Vice President, Claims - Transportation​/Logistics

What is Landstar?

Landstar stands for safe, secure and reliable transportation services delivered by our unique network of small business owners. Independent agents and capacity providers operating under the Landstar umbrella enjoy the strength and support of one of the industry's most stable and successful companies. Our network of independent entrepreneurs provides customers with personalized service at the local level with the global reach and resources of a multi‑billion dollar company.

Location: Onsite in Jacksonville, FL

The Vice President of Claims provides executive leadership of Landstar's Property & Casualty claims function, across liability and cargo claims, with accountability for claim outcomes, litigation strategy, and total cost of risk. You will oversee claims governance, litigation pipeline management, and trial readiness for high‑exposure matters within a self‑insured/captive‑supported structure along with re/insurers. To be successful you will ensure disciplined, consistent, and data‑driven claim resolution, including the intersection of cargo loss, contractual liability, and negligence‑based exposures.

In this role you will partner closely with Risk Management, Legal, Safety, Operations, and Finance to align claims strategy with financial reporting, risk mitigation, and enterprise priorities.

• Lead claims governance, litigation pipeline oversight, and trial readiness strategy, ensuring disciplined case assessment, exposure management, and alignment with authority and escalation standards
• Direct the full claims and litigation lifecycle across liability (BI/PD) and cargo, including complex, high exposure matters and the intersection of cargo loss and contractual liability
• Establish and maintain a forward‑looking litigation pipeline, including severity segmentation, exposure forecasting, and executive reporting
• Oversee trial readiness and resolution strategy, including early case assessment, venue considerations, and alignment with defense counsel
• Direct claims operations to ensure consistent, timely, and effective claim handling and resolution
• Lead data‑driven insights to identify trends, emerging risks, and loss drivers, and translate findings into actionable strategies
• Provide leadership over cargo claims strategy, including loss assessment, coverage application, subrogation, and alignment with liability exposure and contractual frameworks
• Operate within a self‑insured captive structure, including coordination with captive ops, insurers, and re/insurers
• Oversee defense counsel and vendor management, including performance, outcomes, and cost control
• Ensure compliance with regulatory requirements, internal policies, and audit standards
• Communicate material claim developments, trends, and exposure to senior leadership and executive stakeholders
• Lead and develop the Claims organization, including talent development, performance management, and organizational design

• Bachelor's degree or equivalent experience
• 10 years of experience in Property & Casualty claims, insurance, or risk management including:
• 5 years of experience managing litigated claims
• 5 years of experience managing claims teams

• 10 years of experience in transportation, logistics, or trucking‑related claims, including cargo and liability exposures
• 3 years of experience in self‑insured and/or captive insurance structures
• 5 years of experience managing catastrophic and large‑loss exposures

• Knowledge of state and federal regulations governing transportation‑related claim
• Deep knowledge in Property & Casualty claims, including liability and cargo claims handling
• Strong knowledge of claims governance, litigation processes, and trial strategy
• Strong knowledge of cargo claims, including coverage, valuation, subrogation, and relevant regulatory frameworks (e.g., Carmack)
• Knowledge of the interaction between cargo loss, contractual liability, and negligence‑based exposure in transportation environments
• Ability to manage potentially high‑severity litigation portfolios and complex claim…