Episode 203: Fleet Leader AMA: What Top Fleets Do Differently (Live from Connect 2025)

Episode Summary

In this special live panel episode of The Fleet Success Show, recorded at Connect 2025 in Las Vegas, award-winning fleet leaders Sara Burnam, Jesse Ostovich, Jake Johnson, and Chuck Cramer field unscripted questions from fleet managers around North America.

From winning “100 Best Fleets” to improving PM compliance and building data-driven fleet replacement plans, this no-holds-barred Q&A dives deep into the real-world challenges fleet leaders face—and what separates the great from the average.

You’ll learn how to convince senior leadership to invest in technician training, how to tackle resistance from departments that don’t bring vehicles in for service, and why stakeholder satisfaction should be your top KPI. Whether you're rebuilding your fleet program from scratch or trying to fine-tune a high-performing operation, this is a must-listen masterclass in practical fleet leadership.

Key Takeaways

• Data is your greatest weapon in making the case for better budgeting, replacement plans, and leadership buy-in.
• Training isn’t a cost—it’s an investment. Use outsourced costs and industry benchmarks to justify internal training programs.
• PM compliance is more than scheduling. It’s about communication, department accountability, and forecasting capacity.
• Celebrate wins publicly. Recognition, both big and small, drives team engagement and retention.
• Fleet success starts with ‘why.’ From SOPs to annual reports, know what matters and communicate it relentlessly.

Speaker Bios

Sara Burnam – 2023 Public Fleet Manager of the Year and veteran government fleet leader with 27+ years of experience. Known for her innovative approach to performance measurement and team culture.

Jesse Ostovich – Former RTA customer turned RTA team member, with 10+ years of fleet experience across government, private sector, and military operations. Passionate about technician training and operational excellence.

Jake Johnson – Heavy-duty commercial fleet expert with over 20 years in the industry. Known for leading complex system transitions and building high-performing teams from the ground up.

Chuck Cramer – RTA Fleet Consultant with deep experience in both dealership and private fleet environments. Focused on helping fleets use data to drive outcomes and build scalable processes.

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