Women have always had a place behind the wheel and in the industry, but getting recognized at the top hasn’t always come easy. The Women In Trucking Association (WIT) just announced four finalists for its 2025 Influential Woman in Trucking Award, and their work impacts drivers in real ways, from pay and safety to recruiting and representation.
The award, created in 2010 and sponsored this year by TrueBlue’s Centerline Drivers, honors women who are changing trucking through leadership, innovation, and advocacy.
WIT put it this way: “This year’s finalists represent a range of leadership roles across the industry who have made a measurable impact on their organizations and communities.”
The 2025 Finalists
Here are the four leaders being recognized:
- Cindy Ellers, chief customer officer at Fleetworthy
• Dee Dee Cox, vice president of human resources at Old Dominion Freight Line
• Katerina Jones, chief marketing officer at Fleet Advantage
• Leah Shaver, president and CEO of The National Transportation Institute
Cindy Ellers – Supporting Fleets and Standing Up for Women
Ellers oversees customer strategy and growth at Fleetworthy, a company focused on fleet safety, compliance, and toll management. Since joining in 2021, she has helped the company grow fast and manage several acquisitions without losing focus on service.
She has spent more than 15 years leading customer-facing teams and previously worked with compliance tech at RDC, which later became part of Moody’s Corp.
Ellers does not stop at operations. She also created Fleetworthy’s Diversity, Equity, and Inclusion committee and launched internal Women in Leadership panels to help women climb in an industry that is still mostly male. She is known for mentoring others and helping them build careers in transportation and logistics.
Dee Dee Cox – Building Careers from the Ground Up
With three decades in HR and leadership, Cox now leads human resources at Old Dominion. She manages everything from hiring and employee support to training and company culture.
She helped create and expand key programs that help people move up in the industry, including the Management Trainee Program, Supervisor Development Program, internships, and apprenticeships. Those efforts boosted retention and brought more women and underrepresented groups into trucking careers.
When she started, her HR team was one person. Now it is nearly 40 across the country. Cox also built a leadership curriculum that ties in Old Dominion’s core values, long-term vision, and family culture. Her work focuses on helping more people, especially women, see trucking as a place to grow.
Katerina Jones – Driving Growth and Safety Awareness
Jones brings over 20 years of experience in marketing and client relations. At Fleet Advantage, she helped turn the company into a billion-dollar brand and plays a direct role when new private and for-hire fleets come on board.
As part of the senior leadership team, she is involved in shaping operations, strategy, human resources, and company culture. She also acts as a safety liaison and leads demonstrations that show fleets how advanced safety tech can protect drivers.
Her work across the industry has earned her several awards, including “Top Woman to Watch in Transportation” from WIT and “Top Female Professional” from Supply Chain & Demand Chain Executive. Beyond her day job, she is active in charitable work and industry councils.
Leah Shaver – Championing Driver Pay and Retention
Shaver leads The National Transportation Institute, best known for tracking driver pay and helping carriers improve compensation and retention. Her work centers on turning data into real strategies that keep drivers in the industry.
With nearly 25 years in trucking, she has helped fleets address pay structure, driver career paths, and workforce planning. She is also active in efforts to bring more women and younger people into trucking.
Shaver served three terms on WIT’s Board of Directors, sits on the Next Generation in Trucking Association board, and contributes to several capacity and fleet advisory groups.
Drivers may also recognize her from SiriusXM’s Road Dog Trucking Radio, where she speaks directly with drivers about pay, policy, and industry changes. She is widely seen as a leading voice for driver engagement and career stability.
What’s Next
All four finalists will speak during a panel at the WIT Accelerate Conference and Expo in Dallas, Texas, taking place November 9 through 12. The winner will be announced after the discussion.
If you want to look back at who took home the award in 2024, WIT has that story available online.
Sources: WIT and The Trucker
