Insurtech Eye — Insurance Technology News

Freestone Insurance Group Expands Midwest Footprint with 360 Benefits Strategic Partnership

25 August 2026

Press Release: Freestone Insurance Group Expands Midwest Footprint with 360 Benefits Strategic Partnership | Featured Image by FF News

Freestone Insurance Group (“Freestone”), a Scottsdale-based insurance brokerage firm focused on employee benefits and enterprise risk management, and portfolio company of Shore Capital Partners (“Shore”), is pleased to announce its strategic partnership with 360 Benefits (“360” or the “Company”). Located in Chicago, 360 is an insurance brokerage firm specializing in employee benefits and enterprise risk management strategies.

Founded in 2014 by Bill Pragalz, 360 provides employee benefits insurance solutions to privately held, middle-market employers. The firm offers high-quality, high-touch consultative services that enable clients to make informed decisions efficiently. Serving a broad range of industries, 360 combines strategic insight with practical execution in delivering risk management solutions tailored to complex and evolving needs. 360’s advantage lies in its in-depth product knowledge and client-centric approach, and its team of experienced specialists work closely with clients to provide strategies and services that align with their business goals.

“The entire 360 Benefits team is excited to partner with Freestone,” said Bill Pragalz. “As our clients have grown and the employee benefits landscape has become increasingly complex, so has the need for broader capabilities, deeper expertise, and greater resources. Joining Freestone and Shore allows us to continue delivering the personalized service our clients value while significantly expanding our capabilities. Our clients have always been at the center of our mission and Freestone shares our client-first philosophy while providing access to an extraordinary depth of talent, technology, analytics, and specialized resources.” Pragalz will continue to lead 360 as President of the Company.

Backed by the resources, network, and operational expertise of Freestone and Shore, the Company is positioned to scale more aggressively, provide additional value additive services and products to clients, and invest in innovation and talent. The growth strategy will include deepening core service offerings, investing in technology, and partnering with Freestone to provide clients with additional risk management strategies and services.

“Freestone’s partnership with 360 Benefits will allow the Company to accelerate organic growth and deepen client relationships with the support of Shore, Freestone, and targeted talent additions,” said Ben Hayes, Chief Executive Officer of Freestone. “This investment is a complementary addition to our existing employee benefits practice and aligns with our strategy to identify and partner with high character leaders with appetites for aggressive growth.”

  • Freestone Insurance Group, a Shore Capital Partners portfolio company, has partnered with 360 Benefits (Chicago, IL), an employee benefits focused brokerage founded in 2014 by Bill Pragalz.
  • 360 serves privately held, middle-market employers across a broad range of industries, delivering high-touch consultative benefits and risk management solutions.
  • The transaction furthers Freestone's Midwest presence and strengthens its existing employee benefits practice. Pragalz will continue to lead the business as President of 360 Benefits.
  • Backed by Freestone and Shore resources, 360 will deepen core service offerings, invest in technology and talent, and expand access to Freestone's broader risk management capabilities.

Companies in this story: Freestone Insurance Group, Shore Capital Partners, 360 Benefits, GrayStone Insurance Group

People in this story: Ben Hayes, Austin Bockwinkel, Bill Pragalz