August 14, 2025

Mentoring Transportation’s Next Generation of Leaders

WeDriveU recently completed its second annual WINterns Program, hosted by our Women’s Inspiration Network (WIN) employee resource group and allies. The program offers college students and recent graduates a unique, hands-on opportunity to explore rewarding career paths within our business and industry.

WeDriveU 2025 WINterns program celebration in Hyde Park (Boston), MA: (l-r) Billy Shean, Courtney Damarell, WINtern Ethan Kita, Marcy Elliott. Image: WeDriveU

This spring, three exceptional interns joined our Customer Service Centers (CSCs) providing support to transportation programs for public and private sector customers in Charlotte, North Carolina; Hyde Park, Massachusetts; and Austin, Texas.

These accomplished interns rose to the top of a highly competitive pool of candidates vying for these coveted positions:

  • Jaiden Davis | Charlotte, NC – University of North Carolina at Charlotte Undergraduate Major: Finance with a Real Estate focus and minor in Spanish
  • Ethan Kita | Hyde Park, MA – Massachusetts Institute of Technology Graduate Major: Technology and Policy with a Transportation & Urban Mobility focus; California Polytechnic State University-San Luis Obispo Undergraduate Major: Computer Engineering with an Ethics & Public Policy minor
  • Linsy Josita Stephan Jeyaraj | Austin, TX – Texas A&M University, College of Engineering Undergraduate Major: Systems Engineering with a Project Management minor and Procurement & Consulting focus

The WeDriveU Jumpstart

During the six-week program, WINterns gain a unique, immersive experience by working across all functional departments. They receive hands-on training and mentorship from seasoned professionals who are passionate about sharing their expertise in public transit and private shuttle services that are key components in connecting communities, campuses, and workplaces.

The program culminates with a final project presentation, where interns showcase what they’ve learned and receive personalized guidance from their WINternship sponsors on potential career pathways beyond their academic studies. Throughout their time at WeDriveU, interns walk away with meaningful lessons and experiences that leave a lasting impact both personally and professionally.

Establishing Meaningful Connections to WeDriveU Values

WINtern Linsy Josita Stephan Jeyaraj joins WeDriveU’s Ubuntu ERG and Operations team at the 2025 Austin Juneteenth Parade. Image: WeDriveU

WeDriveU’s core values of Operational Excellence, Community, Teamwork, Sustainability, Innovation and Safety resonated with each of our WINterns. Through their projects, experiences at various CSC locations, and day-to-day engagement, WINterns encountered our core values in action. Among them, Jaiden, Ethan, and Linsy each discovered a significant connection to the value of Community, finding shared purpose and inspiration in how it shaped their experience at WeDriveU.

Jaiden developed a deepened sense of connection to our Community value by observing the strong bonds among staff and the seamless collaboration across teams. She also noted WeDriveU’s commitment to sustainability through improvements in public transit, and was especially impressed by the electric bus fleet.

For Ethan, his introduction to the value of Community came through engaging at gatherings such as cook-offs at WeDriveU’s Hyde Park and Quincy, MA locations. These foster meaningful interactions among drivers, office staff, and MBTA personnel, reinforcing the spirit of connection and camaraderie.

Linsy was especially drawn to Community through the teamwork she observed in both the yard and dispatch operations. One of the most eye-opening and heartwarming moments for her was witnessing the strong collaboration between management and dispatch teams during high-pressure situations and everyone’s willingness to help.

In addition, Linsy had the unique opportunity to participate in Austin’s Juneteenth Parade alongside WeDriveU’s Ubuntu ERG members and allies and local Operations team. She described it as an impactful and uplifting experience, sharing how inspiring it was to see “everyone come together on a hot day, marching up and down the hill, and passing out candy to the community. It was a good and inspirational experience overall.”

Making Connections: Where Classroom Learning Meets Real-World Experience

Jaiden never imagined the world of transportation could be so vast until her WINternship experience. Working at one of WeDriveU’s most significant operations in Charlotte, she encountered a special surprise during one of her favorite activities: collaborating with the unions. This experience connected back to a Business Law course she thoroughly enjoyed. She was excited to see the concepts she learned in class come to life during her internship.

“It was interesting to be here and observe the specific processes firsthand, along with how contracts are required to be followed,” she reflected.

