in, I think was like 1997, or 2007. Right? So it was created before the iPad even existed. How much has the world changed since then? And it was created by a company that was at 300 million in revenue. So like, imagine if you're a $10 million company in revenue, $20 million, and you're trying to apply what works for a $300 million company to your business? And it doesn't, it doesn't always work. There's big changes like this difference in infrastructure and all these things. It'd be like, Jeff Bezos does this, we should do it at my $5 million company. Yeah, there's core principles, and there's a work but 9 and a half times out of 10, you can't just cookie cut that. And that's what a lot of people try to do with all this different sales methodologies. So they don't end up with the results they want.

Now, on the topic of sales methodologies, I've heard the comment made before that no one methodology is necessarily better than the other, the most important thing is having everybody on the same page, and using the same vocabulary and and approaching a customer in a common way. Would you agree with that? Or do you see real differences in sales methodologies from your perspective?

I think there's big differences. There's definitely big differences. Some of them are, like, just inward-facing. It'd be like, if you're trying to get into a deep relationship and marry someone. And you're just focused on yourself only and that's it. You're like, does this person meet my qualifications, just like the qualification methodologies. They meet my qualifications? Yes. Okay, we can get married. It doesn't factor interacting with the other person, it doesn't factor connecting with them. It doesn't factor in everything else that's involved with other people. Maybe they have kids, from previous marriage. Not factoring in any of those things and be like, okay, you meet my checklist. So I think we're good to go. There's literally methodologies that are asinine and crazy, where they don't factor in anything else. It's just like, do you meet my qualifications? Yes. Okay, let's go. So I don't know. Gotta have some strong opinions every now and then. But here's some more data behind that, too. I was in a group of 12 different high-performing VPs, or Chief Revenue Officers, and I was in a group with them. And I asked them this specific question: what sales methodology do you think is the best and why? And not one of them used only one sales methodology. And why do you all have two or three sales methodologies for each, each company that you run? And they said it's because none of them are complete. They don't work by themselves, so we have to mix multiple ones together. And when I'm talking about that when I look at an operating system for a company, that's why I said, okay, it's gotta be the process, the strategy, and then the executionI want to call it the holy trinity of sales components. That's kind of what it is when you look at it. And my hypothesis was confirmed from the people I talked to.

I want to go back to a comment you made a little bit earlier that really piqued my interest. You said there's there's always one or two low hanging fruit in every sales organization, that that they can focus on to make the big impact. Is there a most common one that you've seen? Is there is there a mistake that companies are making over and over again, that if they just fix that one thing, things would magically get better?

Yeah. And I have some strong feelings about this as well. So here's what I would say, I think it goes to conditioning, just like the market's conditioned to believe that if you need to grow, you got to throw STRS and create pipeline. And that's like the number one way to create pipeline. And it's a valuable strategy and a valuable approach. However, what you'll see is companies might have 200, 500, 700, 1000, 1300 clients, sometimes even 1000s of clients. And so what they've done with those clients is they built up goodwill, they built up trust because their product works and they like it and they enjoy it. And they they really feel good about it. And then at the same time, they they know them at a personal level, especially in the mid-market up, mid-market plus because this average sales cycle could be three months, six months, 12 months, two years. So you might have deep relationships with nine to 15 people in an account. So all these variables are there, you got someone to trust you, likes you, knows you, knows your product works. And companies don't systemize how they create referrals to their peer network, they just wait for them to come in. Why I think that's a really big mistake is because when you put focus time and energy, people be like: Well, I tried it and it didn't work. That's because you asked once, you know what I mean, and you didn't systemize it. Let me give you an example. This, this is a really cool, a post that I literally wrote, this is coming out in a few days. And this will give you like a real world example of it. So I've had terrible internet issues, soul-sucking internet issues that are terrible if you're a podcast host. So some guy, I hear talking, he was like, you're gonna want to talk to this guy. And I'm like, Who the hell is this? It's a door to door per show. And the guy was selling an internet service. Came to town, and they just put fiber in. The guy's like, alright, well, here's the deal, we'll do this with this, this, this, this, and it's gonna be $80 a month. And I'm like, I don't have a lot of time to deal with this right now, even though I'm having significant pain around it. So the guy throws two or three risk reversal bonuses, no contract, gives me an additional $10 a month free for HBO Max. And, no install fee all this, right? And then, as soon as I agree to it, we set up the date and everything. He literally asked me for a referral right there. Next thing you know, so that's step one, that's one step of the process. Step two, I have my install scheduled for yesterday, two days, 24 hours before I get a call, this will be from an inside salesperson, right? Hey, by the way, we have this offer for home security where you get 800 hours waived if we do that. I didn't need that opportunity. But that was basically probably another $150 a month that person was offering me and they were just confirming the implementation, right? So that's step two. Step three, now, before the implementation, the doorbell rings. And the guy's like I'm here just to make sure that all your apps are set up on your phone, and everything's good to go. And I'm like, okay, cool. And next thing, you know, he's like, Okay, well, we got a program for your phones, like, how are your phones working? What are you doing? And then like, he pulls out his like, iPad, starts doing all the numbers. He's like, you could do this, we could buy this out, give this to you, so on and so forth. And so if you do the math, what was originally an $80 a month deal. If I would have bought all that stuff could have turned into like $450 a month for them. At the same time, there's two processes, where they asked for referrals before I even started using it. I didn't even use the service yet and they asked me twice, right? Because it was built in. So imagine what happens if you apply that not just there. But you apply it to like, hey, we just use SugarCRM, like the program's working good, we love it, our team loves it, boom. You ask them at the right time, you ask them specifically, and there's more to it than that. But imagine what that would do to your customer base. And it just explodes deals close in half the amount of time but twice the rate. So that's a long version. But that's kind of an example of where the opportunity is. And that's a door-to-door salesman. So if you think if someone like that could do it that if you apply at your organization, what do you think the results would be? It's like mind blowing.

