
Celebrating Women in Trucking: 100 Years in the Driver’s Seat
In recognition of Women’s History Month, I thought it would be appropriate to celebrate the history and accomplishments of women in the trucking industry, including the many successful, woman-led moving and storage companies insured with our MOVER’S CHOICE program.
Women Take the Wheel
During World War I, women found themselves in the driver’s seat, filling in for male delivery drivers and movers who had been deployed overseas. Not only did they prove themselves as skilled drivers, many also became mechanics, dispatchers, and advocates for their presence in the industry.
Pioneering Women
One of the most notable names in the early history is Lillie Elizabeth Drennan. In 1928, she co-founded Drennan Truck Lines and became the first female trucking company owner in the United States. Lillie. Despite running her business with safety protocols and delivery efficiency at the forefront of the operation, the Texas Railroad Commission initially denied Lillie a commercial driving license. Cognizant of her own skills and abilities, she disputed their decision, and was eventually granted her license by the state of Texas, becoming the first commercially-licensed woman in the state of Texas.
“I know what it is to wade in mud above my boot tops to get my trucks through to their destination; I know what it is to sit behind the steering wheel of any truck for 48 hours without rest or sleep; I know what it is to have my truck break down on a lonely stretch on one of these cold Texas nights. I am no desk trucker.”
During World War II, Lillie was praised by the U.S. Army for her effort and success in recruiting female truck drivers. Nearly 100 years later, Lillie’s legacy still lives on, and she is considered to be one of the most iconic women in the industry.
Another important figure is Luella Bates, who first started as a mechanic and test driver in New York. Luella later worked as a commercial driver, and was actually the first commercially licensed woman in the United States. To encourage others to consider a career in the industry she went on a cross-country tour, using the tongue-in-cheek catch line that “the truck was so easy to steer, a woman could do it.”
Today’s Trailblazers
After decades of occupying more roles in our country’s economy, women are still in the minority of workers in the moving and trucking industry. As of 2024, women make up about 9.5% of all professional truck drivers, however 34.5% of company leadership roles are held by women.
One of our insureds, Dona Overstreet, president of Security Storage & Van Co. of Norfolk, Virginia, was kind enough to talk to me about her experience in the industry.
Dona has been in the moving and storage business for 24 years, taking on various responsibilities over the years – from dispatching, to warehouse work, to picking up and dropping off trucks at job sites. “We’ve never left a shipment behind, and I make sure everyone here is trained to perform multiple roles; there’s nothing I wouldn’t do myself. Success in this industry relies on being a team player.”
When thinking of her early career, she recalls several challenges that still exist today: a shortage of Class A CDL drivers, long hours, and unexpected delays. “It wasn’t uncommon to work until 9:00 or 10:00 p.m. because, in addition to the jobs we had planned, we also had to accommodate those that drivers couldn’t pick up on the required date.” Drivers for moving and storage operations have a number of responsibilities beyond driving; they also have to “inventory the shipment, load the trailer, and manage their teams,” she states.
Looking ahead to the future, Dona hopes to see better pay for Household Goods drivers to adequately compensate them for their many responsibilities. She would also like to see a more regular flow of customers throughout the calendar year, as currently “70% of our business is done in just four months. It’s tough on the industry when we have to hire so many seasonal employees during the summer.”
Dona’s work ethic, motivation, and enthusiasm for her work is what sets her apart as a modern trailblazer in the industry. “Despite the challenges, there’s nothing more rewarding than knowing we’ve helped a family with their move and taken care of the people who work for us. Having worked for two Fortune 500 companies, I can honestly say I wouldn’t trade the fulfillment I’ve experienced from this industry. The compliments we receive when we do a great job make it all worthwhile. I’m a people person and truly enjoy working with our crews and customers alike!”
Hearing Dona’s insights on the industry, and describing what it takes to lead a company to success, reminded me of Lillie Drennan’s story of perseverance and hard work. These are the stories of just a few powerful women in the industry; in the next 100 years, I look forward to seeing the percentage of women in the industry continue to increase, as more people learn how rewarding this line of work can be.
Sources
The History of Women in Trucking
Women’s History Month: Trailblazers in Trucking
Women Who Shaped The Trucking Industry
Today in Women’s Transportation History – 1928: The First Woman Commercial Truck Driver in Texas
Lillie Drennan – First Woman to Own a Trucking Firm in the US
Women In Trucking Association Releases 2024-25 WIT Index Data
Trucking With Confidence: Building a Trucking Career as a Female Driver

Gabby Boubonis
Senior Underwriter Gabby Boubonis is celebrating her ninth anniversary with Paul Hanson Partners and her seventh year with the MOVER’S CHOICE Program. In her role, she enjoys the challenges of solving problems and meeting the unique needs of her moving and storage customers. Gabby has a Bachelor of Arts in Anthropology and holds licenses in Accident & Health, Life and Property & Casualty.
In her spare time, in addition to being an avid Boston Red Sox fan, she enjoys arts and crafts, cooking and concerts.