Mile Marker 25 – Taming Truck Insurance with Jared Sweeney (Cottingham & Butler)
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Mile Marker 25 – Taming Truck Insurance with Jared Sweeney (Cottingham & Butler)
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About this listen
Jared Sweeney, Vice President, Transportation Group at Cottingham & Butler, joins Beyond the Bulldog to demystify trucking insurance—why costs keep climbing and what fleets can actually control.
Jared breaks down:
-What drives premium increases and how underwriters assess risk (claims history, CSA profile, routes, driver pool)
-Practical ways to lower total cost: top-down safety culture, spec and maintenance discipline, dash cams, smarter deductibles
-Group captives 101: when they fit mid-size fleets, how loss funds work, and why dividends are possible
-Navigating a volatile market: telling a credible safety story to carriers and avoiding jurisdictional “hellholes”
-Why cameras protect drivers and accelerate fair claims outcomes
-Key takeaways from Cottingham & Butler’s Transportation Summit that leaders can apply immediately
Whether you run 10 trucks or 1,000, this episode gives you actionable strategies to manage risk—not just buy insurance.
What’s next?
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