Kendra Tuckers’s Journey in Tech and Logistics

Speaker A: Welcome to Shesess Unplugged, the podcast where we dive deep into the world of female leadership in the private equity SaaS industry. I'm your host, Christine Maslin and I'm on a mission to spotlight the incredible female CEOs who uh, are making waves in our industry. Join us, uh, as we embark on a journey to explore the triumphs, challenges and pivotal moments in the careers of 12 extraordinary female leaders. Over the course of 12 episodes, you'll hear firsthand from these trailblazers as they share their insights, experiences and the secrets to their success.

Speaker B: Today we're joined by Kendra Tucker, the dynamic CEO of Truck Stop. A pioneer in the freight industry, Truck Stop launched the first digital freight matching marketplace, transforming how freight moves across North America. Today it stands as a leading technology provider for the logistics sector, uh, offering comprehensive solutions that power the entire freight life cycle. In 2019, Truck Stop received a majority investment from iconic capital, ushering in a new phase of growth and innovation. Kendra joined shortly after as Chief Revenue Officer and has since played a pivotal

Speaker C: role in scaling the business.

Speaker B: Her, uh, holistic approach spanning product marketing, sales and customer success has been instrumental in establishing Truck Stop as a dominant SaaS player in the industry. Before truck stop, Kendra spent two years at Vista Equity Partners working across their portfolio of SaaS businesses. She also took on the role of Chief Revenue Officer at Vista Portco Upserve, further honing her expertise in scaling high growth software companies. What really sets Kendra apart is not just her impressive leadership track record, but but also her willingness to share the lessons she's learned along the way. Both the wins and the challenges. She speaks candidly about the realities of leadership, the missteps that shaped her growth, and the insights she's gained from navigating complex business transformations. In this episode, Kendra shares her perspective on leading in a traditionally male dominated industry, building high performing teams and fostering a customer obsessed culture in today's competitive market. Join us as we explore Kendra Tucker's inspiring journey, her strategic vision for Truck Stop and her commitment to empowering the next generation of female leaders in sas.

Speaker C: Such a pleasure to have you on the podcast, Kendra. I'm really looking forward to this conversation.

Speaker B: To kick things off, could you share a bit about your background, tell us

Speaker C: who you are and um, what you do?

Speaker D: Yeah, absolutely. Christine, thank you so much for inviting me to be a part of this podcast. I think it's amazing the work that you're doing to showcase women leadership, particularly in tech. So my name is Kendra Tucker. I am the CEO of a company called Truck Stop, sometimes called truckstop.com. if you are an OG in the transportation industry, you might even call us the Internet Truck stop which is how our business started off 30 years ago. So we are a 30 year technology company that serves uh, full truckload trucking on the freight brokerage side as well as on the trucking side. I came to this business as the chief revenue officer in 2020, so smack dab in the middle of the pandemic. It was a totally different experience. And before I came into Truck uh stop, I actually was a part of a private equity ecosystem. So as a chief revenue officer for a restaurant software company which was part of the Vista Equity portfolio, I prior to that, you know, I did a stint in a number of different kinds of companies from consulting to tech enabled services businesses, even did a digital media startup. So I have a massive number of different types of experiences that I regularly draw on in this role and then other fun facts about me Christine because I think all of us as women, we can all say that we are multi dimensional. So I am also a mom to a very active five year old boy. He's incredibly active as well as I have a husband and we live in Arlington, Virginia where I've been for the last 23 years.

Speaker E: So a really long time.

Speaker C: Amazing. Thank you for sharing. I've also got a five year old son, so we've got that in common. And he's also incredibly active so it's

Speaker E: hard to keep up.

Speaker C: And asks about 5 million questions a

Speaker D: second and has all the opinions to go along with those questions.

Speaker C: Yes, absolutely, absolutely.

Speaker B: So could you share some of the

Speaker C: defining moments in your career that led you to becoming the CEO of truckstock?

Speaker D: Actually, so one of the defining moments is that son of mine, which is I ended up unexpectedly pregnant in 2019 where I was doing this crazy stint. So probably like a number of your listeners, I'm a super ambitious person who was very career focused. And it was sometime in my mid to late 30s where I thought, you know what, if I'm going to have a kid, I should probably attempt to have a kid maybe. Let's see what it's about.

Speaker E: And so it actually caught me off

Speaker D: guard when I discovered that I was pregnant and I was in the midst of doing that Chief Revenue officer job, the first one that I had where I am based in D.C. but every Monday morning at 6:42am I um, would take off out of the DCA Ronald Reagan Airport here and land in Providence, Rhode island where I would spend the rest of the entire week running the sales and commercial organizations for that business. I would come back home, I'd land at like 9:30pm on Friday, and I did that every single week. And so in the midst of that, I discovered that I'm pregnant. And the life I was leading was, as you might imagine, pretty hectic and kind of intense. And so I got to about 34

Speaker E: weeks pregnant just before the doctors say, stop boarding airplanes. I was like, I think I might have to tap out. And, uh, for me, that was really

Speaker D: hard because, again, being an ambitious woman who was so career driven, I never thought that I would choose to leave a company. So that way I could, I mean, I don't know another way to say it, I guess, tend to my family, right? Or start a family. But, uh, it was really important. I was thinking about my health. I was thinking about the pace I was keeping. I was thinking about this new life that I was bringing into the world. And I was like, I need some time, I think, to figure it out. So in that, I ended up taking 10 months off, during which the pandemic started and happened. And the best thing, the reason why I think this is such a defining moment for me on the path to becoming a, uh, CEO, is it gave me a lot of perspective on what I was looking for out of my career or in the next phase of my career. So I got to spend time reflecting on what are the things that matter to me most in whatever job I take next. And number one, Christine that showed up on that list was, I really care deeply about the kind of people that I work with. And I hope it's okay to say this. I say this to a lot of people when I recruit them to come work on my team. But my number one criteria, the way I would express it, was no assholes. I'm not working with them anymore. The work day is too long. Life is too short. I spend a lot of hours in a day at work. And I thought, I really want to work with people who are deeply committed to the mission of the company that we're a part of and not just their own personal gain. So to be clear, that's how I define asshole in a business context, is you just cannot be out for your own personal interests. You have to want to be a part of a team. You want to bring your most authentic self to that work every day and win together and as a collective. And so it's so funny because at work people would say, wait, if I'm really opinionated and sometimes grumpy, am I

Speaker E: in the Asshole camp.

