![Erin celebrates building the fleet community with 50 episodes and 11K followers on LinkedIn [Podcast]](https://intellishift.com/wp-content/uploads/2025/03/gfx-STOF-ep-62-wif.png "Episode 50 Thumbnail")
In a recent episode of the Straight Talk on Fleet podcast, Erin Gilchrist, industry veteran and VP of Fleet Evangelism at IntelliShift, led an inspiring discussion for Women’s History Month. The episode featured a powerhouse panel of women in fleet who shared their journeys, challenges, and the lessons they’ve learned along the way, highlighting the importance of leadership, mentorship, and community in the industry.
How They Got Started in Fleet
Most fleet professionals don’t plan to enter the industry—it finds them. That was certainly the case for our guests, who entered the field from diverse backgrounds but found common ground in their passion for efficiency, safety, and leadership.
Sherry Calkins, SVP of Global Strategic Accounts at Geotab, started her career as a fleet administrator, unaware of what fleet management fully entailed. She quickly realized that leadership in fleet required more than just managing vehicles—it required understanding people, processes, and technology. “I had to earn the trust and respect of my team—many of whom were seasoned fleet professionals with years of experience,” she shared. “I quickly learned that I needed to learn from them first before I could lead.” Her career trajectory reflects the evolution of fleet management, where technology and data now play a critical role in decision-making and operations.
Similarly, Mikhaila Baldwin, Fleet Manager at CoolSys, discovered fleet management after working in logistics. She was persistent in pursuing the role, recognizing that her background in trucking and DOT regulations gave her a strong foundation. However, stepping into fleet management came with immediate challenges. “My third day in the position, we got notified we were having a DOT audit. Trial by fire—I learned so much in those first few weeks.” That early challenge not only tested her resilience but also set the tone for a career where adaptability and learning on the go are essential.
Laura Jozwiak, Chief Client Officer at Wheels, entered fleet through an administrative role before quickly moving into leadership. She credits her growth to the people who believed in her. “I had no experience in licensing and title, but someone said, ‘You can do this.’ That kind of encouragement makes all the difference.” Over time, she found herself at the forefront of shaping customer experiences and ensuring that fleet operations ran seamlessly. Her journey highlights the importance of advocacy and mentorship in career growth, particularly in industries where women are still underrepresented.
The Power of Mentorship and Community
One theme that resonated across the conversation was the strength of the fleet community. Initially, Mikhaila felt isolated in their roles. “I didn’t know this huge network existed. Once I found it, it reinvigorated why I love what I do.” The realization that fleet professionals thrive when they collaborate was a game-changer.
Sherry emphasized the importance of mentorship and industry engagement. “When I left Penn State and joined Wendy’s International, my best mentor was at McDonald’s. How crazy is that? This industry is so sharing and so giving of time and knowledge.” This spirit of collaboration, even among competitors, is what makes fleet management unique. The willingness to exchange best practices, share knowledge, and uplift peers fosters an environment where professionals can continuously learn and evolve.
Beyond formal mentorship, professional organizations and industry events provide valuable resources. “Fleet is unique in how collaborative it is,” Mikhaila noted. “You’re not alone. The support is there—you just have to seek it out.” Networking with other fleet professionals opens doors to new opportunities and helps individuals stay ahead of industry trends.
Overcoming Imposter Syndrome
Imposter syndrome is something many professionals face. It can manifest as self-doubt, hesitation in speaking up, or questioning one’s own expertise despite having extensive experience.
Mikhaila admitted, “Even sitting here on this panel, there’s a little voice telling me I’m not qualified. But I remind myself: that’s just a feeling, not reality.” Her approach to overcoming imposter syndrome includes reframing negative thoughts, focusing on facts over feelings, and leaning on her support system when doubts arise. She emphasized the importance of celebrating achievements, no matter how small, to build confidence over time.
Sherry added that early in her career, she struggled to assert herself in meetings. “A key lesson for me was to sit at the table—not just physically, but mentally. You belong in the room. Your voice matters.” Overcoming imposter syndrome often involves a mindset shift—recognizing that expertise is built through experience and that each person brings unique value to the table.
Laura reflected on the importance of trusting oneself. “I was given a seat at the executive table, and at first, I was told just to listen. But I realized—no, I was invited here for a reason. I have a perspective that matters.” Confidence isn’t about knowing everything; it’s about being willing to contribute, learn, and grow.
Advice for Women Entering Fleet
The panelists shared invaluable advice for young women considering a career in fleet:
- Find your people. “Build a network and lean on it,” said Laura. “Fleet is unique in how collaborative it is. There’s always someone willing to help.”
- Get involved. “Join professional organizations early,” Mikhaila advised. “The resources and support are invaluable. I wish I had done this sooner.”
- Push yourself. “Say yes to opportunities, even if you feel unqualified,” Sherry said. “You’ll figure it out along the way. Growth happens outside of your comfort zone.”
- Let go of self-doubt. “Mistakes happen. Learn from them, but don’t let them define you,” Laura added. “Success isn’t about never failing—it’s about always moving forward.”
Celebrating Women in Fleet
These women are breaking barriers and paving the way for the next generation of fleet professionals. Fleet isn’t just a career—it’s a community, one where women are making an incredible impact every day.
As Erin Gilchrist Rugg, VP of Fleet Evangelism at IntelliShift, closed the episode: “We belong here. We are powerhouse women in fleet.”
For those interested in joining the fleet industry, know this: you are not alone. The community is here, ready to lift you up. Let’s keep building it together.