WINternship Revelations: What They Didn’t Expect

WINterns arrived at WeDriveU with a mix of expectations and uncertainties. While some of their expectations were met, many were replaced by surprising discoveries. Jaiden, Ethan, and Linsy were particularly impressed by the complex operations that take place backstage at WeDriveU. They also learned about the stamina, coordination, and resilience required to succeed in transportation careers.

Each WINtern left with unexpected insights, shaped by their individual experiences. Although their lessons varied, all were equally enlightening and impactful, broadening their perspectives in ways they hadn’t anticipated.

As a young adult, Jaiden often rode the campus bus without giving much thought to what made the service possible. But her experience at WeDriveU offered an entirely new perspective.

WeDriveU’s Charlotte, NC Customer Service Center team (left to right): Elena Hopper: Director of Finance, Seyi Osiyemi:General Manager, Jaiden Davis:Intern, Beatrice Cutter:Director of Operations/Assistant General Manager, Stan Thomas: HR Manager. Image: WeDriveU

“I realized that there are so many moving parts to the transit industry. Seeing how they work interdependently was really surprising, and watching the numerous departments collaborate in different ways was truly eye-opening,” she added.

Her time at WeDriveU changed her understanding of transportation from viewing it as just a simple ride to recognizing it as a complex, coordinated system. She reflected on how some passengers rarely consider the intricate behind-the-scenes efforts required to ensure operational excellence and rider safety every day.

Ethan was intrigued by the wide range of contracts and services offered by WeDriveU, but it was the Corporate Shuttle service that especially captured his interest.

He said, “It just didn’t register with me that companies would outsource transportation operations. I had no idea there was such a strong need, or even a market, for this kind of service, until I got to WeDriveU.”

Ethan’s experience shed light on a lesser-known sector of the transportation industry. It broadened his understanding of how businesses rely on specialized mobility solutions to keep their operations running smoothly.

Linsy came into her WINternship expecting a more traditional office environment. Something resembling a scene from The Office, with employees stationed at desks in a centralized space, and her rotating physically between departments. Instead, she was pleasantly surprised by the dynamic and fast-paced nature of WeDriveU’s work environment.

“Everyone was on their feet, constantly moving and adapting to real-time changes,” she said.

WeDriveU 2025 WINtern program at WeDriveU’s Austin, TX Customer Service Center: Keyshana Jackson (General Manager) and Linsy Josita Stephan Jeyaraj (Intern). Image: WeDriveU

She was also struck by the integration of technology, especially the use of virtual meetings that connected her with team members located across the country. These unexpected elements not only challenged her assumptions but also energized her, reinforcing her desire to be in a career that’s active, engaging, and far from sedentary.

The Butterfly Effect

We’re all part of the transportation ecosystem, and WeDriveU’s company values and culture reflect that even the smallest actions can create far-reaching, meaningful impacts.

2025 WeDriveU WINterns program Charlotte, NC

WeDriveU 2025 WINterns program in Charlotte, NC supporting CATS: General Manager Seyi Osiyemi with WINtern Jaiden Davis

Jaiden shared, “I love that something small can change our lives. Transit is a great space for that to happen. You meet so many people, sometimes the same people, and over time, you start to make connections. It’s amazing how it becomes a sense of community. You start looking forward to seeing certain people on the bus or shuttle in the morning. And during your journey, you can meet someone completely new. Meeting someone on the bus can change your life. I love the butterfly effect.”

Her insight captures the profound human potential embedded in everyday moments of transit where chance encounters and daily rituals can blossom into connection, meaning, and change.

The WINternship program complements a range of efforts at WeDriveU to promote career pathways across our company and the transportation industry. Our team members enjoy supporting career days with local school districts, and supporting scholarships through industry partners such as the North American Transit Alliance (NATA) and Latinos In Transit.

New Transportation Career Paths Take Flight

We are thrilled this year’s WINterns have been part of our team leading shared mobility solutions that move communities, campuses, and workplaces, and connect people to the places and moments that matter most.

Congratulations, Jaiden, Ethan, and Linsy, on embracing your WeDriveU journey!

Would you like to experience invigorating careers at WeDriveU? Check out all the places we’re hiring across the U.S.

Special thanks to Marketing content writer Linda Berretta for contributing this piece for our blog.

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