Speaker D: I'm like, no, no, no, no, no.

Speaker E: Totally appropriate to be opinionated and grumpy

Speaker D: and assertive and have vigorous debates with people at work. It's not okay to do all of the politicking and back channeling and all of that. So, anyway, the point is, is when I applied that as my number one criteria, and there were a number of other criteria that I identified as well, it really helped me select, uh, Truck Stop as the place I would work next. And I did not know upon entering, because I joined as a Chief Revenue officer in August of 2020. I didn't actually know that it would turn into a CEO role. Right at that point, I had no idea. I just knew I was choosing the company I thought best reflected the values I had, uh, and what I wanted to be a part of.

Speaker A: Thank you so much for sharing.

Speaker C: I really love your perspective, and it really resonates with me, actually. Similar story to mine, and we were obviously pregnant at the same time. I don't know about you. My boy was born in April 2019. So right before the pandemic. And we, you know, I was running a business, and it was kind of early stages for the business that I was running at the time. And actually, Covid ended up being one of the biggest gifts that I could have ever been given because everything went from being in the office, like, you know, commuter trains early in the morning, back late in the evening. Having a young child, barely had any maternity leave. And then I ended up with so much time when he was about nine months old, just kind of. The lockdowns all started to hit in the uk, so, you know, it really, really resonates with me. And I love the no assholes bit around, you know, the culture and the people that you, you know, you choose to work with. And even better, you went a step further to define what also actually is means to you in a work context.

Speaker E: We had to norm on it as a team, right? We had to norm. I was like, here are my standards. How do they match your standards? So, yeah, it's. Those are fun conversations at work when it's like, I've item define asshole at work.

Speaker D: Uh, but I agree with you on the COVID experience, by the way. My son was born December 2019, so just before the, uh, lockdowns, and I did not leave him for 18 months. Right. Like, we were never apart for 18 months. And so while Covid had a lot of very negative elements to it, a, uh, silver lining in Covid was the amount of just uninterrupted time I got to spend with my son.

Speaker C: How was your. How has your education, and particularly your MBA shaped the way that you approach leadership?

Speaker D: It's a good question because I don't really think about my education a lot in my leadership. What I mean by that is I went to University of Chicago for my undergraduate degree and then Georgetown for my mba. And I think what I took from both schools was the ability to do lots of really quick information processing. So people on my team have commented, you can put a lot of data in front of me really and really quickly. I can digest it and get the crux of it and use it to make a lot of secondary decisions. Uh, and actually that. That sometimes, particularly in context where I have to communicate decisions I make really clearly, it can be a detriment. So me moving too fast and not slowing down to explain how I processed the information that I've taken in, I can leave people behind and I have to really think about, as a leader, how to keep them, um, tracking with me. So it's almost like in that regard, it's very good that I've learned how to process information differently. It also then requires me to manage that closely. So I think. I think my most profound leadership education has come from my work experiences. I was just saying this this morning to another CEO in the D.C. area. We were comparing notes about where we were working when we first started in the professional arena. And my first job out of college was at the Gallup Organization. They're known for the Gallup whole, but they also have these amazing human resources consulting and data solutions. And one of the things they do is called the strengths Finder. They do this employee engagement survey called the Q12. And right out of school, I got thrown into learning the ins and outs, the science behind the strengths finder, which is this almost like personality assessment, for lack of a better way to quickly explain it. And I learned about the filters that individuals have and how they show up at work. And I have to tell you, that has been probably the body of work that I draw upon the most. It gave me such an appreciation for how each person on my team is different, how I think about our customers, or different audiences I'm in front of. I'm always thinking about the different kinds of filters that individuals have and how to tailor my messages in order to hit different filters differently. So that's been really impactful and something that I've drawn upon for over 20 years.

Speaker B: Wonderful.

Speaker C: Thank you. Was there a particular moment or mentor that made you believe you were ready to take on the role of CEO.

Speaker D: Funny, uh, enough. It was the CEO right before me, the one who hired me into Truckstop.

Speaker E: Because m. Here's the story about me becoming CEO at Truckstop.

Speaker D: Like I said, I didn't see it coming.

Speaker E: I don't get me wrong, I'd always

Speaker D: thought if I can get there and if it makes sense, I would be the CEO for a company. But I still had some trepidation about it. It's kind of like it's a major responsibility. Honestly. It's like a really significant relationship. It's like being married, but except to, uh, kind of your job.

Speaker E: It's a significant relationship.

Speaker D: So anyway, one of the reasons why I really felt connected to the culture at Truck Stop was because of the then CEO, Paris Cole. He's the second CEO for Truckstop. And when you meet him, this band just exudes integrity and generosity and humility. He's just got so many wonderful qualities about him. When I met him, he was the CEO on top of a high, ah, growth tech org that I'd never heard of before. So anyway, we get to maybe I'm 18 months enroll, and I move from being chief revenue officer to being chief Operating officer. And he, he lives in Idaho where the company is headquartered and I live, you know, just outside of D.C. and so he's like, I'm going to come see you. And he's like, we've got some things we need to talk about. It was December of 2021. He's like, we need to do some planning for next year and I really want to take you through. And I said, okay, sounds good. He shows up. I've got a full blown agenda, you

Speaker E: know, again, I'm prepared.

