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Podcast Pit Stop: Casey Jacox on Unlocking Long-Lasting Clients Through Relationships

Unlocking Long-Lasting Clients Through Relationships

In episode 95 of Pit Stops to Podium, we sit down with Casey Jacox.  As a Sales & Executive Leadership Coach, Author, Podcaster, and Keynote Speaker at Winning The Relationship, LLC, Casey's diverse skills and knowledge bring tremendous value to our show.

Throughout this episode, we'll delve into the theme of Cultivating enduring client relationships. We'll explore the crucial qualities that define outstanding sales professionals, underscore the "Win the Relationship, Not the Deal" philosophy, and shed light on the fundamental role of relationships in shaping a thriving portfolio and career. Additionally, Casey will impart his "6 Principles for Fostering Strong Client Connections," providing actionable insights for establishing and maintaining meaningful bonds.

If you’re ready to learn from one of the best, then buckle up and hold on!


Pitstop Highlights

Traits for Successful Sales with a Focus on Relationships

There are three traits:  curiosity, humility, and vulnerability.


Instead of being overly excited to talk about a product, make sure that you're asking prospects questions about their business, their needs, and their challenges.


Having more and more success should result in becoming more and more humble.  The goal is to be a good teammate, which means making things easier for those around you and realizing your success comes from their support.


It's ok not to know every answer, it's not ok not to do anything about it.  When you're vulnerable, it's a lot easier to work on your shortcomings and make improvements.  Don't try to fake it 'til you make it.

Distinguishing Between Hearing and Listening

Listening is a skill and requires practice.  Most people aren't good at it, it's an uncommon skill that can set you apart.  Hearing is subconscious, it's something that most everyone can do.

When you listen, you are prepared to ask questions about what was just said.  In addition, listening enables you to write up detailed meeting recaps to send to buyers to show them you're interested and care about their problem.

Connect with Casey




Full Transcript

Brendan:  Hey everyone. Welcome to Pit Stops a Podium, the RevPartners podcast where we talk to execs who have competed and won in taking their companies from high growth to high scale. My name is Brendan Tolleson. I serve as the co-founder and CEO of RevPartners and I'm delighted to have with me today, Casey Jacox.

Casey:  Appreciate you having me on. I'm honored to join you guys.

Brendan:  Yeah, this is gonna be a lot of fun. We didn't prep too much about this, but for those that are Ted Lasso fans, I see two of my favorite lines behind you. And I was playing pickleball with my nephew and I had to keep reminding him to be a goldfish. So it's a good reminder to see in your background.

Casey:  It's hard, it's sometimes hard to do, but super important in all walks of life.

Brendan:  Yes, especially for a teenager playing a sport.  So, well, for those of you who may not be familiar with Casey, Casey is a sales executive and leadership coach, an author, a podcaster, a keynote speaker, but really the founder and CEO of Winning the Relationship. And so Casey has a lot to communicate. And so I'd love for you to just share with our audience a little bit about your origin story in terms of how you got to Winning the Relationship. And let's start there.

