Vice President Landstar Agent Jobs (NOW HIRING)

Landstar Risk Management, 13410 Sutton Park Dr S, Jacksonville, Florida, United States of America

Posted Tuesday, June 30, 2026 at 4:00 AM

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 environments
• Strong financial acumen, including reserving, loss cost management, and recovery optimization
• Ability to leverage claims technology, data analytics, and automation to drive operational efficiency and improve claim outcomes
• Strong executive presence with ability to communicate effectively with senior leadership
• Ability to manage defense counsel, vendors, and legal spend
• Strong leadership, organizational, and stakeholder management skills
• Ability to operate effectively in high-profile, time-sensitive environments
• Proficiency with claims systems (Origami preferred) and Microsoft Office tools

** This job posting is not designed to cover or contain a comprehensive listing of all activities, duties or responsibilities that are required of the employee. Duties, responsibilities and activities may change, or new ones may be assigned at any time with or without notice.

Landstar provides competitive compensation, robust benefit plans including affordable medical plans, employer 401(k) match, paid time off, tuition assistance and much more.

Landstar is an Equal Opportunity/Affirmative Action employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin or any other characteristic protected by federal, state or local laws. Landstar will provide reasonable accommodation to applicants with disabilities where appropriate. Applicants requiring reasonable accommodation for any part of the application and hiring process should send an e-mail to employment@landstar.com.