Landlord-focused insurtech Obie lands $25.5M led by Battery Ventures

Obie, a real estate-focused insurance technology company, has raised $25.5 million in a funding round led by Battery Ventures.

Since the company’s last raise — a $10.4 million Series A — nearly two years ago, the startup says it has gone from securing insurance for over $3 billion worth of property to $20 billion worth. It has now raised a total of $39 million since its 2017 inception.

Obie’s software specifically targets small-to-medium size apartment landlords who own single-family rentals and/or larger apartment buildings.  

Chicago-based and Y Combinator graduate Obie says its platform stands out because it offers instant quotes (by instant, they mean in about five minutes). The company also claims to save policyholders up to 25-30% compared to other insurance premiums.

While the startup declined to share its valuation, COO and co-founder Aaron Letzeiser said Obie “was able to achieve a significant increase in valuation” from its 2021 Series A round.

“Our team has pioneered an embeddable solution that seamlessly integrates insurance offerings into our partner’s channels, including any place a real estate investor is buying or managing their investment property online,” said CEO and co-founder Ryan Letzeiser.

Obie says it has “thousands of customers” and is now partnered with more than 75 proptech companies to offer insurance, such as Roofstock, Flock Homes, Baselane, Awning and Marketplace Homes. It has seen 300% growth in written premium over the past two years, Aaron Letzeiser said.

Within the last year, the company has increased its margins by 40%, and is on track to improve another 25% by the end of 2023, he added.

“Our bread and butter is the 1-4 unit single-family rental market and we offer coverage in all 50 states,” Aaron added. “There are over 18 million residential real estate investors in the U.S., and more than 90% of them are small ‘mom and pop’ investors who spend over $60 billion a year on insurance premiums, so there’s plenty of room for Obie to run here.”

Battery Ventures General Partner Michael Brown believes there are “very few digital competitors to Obie, as landlord insurance is a nuanced, specialized insurance product.”

He wrote via email: “Obie’s focus on this market — and its savvy use of data, proprietary risk-management tools, and embedded industry partnerships — has allowed it to develop a unique system to generate near-instant, competitive quotes that landlords can access anywhere they’re buying or managing property, such as within their broker’s portal or their own property-management system. We feel Obie is on a path to building a valuable, next-generation, digital landlord-insurance brand.”