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Meet a WEXER: Jason Simpson
Inside WEX

Meet a WEXer: Jason Simpson

September 22, 2020

Occasionally you might happen to come across someone from whom you have much to learn. Often when this happens it can be a matter of time and place and where you are in your life when you encounter that person which makes the moment just right for you to learn from them. Once in a great while, you meet someone with the kind of wisdom that is so rare it will be of value to anyone, anytime, anywhere. Most who have the fortune of spending time with Jason Simpson will soon become aware of the valuable lessons he has to share. 

Born and Raised in Nashville 

At eighteen, Jason Simpson could not wait to get out of Nashville, Tennessee, where he spent his early years. He left for college in Kentucky, studied meteorology, and was taken aback by the changes he saw in his hometown after he left. As Simpson puts it, “The economy was not very promising at the time, and I graduated from college on the front end of this renaissance that’s happened in Nashville over the last 15 years.” On trips to visit his family, Simpson watched Nashville grow into a place to which he could imagine returning. Today, he works in WEX’s Nashville office as a client relationship manager.  

Traveling as a Client Relationship Manager for WEX

As a client relationship manager for WEX, Simpson sells and manages Fleet cards and other WEX EFS programs and services nationwide to third parties.  And then those companies collaborate with WEX to create a shared brand to distribute these products and services to the third party’s customers.

Simpson especially loves the travel he gets to do working for WEX. “I like to see the country, and I like interacting with a multitude of different people, personalities, and nationalities.” As a client relationship manager, Simpson has gotten the chance to travel throughout the US, from Florida to California with many trips to other locales in between as well. Simpson has come to know a lot about our country’s distinct geography, cultures, climates, and cuisine.

Simpson has particularly fond memories of a 2014 work trip to New Orleans. At the time, he was managing a small team for WEX and was responsible for hosting a customer event called “Bayou Blast.” This event consisted of a fishing trip, orchestrated and led by Simpson, that took a group of WEX customers south of New Orleans and into the Bayou. Simpson describes, with particular appreciation, the view from the boat when they first got onboard at the landing spot: what he saw was a line of houses with canals separating them. Instead of streets between houses, there was water. One of the fishing guides, a local, told Simpson he owned a boat before he ever had a car because “around here you get around on a boat.” Instead of walking or driving in a car to visit a friend like most of us do, residents in this part of Louisiana hop in their boats to travel down the lake a little way to their neighbor’s house, dock the boat, get out on the dock, and walk inside for a visit. 

WEX Bayou Blast Canals

Houses On Canals at WEX’s Bayou Blast

During Bayou Blast, they were fishing for rainbow trout, redfish, and snapper. They would also catch the occasional catfish but they’d always throw those back. “One of the guides one time actually caught a small alligator – it was probably about three feet long so it was a baby but that was exciting and we would catch stingrays every once in a while as well.”

WEX Bayou Blast Fish

Trout, Catfish, And One Of Many Stingrays Caught At WEX’s Bayou Blast


WEX Bayou Blast Welcome Sign

Welcome Sign To WEX’s Bayou Blast

Most importantly, Bayou Blast served as an opportunity for Simpson and other WEXers to bond with their customers: “The Bayou Blast experience with the customers was great. There was “shop talk,” but it was the exception and not the rule. Deep discussions of hobbies and family were common, and then there were just times in which not much was said at all as we were at peace with nature and zoned in on fishing and simply enjoying the trip. Even though I don’t manage some of these companies any longer, they will still reach out to me from time to time to check in. And they always know that I can be contacted in those “in case of emergency, break glass” type situations. At the end of the day, these trips formed a special bond because of the quality time that was spent and the friendships that extended beyond business that were made.”

Simpson’s time spent traveling to visit customers and on extracurricular trips with customers illustrates the learning and adventure he’s been able to participate in as a WEXer, as well as the experiential and bond-forming outings client relationship managers enjoy with WEX customers company-wide. In addition to his time spent on Bayou Blast, Simpson mentioned customer trips to Casscoe, Arkansas for a “Sportsman Series” where they invite customers out to skeet and trap shoot on the first day and hunt pheasant and chukker the following two days. He also speaks with fondness of trips to Scottsdale, Arizona for trucking conferences where he was able to enjoy a climb with fellow WEXer Bill Cooper up Mount Camelback. Another favorite for Simpson has been his travels in Oregon including a scenic spot he loves in Coos Bay, Oregon.