Speaker D: I got my PowerPoints, I'm ready to go. And he's sitting across the table from me. He's like, look, before we get into any of that, that you've prepared, he said, I need to tell you I'm gonna, um, retire. And I was shocked. I was like, oh my gosh, who am I gonna report to? And he's like, well, I was thinking you would be the CEO.

Speaker C: Wow.

Speaker E: And I was stunned. I was absolutely stunned. And so funny because people at trackstep were like, why were you so surprised? It's like, because I don't do this

Speaker D: job every day thinking I'm going to be the CEO.

Speaker E: Truck Stop. I didn't, I really didn't see it

Speaker D: coming, what he done for me though, because obviously we didn't get to my

Speaker E: PowerPoint during that conversation.

Speaker D: He hands me then a three page single spaced document that says, here's what, what it would mean for you to be the CEO at Trucks Up. And it was really, I still have it. It's, it was really interesting. It started off with, first you need to assess are you in a good mental and emotional place to take on the responsibility of being a CEO. And he had this stat, this was like the second bullet in his three page document. The stat that said 47% of CEOs present with a mental illness at some point across their tenure. And I was like, oh my God.

Speaker E: And that really stuck with me.

Speaker D: In fact, as I made the decision to take on the CEO role, I said, look, we've got to surround me with pillows. And what I meant with by that is again, because I have a small child, when they're learning how to sleep, move from a crib to a bed, you surround their bed with pillows. So that way if they fall out, they don't hurt. It's okay to fall, but I don't want them to hurt. And so I was like, as a

Speaker E: new CEO, I need pillows.

Speaker D: So here my pillows were, here's who I want to be my people leader. Because that's so important. Here's what I need from a finance leader. Here's the type of executive coaching I think I need, here's the type of partnership I think I need to build with the board. So they weren't even necessarily all requests from either him or our investors so much as I was saying and uh, really contemplating what's the structure I need to put in place for me to be successful even when I fall off

Speaker E: the bed, which is bound to happen.

Speaker D: And do I have, you know, do I have a support system that can help me? So, so he really one helped me see myself as the CEO of now a 30 year old business that is in transportation and logistics technology. And then even helped me to think about what does it mean to assume this role. Right. To step into it and ultimately to be successful, hopefully. And so it was a very defining moment.

Speaker C: Wow, what a lovely story. And Paris. Paris sounds wonderful.

Speaker D: Yes.

Speaker C: And it goes back to what you're saying about the people, right? That's why you joined in the first place. And it's funny to listen to how surprised you were to be asked to become this.

Speaker E: Who am I going to report to? It's literally myself. That's why, that's why it's funny.

Speaker C: And is it, is it lonely at the top? I mean that's a lot of people say, don't they difficult Difficult job to be the CEO. Uh, to not have that. Well, you obviously report to the board, but can be a lonely, a lonely role.

Speaker D: So here's what I said to people about that is it's lonely in that the buck stops with me. Right. That I am uniquely accountable, whether or not I've done a thing or not. I end up being very accountable for sins that were committed before my time,

Speaker E: sins that are committed on my watch.

Speaker D: I'm very uniquely accountable for, for that. And there's not a whole lot of glory or even in the moment praise that comes with the job. That's, that's not. I think that a lot of CEOs would tell you that. But as far as having that support system or the network around me, I'll have to tell you that there are so many CEO focused things because I think everyone has recognized that it can be quite lonely, that there's a lot of infrastructure to help CEOs tap into other CEOs. So I was just at a breakfast this morning that was specifically for CEOs in the, uh, Washington, D.C. area to learn about how, you know, the change in the administration could impact corporations of all sizes. And that's through the CEO network that I'm a part of. And I regularly attend events and Talk to other CEOs of all kinds of companies to get advice, to bounce ideas off of. And it's, it's actually different even than when I was a Chief Revenue Officer, where I didn't have that same deep network the way I have a deep network of CEOs today. So in some ways it's super lonely in the buck stops with me. I guess that's a form of loneliness. But in terms of having friends, I

Speaker E: have a lot of CEO friends at this point. Yeah, it's.

Speaker D: It's really good.

Speaker B: Yeah.

Speaker C: Yeah. Which is great.

Speaker E: Yeah.

Speaker C: And the other thing you've said, which I've never heard before, which is really worrying, is the 47% of CEOs have some level of mental illness.

Speaker D: Either it develops.

Speaker E: It.

Speaker D: It basically develops, apparently during their tenure. Yes, it is. That is worrisome. That's speaks to the unique responsibility of the CEO that I'm describing is, I think, without being quite intentional and purposeful about how you manage the stress and responsibility, the obligation that comes with the job, it is always overwhelming. How you manage it, in my experience, is what matters. And the other thing too is, you know, life around me doesn't stop. So it's not just what I find in talking to other CEOs. Yes. We talk about our work, but we talk about so many other things that are happening alongside it. Uh, which is things like raising a small child, managing aging parents, talking about spousal relationships. Right. All of these dynamics are all conflating together. And so to have such high responsibility role just adds to the intensity.

Speaker E: So it makes, you know, being here

Speaker D: in the role, I can understand why that statistic could be true.

Speaker C: You've championed a customer obsessed approach and often emphasized the importance of empathy and leadership. My favourite example of that with you is when you spent time on the road with a trucker. Can you share that experience and how it shaped your understanding of their challenges and how it influenced the culture and strategy of Truck Stop?

