Freestone makes first acquisition, buying Chicago's 360 Benefits
What's the deal? Freestone Insurance GroupDealroom has a profile for this one. Try Dealroom → has acquired 360 BenefitsDealroom has a profile for this one. Try Dealroom →, a Chicago-based employee benefits firm founded in 2014 by Bill Pragalz. The deal gives the Scottsdale-based brokerage a direct Midwest presence to complement its Arizona base. Financial terms were not disclosed.
Why now? Freestone is backed by Shore Capital PartnersDealroom has a profile for this one. Try Dealroom →, which took the brokerage private in June 2025 with geographic expansion and selective acquisitions as stated objectives. The 360 Benefits deal is the first publicly announced add-on since that investment.
What's the endgame? 360 Benefits serves privately held, middle-market employers across Chicago and the broader Midwest, consulting on group health and welfare plans across self-funded, level-funded, and fully insured frameworks. Pragalz will remain as president. Chief executive Ben Hayes said the deal fits Freestone's strategy to partner with principals who have "an appetite for aggressive growth."
Why the price holds up: Employee benefits agencies with revenues of $1 million or more are the highest-multiple insurance category in 2026, trading at nine to 12 times EBITDA, according to CT AcquisitionsDealroom has a profile for this one. Try Dealroom → data. That reflects a specific trait: group health books renew at 92% to 96% retention, making commission revenue durable in a way property and casualty books are not.
High retention means an acquired book is a recurring revenue stream, not a one-time transaction — one private equity investors can model against acquisition multiples. The same rising-cost environment pushing mid-market employers toward more sophisticated advice is making the advisers who supply it more valuable to consolidators.
Alongside Freestone: The 360 deal is not Shore's only benefits move this year. In July, it separately acquired ThrivePass, a Denver-based benefits administration technology platform. Freestone and ThrivePass operate as separate businesses, but Shore now holds a brokerage platform and a technology platform under the same ownership.
The signal: That pairing is what matters most for independent mid-market brokers. When a PE-backed consolidator combines brokerage with administration technology, it builds a vertically integrated offering competing on advice, carrier relationships, and the data infrastructure that increasingly drives renewal decisions — a value proposition independents without equivalent tech will struggle to match.
Read more: insurancebusinessmag.com
Image credit: DaltonKat2