WEX Sportsman Series Casscoe Arkansas

WEX Sportsman Series in Casscoe, Arkansas: The Hunters In Orange Posing Inside the Lodge

Thriving in Relationship Management as an Introvert

Whether it be during events like Bayou Blast, or in his visits to WEX partners around the country, Simpson enjoys engaging with the partners with whom he works. As he describes it, “It’s a different type of relationship than just going directly to a carrier, because you really have to develop a meaningful bond with that partner.” Simpson is a self-professed introvert, so his work with others, which can be quite social, has often been a surprising addition to his life. The relationships Simpson has formed with clients and the sensation of participating in the joint success that WEX and our partners have together is motivating and inspiring to him.

How to Manage a Team as An Introvert and Be Your Authentic Self

Simpson knew that going from account management to managing a team of people and becoming a representative to WEX’s clients would push him out of his comfort zone. It was important to him that whatever happened, and whatever way he had to adjust to make it work, he still needed to be true to his natural instincts and personality. “What I didn’t want to do was create a fake version of myself to fit the scenario that I found myself in – the trick was to find a way to still be me while being successful in my new role. I knew that if I could master that it would be something that I could continue to develop and refine versus something that was going to be a flash in the pan, work for a finite period of time, and then I’m stuck. And I think the most hurtful result would be for somebody to identify me as being inauthentic. Because then everything else I’m involved in would be questioned.” Simpson has worked hard to develop this more outgoing side of himself while always adhering to what feels right to him as an individual. The process is one of discovery and learning, even after years on the job.

Developing a Meaningful Bond with Customers is Key to Success

Being successful as a Customer Relationship Manager requires two things according to Simpson: first, you need to gain the customer’s confidence in WEX and secondly, you have to gain the customer’s confidence in you as an advisor. You are responsible for growing their card program and they need to be assured you are completely dedicated to that effort. “There’s never a day that is the same when I’m out in the field. I’m connecting and making these bonds with our partners and their sales teams. There are several places I visit around the country where I walk into their offices and I’m embraced as if I’m one of them. That’s pretty powerful.” 

Simpson explains that the trickiest aspects of forming a client relationship come at the beginning. “Going back to my comment about being an introvert, I am by no means a social butterfly by any stretch of the imagination. So the beginning of building a client relationship can be the most challenging for me.” He tries to find common bonds or shared interests to start a dialogue: “Frankly, I open myself up and as we find common ground, free-flowing conversation can take place. Being vulnerable to a point and allowing them to see me as an individual really helps the client understand that I’m being genuine with them. Long term this helps develop a foundation in which trust can be created.”

Science, Engineering, and Technology as Hobbies

It is fitting that a meteorology major would explore a love of science in his downtime. Simpson has had a long term love of cars. “I am just a big car nut all the way around. I always describe myself as a car nerd. I really kind of geek out about some of the engineering and technology and materials used on cars, and the different ways to extract performance out of a vehicle or the set-up of the vehicle. That’s fascinated me all my life.”

He is also interested in horology, which is the study and measurement of time. “I have an affinity for the science and engineering of things. Over the past five years or so I’ve really gotten into horology. I sometimes catch myself and have to laugh because I’m really fascinated by the inner workings of a wristwatch, for example. Just the idea that all these little gears and springs can be created to keep time and then the more sophisticated pieces are able to track a calendar year, or the moon. It’s amazing that with a bit of engineering and math we can develop little mechanical pieces that work off inertia to keep track of something that effectively we made up – the sense of time – but these devices we’ve invented can do so accurately over a long period of time.” Simpson’s interests while off the job are distinct from his work, a commonality among many WEXers, whose hobbies range widely from birding to motorsports to gaming.

Simpson is part of a local watch enthusiast group in Nashville that was formed a few years ago. Some of their founding members have a podcast and FaceBook page called Tenn & Two which is a treasure trove for a fanatic like Simpson. “I can be found regularly watching YouTube videos and listening to podcasts about horology for hours during my free time. My wife thinks I’m crazy.” And he has an extensive watch collection: “The inevitable question of  “Do you really need another watch?” comes up more times than I can count.”

A Mom Who Taught Optimism, Humility, and Work Ethic

Simpson’s parents divorced when he was eleven years old and his younger brother was five. He and his brother then lived with his mom and “she kind of just made a commitment to us that she was going to do her absolute best to make sure that nothing changed for us. We didn’t have to move, and we stayed in our same schools.” His mom worked at the post office and there were many years she had to work the third shift which was difficult for the family. But Simpson learned so much in those years, “She showed me the meaning of sacrifice, devotion, and grit. She was an example to us of being persistent about making sure those she really cared about and loved were taken care of. And the overall drive she exhibited and I learned from watching her continue every single day to make it happen was really just profound for me.” 

Simpson goes on to describe how his mom always had a positive outlook about life: “No matter how bleak things looked she always saw each phase in our lives as a season that we were all going through and that there would be another season to follow the season that we were in that would be brighter, that would be much more favorable. To this day when I’m feeling down I know, I can pick up the phone and call her and she will give me an alternate lens through which to see whatever situation I find myself in.” His mom taught him to keep things in perspective and look for opportunities in every difficulty and Simpson carries that advice with him.