The takeaway I get from that, Ryan, is timing can be everything in this situations where you think, at one point in the moment or the journey, I haven't used it yet. I'm not going to approve, but someone else might say sure, why not? You just never know. Right? So asking is the first step I think.

It's like consistency, you know, you nailed it, Lizzy. So there's really there's what's the incentive or what's the pathway? What's the peak, the emotional peaks that they have during the process? Like, that's the buyer side? What's your sales process? And how do they align? Then what's the persuasion you use? Like, that taps into the 90%? Because once people are over the age of 30 to 90% of our decisions are automated. So it's like tapping into that 90%, which is what like, they applied it pretty good. They didn't hit on all those areas. But that's kind of like the core framework that you leverage. And so, so yeah, so that's, yeah, that's exactly it. All right.

Last segment that I want to dig into here for a moment with you, Ryan, about Ryan Staley, the sales leader. What are the top two or three mistakes that you made in your career as a sales leader that you'd like to pass on to our audience to encourage them not to do the same?

I'll give you the unfiltered number one response: Don't take what your team does personally. Even no matter how frustrating it is. By nature, salespeople are some of the biggest risk-takers, I should say, extroverts. Sometimes it's like trying to tame a caged animal. So you have to basically sometimes take what they're doing with a grain of salt because they're just trying to look out for themselves, and so that's what I would say is the number one biggest—I used to take this stuff personal like, why is this person doing this, like, getting all torn up and about it, you know because I invested deeply into my people. But that's something that you have to be very careful about. So I would say, that's, that was number one. And then number two, is that I think I noticed the biggest it was my team work harder for me and do their best when I looked at customizing how I supported each one of them individually, based on their strengths and weaknesses was one. And the other thing that I noticed that really just drove them crazy style, and then also develop deeper relationships is when I did the same thing with like, what their vision and their outcomes were for their life, right, like I had a rep on my team that wanted to get pregnant in a year and a half and wanted to basically make X amount of money before she got pregnant because of maternity leave later. And so we built a plan around that, you know, where I had someone else who wanted to buy a house in X amount of time. So once I individualize the support, and then the alignment with their goals and visions that that really made things take off. And I didn't do that early in my career.

It's similar to what you were pointing with making the connection with your prospects and meeting your connection with your team members too. At the end of the day we're all people working with people.

Lizzy nailed it. So I'm sure you're good at it.

Lizzy is the people side of the equation. I'm a quant. And she's more of the qualitative side. So so we make a good team here. Well, I got to thank you, Ryan, for your outstanding insights today. Before we wrap up today's episode, how do we find you?

So podcast listeners, join The Scale Up Show. That's, that's number one. You want to listen, I interview founders who deconstruct their biggest revenue growth, hacks and paths and things that they do. So if you're an audio person, listen there. Otherwise check it out on LinkedIn, and DM me if you want to if you need help, or have questions. I post daily, trying to post daily at like 8am Central time. So that's good to find me and then you can see my content and then you know, take it from there.

Outstanding. Thank you very much Ryan, Staley, CEO and founder of Whale Boss Consulting. You've been a really insightful and fun guest here on today's episode.

Absolute pleasure, Ryan.

Thanks, Lizzy. Thanks, Clint. That was awesome.

Have a good one.