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Wit Kendra Tucker

Truckstop CEO finds her fit

Aug. 26, 2022
Kendra Tucker, who joined in 2020, brings 15 years of software expertise to the trucking industry.

Kendra Tucker got into trucking by chance. After working at software companies for 15 years, she was looking for a change, but she had three criteria for her next move.

The first was around company culture. Tucker was looking for a company that emphasized business and financial success, but not at the expense of its workforce. She also wanted to know she was with a company that built technology products to help people in their industry succeed. Third, she sought a company that demonstrated a strong product market fit and need.

Truckstop checked all three of those boxes really well,” Tucker said. “From the first interaction I had with the executive team here, they just exuded integrity. The culture was just palpable based on the few conversations that I had and the more that I got into it, I just appreciated it.”

“Transportation as an industry is different than other industries I’ve served,” she added. “I love the complexity of it. I love that mission-critical nature of it.”

Tucker joined in 2020 as chief revenue officer. In 2021, she was appointed chief operating officer, and just this year, Tucker took on the role of CEO, succeeding Paris Cole, who retired from his long-term position as CEO in April.

See also: Women in Transportation 2022: Trailblazers in trucking

“I was both honored and humbled to move into that position,” Tucker explained. “Truckstop has been around for 27 years. To follow our first two CEOs, I am honored to carry the baton forward.”

“There is a lot of responsibility that comes with running a company the size of Truckstop as well as with the growth opportunities we’ve got," she added. "We have so many opportunities ahead of us as a company—so many so that Paris Cole and I have talked about figuring out which opportunities to pursue, which is a fortunate position to be in.”

Tucker’s vision for the company is to continue that growth path. Over the last five years, Truckstop has multiplied in size as a software provider, offering additional automated services on top of freight-matching capabilities. When Truckstop got its start in the industry more than two decades ago, it was the first company to put a load board on the internet, Tucker said. The company was initially called Internet Truckstop.

Tucker is focused on leveraging the company’s roots in innovation to continue helping trucking companies streamline efficiencies.

“Right now, there are so many automated and disconnected processes that whether you are on the carrier side or the broker side, sometimes you’re trying to connect systems manually,” she said.

“At the same time as we have grown the business, more opportunities continue to illuminate,” Tucker added. “There are still parts of the industry on the trucking side that don’t use us. That’s a big opportunity for us that we will pursue quite a bit this year and into the next three years or so.”

From her start working as an individual contributor in software to her more recent leadership roles, Tucker has had to learn how to put the needs of her team and the entire organization ahead of her own personal successes.

“I remember getting a lot of coaching and feedback as I went through that process, some of which I sought and some of which was proactively given to me because I wasn’t doing it right,” she said with a laugh. “That was a good learning experience, and it was humbling because I knew way less than I thought I did. I had a lot to learn from other people.”

Another major learning experience happened when she became a working mom.

“That is hard,” Tucker emphasized. “It is the pinnacle of multitasking—being able to manage and care for a newborn while simultaneously making really tough business decisions."

“I feel like it rounded me out more. I am so driven as a professional that having a child added balance. Being able to have both at the same time required a lot of flexing, introspection, and constant and continuous reflection on whether I am doing it right. Probably not, but we’re making it,” she quipped.

At the end of the day, what Tucker finds most appealing about the industry is that it is the heart of America. Moving ahead in her role as Truckstop CEO, Tucker takes to heart some advice she was given when she first joined the industry.

“Transportation is an industry that rewards the ‘good guys,’” she said. “Because transportation does recognize the heart and the intent of the actors within it, being authentic matters more in this industry than any other industry that I have been part of. My advice is to bring your authentic self to work every day because you will be rewarded for it.”

About the Author

Cristina Commendatore

Cristina Commendatore was previously the Editor-in-chief of FleetOwner magazine. She reported on the transportation industry since 2015, covering topics such as business operational challenges, driver and technician shortages, truck safety, and new vehicle technologies. She holds a master’s degree in journalism from Quinnipiac University in Hamden, Connecticut.

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