Obie Acquires Commercial & Multi-Family Brokerage, Skylight Insurance

Venture-backed insurance and risk management platform for real estate investors acquires Chicago-based specialty insurance brokerage to expand nationwide.

CHICAGO - September 17, 2020 - (

​​Obie, a Y Combinator-backed insurance and risk management platform for real estate investors today announces the asset acquisition of Skylight Insurance, an insurance brokerage specializing in commercial and multi-family coverage and risk consulting. Terms of the transactions were not disclosed.

Located in Chicago, Skylight Insurance was founded in 2017 and led by CEO Matthew Sutika, formerly one of State Farm’s top agents in the United States and a consultant to many of the top names in InsurTech today. Since that time, Skylight has placed millions in premium and grew to become a recognized brand in the multi-family investment space.

“We’re excited to welcome the Skylight team to Obie. We’ve worked closely with Matt and his team over the last year and have been extremely impressed with their knowledge of the space, dedication to clients, and interest in the next generation of insurance,” says Aaron Letzeiser, Co-Founder and COO of Obie. “It’s hard to find a brokerage that both specializes in what we’re working on and fits the culture we’ve built at Obie. We found that in the Skylight team.”

Through this acquisition, Obie will be able to continue a nationwide expansion of their tech-enabled insurance platform. Already tripling in size over the last six months, the new additions will provide expanded support to both the sales and service team, as well as a deep network and expertise in commercial and multi-family insurance.

“Technology is going to dramatically change how insurance is bought, sold, and managed over the next decade. I’ve seen what’s possible in the personal lines space and am excited to be at the forefront of what can be done to improve and enhance the commercial property insurance vertical. We always strive to provide a fast, transparent, and consultative process for our clients and Obie’s capabilities will take that even further,” says Matthew Sutika, formerly CEO of Skylight Insurance and now Obie’s first Chief Insurance Officer.

By combining property or portfolio data with the insurance process, Obie has been able to save customers more than 15% on insurance premiums and in many cases, within 72 hours or less, compared to the industry average of 2-3 weeks. When every dollar saved while operating an investment property instantly increases the value of the asset, cutting insurance premiums by 10-15% can sometimes add millions to the value of a portfolio overnight.


About Obie

Obie is building the next generation real-estate insurance platform, consolidating and democratizing technology while connecting the community to intelligent and seamless insurance and risk management tools. This is a huge, important part of our economy yet commercial real estate operates in the same way it has for decades — through opaque systems. That’s why Obie is re-engineering the CRE insurance process from the ground up.


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Original Source: Obie Acquires Commercial & Multi-Family Brokerage, Skylight Insurance
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