Mile Marker 25 – Taming Truck Insurance with Jared Sweeney (Cottingham & Butler)
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…
The skinny
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