Specialty Program Group Acquires Proper Insurance, Expanding Its Specialty Property Insurance Platform

CHICAGO, Feb. 26, 2026 /PRNewswire/ — Specialty Program Group LLC (SPG), a leading operator of specialty insurance distribution, underwriting, and consulting businesses, announced the acquisition of Proper Insurance (Proper).

Founded in 2014 and headquartered in Bozeman, Montana, Proper provides insurance coverage designed specifically 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®. Proper offers a commercial insurance solution that replaces traditional homeowners or landlord policies. The program is supported by leading insurance markets, including Lloyd’s of London and Concert Specialty, and is available nationwide, with Proper licensed in all 50 states.

As part of the transaction, Michael Grimland has been appointed 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. During his tenure, he has been involved in the development and scaling of Proper’s underwriting, claims, and operational functions, and brings experience in commercial underwriting, reinsurance, and the Lloyd’s of London marketplace.

“We are very excited by Proper,” said Chris Treanor, President & CEO of SPG. “It has the key ingredients we look for in acquisition. It is an industry leader with a strong brand and track record. It is in an attractive market segment with good long-term growth potential. It has a great management team that will lead it into the future.”

“Proper has been built on disciplined underwriting and a deep understanding of the risks unique to short-term rental properties,” said Michael Grimland, President of Proper. “Becoming part of SPG provides an opportunity to further align our capabilities within a broader specialty platform while continuing to focus on delivering insurance solutions designed for this market.”

The acquisition further strengthens SPG’s specialty property insurance platform and expands its capabilities in the short-term rental market.

About Specialty Program Group LLC

Specialty Program Group LLC (SPG) is a leading specialty platform headquartered in Chicago, IL, with a diverse portfolio of specialty insurance operations spanning underwriting management, digital solutions, wholesale and specialty retail brokerage, and insurance services. SPG has a track record of scaling industry leading businesses by providing access to business resources, technology and process efficiency, capital and investment, deep carrier relationships, and a broad distribution network. Visit specialtyprogramgroup.com to learn more about how SPG can help you scale your specialty business.

About Proper Insurance
Proper Insurance provides insurance solutions designed specifically for short-term rental properties. Backed by Lloyd’s of London, the company offers coverage that replaces traditional homeowners or landlord policies and addresses the unique risks of vacation rental ownership. Proper Insurance operates nationwide and is licensed in all 50 states. For more information, visit proper.insure.

CONTACT:
SPG Media: Lea Prses
[email protected]

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SOURCE Specialty Program Group