Freestone Insurance Group has acquired 360 Benefits, a Chicago-based employee benefits firm founded in 2014 by Bill Pragalz. Freestone is a Scottsdale-based brokerage backed by Shore Capital Partners, which took the platform 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.
360 Benefits serves privately held, middle-market employers across a range of industries. The firm consults on group health and welfare plans across self-funded, level-funded, and fully insured frameworks. Pragalz will remain as president under the new ownership structure. Financial terms were not disclosed.
Shore Capital Partners, which has approximately $17 billion in assets under management, targets lower middle market companies in healthcare and business services with potential for industry consolidation. The Chicago acquisition gives Freestone a direct Midwest presence to complement its Arizona base. Freestone CEO Ben Hayes said the deal fits the firm's strategy to identify and partner with principals who have an appetite for aggressive growth.
The retention of Pragalz as president follows a standard structure in PE-backed brokerage acquisitions. In benefits brokerage, client relationships are the primary asset. Acquirers routinely keep founders in place to preserve continuity through the ownership transition.
The Freestone-360 deal fits a documented market pattern. Employee benefits agencies with revenues of $1 million or more are the highest-multiple insurance category in 2026, at 9 to 12 times EBITDA, according to CT Acquisitions data. Group health books reach those valuations because renewal retention typically runs at 92% to 96%. That retention makes commission revenue durable across renewal cycles and makes independent benefits brokers a primary target for PE-backed consolidators.
The same healthcare cost environment driving employer demand for consultative benefits advisory is also driving consolidator appetite for the advisors who supply it. 360's focus on middle-market employers sits in a segment under sustained acquisition pressure.
The 360 Benefits acquisition is part of a wider Shore Capital move into the employee benefits sector. In July, Shore separately acquired ThrivePass, a Denver-based employee benefits administration technology platform. Shore now holds a benefits brokerage platform in Freestone and a benefits technology platform in ThrivePass, though the two operate as separate businesses. Freestone and 360 Benefits plan to deepen service offerings and invest in technology and talent, though no timeline or investment figures were disclosed.
PE-backed benefits consolidation is accelerating across the market. Mid-market employee benefits brokers serving the same employer client base as 360 Benefits have been acquisition targets for national brokers, private equity-backed consolidators, and regional firms throughout the current cycle.
