Key takeaways
- Samantha Thompson transitioned from a creative arts background to become a key leader in transportation technology at Penske.
- She spearheaded innovative projects like Catalyst AI, enabling fleet benchmarking and data-driven decision-making.
- Thompson emphasizes the importance of mentorship, diversity, and inclusion for women in the transportation industry.
For over a decade, FleetOwner has looked at ways to shine a light on how women are shaping the transportation industry in the 21st century. This year, the team profiled six women from different parts of the industry, showcasing their accomplishments and how they have overcome. You can view all six profiles here.
Samantha “Sam” Thompson, VP of telematics and customer success for Penske Transportation Solutions, is a multitalented leader. Her interests span the academic spectrum, from artistry to technology, which helped guide her to the position she has today. While she noted her journey into transportation was a surprise, it wasn’t one she’d change, as now she applies her creativity and connections with others to pushing Penske, and the trucking industry, into the future.
Thompson started her journey in art and design, where she taught, worked in photography studios and print shops, and freelanced. But when she wanted a career that paid enough to “eat, pay bills, and maybe travel a bit,” Penske was her opportunity.
“I didn't think about transportation specifically as a career,” Thompson laughed. “I genuinely didn't have any idea that people actually went to school to get degrees in transportation, logistics, and what have you. That was shocking to me. Once I joined Penske, I said, ‘Oh my goodness, the rest of you didn't end up here by accident, like me?’”
But while this career juncture was a surprise, the company itself was not. Thompson hails from Reading, Pennsylvania, where Penske is headquartered.
“Penske has always been well known as a place to get a really good job or even start and build a career,” Thompson noted. And the company served the same purpose for her after her starving artist days.
Thompson began her journey with Penske as a rental clerk in 2012. She soaked up as much information as she could about the business and the transportation industry, but she also didn’t forget her creative roots.
“I did have that ambition to do something creative,” Thompson recalled. “So the first opportunity that I saw open up in the marketing department, I took it, and I thought, ‘This is another opportunity for me to learn more and maybe move into a creative space.’”
This is how Thompson joined what she called a “small but mighty technology team … where they were tinkering with what's next for Penske and technology.”
Thompson now leads this team as VP of telematics and customer success, where the group helps develop technology to make fleet operations easier.
“A lot of the things that we're doing are forward-looking or innovative,” Thompson explained. “So one of the greatest challenges, and something that we’re still trying to overcome today, is walking that fine line between practical innovation and thought leadership.”
Walking this line is what helped Thompson’s team release Catalyst AI in 2025, a program that allows users to compare their metrics, like maintenance, fuel efficiency, and fleet utilization, to similar fleets. The input for the program is collected from the logistics and maintenance provider’s fleet data from over the years, and it is entirely anonymized.
“It's us reimagining how we can offer prescriptive benchmarking to a fleet so they really have that outside-in view of how they're performing relative to similar fleets, versus just their own internal performance over time,” Thompson explained.
Mentorship and the female workforce at Penske
But while her team’s technological success is something she’s proud of, Thompson counted “one of the greatest privileges and honors of [her] career” is leading and developing her team.
For Thompson, mentorship is a mutual investment and effort from leadership and mentees.
“[In] my team, we have an inter-team mentorship for newer associates, and then, as they stand up on their Bambi legs and they get off into the world and start doing things, we get them more professional development mentors that have experience in spaces where they have opportunities for improvement,” she explained.
This kind of investment prepares them for future opportunities, just as Thompson’s mentors, Ann Walsh, SVP of Penske Digital, and Sherry Sanger, Penske’s EVP of strategy and marketing, helped prepare her. Together, the two women helped Thompson take on more responsibility and focus on organizational strategy.
Having this female leadership in a male-dominated industry is very helpful, Thompson believes. She also credited her success to Penske’s investment in making sure women have the chance “to seize the same opportunities as our male counterparts.”
This inclusivity doesn’t just come from Penske’s female leadership. Thompson remembered Art Vallely, who led the rental product line when Thompson worked as a rental clerk, and is now the current president of Penske Truck Leasing. Valley spoke passionately about getting women into the field program and the management trainee program.
“He was pretty adamant that we need the best talent, and that couldn't just be from men,” Thompson recalled. “I very much remembered that, and still hold on to that. To this day, I have never heard a leader speak so passionately or dynamically about the importance of including women in your organization.”
It was after this that Thompson went on to join the marketing and strategy team “led by these powerhouse female leaders,” Walsh and Sanger, which “changed my perspective and my life quite a bit,” she explained.
Now, Thompson is a powerhouse leader herself and is looking forward to seeing how greater technology implementation will impact the industry, from smart trailers to SaaS platforms and AI.
“With technology being more affordable and accessible to fleets of all sizes today, I think we're just starting to scratch the surface of what's possible if more fleets adopt this technology,” she said.
And, of course, Thompson also noted that she hopes to see more women in the industry. “I think that would be impactful," she said.
For women looking to join her in the industry, she advises that they “show up and take up space, sis. The industry needs you, full stop.”
About the Author
Alex Keenan
Alex Keenan has been associate editor for Endeavor's Commercial Vehicle Group, which includes FleetOwner magazine, since 2022. She has written on a variety of topics for the past several years and recently joined the transportation industry, reviewing content covering technician challenges and breaking industry news. She holds a bachelor's degree in English from Colorado State University in Fort Collins, Colorado.