[Webinar] 2026 Insurance Outlook for Fleet Risk & Compliance

Thursday, January 29, 2026 |1:00 PM ET

2026 Insurance Outlook: What Fleet Risk Looks Like Now — and What You Can Still Control

How CSA scores, driver oversight, and compliance data are shaping insurance outcomes heading into 2026 

Insurance markets remain tight, premiums are under pressure, and underwriters are scrutinizing fleet risk more closely than ever. For midmarket and enterprise fleets, the conversation has shifted from what happened last year to what your data says about risk right now.

In this educational webinar, Foley and McGriff break down what insurance carriers are watching as fleets head into 2026 renewals — and how compliance performance, CSA scores, and driver oversight are directly influencing premiums, capacity, and underwriting decisions.

You’ll hear practical insight from Mike Hulsey from McGriff, a transportation insurance advisor who has seen firsthand how underwriters evaluate fleet risk across trucking, construction, and private fleets, alongside Mary Martin from Foley, who works closely with fleets on the operational and compliance data that increasingly shape insurance outcomes.

What You’ll Learn

• How CSA scores are being interpreted by insurers and why they matter more than ever

• The role of Clearinghouse compliance and Part 382 enforcement in fleet risk profiles

• Why MVR monitoring is becoming a baseline expectation for midmarket and enterprise fleets

• How digital driver files and documentation quality influence underwriting confidence

• What fleets can realistically improve before renewal to help manage premium increases

• What insurance markets may do regardless of performance — and where fleets still have leverage

Why This Matters for Midmarket and Enterprise Fleets

Insurance decisions are increasingly data-driven. Fleets with strong operational discipline, consistent driver oversight, and clean documentation are better positioned to demonstrate control — even in a hard market.

This webinar is designed for safety leaders, risk managers, and operations teams who want a clearer picture of how insurers assess fleet behavior today and what actions can meaningfully impact outcomes heading into 2026.

Meet the Speakers: 

Mike Hulsey

Transportation Insurance Advisor, McGriff

Mike advises transportation and construction fleets on risk strategy, underwriting expectations, and renewal planning. He brings a candid, real-world perspective on how insurers evaluate fleet safety, compliance data, and loss trends behind the scenes.

Mary Martin

Senior Program Manager, Growth Marketing, Foley

Mary brings a background in the construction sector to her work at Foley, where she partners closely with midmarket and enterprise fleets on compliance, risk, and operational visibility. As part of Foley’s demand generation team, she works hand-in-hand with channel partners, including insurance advisors, to help fleets understand how safety and compliance data influence business outcomes. Mary has been with Foley for more than three years and is based in North Carolina.

Who Should Attend:

• Safety Directors and Managers

• Risk Managers

• Fleet and Operations Leaders

• HR leaders involved in driver hiring and oversight

• Finance leaders preparing for insurance renewals

Reserve Your Spot

Join Foley and McGriff for a practical conversation about what fleet risk looks like now — and how to head into 2026 with greater clarity and confidence.

Register now to attend this free webinar.