Casey:  Yeah, well, I always do who Uncle Rico is from Napoleon Dynamite. I gotta give love, you know, anytime I reference I played quarterback in college, you gotta give love to Uncle Rico because I can throw the ball with that mountain probably. But no, joking aside, I was a collegiate athlete which taught me a lot about this life skills, leadership, grit, resilience, communication, all these great things that I used in corporate. I spent over 20 years in the staffing and consulting industry, worked for a company called K-Force that acquired Hull Canyon in June of 2004.  I would say right guy, right time, right place. But I was our number one rep nationally for 10 consecutive years, um, before moving into a executive role where I was, um, executive sponsor over certain accounts helped take the firm for more like a staffing service into more services work, um, which is a more of a consultative value-based cell. And then I started doing some writing and some speaking and at the end of that three year run company I was with, we're looking to have me go into a different role in it. I just didn't know if that was what I wanted to do. And so we agreed to part ways back in March of 2019. And 10 years before that, I knew I wanted to write a book, um, which is, it was in my head for 10 years and I didn't want to do it when I was still working in corporate because I thought that would be an excuse or distraction. So I just waited and my mind, it was always there. And, and then for four months, probably about four months. Um, once I kind of cleared my mind, as it got my head right after I left, I wrote for two hours every day for four months. And then four months later, the book was done. And then in that journey, I thought I wanted to start a podcast, which I launched both those book, launched in January of 2020, podcast launched January 2020. And then maybe later than 2020, coaching found me. I did not plan on doing this. I didn't say, I'm gonna go to coaching school. It literally, I think it found me. And I had a powerful conversation with a gentleman named Andrew in Toronto who I asked, I reached out for advice because I was getting people to ask me about coaching and I didn't even think of myself, mainly because I wasn't quote unquote certified. And so I asked him for his advice and I go, Andrew, what do you think I should do? I think I have these coaching opportunities but I'm not certified. And he looks down on Zoom, he goes, Casey, can I be honest with you? I said, yeah, that's why I called you. He's like, okay, good. But I'm gonna be really honest with you, man. I know if you're gonna like it. I said, I can take it. I've thrown four interceptions in the first half. I've been part of the biggest, one of the biggest deals in company history, biggest flunks.  I can take it. He's like, okay, good. He goes, so what I heard about you Casey, is you've done A, B and C, you've achieved D, E and F, you've done all these things, nonprofit world, executive world, I'm like, yep. He goes, good, then I want you to get out of my quote, mother effing face and stop wasting my mother effing time. And he holds up a copy of my book. He goes, hey, dumb, A, S, here's your certification. Seriously? And I was like, oh my God, thank you. And I hung up with him, called a CEO back and I said, Leslie, are you still looking for a coach?  She says, yes. And I said, I think I found him. Can I tell you more about who I'm thinking for you? And I described myself on third person. She was like, oh my God, who is it? I go, it's me, when do I start? And that was two and a half, three years ago and I haven't not looked back. So that's how we are today.

Brendan:  That's great. And I think it's a good summation of the believe quote right behind you. So now I understand why that's up there.

Casey:  It's mainly there for, yeah, selfishly for me, it reminds me, I believe what I do matters. I got him. John Kaplan taught me that question at age. I'm a little older now at age 41. And I'll tell me age I'm 47 now, but at, uh, he used to always ask us that question. He was my client. I, we, we were leading a sales transformation and I was his customer actually. And, um, I think too often sellers don't ask them, ask themselves that question.  Like if you truly believe what you do matters, then you should have the confidence to call anybody, ask anybody, anything, email anybody, do any, do any outreach because you believe what you do matters, I think slowing down to have the right seller's mindset is something I work on in my, in my coaching.

Brendan:  Well, I'd love to unpack that a little bit further as we get into one of our big ideas for today. But before we do that, love to get to know you a little bit outside of work. I know you kind of weave some of that in terms of your background from a sports perspective, but that's college. So now you're, I think you said you're 47. I hope that's the right number. And so, yeah, what's going on now in your life? What are the things that keep you busy or that you're passionate about?

Casey:  Well, I'm very grateful to I'm still working from home as a sole proprietor. Uh, I'm very grateful for time with my kids. I have a 17 year old son who's a, she's a great, great kid. He's a little bit of a part of my French smart ass like I am. Um, but he has a lot of fun, diehard Seattle sports fan, like he lives and dies by every loss and we're actually going to the Mariner game tonight. So hopefully they win. So for his psyche, uh, been married to be 25 years in February.  And my daughter, Riley, she's a scrappy little, why we say the toughest one in our family, but she's point guard, shooting guard, and keeps us busy chasing around the country playing AAU basketball.

