In light of International Women’s Day on March 8, Automotive Fleet is recognizing the women who have shaped not only the fleet industry, but the workforce. 

Kathryn Schifferle, serial entrepreneur and fleet pro, shared her thoughts on the profession. 

Leadership Spotlight: Kathryn Schifferle

AF: What’s the biggest change you’ve seen in fleet over your career? 

Schifferle: I have had a very long career as an entrepreneur, and, of course, the biggest change has been in technology. Adopting and adapting is a very real challenge.

AF: What challenge shaped you most as a leader? 

Schifferle: At a previous company, I failed to foster the best culture, and when I started Work Truck Solutions in 2012, I made it my priority to build a collaborative, appreciative, hardworking, and iterative environment. This is the one thing, as a leader, that I am most proud of, and it has continued to shape me as the benefits of the culture accrue.

AF: What skill is most critical for fleet professionals today?

Schifferle: The ability to step back from the day-to-day and accept that reviewing new ideas and technologies is an important part of what makes a company resilient and successful.

When asked what advice she’d give to women in the industry, Schifferle’s answer was direct and effective. “Don’t be defensive,” she said. “Do be yourself.” 

Leadership Spotlight: Lori Olson

Lori Olson, the signature team lead at Geotab, is a strong, energetic, and leading figure in the fleet. Here’s what she had to say. 

AF: What’s the biggest change you’ve seen in fleet over your career? 

Olson: On a technical level, we’ve moved from basic tracking to a massive expansion of data-driven insights. We are entering an era where AI tools and autonomous agents aren't just 'features'—they are becoming our strategic partners. However, the most profound shift I’ve witnessed is human. 15 years ago, the landscape looked very different. Today, I am inspired by the sheer volume of women not just attending national conferences but leading the conversations. We are seeing women head up panels, drive diversity of thought within global organizations, and redefine what leadership looks like in the automotive industry. The 'room' has grown, and the quality of our collective innovation has grown with it.

AF: What challenge shaped you most as a leader? 

Olson: Several years ago, I faced a setback that felt like a dead end: I was denied a role I knew I was right for because the hiring team felt I was 'over-qualified.' I called my mentor in a state of shock, and she gave me the perspective and confidence I needed to reframe the value that I brought to the table. She challenged me to call them back, and, professionally and confidently, I re-stated why I was the right person to hire. They called the next day with an offer. That moment taught me two things: first, that you must believe in yourself because others—especially your mentors—already do. Second, never be afraid to stand up and speak your truth with confidence. A 'no' is sometimes an invitation to provide more clarity. 

AF: What skill is most critical for fleet professionals today? 

Olson: The ability to synthesize complexity into clear communication. With the deluge of data we face in this industry, the real skill lies in identifying the specific data points that matter most to each unique stakeholder. Beyond the numbers, you must be a collaborator. 

Modern fleet management is a team sport involving providers, peers, and internal stakeholders. Every person brings a unique value to the table; our job as leaders is to facilitate that dialogue and constantly make room for new thought leaders to contribute. If you can bridge the gap between high-tech data and human-centric collaboration, you’re future-proofed.

AF: What advice would you give women entering the industry? 

Olson: Be bold and be visible. The only person who can truly hold you back is you. My best piece of advice is to find someone you admire professionally and be intentional—request a monthly meeting, whether formal or informal. Finding mentors you respect is the single greatest catalyst for personal growth. Don’t wait for an invitation to lead; keep learning from others, push yourself toward the levels that scare you, and remember that your perspective is a necessary asset to this industry. The future of fleet isn't just driven by algorithms and AI; it’s driven by the humans who have the courage to interpret them. 

To the women entering this space: Don’t just look for a seat at the table—bring your own chair, bring your data, and never apologize for the experience that got you there.