Speaker D: Yeah, well, I know your listeners can't see me, but if they could, they'd be like, that girl's not a trucker.

Speaker C: They would definitely say that. And they will see a picture of

Speaker E: you

Speaker C: far too clever.

Speaker E: They're gonna be like, that girl is not a trucker.

Speaker D: And it's true, I am not a trucker. So I, in all of my roles have had a customer obsession. I think what my first product manager role, I was actually building a product for chief accounting officers and corporate controllers. And my dirtiest secret was I'd never taken an accounting class because I did

Speaker E: that job before I went to business school. And so in order to be credible

Speaker D: and, I don't know, build valuable products, you then have to actually get incredibly close to your customer. So I'm undaunted by the fact that I'm not a trucker. But in order for us to do anything that makes their lives better or easier, helps them get jobs every day, we have to get exceptionally close to them. And how close, Like, I mean, the

Speaker E: closest you can get is being in the cab. And so I've done it a few times.

Speaker D: I, uh, really enjoy it. I was just thinking this week, I've got a plan, the one for 2025. I didn't get a chance to do one in 2024 and I really want to because truckers. So those individuals that are choosing the lifestyle of being on the road, they have different things that motivate them, um, from the people who choose to be in the digital sphere, right. Choose to be behind screens, coding and building the technology that supports them, they can, uh, they really don't want to be over teched. So one of the things I describe is, you know, we've been around for 30 years, which means some of our, some of our tech has looked like Windows 97 technology.

Speaker E: And when We've changed that, you know, in a text message, like, you can't have the thing. So it's like Windows 97. But here's what'll happen. I got in that cab. The first.

Speaker D: The first trucker I rode with, the

Speaker E: first thing he did was say, why did you change that platform? I was like, it was a technology that we literally called classic. We can't have classic technology anymore. We can't support it from the technical perspective. He's like, but then I have to

Speaker D: go relearn the whole thing, and that makes it hard. So it is really important that I get close to them to understand why does that feel painful and how can I make it easier. And then, you know, riding with them for hours. So truckers, they can.

Speaker E: They can keep a conversation going because

Speaker D: they're in a cab for hours and hours. And so you learn just like a lot, you learn about how important finding showers on the road are and how hard it is to find clean showers. Or. I rode with a female driver who was explaining to me, you know, they sleep on the road for when they're doing various hauls. And she explained to me some of the safety things that she does, so, uh, that way she doesn't get broken into in the cab. You learn a lot about how they think about relationships in the industry. So they're not particularly trusting, I would say, as a community. And one of the things that we help them do with our services is figure out who are the people in this industry that I can trust, that I can build trustworthy relationships with. And I wouldn't know all of those things if I didn't sit with them and hear them tell me their stories, tell me why they chose to do trucking over the other opportunities that they have. Tell me about how they work really hard to make money, the puts and takes and how they make money. All of that is just really influential. And then probably the last thing I would say is I work really hard at, uh, at trucks out then to always keep the spirit of the trucker front of mind, because I obviously am hiring technologists to build tech products. So they too, are not truckers.

Speaker E: And so many people are so used

Speaker D: to, you know, the environments that we operate in, they. They don't even realize that they do it. But they will translate really common language into more, I don't know, just. I want to say, like in the office language. So a trucker might say, man, I gotta. I gotta make some money on my loads that I move.

Speaker E: And somebody in our type of environment

Speaker D: will Translate that to they really want to expand their profit margin. I'm like, no, no, no, no, no. Truckers do not say that.

Speaker E: Do not build things that expand their profit margin. Or at least don't say it.

Speaker D: You have to say they want to make money. What are the things that we can build that make them feel like, this helps me make money. Right. Like that's. We have to keep that spirit alive or else we're going to build the wrong thing. And that's costly to do. Uh, in a tech world, that takes a lot of time and resources and money. So getting it right, we've got to stay super close to our customers so we can get it right for them.

Speaker C: Yeah. Another brilliant story. I love it. The Windows 97 thing killed me. You know, it's like when Apple do an update and you're like, why have they done that?

Speaker E: Totally. It is exactly like that. And the thing is, truckers use our

Speaker D: app to make money. So it's not just like you and me logging in to like, check our email. No, no.

Speaker E: They come to our app.

Speaker D: Cause they're like, I'm looking for freight. I need to move, like tomorrow. And so if it's changed and they're like, now, I can't figure out how to find the freight. They are not. So when we do, we have to be really careful about how we think about releases. And our tech doesn't have to be the prettiest. Like, we're not winning truckers by being the prettiest tech that is not being the most usable, being frictionless in their day. That. That is super important.

Speaker C: Yeah. And probably not the most tech savvy. You know, some of them will be, but some of them definitely won't be. So. Yeah, well done. Good for you. Getting in the cab. I'll look out for the 2025 version. Can you share an instance where feedback from a colleague or a customer shifted your perspective as a leader?

Speaker D: Yeah, you know, I've kind of. I've described. I've described it a little bit. I've reflect on this a lot. This is sometime in my product manager days where I had this manager. You know how you have managers in life where you're like, man, I did not like that manager.

Speaker E: And this person was in that camp for me.

Speaker D: But what I, what I reflect on is at one point during my time working on her team, she gave me really valuable feedback and I reflect on it a lot. So here's the situation was I was a product manager and I was working alongside a guy on like, Our research, I think he was on our like market research team basically. And he likes uh, to move slower than me and. But he liked to poke me a lot about it and would do kind of that like back channel politicking thing and I wasn't for it.

Speaker E: And in my younger days I, I'm

Speaker D: a fairly assertive person and sometimes that might have skewed to a little aggressive.