WEXer Jason Simpson with his Mother

WEXer Jason Simpson with his Mother

Advice for His Younger Self

If Simpson were able to give advice to his 18-year-old self he’d tell him to “Find ways of being comfortable with being uncomfortable.” His natural bent is to be analytical and he can sometimes analyze a situation to a point of paralysis. In the past, that paralysis would extend into whatever it was he was struggling to accomplish, making it hard for him to take action. He was either too scared to fail or scared of what others might think of him. “You know hindsight’s always 20/20 but it took me years to be able to understand the importance of figuring out how to get out of my own way. To step out of my shell and just take risks.” 

Risk-Taking as Second Nature

Simpson had an epiphany one day when looking back at his life and analyzing the challenges he’d faced successfully. He saw that anytime he truly applied himself to whatever it was that he wanted to do he succeeded. If he could get beyond doubting himself and just get to work, he could accomplish almost anything he set his mind to. “I realized that if I applied myself I would eventually figure it out. It may not work out the first time around, and that’s okay. I’ve learned more from my failures than I’ve ever learned from my successes. When you fail you have to be courageous and say ‘Ok, yep, I took that womp on the head and now I know how to adjust and not make that same mistake again.’” Simpson advises having the confidence to be okay with failing. “Know that you are resilient and resourceful enough to push through to that point of success. Trust your instincts and allow yourself to say ‘Okay, I really don’t feel comfortable here but I’m going to keep pushing forward and see this through.’” 

At WEX Simpson has found a culture that fits with his life philosophy. In his career at the company, he has been encouraged to be bold and learn by doing. WEX promotes a culture of not being afraid to fail.  

Opportunity at WEX for Pushing the Envelope

Simpson started his career at WEX in SMB Fleet card sales and after having worked in that capacity for a while, he came to the point where he was ready to move on. He was contemplating leaving the company and one day had a chance encounter with a manager who asked him, unprovoked by Simpson, if he’d ever consider moving into an account management role. This would move him into the large fleet arena, which was a completely different animal and would require a fairly steep learning curve. This WEX manager, by suggesting the move to Simpson, not only saw potential in him, she was also willing to take a chance on him and was pushing him to take a chance on himself. 

Simpson experienced this same kind of propulsion years later when he was hired in his first management position for WEX. “Even applying for that role was very daunting for me at that time. And I’ll never forget it, during the interview process I was so scared, so nervous. I didn’t think I was going to get the job because the person I was up against had been in the industry for 15 years and had an abundance of experience. And then I was selected.” For Simpson this was a major confidence boost, and pushed him beyond his boundaries. WEX’s management was once again encouraging him to stretch himself.  

WEX Jason Simpson With His Team

WEX’s Jason Simpson With The Original Account Management Team He Managed For WEX

What Simpson did with that push is indicative of his character: “I’ll never forget the first team meeting I conducted. In the team of individuals I was leading at the time were all people I had worked with over the years so we were all familiar with one another. And in my first team meeting I told my team, I said ‘Look, I really don’t know what I’m doing but I’m just going to go off my instincts and we’re going to figure this out. And I’m not going to have all the right answers and sometimes I’m going to come to you all and say ‘what do you think?’ but we’ll figure this out together and I’m just going to keep faking it until I make it and make this work,’ and they kind of chuckled a bit. Over time I got into my stride and I got comfortable with it. Having that opportunity to go into management when I thought I wasn’t going to be the person selected was very meaningful to me. I didn’t have the experience, the time in the industry, nor the credentials – I think I was selected for the potential that I showed.”

Honesty, Openness, and Humility as a Leader 

The openness and humility Simpson displayed when facing his team for the first time is remarkable. He attributes that to his mother’s guidance. “My dad was very black and white. Very much a person of principle. Former farmer, former marine. He was very no-nonsense. So I have a lot of my father in my personality and I always say the part of me that I attribute to my mother is the part that rounds off the rough edges I get from my dad. Once I get confidence behind an idea I have I’m laser-focused on it and that comes from my dad. But yeah, those sweet spots are all my mom. She’s never met a stranger and she’s just very down-to-earth and she herself is very humble. She’s always just taught me ‘You are who you are.’ She would say, ‘We all wake up, get out of bed, put two feet on the ground, and start moving about our day the same way – just be your authentic self as much as you possibly can be.’”

Simpson’s lessons about living a full and meaningful life, about nurturing relationships, and about how to be an authentic person are timeless and invaluable. We are so lucky he contributes every day to WEX, as a company, and as a group of people working together and learning from each other.

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