BY SUSAN ROSE
Cover Art: The Jax Black Car team at their new facility in downtown Jacksonville, Florida. Photography by Chris Weiss. It’s a few days after the CD/NLA Show in Orlando and Theresa and Kelly Callahan are playing catch up at work following the four-day event. Although it was a short trek down I-95 from Jacksonville for the chief administrative officer and vice president of operations (respectively), it’s never easy when one-half of the family-run Jax Black Car team is out of the office. Plus, the 11-vehicle company is busier than ever while handling a growing list of clients, settling into their new headquarters, and migrating their software to Santa Cruz—a big move for them.
“Richard and I always go to the shows, but we’re in and out,” says Theresa, referring to her husband, who is the president and co-founder of Jax Black Car. This time, he and their son, Fleet Manager Connor, held down the fort while the ladies headed south to network with affiliates and industry friends.
They returned just in time to celebrate Richard’s birthday—a milestone one at that—as the inevitable rumblings about potential retirement came up. But he had tried that once before, and it resulted in the couple launching Jax Black Car, partially out of boredom. He still loves the business and getting behind the wheel (he’s one of the company’s CDL drivers), so the idea of retirement is once again shelved. Road trips and European vacations are definitely on the short list though.
It’s been just 10 years since the Callahans opened Jax Black Car, and now the next generation is quickly becoming indispensable leaders within the company, enough to give Richard and Theresa a bit more freedom and time away from the business.
“Rich and I have two completely different management styles. And I am a get-it-done-right-the-first-time-because-I-told-you-to-do-it type of person. I’m direct. My husband, on the other hand, is more like a coach and allows Kelly and Connor to argue back, which, of course, drives me crazy. But his style has had an impact on them,” says Theresa.
Kelly and Connor have gravitated toward specific responsibilities within the business, where they can best showcase their natural strengths and make the greatest impact. Plus, being a second-generation leader in this industry is hardly rare, so they have plenty of up-and-coming peers in their own right to swap ideas with.
Front Row (L to R): Allyson Poe (Connor’s girlfriend), Fleet Manager Connor Callahan, Chief Administrative Officer Theresa Callahan, President Richard Callahan, Vice President of Operations Kelly Callahan, and Customer Service Manager Kristina Crumiel. Back Row (L to R): Chauffeurs Eddie Madden, Omar Crooke, Mike Mulqueen, Jethro Francois, and Ron Frisina. Kelly was first to join the company full time as affiliate manager, and spearheaded Jax’s national affiliate network expansion tremendously, but she had several years to branch out on her own and build a career beforehand. In her previous position, she was fast-tracked through management and was leading one of the region’s best-performing locations before deciding to tackle her next challenge.
“Leaving my previous job was a hard decision, but it was a necessary one since there was a lot of potential for Jax to grow and thrive,” says Kelly. “I can do a lot of the heavy lifting so that Theresa and Rich can work on the business while I work in the business.”
When times were difficult, Kelly fell back on her training as well as the sense of entrepreneurship that her parents had instilled in her—she can be blunt like her mom, but also mentor others like her dad. In fact, she’s always eager to share her own hard-earned experiences with new faces in the industry as much as she is a sponge soaking up knowledge from her established peers.
Kelly Callahan (left) and Kristina Crumiel at Jax Black Car’s new office “I learned so much in my previous position. I got to see behind the scenes what running a business is really like, including HR. I saw what not to do or how not to run a team. One of my biggest assets was empowering and building a team, and I was especially good at it that other managers would send me in to see what was happening in their own stores. I was able to tell someone that they suck at their job, but that they were important so they would want to stay, do better, and grow. I apply those same principles here because I firmly believe that employees don’t leave bad companies; they leave bad management,” says Kelly.
Kelly is the new vice president of operations, overseeing everything from reservations and affiliate relations to dispatch and fleet. With Richard and Theresa laying a solid foundation, Kelly carved a path for herself where she has catapulted Jax from a regional transportation service to a nationwide affiliate, magnifying the company’s profile on the national and even international stage in the process. She works closely with Richard, and together, they are a formidable team.
Connor is much newer to the company but has taken on the critical fleet management duties while also stepping in as a chauffeur—a role that made Richard somewhat of a local celebrity with his clients and Florida-based affiliates. As he’s growing into his position at Jax, his role is largely behind the scenes and often less visible than his big sister. Plus, their age gap of nearly a decade means that they are in different stages of their careers.
L to R: Connor Callahan, Omar Crooke, Mike Mulqueen, Jethro Francois, Ron Frisina, and Eddie Madden “Kelly and Connor are the exact opposite when it comes to personalities,” says Theresa. “Kelly is great at building relationships and managing the team. Connor is meticulous, he thinks everything through. He’s good with details, which is why he does well with our fleet, but he also makes sure that all the chauffeurs are on time. He’ll be out there at 5:00 a.m. scrubbing down a vehicle because it has to be perfect for a wedding that day, and he’s always thinking outside of the box, suggesting things we didn’t even think of. But they contribute equally in the sense they give the best of their individual talents.”
“Connor and I are polar opposites, but we complement each other. He does things better in some areas than I do, and I do things better than he does in another, but we have the same goals as a company and a family,” says Kelly.
