Alternative Risk Captive Insurance and Programs

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Reduce Costs | Take Control | Create Stability


If your business experiences repeatable, consistent risk, this is where an alternative risk solution, such as a captive, can offer:

  • Reduced Costs: Return of unused premium and investment income can lead to potential lower costs and lower net effective costs.
  • Control: A captive can offer leverage against insurers, program and coverage flexibility, insulation from “the pool” of other risks and more control over claims through advanced risk control, safety practices and culture.
  • Stability: Minimize unpredictable insurance pricing, mitigate shock losses and provide asset protection.

Oswald has access to group captives for just about every industry and we build specific programs for companies that don’t fit in a group, or don’t want partners in their insurance program.

Oswald has the industry knowledge, marketplace leadership and proven solutions, to get started on a custom program for you today.

To learn about Oswald’s specialized Alternative Risk practices, our proprietary strategic process, and our solutions at work for hundreds of businesses, contact Jason T. Stevenson, CIC, CPIA, Alternative Risk Strategies Leader at Oswald Companies.

His diverse background in Finance, Insurance, Real Estate, Restaurants and Technology puts him in perfect position to effectively develop and implement alternative solutions for his clients and for Oswald. He has a passion for innovation and has been in the Alternative Risk and Captive space for over a decade. During this time he has developed and implemented strategic products and programs in Real Estate, Construction, Active Assailant Cover, International Transportation, and Franchisors industries to name a few.

Key Service Areas

  • Captive review, consulting and placement: Don’t go it alone. Let us review, consult and place coverage as needed.
  • Reinsurance negotiating: Are you already taking significant risk? Let us place your reinsurance.
  • Program Development: We can build a new program or manage and develop one you already have.
  • Alternative Services: We can source actuarial, legal accounting, domicile, or management as needed.

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.