Brendan:  That's great. Did you say your wife's name was Carrie? Oh, that's my wife's name, which is kind of odd. That's cool. Yeah, you're a little bit further ahead than I am. My kids are like nine, seven, and five. So we'll have to maybe discuss another podcast, How to Parent Kids Through the Adolescent Years, because I'm gonna need a lot of help.

Casey:  It's yeah, it's no easy task. I just have to remind my kids that this is your journey, not mine. Dad has no eligibility left. I'll help get you there. Help provide opportunity, but you got to put in the work.

Brendan:  It sounds like you're taking your sales coach methodology and applying it to your parenting, which I appreciate. Well, that's a good segue, Casey. Let's talk a little bit about some of what, I know you're passionate about when it gets into the work perspective. And that's really, as we think about sales, you talked a little bit about, you had to believe in it. But also there's an element too that I wanna talk about is the relational component where we treat these really, these are not transactions, these are relationships when we talk about our clients. And so I wanna talk a little bit more about that because I think there is a tendency, especially in high volume, in technology, where it becomes very much churn and burn and just get the deal. I think this is a powerful concept to be thinking about, to really drive not only what's sustainable and what's gonna make you successful, but what ultimately is gonna make the customer successful. And so maybe as you think through that concept, we'll get to some of your key principles for it, but you described yourself at the beginning in terms of selling yourself in the third person to your first customer as a coach. What do you, like you talk about grit and tenacity, what are some of those traits that you look for or that you coach about to make a great salesperson where they're putting that relationship front and center?

Casey:  I think these are three, everybody has them. Most, some of these skills, unfortunately for people, they lay dormant. Some of these skills are present. Sometimes they're not always present. But I believe these are superpowers and they're curiosity, humility, and vulnerability. Michelangelo is 87, he said he was still learning. Guy named Walt Disney, he said curiosity was the key that led him to all the success.  You know so many people in through life have been Successful based on curiosity, you know, they always say, you know, you know a man or woman is not judged by his or her answers But by his or her questions I always when I'm coaching people I always talk about how often are you hearing a client or prospects say a great question and are you allowing space for that question to sit in or you just so excited to talk about the deal talk about what?  I got taught a framework called TED, which is tell me, explain, describe. That's what I teach now and sounds really simple. Three-letter words and three words really hard to do because when we go into meetings, I see a lot of sellers, they go in with sometimes fear, self-doubt, um, unprepared, not knowing about the business and they just think they have to tell everything versus I'd rather you know nothing about what we do and know more about their business and just keep asking questions to get the client talking about what his or her challenges might be, why they're a challenge and really dig deep what I call second, third level Ted. Like phrases like, tell me more about that. Describe what that could be of a value to you. Tell me what would happen if that went away. Explain why that problem's impacting you and your organization. And I think to ask those questions, you got to pointing, got to believe what you do matters, but you got to be prepared and be confident to be able to ask those, which takes practice, which most sellers again, don't like to do. We like to wing it.

Brendan:  Yeah, I think I wholeheartedly agree with the curiosity concept. I really like the TED framework. I think you said what's tell, explain, do for those the describe, excuse me, tell, explain, describe. Okay, so that's that is the curiosity. And then you talked a little bit about humility and vulnerability, correct? 

