SPG Acquires Property Specialist Proper in Montana

February 27, 2026

Specialty Program Group LLC has acquired Proper Insurance headquartered in Bozeman, Montana.

As part of the transaction, Michael Grimland has been named president of Proper. Grimland will lead the business and oversee day-to-day operations, underwriting strategy and continued development of the platform. Grimland has been with Proper Insurance since 2017 and previously served as director of operations.

Proper provides insurance coverage for short-term rental properties, including homes owned by individual hosts and professionally managed portfolios, as well as those listed on platforms such as Airbnb and Vrbo. Its program is supported by insurance markets, including Lloyd’s of London and Concert Specialty, and is available nationwide. Proper is licensed in all 50 states.

SPG is a specialty platform headquartered in Chicago, Illinois with a portfolio of specialty insurance operations spanning underwriting management, digital solutions, wholesale and specialty retail brokerage and insurance services.