This is Roadrageous, the podcast for safer drivers, smarter training, and bold ideas. Featuring innovators and thought leaders from the driver training industry, we're here to inspire and educate.
Knowing the risk is not the same as learning to control it
Fleets have more information about risk than ever before. Telematics, camera systems and claims data can reveal patterns that were once difficult to see. But identifying a risk is only the beginning. The real challenge is turning that information into action and building the habits and processes that make improvement last.
In this episode of RoadRageous, host Chad Lindholm speaks with Dave Strickland, Vice President and Head of Casualty Risk Engineering at Zurich Resilience Solutions. Drawing on nearly four decades in risk engineering and insurance, Dave explains why effective safety management requires more than technology or compliance. Organizations need clear priorities, documented processes, sustained behavior change and the right people involved in making improvements.
Here's a glimpse of what you'll learn
11:45 — Why organizations may want to become proactive about safety but need help determining how to begin.
14:28 — How to turn telematics data into useful insight instead of becoming overwhelmed by information.
17:29 — Why identifying a risk creates a responsibility to respond.
24:09 — Why compliance is a baseline rather than the ultimate standard for managing risk.
44:48 — How technology and AI can create more room for human judgment and connection.
46:43 — Why risk engineering works best as a collaborative, ongoing partnership.
54:49 — How external expertise can help organizations advance and validate safety initiatives.
In this episode
Dave and Chad discuss the changing risk environment facing fleets, the growing importance of managing both the frequency and severity of losses, and the challenges organizations face when they have more safety data than they can effectively use. They explore why one-time training and short-term improvements may not lead to lasting behavior change, how structured and documented processes can help organizations respond to known risks, and why technology is most valuable when it supports not replaces human interaction. The conversation also examines the role of insurers and risk engineering partners in helping organizations prioritize improvements, learn from industry experience and build more sustainable safety practices.
Key takeaways
Information must lead to action. Data is valuable when it helps organizations make better decisions and address identified risks.
Compliance is not the finish line. Effective programs need processes that are implemented, documented and reviewed.
Lasting improvement requires reinforcement. A training event may create an initial change, but sustaining it takes ongoing attention.
Technology should support people. Data and AI can help focus efforts, while judgment, empathy and communication remain essential.
Partnership can accelerate progress. External expertise and industry benchmarking can help organizations find practical ways to improve.
Resources and topics mentioned
Zurich Resilience Solutions
Telematics and camera data
Claims and loss analysis
Industry benchmarking and risk engineering
Dave Strickland on LinkedIn
Chad Lindholm on LinkedIn
SPIDER Driver Training by IMPROV Learning
Listen to the full conversation with Dave Strickland on RoadRageous for a deeper look at how fleets can move from identifying risk to managing it more effectively.
6 Oct 2026
What It Really Means to Be a "Chaos Controller" in Fleet
Fleet operations rarely go as planned. Vehicles break down, priorities shift, emergencies arise, and new information can quickly change decisions.
Desiree Taylor, Fleet Administrator at the California Governor's Office of Emergency Services, joins Chad Lindholm on Road Rageous to discuss how to manage this uncertainty. She explains that effective fleet leaders oversee not only vehicles, but also people, priorities, risk, and change.
Here's a glimpse of what you'll learn:
[1:24] How Desiree unexpectedly found her way into fleet
[4:19] Why persistence, training, and NAFA helped shape her career
[6:08] Why she describes herself as a "chaos controller"
[8:16] How fleet professionals prioritize when everything seems urgent
[10:15] Why preventive maintenance is essential to staying ahead of reactive problems
[13:24] How telematics and video have changed fleet decision-making
[18:37] Why driver safety requires more than one-time training
[21:38] What fleets should do when technology reveals unsafe driver behavior
[22:18] How professional networks and continuous learning support fleet leaders
[31:50] Why fleet is far more important to business operations than many organizations realize
[33:05] The advice that shaped Desiree's approach to fleet leadership
[34:18] Why trusting yourself and persevering still matter
In this episode…
Taylor describes fleet as a dynamic environment where constant movement and attention are required. The discussion covers preventive maintenance, emergency response, driver training, telematics, AI, and professional development, highlighting how leaders anticipate issues and respond to the unexpected. The central message is clear: technology improves visibility, but people must decide how to act on the information they receive.
Key takeaways
Fleet leadership requires constant prioritization and adaptability.
Preventive maintenance can reduce the need for reactive problem-solving.
Telematics and video provide valuable visibility into vehicles and driver behavior.
Driver training should be reinforced continuously rather than treated as a one-time event.
Technology does not replace human judgment or the need for meaningful coaching.
Fleet is a critical part of operational performance, not simply a function that manages vehicles.
Professional networks and ongoing education help fleet leaders adapt to change.
Sometimes the most important leadership skill is trusting your judgment and persevering.
Resources Mentioned
Chad Lindholm on LinkedIn
Desiree Taylor on LinkedIn
NAFA Fleet Management Association (https://www.nafa.org/)
IMPROVLearning
Listen to the full conversation for more insights from Desiree Taylor on managing fleet operations, safety, technology, and ongoing uncertainty.
28 Aug 2026
When Fleet Stopped Being Just a Cost Center: The Technology, People, and Decisions Shaping What Comes Next
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:
[1:41] How Sherry accidentally fell into fleet — and turned an operations manager role into nearly three decades in the industry
[3:11] Why fleet has evolved from a cost center into a strategic asset, and how technology changed the role of the fleet manager
[6:54] How globalization, technology, and industry collaboration are changing the fleet community
[8:30] The mentorship advice that shaped Sherry's career — and why she still believes nobody is too experienced to learn
[11:41] How data is helping fleets lead with evidence instead of assumptions
[12:06] Why AI could change the way fleet professionals work with data — without replacing the human element
[17:27] What tomorrow's fleet leader will need to know about AI, data, and technology
[24:37] Why the vehicles of the future could become purpose-built platforms for individual fleet operations
[27:29] How technology, automation, and AI are changing fleet maintenance and vehicle operations
[28:56] The biggest challenge in fleet safety: changing driver mindset and behavior
[29:19] What telematics can tell you, and what video intelligence reveals that data alone cannot
[30:40] Why positive reinforcement and recognition can be more effective than punishment when coaching drivers
[37:29] Why Sherry says the industry needs to move faster — and what success looks like to her today
[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
Fleet has shifted from a cost center to a strategic business asset.
AI reduces data overload and helps fleet professionals act on insight instead of drowning in dashboards.
Video intelligence reveals context telematics data alone can miss — including seatbelt compliance and true root causes of harsh events.
Positive reinforcement tends to change driver behavior more effectively than punishment.
A strong professional network is one of the fleet industry's most valuable resources for learning and staying current.
Resources Mentioned
Chad Lindholm on LinkedIn
Sherry Calkins on LinkedIn
Geotab on LinkedIn
SPIDER Driver Training by IMPROV Learning
Who has been a guest on Roadrageous
Names identified in recent episode analyses. Showing up to five guests.
Eric Winterset
Nancy Bendixson
Phil Kozdemba
Emily Garza
Rob Matthews
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Apple Podcasts (US)
5.0 / 5
1 ratings
Spotify
5.0 / 5
2 ratings
Podcast Authority Score: 45 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
77
Social presence
0
YouTube
0
Engagement
32
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Questions about Roadrageous
Who hosts Roadrageous?
Chad Lindholm and Liam Hoch host the show. Published by IMPROVLearning.
How often do new episodes come out?
The show publishes bi-weekly, based on its RSS feed.
Does Roadrageous take guests?
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