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Freestone acquires 360 Benefits in first add-on since Shore buyout
Financial terms were not disclosed, and the deal gives Freestone a direct Midwest presence beyond its Arizona base.
Freestone Insurance Group has acquired 360 Benefits, a Chicago-based employee benefits firm founded in 2014 by Bill Pragalz, marking Freestone's first publicly announced add-on since Shore Capital Partners took the brokerage private in June 2025, according to Insurance Business.
Freestone, which is headquartered in Scottsdale and backed by Shore Capital, said the transaction supports its expansion goals through selective acquisitions. 360 Benefits serves privately held, middle-market employers across industries, consulting on group health and welfare plans across self-funded, level-funded, and fully insured frameworks.
Pragalz will remain president under the new ownership structure, a setup that Insurance Business notes is common in private-equity backed benefits brokerage deals to preserve client relationships during ownership transitions. The acquisition also adds a direct Midwest footprint for Freestone to complement its existing Arizona base.
Insurance Business further linked the deal to broader consolidation trends in employee benefits brokerage, citing CT Acquisitions data that benefits agencies with at least $1 million in revenue are among the highest-multiple insurance categories in 2026 at 9 to 12 times EBITDA, supported by group health renewal retention typically running 92% to 96%. It said Shore has pursued the sector through both brokerage and technology investments, including acquiring ThrivePass in July.