Specialty Program Group (SPG), a Chicago-based specialty insurance platform, has acquired Proper Insurance, one of the most widely used insurance providers in the short-term rental industry.
Proper Insurance was founded in 2014 in Bozeman, Montana, and offers commercial insurance policies designed specifically for STR properties. The company reports it has written over 200,000 policies across all 50 states and Washington, D.C. Its policies are backed by Lloyd's of London and Concert Specialty Insurance Company.
What Proper Covers
Proper's policies are built to replace traditional homeowners or landlord insurance, which typically don't cover short-term rental activity. The company is endorsed by Vrbo and has positioned itself as a specialist in the gap between residential coverage and the commercial exposure that comes with operating a rental business.
What the Acquisition Means
SPG's portfolio spans underwriting management, digital solutions, wholesale and specialty retail brokerage, and insurance services. The acquisition brings Proper into that broader platform. The deal terms for the acquisition were not disclosed.
As part of the transition, Michael Grimland has been appointed President of Proper Insurance. Grimland joined the company in 2017 as Director of Operations and has overseen underwriting, claims, and operational development since then.
Grimland said the move gives Proper an opportunity to "further align our capabilities within a broader specialty platform" while continuing to focus on insurance designed for the STR market. SPG's CEO Chris Treanor called Proper an "industry leader with a strong brand" operating in a segment with long-term growth potential.

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