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Vice President Risk Management

Landstar
paid time off, tuition assistance, 401(k)
United States, Florida, Jacksonville
13410 Sutton Park Drive South (Show on map)
Sep 11, 2025

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 provide customers with personalized service at the local level with the global reach and resources of a multi-billion dollar company.

What work will you perform?


The Vice President of Risk Management is a key leadership role responsible for directing and administering Landstar's risk-management programs, including the oversight and guidance of claims management, insurance administration, and the fraud operations & analytics teams. The ideal candidate is an executive leader with experience leading teams responsible for managing a highly complex claims and insurance environment. The ability to influence outcomes while creatively solutioning across claims, insurance and fraud is paramount. We seek a relationship builder who understands the importance of elevating the level of service. Bring your subject matter expertise and your drive to make an impact at Landstar.



Essential Responsibilities:



  • Develop strategies, controls, and measures to monitor and mitigate the risk exposure of the organization and enhance customer experience.
  • Oversee the building of financial models to predict the risk exposure of the organization.
  • Lead and develop a high-performing team of risk, claims, and insurance professionals
  • Ensure compliance with all relevant regulations and industry best practices
  • Design and deliver comprehensive risk reporting and analysis for executive leadership and board-level meetings
  • Track key performance indicators (KPIs) related to frequency, severity, exposure, and insurance costs
  • Direct the end-to-end claims management process, ensuring timely reporting, investigation, and resolution of claims
  • Serve as subject matter expert for high-severity liability, contractual and coverage exposures.
  • Liaise with insurance brokers/carriers, lawyers and corporate team on litigation and complex claims matters.
  • Oversee design, placement, and renewal of all company insurance programs, including, but not limited to, auto liability, cyber, FINPRO, physical damage, cargo, general liability, worker's compensation, property and third-party insurance programs.
  • Lead the development and implementation of fraud detection and prevention tools



Required Minimum Experience and Education:



  • Bachelor's degree in Risk Management, Insurance, Business, or related field
  • 10+ years of progressive insurance/claims management experience



Preferred Experience and Education:



  • MBA or JD
  • Trucking, logistics, or transportation experience
  • Experience with risk management information systems (RMIS) and telematics data
  • Experience managing existing relationships with major brokers, insurers, and third-party administrators
  • Experience with risk management information systems (RMIS) and telematics data
  • Experience managing large self-insured and/or captive programs



Knowledge, Skills, and Abilities:



  • Deep knowledge of auto liability, cargo, and worker's compensation insurance programs
  • Strong experience handling transportation claims, litigation management, and fraud investigation
  • Exceptional negotiation, analytical, and communication skills
  • Ability to travel as needed
  • Ability to respond to critical incidents and high-exposure claims on short notice

Why work at Landstar?


Landstar is seeking hard-working and dedicated employees committed to exceeding the expectations of those we serve. We employ a highly diverse workforce and welcome employees from all cultures and backgrounds to our team.



Our workplace culture is second-to-none. Landstar provides a safe and professional work environment in which to thrive and grow. We offer competitive compensation, robust benefit plans including affordable medical plans, employer 401(k) match, paid time off, tuition assistance and much more.



If you want to be part of a top-notch transportation company with an emphasis on safety, service, teamwork, and dedication then Landstar is the place for you!



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.



Privacy Policy

Landstar uses application information only for employment related purposes, including background investigations and regulatory compliance. Landstar will not disclose the information to any other person or entity, unless compelled by force of law. Landstar stores your application information on computers operated by Ceridian. This on-line application software is provided by Ceridian under an agreement which specifies that Ceridian will not disclose or make any use of application information stored on its secure servers.

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