Speaker E: So he, I needed to deploy him,

Speaker D: I needed him to go see a uh, customer. He was giving me a super hard time about the travel arrangements and so he was the one that was supposed to book his flights. But I just got really irritated and so I went online, I found all these flights, I screenshotted them and I said how about this one?

Speaker E: How about this?

Speaker D: So I just sent him, they sent it to him like one after the other.

Speaker E: He got like four emails from me, kind of attacked him a little bit on it. So that's one example and. Cause he was taking too long.

Speaker D: He was like hemming and hawing and trying to make this decision. I'm like, it's a really important customer. Here are the reasons why you need to go. And this is really, this is important, this is important for our business. So he and I would have these fights a lot. So anyway, the manager who was, who was uh, I was reporting to at the time, she uh, she pulls me aside and she, or maybe it's in a one on one or something. I was just sitting in front of her and she said, you know Kendra, your approach with him, it's not good. And I was so irritated with her where I was like, why aren't you talking to him? He's obviously demonstrating really bad behavior. And she said to me, she's like, look Kendra, I know that where you get super convicted is you believe you're right.

Speaker E: And she said the truth of the

Speaker D: matter is you are right most of the time. She's like, I'd say 85% of the time you are right. She said the problem is, is that you push that onto other people and you're not bringing them along with you. And so uh, her feedback to me was just because you've gotten to the right answer faster than other people doesn't mean then you get to force it upon them. And actually part of your job if you're going to be a good leader is to bring them along with you as opposed to the overly assertive tactics that you are taking today. So I think about this a lot. It's how I, it's. She was at least the Catalyst to help me realize that when I get to answers faster, it doesn't mean one, they might not be the right answer. Thing one, thing two is, even if it is, there is something in understanding that other people have to go through their own journeys. And particularly as a leader I have to help facilitate that journey and that's important. So I constantly think about her saying like I think you're, you're right 85% of the time, but the way you approach it is wrong. And I'm like uh, and I did not like her.

Speaker C: I wonder why.

Speaker E: Right. So, but it was uh, a, it

Speaker D: was really valuable feedback that caused me to reflect on what's the best way to bring people along on the journey with me, to like even before that to validate the information I'm receiving and the decisions I'm making and then ultimately to bring people along differently. Brute force is not typically the answer.

Speaker C: Yeah, no, great. Thank you for sharing and very good honest story and good, good self reflection. Right. And I, I imagine m. The more difficult thing that you've obviously done successfully would have been actually executing on don't use the brute force. You know, people irritate you and then you are right and you know you're right on certain things, especially when it comes to the customer and you're very passionate about the customer and stump that person's just not keeping up with you on the, the journey but then actually taking the feedback on board and then acting on it and doing it differently. I imagine that was probably quite a journey in itself.

Speaker D: It is, um, it has been. It still is. It's one of the things we talk about at our leadership level is there's I think two really important pillars of being a leader, which is self awareness. So knowing oneself really well. And then the second pillar is discernment. So knowing when to use brute force because it's time, knowing that it comes with consequences. Right. Like the. You have to understand I think both things intimately and I find both the uh, journey of self awareness and the exploration of discernment to be just an ongoing set of lessons and reflections. It's constant in the work that I do.

Speaker C: Interesting. What are the unique challenges you faced as a female leader in the tech and logistics industries?

Speaker D: So the unique challenge I face is it just so happens that I'm a woman. It's not specific to gender at all. It's that transportation and logistics is an industry that has an incredible depth of knowledge because as people in the industry say, once you get into transportation and logistics, it gets into your Blood. And so most of my customers, a lot of our partners, have decades of experience in transportation. Even my company has three decades of experience in transportation. I have five. And so, uh, in other realms, like in the tech world, I think five is pretty good.

Speaker E: But in transportation, I think there's a decent chunk of my population that still

Speaker D: looks at me like I'm a newbie.

Speaker E: And so because I haven't actually led

Speaker D: a logistics firm or trucking company, there is almost like I have to prove that I know the industry enough to be at the helm of a company like truckstep. Right. And so that's not got to do with me being female. There are a number of female leaders across the industry still. Obviously not as many as you'd like to see, but you know, that's endemic to where we are as a society. It's more the transportation experience that has been, I think, the challenge, my hurdle to clear. So it again speaks to why it is so important for me to spend time with truckers or to spend time with freight brokers and then even the shippers that uh, distribute the products to make sure I understand from their point of view what they care about, what they want to see us doing in the industry. It's, it's really important for me to stay as close to them as I can because they've got the depth of knowledge and how the industry works. And then I can steward the resources at, uh, Truck Stop to create tech products that align with what that.

Speaker B: Wonderful.

Speaker C: Thank you. Can you recall time when a setback or failure taught you a key leadership lesson?

Speaker D: I had this pivotal moment when, um, when still on my journey from being like a mid level product manager into real leadership where, you know, I was managing a team of greater than 30 and you know, it's kind of like where you cut over from being a manager to being a director or senior director or something like that. So I was on the product side of the business I was a part of for probably about six years. And I knew that part of the business really well. I had gotten really good with talking to customers and understanding their points of view and how to build product for them. The sellers used to love to have me on their calls. And so the more time I spent with the sales team, the more recognition I was getting for being really good at sales things. And so 1m day, ah, one of the senior leaders in the company, he calls me up and he is like, I want you to come run the sales team for me. He's like, you can make more money doing It. And he's like, you know, all the things. He's like, I can teach you the things you don't know. Come try to do this. I was like, that's kind of interesting. I might do that. And so I go through the interview process and don't forget, this is still in the, like, it's still in the same time frame when I was telling you about, like, I'm right. And, um, I feel very good about

Speaker E: being right, very confident about myself during this time. So anyway, I go through the interview with like, flying colors, right? Wow. All the people I'm like, this job

Speaker D: I'm a shooting for.