Casey:  Yeah, I think the best what motivated me as a number one seller for 10 consecutive years was not winning every year. What drove me was when my CEO after I spoke on stage would say, you're more humble this year than you were last year. I don't know if it's the quarterback in me wanting to make sure that 10 other guys in the huddle respected me, know I was in it for them. Just same mindset I took to corporate, whether it's making sure I'm getting making life easy on AP, making sure I'm making life easy on my admin, making sure I'm making easy on my support staff, just going out of my way to be a good teammate, which cry and realizing that if any success I have, it's because of the team, not just me. I'm sure obviously I know I'm, I have gifted with certain talents, but quarterback doesn't throw the ball to himself. Quarterback can't make tackles on defense unless he's throwing interceptions. So humility is one of the biggest attractive skill sets, I think in any elite seller or in a leader.  And I think I mentioned vulnerability because, you know, one of my mentors said, Casey, it's okay not to know every answer. It's just not okay not to do anything about it. When we get into pipeline reviews, sometimes people pucker up, they get nervous, they go, shoot, I got to have the perfect pipeline. No, you don't. No such thing as a perfect pipeline. But you have maybe a follow-up sales process or when you go meet with your sales leader or he or she, are you saying, man, I feel really good about these two deals, but I just, I don't know, something's not happening because of this one or tell me what I should be asking differently. Or can you look at my emails? I'm just not getting the meeting acceptance rates I want back. Tell me what I'm doing wrong. Like, are we vulnerable enough to show our gaps? Or are we gonna follow, which I think is the worst piece of advice in life, was when you fake it till you make it. I can't stand that. I think it's the worst thing people can do. I always tell people, no, be your true self. Show up who you are, realizing that we all have gaps. Me as the coach, I got gaps. Things that I'm working on every day. I even have my own coach. So too often, I think we as sellers, our ego gets in the way. We think we're more important than we are. And I always joke now, I say, you know, believe it or not, when I left K-Force, believe it or not, they didn't go out of business. They're still around, miracle, right? They're doing great. Maybe they were ramped up more without me. So I think though that's why I'm so passionate about those three skillsets because those are leaders I wanna follow. Those are the people I think have proven to me over time.  Consistently those are skill sets and traits that I think are very important for a sales leader or salesperson

Brendan:  Yeah, I like that curiosity humility and vulnerability it might we have a value at our at our organization called fail forward and it's really trying to capture some of that of It's okay not to know the answer And to ask for help but we can't know how to help you if you don't tell us and I think that a lot That's part the culture too When you think about the vulnerability is that is that accepted or not? Because that can also be a hard part for the sellers if they go to a meeting and they know they're gonna get a you know obliterated by their manager it's hard to feel the freedom and the space for that to actually get expressed and ultimately be experienced. 

Casey:  Yeah, well, I was gonna say real quick it's one thing to say it, but as the leader, he or she, if you're as a sales leader out there, when's the last time you've, if there's sales leaders listening, when's the last time you've maybe shared one of your gaps with your team, your sellers, your AEs. Maybe you've shared an area of your game that you're looking to get better at, just to bring this normalcy of we're all human, we all got gaps, no one's perfect. You might be better than someone more experienced, but there's still things you're working on. And I think when we slow down to go faster and slow down to share these um, experiences with our teams. I think it brings them a tighter connection. It brings us level of like, okay, I can't wait to get to work and, and attack these gaps versus pretending we don't have them.

Brendan:  Yeah, and that reminds me of the whole, I think, yes, it's what's rewarded repeated and or what's modeled is repeated. And if you as a leader aren't going to model that and there's no way that the reps or the SDRs or whoever it is that you're talking to is going to do that. So you set the tone. I think it's a good reminder for our management and leadership that's listening to the podcast. So we talked a little about the traits of an effective salesperson, but there's also the element of how to approach the actual engagement.  And so a lot of what you talk about is winning the relationship, not the deal. So what is, you know, in light of those traits, now how should they apply those with the belief that what they have to provide is ultimately in the best interest of the customer? Let's talk through that.

