Driver turned shop owner embodies grit and independence

When Jennifer Wilson, co-owner and operations manager of Inland Empire Fleet Maintenance, first walked into the shop she and her husband owned in 2019, she had already been in the transportation industry for over a decade. After holding a bevy of positions, from driver to dispatcher to terminal manager, it was safe to say she’d already faced all kinds of challenges.

“I’ve been dealing with the ‘women have to do it twice as good to be equal to a man’ the whole time,” she noted at a conference panel discussing women in the heavy-duty repair industry in 2024. “No matter what it was, driving, turning wrenches, etc.”

“You have to prove yourself a little bit, but when you know your stuff, you know your stuff. It doesn’t matter who you are,” Wilson added. “You just have to be confident that you know what you’re doing and that you get it.”

But looking at the shop she and husband Steve Wilson built together, she knew she’d found her place and was determined to succeed, no matter what it took.

“It's just my own stubbornness of, ‘You know what? We're not going to fail at this,’” Wilson recalled later.

Luckily, the 51-year-old has practice handling the unexpected problems that pop up in commercial maintenance. She’s cultivated a cool head in crisis situations and while volunteering as a firefighter over the years. This grit and tenacity have seen her thrive in a field where only 10.4% of truck and tractor operators and 21.8% of transportation, storage, and distribution managers are women, according to the U.S. Bureau of Labor Statistics.

Women in Transportation 2025

For nearly a decade, FleetOwner has looked at ways to shine a light on how women are shaping the transportation industry in the 21st century. During Women's History Month, we'll be profiling six women building impressive careers in various trucking and maintenance fields, along with a Women In Transportation: By the Numbers.

As those stories roll out in March, we'll update this page with links.

From driver to owner

Wilson has certainly proven her expertise, starting from day one behind the wheel of a truck pulling refrigerated trailers across the country and Canada. She started driving professionally when she was 21, attending a neighbor’s truck-driving school after graduating high school in San Bernardino, California. Even as a new driver, she was dedicated to putting in the work so that she could finesse the 53-ft. trailers carrying food, chemicals, ice cream, and more on her own.

“Everything I do, I do with full intentions of doing it the right way the first time,” Wilson said. After driving with a trainer for a while, “I always worked on trying to do it better than the average person. I took to heart [being able to back] the truck up, putting those 53-ft. trailers in tight little spaces so I didn't have to rely on anybody else.”

After driving for eight years in one fleet, Wilson knew she was ready for the next step. She applied for a dispatch position at the same fleet. She found that learning the system used outside the truck instead of within was not tricky, so much so that her then-supervisor—her future husband Steve—claims she hip-checked him out of the way after about five minutes of training.

“I said, ‘I think I got this,’” Wilson laughed, “and he backed out of it, and that was the last training I had.”

However, the experience was even more valuable because it helped her learn the big picture of running a fleet. “It gave me a sense of what it's like to run a business,” she explained.

For a year, Wilson continued to work dispatch while taking on additional management responsibilities when Steve had to help out at another location. This led to her becoming terminal manager. However, when another company acquired the fleet where she started her career, Steve and many others were laid off.

“I think because they had me so much cheaper, they were going to have me do his position,” Wilson recalled. “So the day that they laid him off, I walked out with him.”

“By that time, we had become pretty close friends,” Wilson added. “A relationship grew after that.”

Even while employed as a dispatcher, Wilson has split her time between work and the San Bernardino County Fire Department since April 2018. She handles middle-of-the-night calls, rescues hikers, and checks out downed power lines. Wilson also helps with some maintenance tasks for the fire engines around the station, and after the fleet’s layoffs, she plays a more prominent role there, too.

While Wilson has stepped back from her volunteer firefighter work now, “I'm still pretty involved; I just don't actively respond to calls,” she explained. “But they’re still my firefighter family.”

After a few months of recuperating from the layoffs, the Wilsons found a truck repair dealership selling its territory and offering to help the buyers establish themselves. The opportunity allowed Wilson to flex the high-level business understanding she gained from working as dispatch and terminal manager but this time on her terms. So, the couple attended the training they needed, made a down payment, and got to work opening Inland Empire Fleet Maintenance.

The shop got its first customers in September 2019, and they were able to add another technician near the end of the year. Since then, the shop has only continued to grow, even through COVID-19, and in 2024, they moved to a bigger shop with 6,000 sq. ft. of repair space plus 3,000 sq. ft. of offices.

Nowadays, even when shop life is challenging, and Wilson has to contend with hiring difficulties and training, she relishes the independence she’s forged for herself.

“I probably could never work for another company again,” she said.