ABOUT THIS EPISODE
Sherry Calkins is a recognized leader in the fleet industry with nearly three decades of experience across government and private-sector fleet operations before moving into technology leadership at Geotab. She is a prominent voice in connected mobility, fleet data, AI, and strategic partnerships, has served on numerous industry boards, and was inducted into the Automotive Fleet Hall of Fame.
Here's a glimpse of what you'll learn:
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[1:41] How Sherry accidentally fell into fleet — and turned an operations manager role into nearly three decades in the industry
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[3:11] Why fleet has evolved from a cost center into a strategic asset, and how technology changed the role of the fleet manager
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[6:54] How globalization, technology, and industry collaboration are changing the fleet community
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[8:30] The mentorship advice that shaped Sherry's career — and why she still believes nobody is too experienced to learn
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[11:41] How data is helping fleets lead with evidence instead of assumptions
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[12:06] Why AI could change the way fleet professionals work with data — without replacing the human element
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[17:27] What tomorrow's fleet leader will need to know about AI, data, and technology
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[24:37] Why the vehicles of the future could become purpose-built platforms for individual fleet operations
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[27:29] How technology, automation, and AI are changing fleet maintenance and vehicle operations
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[28:56] The biggest challenge in fleet safety: changing driver mindset and behavior
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[29:19] What telematics can tell you, and what video intelligence reveals that data alone cannot
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[30:40] Why positive reinforcement and recognition can be more effective than punishment when coaching drivers
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[37:29] Why Sherry says the industry needs to move faster — and what success looks like to her today
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[38:24] Her advice for the next generation: have a voice, believe in yourself, and build your network
In this episode…
Fleet used to mean spreadsheets, service intervals, and a manager who had to know every diagnostic code by heart. Sherry Calkins joins Road Rageous to explain how that world gave way to one driven by AI, video intelligence, and connected vehicles — and why, even with all that technology, the hardest problem in fleet is still the same one it's always been: changing driver behavior.
Key Takeaways
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Fleet has shifted from a cost center to a strategic business asset.
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AI reduces data overload and helps fleet professionals act on insight instead of drowning in dashboards.
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Video intelligence reveals context telematics data alone can miss — including seatbelt compliance and true root causes of harsh events.
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Positive reinforcement tends to change driver behavior more effectively than punishment.
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A strong professional network is one of the fleet industry's most valuable resources for learning and staying current.
Resources Mentioned
