Geotab group at a tradeshow

From Operations Manager to the Fleet Hall of Fame

Published on November 29, 2023

A Reflection on My Career

Geotab group at a tradeshow

As I take a moment to reflect on the past 27 years in the transportation industry, I am drawn back to my early days when I was fresh out of university and was taking my first steps into the fleet world. It is sometimes hard to believe that a young twenty-something with only a few years of dealership experience would find herself as a fleet operations manager at a major university. Yet, it was that chance - the university having faith in me - that paved the way for my career in an industry that I have grown deeply passionate about.


My entry into the fleet was more than a job; it opened the door to a world where collaboration and community became two pillars of my success. My first manager instilled in me the importance of benchmarking, of comparing and contrasting our work with others to improve. He advised me to immerse myself in associations, to network, to learn and to grow alongside my peers. I took his advice and found myself in an ecosystem that was supportive and empowering. 


For example, in any other category, Wendy’s and McDonald’s are fierce competitors, but not in the fleet world. When I was the fleet manager for Wendy’s, I often collaborated with the fleet manager at McDonald’s, sharing insights to enhance safety and optimize operations. That’s the fleet industry at its core — an industry that transcends traditional boundaries and fosters an environment for shared success.


Yet, as I navigated the industry, I did so as one of the few women in a male-dominated field. It was a reality that never deterred me, thanks to the mentorship and support I received from day one. I was fortunate to collaborate with people who advocated for diversity and valued varied perspectives. Today, this advocacy has grown; formal groups and networks are in place to bolster women in fleet. It is essential that we continue to forge paths for young women, empowering their success and nurturing their contributions in an industry that flourishes with collaborative efforts and a wealth of different viewpoints.   


Since mentorship has been a cornerstone of my professional journey, I have developed a strong commitment to mentoring others. Paying it forward became a personal mantra. I was fortunate to receive guidance, to have doors opened for me, and to be taught, coached, and mentored by incredible people. It's this invaluable support system that I strive to recreate for the next generation, who are carving their path in fleet.


I often share the importance of being assertive and vocal about their goals with my mentees, particularly young women. In my early days, I mistook hard work for self-advocacy. It took time to realize that visibility and vocal presence were just as critical as performance. Encouraging emerging professionals to advocate for themselves and to be assertive and confident is a message I cannot emphasize enough. It's transformative when you speak up for what you want; it's when you truly begin to steer your own journey.


Reflecting on the industry today, I am pleased to see the strides we have made but equally aware of the road ahead. Serving on the board of the Hourglass Foundation,  which provides scholarships to young individuals in automotive trades, I've witnessed the persistent biases that still challenge women. But change is happening, and success is possible; with every scholarship and mentorship opportunity, we're driving toward a more inclusive industry.


Being inducted into the Fleet Hall of Fame is an honor I share with every individual who has been part of my journey. It is a testament not just to a personal career but to the spirit of an industry that thrives on collaboration, continuous innovation, and a collective drive for excellence.


As I look to the future, I see an industry that continues to evolve, embracing new technologies and facing challenges head-on. It's an industry ripe with opportunity for all people. I'm proud to be a part of this journey and even prouder to help shape a path for those who follow. Because when we drive forward together, there's no limit to how far we can go.


-Sherry Calkins, Vice President, Connected Car & Platform Solutions

Media Contact

Hanna Corrente

Manager, Strategic Communications & Public Affairs

About Geotab

Geotab is a global leader in connected transportation solutions. We provide telematics — vehicle and asset tracking — solutions to over 50,000 customers in 160 countries. For more than 20 years, we have invested in ground-breaking data research and innovation to enable partners and customers, including Fortune 500 and public sector organizations, to transform their fleets and operations. With over 4 million subscriptions and processing more than 75 billion data points a day, we help customers make better decisions, increase productivity, have safer fleets, and achieve their sustainability goals. Geotab’s open platform and Marketplace, offers hundreds of third-party solution options. Backed by a team of industry leading data scientists and AI experts, Geotab is unlocking the power of data to understand real-time and predictive analytics — solving for today’s challenges and tomorrow’s world. To learn more, visit, follow @GEOTAB on X and LinkedIn or visit the Geotab Blog.

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