As part of their aggressive growth strategy, Kelly insisted they migrate to Santa Cruz software to connect with larger clients on the network, although it was a considerable expense for Jax. Reducing errors and having seamless connectivity with affiliates are among the benefits, but when it comes to automation for their clients, they give thoughtful consideration to whether it will improve customer experience. As a boutique, high-end provider, they want their service to stand out for the right reasons.
“I think it’s really about bringing the human experience back and focusing on what we do that makes us different than other industries that offer transportation,” says Kelly. “Everyone [in the hospitality industry] is all about the technology, but you can have the best freaking app in the world and not have a relationship with your clients. If you are not able to connect with that other generation who needs that human touch, then who is this for? I love automation, and I think it’s amazing, but it should always be trying to make us better.”
Kelly may have her hands full at Jax, but she has also made it a point to become more visible in the industry. When she first joined Jax, she got involved with Driving Results’ Going Global group, which offered specific education and training to help affiliate managers expand their networks. Kelly was able to make many valuable contacts and learn more about the industry through the group as they met across the country several times a year.
The Callahan family at the EverBank Stadium (formerly known as TIAA Bank Stadium), the home of the Jacksonville Jaguars Lately, she’s been expanding into other roles like speaking on panels or moderating groups. She was invited to be a Mentor during the CD/NLA Show’s Operator Mentoring Program and stepped in to help moderate the Women in the Industry Networking Event. Over the summer, she also spearheaded a session at a regional association event. But don’t be surprised if you see her on a bigger stage someday.
“I’m goal oriented,” says Kelly. “If I can impact one person in the audience or offer them a piece of information that will help them look at something differently and in a positive light, then I’ve succeeded. I have some off-the-wall ideas that you wouldn’t even know make sense to do, but I am unbelievably comfortable speaking and teaching about that.”
“I wouldn’t bet against her being on a speaker tour eventually, whether it’s in this industry or not,” Theresa agrees, adding, “She’s also been opening new verticals for the company. She’s great at travel planning and events, and there are a lot of big events here in Jacksonville. We’ve become a destination, especially in the last three years, which is in part because our football team has gotten better. Plus, we have a ranked soccer team that’s going to be coming to our area, so it really is true that if you build it, they will come.”
The Jaguars doing well is certainly good for all local businesses including Jax. The AFC South franchise is currently ranked #1 in their division, and the team’s principal, Shad Khan, is investing heavily in the surrounding area. But he’s one of many who sees the potential for a revitalized downtown as numerous multimillion-dollar projects are in the works, from mixed-use buildings to commercial spaces to greenways to complement the city’s lush surroundings. Plans also include a renovation of the EverBank Stadium (formerly TIAA Bank Field) into the “Stadium of the Future,” with upscale hotel space to accompany it. Designs were unveiled earlier this summer and construction is expected to get underway in 2025, while the highly anticipated Four Seasons Hotel is projected to open in 2026. Jacksonville is transforming so quickly that it might be unrecognizable in just a decade.
Kelly Callahan in Jacksonville’s Phoenix Art District “It’s nice having successful sports teams in our city, and it’s especially good economically. They’re not kidding when they say billions of dollars will come to the region because of it. The outlook for this city is amazing. It’s very exciting,” says Theresa.
But it’s definitely more than just athletics or the center city rehab that’s keeping the Callahans on the go. About a year ago, the company moved into its new headquarters, a gem of a find located close to the stadium and downtown. Richard and Theresa had been searching for a while and were thrilled when they stumbled upon this listing in November 2022.
“The previous owner had just passed away, so they were looking to get out quickly to settle the estate,” she says. “He had totally rehabbed the inside, from floor to ceiling, and the HVAC is brand new, so we’re currently working on the exterior. We’re having the lot repaved and fixing the fencing. The building is small—about 1,000 square feet—but it’s beautiful, and it’s on a corner lot with parking for our fleet. We look at it as an investment in the company; it’s a great steppingstone for us.”
And you know what they say: Location is everything, and their downtown location is pure gold.
The Callahans are all in for Jacksonville, so much so that you’d think they’d lived here for generations rather than relocating from Chicago in 2010. More than just business owners, they have been highly involved in their local chambers of commerce and professional organizations to become a significant part of the community and share in its prosperity.
“I’m proud to be building our business in Jacksonville; I love being a part of this amazing community,” says Kelly. “I wanted to reinvest in my local relationships, which has been a challenge that I’ve taken on. So, we’re out there supporting the opening of new hospital wings and going to ribbon cuttings.”
For Richard and Theresa, seeing Kelly’s drive and Connor’s passion for their business and the industry has been a joy to witness, and they know that Kelly is in it for the long haul after the impact she’s had in just five years at Jax.
“It does sound like it all kind of fell together perfectly, but it never feels like it when you’re in the middle of it because a business is a lot of work. And we’re still doing it, so it must not be broken,” says Theresa. “Richard and I had a vision initially, but as things came together, we thought, this is something we should do for our kids. Kelly has shown that she has the drive and determination to be successful and help the company thrive. We broke the ice, but Kelly is diving right in.” [CD1123]