Casey:  Well, sure. Let me so me before I tell you that I want to say I did. I'm not a I did not predict the future. I did not guess that sales leaders would be going to virtual selling back in 2019. I did not know that we would have to go back to the basics. I did not know that we would forget how to sell. If I knew that now I was I wrote the book back then actually, I think it's been received very, very well given what people have gone through as of late because they almost forgot how to talk to people build relationships with people and my book talks about six key principles that I focus on every single day to be my best version of me. As the author, I've read the book over 10 times through the editing process. When I did the audible version, I still learned something from myself and I'm the author kind of embarrassing to say, but the idea came about, we'll call it 10, 12 years ago when I was traveling, I was in Dallas working with a younger group of folks, less experienced group of folks, and they were so competitive. They wanted to win every deal they w which I love. And I said, I know that you want to win. I want to win, but how can you win a person?  When you lose a deal and they looked at me like I had a screw loose. I said, think about it. Like how can we win a customer when we lose a deal? Like you might win the relationship, but you don't, you don't win the revenue. And I said, for example, let's say that we lose a deal to ABC company, but in two weeks you follow up with that customer. You say, Hey, Brandon, it's Casey with ABC company. I, you know, I wanted to follow up with you. I know I was bummed that we didn't get it done or we weren't the one you chose, but I wanted to follow up to make sure that the product you chose or the service you chose is everything you wanted it to be. And you're getting the service you requested.  The number of times I would do that, sometimes client would say, Casey, I haven't even heard from the people we want to do. Thank you for following up. Or they'd say, actually, it's not going good at all. Is your, is your consultant still available? Well, I'd rather work with you. I would pick up easy deals just by because I truly cared. I wanted to follow up. And so when I said that, I said, you guys, it's more important was we got to win the relationship, not the deal. And when I said that to my team, I was like, that's it. It was almost like if you've seen Christmas vacation, when Griswold Sees His Tree, when he kinda like just glows, that's what I was like, that's the name of the book. I knew it, knew it wholeheartedly. And then from there, when I decided to write it, I went through like a word mapping exercise and I thought about what were the things that helped me be successful over 20 years consistently. And I was starting chapter one, starting the day with positivity, entering a huddle with the type of character and type of energy that people wanna be around.  Are you, are you like adding to it? Are you detracting from it? Chapter two is a store power of expectation management, setting expectations, just like I did with you, like your boy, Igor, I said, I might be late today. Luckily I wasn't, but I said expectations. So you guys would know, I didn't just want to show up two minutes late and just assume that worked for you guys. So it's too often sellers don't take time to think about that. Chapter three is all about the difference between hearing and listening. I think listening is all about, you know, two ears, one mouth, let the bigger number do the work, uh, chapter four is about the power of a CRM and why using a CRM made me look way smarter than I am, uh, I love document. I love documenting cause it just gives you data to ask great questions. Chapter five is about ditching your ego, letting your authentic self shine and embracing practice. Most sellers don't like to practice. We like to practice on our clients and imagine how they would feel if we went and told them that. And then chapter six is patience. Relationships take time. And Brendan, this book, it's not a book of let me sit on top of this pedestal and tell you how great I am. It's a book of let me expose where I sucked. Let me expose where I struggled. Let me tell you where I had to learn lessons. Let me share stories of my own team's failure, my own team's successes, my own failures, my own successes. And I wrote it from a style of writing that I didn't know existed because I've had a lot of authors who are trained say, where did you learn to become a conversational style writer? I said, I have no idea what you're talking about. But it's my voice that comes out when people read it. So hope that answers your question about why I did it and the power of it because it, yeah.

Brendan:  Yeah, it does. And I think to your point about getting back to the basics, you outlined what those six key attributes are for really putting that relationship at the front center. I love the idea of kind of that insight of even that next step that some people can take in terms of reaching out to that customer or that relationship, probably shouldn't use it with customer because you didn't win the deal, but it shows care. And I think, if you look at something we talk a lot about on this podcast, like, and I talked to Horst Schulze, the former CEO of the Ritz Carlton, the number one question for customer satisfaction is not quantifiable, it's actually qualitative and it's, do you care about me? And what you're describing is that whole element of, do you actually care about that person? Because if you do, that's a natural thing to ask somebody afterwards, hey, regardless of whether you use this or not, I wanna make sure that your problem got solved and that you're seeing that and experiencing that.  And so that is, you know, that, so I love that kind of concept because I think it's, people don't expect it and it truly shows and reflects what you really believe. So thank you for sharing that. Look, we don't have time to go through every one of those six. It's probably picking your favorite child. That's not a fair question. So I'm going to pick one for you. Let's get into, you mentioned there's a difference between hearing and listening. I think that'd be a really good one for our audience to understand what, how you distinguish between the two, and then how our sellers can apply that into their future sales engagement.