Speaker E: But then it starts, the process starts to slow down.

Speaker D: Don't forget this is like an internal interview process that I'm in. I was like, hey, why, why haven't I heard anything about this job? And so the guy who was recruiting me, he's like, well, look, there's a small wrinkle. He's like, but it's going to be fine. He's like, you need to interview with our new Chief Commercial officer. Which I thought was kind of crazy. This was a publicly traded company.

Speaker E: We had.

Speaker D: What was it like at that point? 3,000, 4,000 employees around the world. So it wasn't small. And I was like, why do I

Speaker E: have to interview the Chief Commercial officer? Like, uh, I was becoming a director, not a bpe. It wasn't. It was. Anyway, so I, I get all ready

Speaker D: for the interview and I show up, uh, at a chief Commercial officer's office and we're scheduled to have a 60 minute interview. So I go in and he, and I start talking. He's got a folder in front of him and he asked me some cursory questions. We hit the 20 minute mark and he looks at me and he's like, well, Kendra, I think I have everything I need. And it caught me really off guard because I was like, but wait, we were scheduled for an hour and it was only 20 minutes. So I said to him, I was like, oh, I'm kind of surprised. We were scheduled for an hour and it's been a third of that time. He's like, I know, but I think I have what I need. And I said, oh, that's, that's surprising. We just haven't covered that many of, you know, my experiences. And he said, well, the thing is, Kendra, uh, I have done a lot of, I've done a lot of research on you outside of this interview. He said, I've talked to a lot of people that you work with and I've gotten a lot of feedback about your performance outside of this conversation. And I want you to know my

Speaker E: heart just like dropped to my feet and I was like, oh my gosh, what. What did you hear about me? And then he proceeds to tell me

Speaker D: what he heard about me for like the next 25 minutes. And it was brutal. It was, it was brutal. And I mean that to say, like, don't forget I was a confident person, highly assertive, and sometimes a passive aggressive organization. So he and I end up having this back and forth conversation and what I would call no longer an interview, but a performance review that I had never received. And it was, he, he had one point of view from a certain set of individuals where I would say, but look, here's why I did those things. Here's why I reacted. And so we went back and forth and back and forth about like, how I had reacted to certain situations. And he said, as we neared the end of the time of this incredibly dynamic conversation, he said, kendra, look, I. The reason why I wanted to meet with you is, he said, I'm inspecting every single manager or leader that comes into the sales organization. I am intent upon changing the culture of it.

Speaker C: He's.

Speaker D: And I said to him, I, I appreciate that and I'm willing to learn how to do it, but know that you're like, what you're talking about. That's not been how the group has operated. And he's like, I can appreciate that. But he said, some of your behavior has not been above board. Some of it has been this back channeling and politicking. And I was, um, like, I will own that. At the same time, know that this is like the mo m for how this org works. And so we hit the end and I said, I hope I've done everything I can to help you understand. I'm willing to learn, I'm willing to be coached. He said, I appreciate that. I'm not sure if you've got, if, if you have enough for the type of Runway, for the type of time that we have and we need you to upskill in. And I said to him, his name was Steve. I said, steve, I'm just asking to take the bet on me. And he's like, I'll let you know. So I leave that office and I go back to my own office. And I never cry at work because I don't think work is a thing to cry about usually. I want you to know, I shut my door, I turned my face around,

Speaker E: I was like, oh my goodness. And I shed so many tears in that office where it was like, I

Speaker D: didn't see that coming. It was just so.

Speaker C: Oh, man.

Speaker D: It was a tough life experience at work. But the story ends well because later on that day, the recruiter calls me and she says, kendra, I want you to know that you're going to get this job. And so we came up with this whole construct where for the first year I had an executive coach. I had certain milestones that I needed to hit in order to get the promotion. Like, you know, actually get a title, promotion change. And honestly, to this day, his name is Steve Meyer. He is one of my mentors, and I have told him this story. He knows, actually.

Speaker E: It's so funny. He's like, oh, yeah. I remember this when I was, you

Speaker D: know, when I was thinking about taking the CEO job, I talked to him about it because he ultimately became a CEO for another organization as well. But he taught me so much. He helped me turn into the leader that I am today. I mean, uh, part of what we talked about was cutting over from being this individual contributor on one path and then being a leader on another path. And because of that conversation and, uh, because of the investment he then later made and me, I could make the cutover to. From IC to leader. But, yeah, that was. That was a tough and truly memorable day experience. Yeah.

Speaker C: I mean, what. M. An incredible story.

Speaker E: It's. Yeah.

Speaker C: I wasn't sure where that story was going. I think when you.

Speaker E: You're like, is she gonna get.

Speaker C: I was on the edge of my seat as I was listening, as I was listening to you, so what's gonna happen next? But when you talked about it being so brutal, I mean, a few things going through my mind, but, like, first of all, how, um, amazingly honest you are. It's so refreshing to listen to those lessons and, you know, they're real, real life stories. And I hope that would resonate with a lot of our listeners. That kind of self reflection and, you know, good for Steve to actually tell you. I mean, I wonder if he sat there like, is she gonna ask me, like, how is. Cause you. You had to get it out of him, right? Otherwise you could have got up and said, okay, great, I'll wait to hear. But you did. You. You got it out of him and you kind of made your case and you listened and said, right, m. I'm gonna learn. And you got an executive coach and great that you got the. You got offered the job in the end. And that's been a real pivotal moment in your career towards Becoming, you know, the CEO of Truck Stop, where you are today. Thank you so much for sharing that. Truck Stop was recognized as one of the best companies for women in transportation. Congratulations. What steps have you taken to foster a culture that supports and empowers women?

