Group Health Captives & Shared Risk Services

Running a business has never been harder. Companies face an ever-changing landscape of challenges – inflation, supply chain disruptions and heavy competition in recruiting and retaining employees, to name a few. Offering a competitive benefits package while maintaining spending as health care costs rise leaves even the savviest employers having to get more creative.

Rest easy. Oswald understands those challenges, and we’re here to make life easier by offering a variety of benefit options that enable your company to save money by sharing risk.

Gene PompiliGene Pompili, VP, Risk Leader

As the Risk Leader for Group Benefits, Gene Pompili builds and manages captive and risk sharing programs. Gene has relationships with the reinsurance markets and designs reinsurance treaties to support the risk sharing and risk transfer elements. From a programmatic perspective, he also helps evaluate and implement cost containment strategies and supply chain partners that drive economic efficiencies to reduce health care costs for program participants. As part of these efforts Gene strives to understand the landscape of next generation digital health care solutions, precision medicine, pharmacogenetics, and predictive risk modeling tools. Prior to joining Oswald in 2021, Gene spent over 28 years with group insurance stalwarts MetLife, Prudential, and Nationwide. He was also part of the leadership team at Roundstone Insurance, an MGU and captive manager focused on middle-market healthcare captive solutions. During that time Gene has held positions responsible for P/L management, strategy development, sales leadership, and agency production.

Contact Gene or connect with him on LinkedIn.


It often seems that big companies get all the breaks, but it doesn’t have to be that way. Companies of all sizes can fund their own health care plan by forming a pool to share risk. Member companies pay for predictable claims such as office visits and maintenance prescriptions and buy insurance to cover only catastrophic health events. We’ll design a flexible plan that provides for your employees’ needs while saving money. Learn more.


Public entities have a unique challenge. They must offer attractive employee benefits to compete for top talent and budget for necessary public services – all on a fixed income. PublicSmart helps you reach these goals through access to exclusive provider networks, predictable health care costs and collective bargaining. Learn more.


The ISBC is an employee benefit solution that focuses on cost control through innovative funding and cultivating a culture of wellbeing. The ISBC concierge approach to your benefit needs provides you with cost control, flexibility in plan design and market strength – regardless of your school’s size. Learn more.