Casey:  Listening is a skill, listening requires practice, hearing is subconscious. We hear planes, we hear wind, you know, listening is conscious. I I'm, I'm focused. I'm, I'm listening for key words. Listening requires me to use. That's why Ted's in my mind gold, because then we can say, huh, tell me more about why that's important to you. Or, and we might go off script in our meeting and that's okay. Because if we're talking about what our customer wants to talk about, what's important to he or she.  They're going to be much more likely to engage because we're making them feel heard. Um, and then when I specifically, when I, when I document all those things, which I talked about in chapter four, and I use that follow up for questions showing, I listened showing I was different. Maybe I write a tight meeting recap, uh, to my, my client post meeting. And I, and I tell them in the meeting recap what I heard today. And I document specifically most sellers aren't willing to, willing to do that. Um, I like being uncommon.  I like making people, I like being on people's mind, hopefully a couple hours after they spend time with me. How did I make them feel? How did I show up? And I think listening is the way you do that because most people are not good at it. And one of the things I learned from one of my mentors, John Kaplan, he said he had this phrase called seller deficit disorder, which I gave him credit for in my book. And there's two symptoms, why clients or customers do not like salespeople. And the number one answer is they don't understand my business and the second one is they don't listen.  That comes directly from a client's mouth. So these are two things we have control over too. 

Brendan:  It reminds me of going back to the three traits of a successful sales rep. And I think that's where humility comes into play. And being reminded as even Donald Miller, who wrote Story Brand, talks about the customer is the hero, not you. And so you need to understand their business, understand what their needs are. And it's something we talk a lot about even here, when you talk about the whole idea of recap, it's like, go the extra mile, take the extra step. Because the reality is if you don't do the recap, you lose the deal.  At least that's our opinion. And if you look at the data, you forget 50% of what you learned 24 hours later and then 90% a week later. So if you don't, to your point, document, leverage things like CRM, and ultimately communicate that out, it's a way not only to show that you listen, but that you truly understand their business. So I think it's a great piece of advice that our audience should take with them on their next engagement. All right, well, Casey, as we wrap up, final lap question, if our audience wants to learn more about your coaching or to see something about your book, what's the next step they can take?

Casey:  Best way I'm very active on LinkedIn people can I love connecting. I love helping others. I love going out of my way to connect others is one of my I know I just I get joy out of it. And I teach that I teach is called a boomerang mindset. So like, the more you're serving positive boomerangs of others and not keeping score, most likely boomerangs are going to come back to you. If you're interested in buying the book, you can get it on Amazon. It's in there in Kindle, audible and paperback.  I have a weekly podcast we mentioned earlier called the quarterback diecast comes out every Thursday wherever you can consume podcasts on all major platforms. And I also want to let people know in the fall myself and my colleague, entrepreneurial colleague Marsha Stout, who had 20 years sales executive leadership, top salesperson. We're starting a mastermind in the fall to be really intentional. Like what does the intentional seller do to be successful? And we're going to talk about, you know, whether your mom or dad.  And really talk about the key attributes that have helped us on our journey. And it's going to be very interactive. People can learn more about that at slash mastermind.

Brendan:  All right, well, we will be sure to share that mastermind opportunity with our audience. As Casey said there, it's limited. So we're gonna make sure that our audience has access to that as it launches in September. So please take action on that. I think that'd be a great next step for our audience to take and then ultimately get your book as well. So Casey, thanks for stopping by, reminding us of the power of the relationship and some of those key attributes that not only make people successful, but things that they can apply into their engagement to really be a win-win for all parties. So thanks a lot. Really do appreciate it.

Casey:  You bet. Thanks for having me.

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