Speaker D: So, um, Truckstop, I think, is really unique in that I have said this to our company. Sparkstop is probably the most inclusive company I've ever been a, uh, part of. And what's really interesting is when I joined, we had no structured DEI program at all. And the reason why I think that is notable is because it's not because we've set up programs that are world class or outstanding, but it's really because of the culture.

Speaker E: Right.

Speaker D: So Paris, who brought me into the org, one of the things that he and I had talked about or I talked about with the recruiter that had found me for truckstaff was how committed Paris was. And this is just in our. This is in our DNA, how committed he was to finding the right person for the jobs that we have. And when you do that and you kind of take off the other filters, it really, I don't know, it's. It's just really helped us. So one of the things that people comment on is really significant percentage of our leadership team is female, and it's varied. I haven't done the stats on it recently because, again, it's, uh, not actually something I really keep tabs on, but it's been 50% or greater for the most part. And even when Paris was here, it was 50%. And so it's not even just me. I guess what I'm saying, it is a culture where we're super committed to having the right people with the right experiences to help us realize the opportunity in the truck stop business. And as a result, we are totally willing to cast a pretty wide net that gets us pretty diverse profiles. So I am proud of the diversity that we have across our business, but not just in the diversity that you can see in terms of gender or race, ethnicity, et cetera. We have diversity in terms of people's college education level. Right. So I think it's amazing that some of our most senior people at Truck Stop never, um, got a college degree. Right. I think that. I think that is just a totally different type of diversity. And so when you think about not everyone around the table has an Ivy League education that's really, really good. Or when I think about the people that we hire who, uh, become our top sellers, some of them came out of brokerages or out of trucking. Companies or their dads were truckers and they too didn't complete college. This is good. This is very good. So it's not just, it's not just about gender or race. Like I said, it is about creating an environment that supports and embraces all kinds of diversity. And I think that allows women to flourish and just a lot of others to flourish as, as well.

Speaker C: Yeah, great. Really, really interesting. And I noted that you've got a good percentage of female leaders on the leadership team. Well done. And you know the point around the whole college degree thing, I couldn't agree more. And it goes back to what you were saying at the beginning when I asked you how your education has shaped your approach to leadership and you sort of said actually it was more the experiences that I've had at work that has shaped that. Um, right. So that's really important one. I actually didn't have a college education. I started work when I was 16 after finishing school. So yeah, I definitely resonate with that. Okay, so onto advice for our aspiring leaders, uh, who are listening. What advice would you give to women who aspire to become leaders in the SaaS, DAS or tech sectors?

Speaker D: Use really practical advice for women. Women who are ambitious and over time do want to climb the ranks or create whatever success looks like for them in this space is developing and mastering a set of skills that can transfer from one company to another. So part of what has helped me is I got really good in the commercial realm. So understanding particularly how SaaS revenue models worked and how sales, marketing, customer success teams work in SaaS, that has helped me a ton. And it is a skill that I honed and fine tuned and really invested in. And so what I mean by that is, is I've had roles, I've taken roles at some point that ended up being lateral instead of promotion roles to exp my knowledge and skillset. So when I moved out of my tech enabled services business and into the private equity ecosystem, I didn't get promoted. I actually just went into a different construct where it gave me greater exposure to things like marketing which I'd had less exposure to and professional services like post sale. And I got to do it in a pe, uh, context, which means I was working with like, you know, 14 to 16 companies and learning how they were doing it. And so it just added to my knowledge. And so when it became time for me to try to take on uh, more senior leader positions, I could draw on this variety of experiences, but all still around a particular skill set, mine being like go to market Models for software companies that got me, I think, just into places I otherwise didn't expect to. So it was really choosing this is the skill set I am going to become a master of. And I know that it can transfer from company to company. It helped me develop a sense of professional worth that was independent of the company I was working for. So you know how earlier in a career, at least this is my experience earlier in a career you can be really wedded to the company that you've been at and the accomplishments you've had there. I found that by deepening my skill set, I began to realize, oh, I can leave this role or this company and move from one company to another or from one role to another and advance my career differently. What I have is really valuable beyond a really narrow construct of the one business you might work for. So I think that has helped me. And if you're at the beginning of your career, sometimes you feel pressure like, am I going to stay in finance? Do I need to choose marketing? And the answer is you don't need to at the beginning of your career. But look for those things that create the skill sets that give you energy and then work to deepen and master them because that's going to make you really valuable in, in your space.

Speaker B: Yeah.

Speaker C: Brilliant advice. Thank you. And really interesting way to, to look at it, you know, the whole deepening your skill set. If you could offer your younger self one piece of advice at the start of your career, what would it be?

Speaker D: Pay attention to being self aware.

Speaker E: So I've just, you know, I've given

Speaker D: you a few examples of where I

Speaker E: was overconfident and overzealous and it's really,

Speaker D: honestly, it's a good laugh to look back at it now to be like, what were you thinking?

Speaker E: 22 year old Kendra, right? It's good, it's great. There's a lot of distance between me and her now. And so look, part of me knows

Speaker D: that I wouldn't be able to give the advice of be, uh, more self aware if I didn't have those tough experiences though. Like you need people to call you out for you to say, oh dear, I could have been way more self aware of how whatever I'm doing will be perceived by others. You kind of got to get knocked down a bit. So I wouldn't avoid having the experiences. It's more like it's taken, as you noted, a lot of self reflection to pull it out. And I'd want to be, I'd want to be a guide to myself. That says now a way you could do this differently is to think about how you come across.

Speaker E: Right.

Speaker D: Like just be aware of how you come across to others. Earlier in my career that the awareness would have been great.

