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On the Move | Transportation Risk and Insurance Solutions

Oswald has the industry experience and advisory to help you control your fleet insurance and loss costs for years to come.

In addition to leveraging our underwriting relationships to bring you competitive premiums we bring a greater depth of expertise to help reduce your costs: workplace safety and loss control services; experienced claims management and advocacy and more.

We uniquely invest in our talent and technology to simplify the world of our clients and optimize their business success.

As a result, our clients can achieve best in class status, which translates into best in class risk management programs that differentiate their business in the insurance marketplace.

Key Service Areas:

  • Policy Oversight and Management, Specialized Market Access & Claims Management
  • Productive Data: Quantifying Efficiency and Value.
  • National Fleet Redundancy Services: Protecting Strategy, Not Just Assets.
  • Benefits, Work Comp, and Casualty: Harnessing the power of bigger, better data means better loss and expense management, healthier employees, lower turnover, and more efficient operations.
  • Alternative Risk Solutions: Captives – Single Parent, Group, New/Formation Services, Development, Management and Self Insured Retention (SIR) Programs.
  • Safety and Compliance: With a comprehensive media library of more than 2500 documents, videos, and presentations, and on a broad range of topics, our team is ready to help.

Download our full program brochure.

oswald transportation

Contact us today to learn more about our:

  • Captive Solutions
  • Deductible Analysis
  • Written Service Contracts
  • Compliance & Safety Reviews and Meetings
  • Dedicated Claims Team
  • 24/7 Online Certificate Service
  • Owner-Operator Specific Coverages
  • NTL and Physical Damage Master Plan
  • Ohio and all States Workers’ Compensation
  • Trucking Specific Insurance Markets
  • OSHA and Driver Safety Management
  • Contract Review
  • Environmental Compliance


Jason Stevenson, CIC, CPIA, MBA

Vice President, Practice Leader – Captives, Programs & Alternative Risk

Jason Stevenson is the Vice President and Captives, Programs, and Alternative Risk Practice Leader for Oswald Companies, a nationally recognized (top 50) insurance and risk management firm based in Cleveland, Ohio. Jason serves clients with exposures and operations in many states throughout the U.S. and Canada.

He has more than 12 years of advanced business experience and has served hundreds of clients with diverse risks across many industries. His expertise lies in all lines of insurance related to the captive and program segments of the industry domestically and internationally.

Jason is a thought leader in the industry, a frequent attendee and speaker at industry events worldwide, and a mentor in the CICA Mentorship program, established in 2017.

He also frequently advocates on behalf of the insurance industry, including an appointment to the Ohio Insurance Agents Association’s committee to advise the Ohio Bureau of Workers Compensation on interjurisdictional workers’ compensation issues. Jason has testified in front of both the Ohio and Senate Finance subcommittees at the Ohio State House.

Email Jason Stevenson and connect on LinkedIn.

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