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From Administrative Assistant to UPS Feeder Driver: Esther Parsons' CDL-A Journey

How a former office worker earned her CDL-A to support her family, built a career with Yellow and UPS, and now mentors the next generation of women in trucking.

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MIDDLETOWN, Pa. — In 2017, Esther Parsons traded 15 years behind an administrative desk in the lawn care sector for the driver's seat of an 18-wheeler, earning her CDL-A to financially support her two college-bound children. That career pivot launched a remarkable trajectory through the heavy-duty freight industry, taking her from local student to a five-year stint as a linehaul driver for the now-defunct Yellow Freight and eventually to her current role as a Feeder Driver for UPS at the Eastern Zone Regional Hub in Middletown, Pennsylvania.

Parsons did not make the leap alone. A close friend and industry mentor spent six months providing the practical insights and confidence she needed before she enrolled in truck driving school. That mentorship demystified industry terminology, answering foundational questions about operations like drop-and-hook freight. Her education paid off immediately when she outperformed her mentor on school exams, proving her readiness for heavy-duty commercial driving.

Her introduction to the wider industry expanded rapidly after graduation through Women In Trucking. Ellen Voie, founder of the organization, connected Parsons with a reporter on her birthday, setting the stage for her involvement with Yellow Corp. as a sponsored attendee at the Accelerate! Conference & Expo. That exposure led her to join the Image Team, serve on the Women’s Inclusion Network Employee Resource Group, and work as a professional driver trainer before transitioning to UPS in May 2023.

What This Means for Drivers

Parsons' trajectory demonstrates the viability of second-career transitions for individuals seeking stable employment in the transportation sector. Her path highlights the critical value of structured mentorship programs, such as the WIT Mentor Match initiative where she now volunteers to guide newcomers through their initial years on the road. For CDL-A holders and aspiring drivers navigating complex carrier operations, finding experienced guidance remains a proven strategy for long-term retention and success. Commercial carriers increasingly rely on internal employee resource groups and mentorship frameworks to support driver development and reduce turnover across linehaul and feeder divisions.

Industry Reaction

Advocacy groups continue to push for expanded representation across commercial fleets, recognizing that intentional recruitment and peer support are essential for onboarding new talent. Recognition programs, such as Women In Trucking naming Parsons one of the Top Women to Watch in Transportation in 2023, underscore the growing visibility of professional drivers who also serve as public ambassadors for the trade. Industry leaders frequently point to outreach efforts—ranging from classroom pen-pal initiatives like Trucker Buddy International to high-profile media appearances—as vital tools for shifting public perception and attracting dedicated operators to trucking companies hiring today.

Key Points

  • Esther Parsons transitioned from a 15-year administrative career to commercial truck driving in 2017 to fund her children's college education.
  • She spent five years as a linehaul driver for Yellow Freight before joining UPS in May 2023 as a Feeder Driver in Middletown, Pennsylvania.
  • She was named one of Women In Trucking's Top Women to Watch in Transportation in 2023 and serves on the organization's Mentor Match program.
  • Parsons is actively involved with Trucker Buddy International, connecting professional drivers with school classrooms as a pen-pal.

Looking for a better trucking job? US Trucker's free job-matching service connects CDL-A drivers, OTR drivers, regional drivers, and owner-operators with 500+ top US carriers. Leave your details in the form on this page and a recruiter will call you within one business day. Trucking companies are hiring now.

Photo by Wahyu on Pexels

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Dave Kowalski
Owner-operator and industry commentator. Runs his own flatbed operation out of Ohio.