Speaker C: Earlier on how do you balance the pressures of leading a company with. And um, you Talked about your 5 year old son and your husband. So with, you know, your personal well being but also your family life.

Speaker D: I have a lot of structure to my life and I have received the feedback which is sometimes questionable in how it's delivered, but the feedback that I have really strong boundaries which I think is really important. I learned, I think in the first year of being a CEO that this job can be truly all consuming. If it wants me to work 36 hours a day, I can let it have me working 36 hours a day. And so I keep 80% of the time, I would say I keep a pretty structured schedule. It does get disrupted and everything has to be flexible. But I spend a lot of time with my son in the morning before he goes to school, before, before most of my company wakes up because we are headquartered in mountain time. I live in eastern time. So that is a very good arrangement. I end up working later so I can work till you know, 6:37. You know, some nights I'm on the phone at 10 or 11 o' clock at night. And so I purposefully protect the mornings to do family things to do, exercise, mindfulness, all of that. I protect the mornings for, for that. And it's funny, you know, when I onboard a new ea, they'll try to schedule a meeting for me at like 9:30 and uh, I will automatically decline it.

Speaker E: And they'll be like, what? Why, why can't I schedule that? You're free.

Speaker D: I'm like no, no, no, it only looks free on the calendar. Okay, that's a, that's a truck stop calendar. I'm running this whole other life that needs its own oxygen. And so the boundaries, like the boundaries are really strong. In order, in order to keep me in the right emotional and mental state to take on the things I need to take on for the business on a daily basis, I have to be in a good place in order to do my best. And so I get very protective about the time that I set aside.

Speaker C: Yeah, brilliant. It's, I mean I again like, I can relate to that so much. I think boundaries is something that I particularly struggle with in terms of, you know, I set the structure that you talk about and then like you say, it always needs to flex. But um, I Kind of immediately cave and go, oh yeah, okay, I can do that call. Or, you know, it's, it's definitely something that I'm working on. But it's great. It's very good advice. You know, by doing this podcast series, actually, I found it's been the most incredible coaching sessions for me as I'm asking these kind of questions and just getting the insights from, you know, successful CEOs like yourself on how you manage, you know, on how you manage life, family life and personal well being. And that exercise piece has to, it's just, it's so important for mental health, isn't it? It's not just about keeping fit, it's about, it's about your mental health as well and finding something that you enjoy doing.

Speaker B: So thank you very much.

Speaker C: So that brings us to pretty much to the end. I've got a quick fire round of questions if you're ready for that.

Speaker D: Let's m. Do it.

Speaker C: One skill you wish you'd mastered earlier in your career.

Speaker D: Networking.

Speaker C: One habit that keeps you productive.

Speaker D: Morning walks.

Speaker C: Nice.

Speaker D: Night or day really depends on the activity. Day is for all the thinking and work related things. Night is for the recreational, uh, things. But day for work things.

Speaker C: Yeah. Good. Are you dream dinner guest dead or alive?

Speaker D: I think my dinner guest is currently alive and his name is Adam Levine.

Speaker C: Wonderful.

Speaker D: Because he's very attractive.

Speaker C: I hope your husband doesn't listen to this.

Speaker E: I've already told him.

Speaker D: No, no, no, he knows, he knows.

Speaker E: Oh, that's okay.

Speaker C: Brilliant.

Speaker E: That's all right. He's at the top of the list.

Speaker C: The last thing that made you laugh out loud, actually.

Speaker D: This is funny. This just happened this morning. So I, I was at this breakfast for CEOs in the D.C. area. It was about what changes should we expect now that Trump is in office again, right? So as you can imagine, people can talk for a really long time about the, about the changes. And it's this esteemed panel, right? So it's woman who's a senior government relations officer from credit card company, a guy who's like run a political consultancy that supports the Fortune 500. Like they're very esteemed. Anyway, so they open, they open it up to questions from the audience at the very end. And the last question that gets us is a guy who's like, look, what should we expect from the midterm elections, right? That'll happen in a year or so. And you know, one guy who's a

Speaker E: CNN correspondent on the panel, he responds,

Speaker D: he's like, let me give you the answer and blah, blah, blah about midterms,

Speaker E: whatever, the government relations and the credit card company.

Speaker D: She's like, I've been waiting for a question like this. And she's like, and when I have truly ponderous questions, such as the one that you've asked about what will happen to the midterm elections as a result of the Trump presidency, she's like, I like to take these ponderous questions to, uh, one truly reliable source. And she pulls out a Magic 8 ball.

Speaker E: You have the toy Magic 8 ball that you shaped.

Speaker C: That is brilliant.

Speaker E: Yeah, she had a, uh, Magic eight Ball. She's like, so let's ask the Magic eight Ball, what should we expect from the midterm? She shakes it and she goes, ask again later. That's what it says. Ask again later. And we all laughed because that is hilarious. And I was like, why am I

Speaker D: not using a Magic 8 ball in my job?

Speaker E: I should be prepared at all times.

Speaker C: I'm going on Amazon after this to order a Magic 8 ball.

Speaker E: It was great.

Speaker D: It was really great.

Speaker C: Anyway, what a brilliant way to finish off, uh, Kendra. It's been truly fun and engaging, and I've really enjoyed every minute. So thank you so much for coming on the podcast.

Speaker D: Thank you so much for doing this podcast and just creating the opportunity to have conversations like these. Christine, you're doing good work.

Speaker A: Thank you for listening to this episode of she says Unplugged. I hope it. It inspired you in your personal journey. If you enjoyed listening, please subscribe and share this episode with others. You can find out more about Shesas at our website, shesas.

Speaker D: Org.

Speaker A: You can also find us on LinkedIn.