Obie Raises $25 Million in Series B

In a sign of momentum, Obie secures a second round of funding, showing investor confidence in embedded insurance solutions for real estate investors

CHICAGO–(BUSINESS WIRE)–Obie, an industry-leading insurtech startup, announced today that it has raised $25.5 million in a Series B funding round led by Battery Ventures, with participation from Brick and Mortar VC, DivcoWest, and several real estate funds and investor groups.

Founded in 2017, Obie is focused on providing insurance to residential real estate investors. The company has seen success from, and is now doubling-down on, its industry-first embedded insurance distribution strategy. The Obie instant quote process leverages data enrichment, accessing multiple databases to apply unique algorithms and analysis to over 1000 data points. The proprietary methodology of this data analysis allows for a more accurate assessment of risk and the ability to more efficiently underwrite policies, resulting in faster quote generation. With this innovative technology, Obie delivers instantly bindable quotes that meet the distinct needs of each investment property, enabling a superior customer experience and positioning the company as the leading digital provider of landlord insurance.

“We’re excited to have the ongoing support of our investors as we continue to build insurance products that drive efficiency and change the way insurance is bought and sold,” said Obie Co-founder and CEO, Ryan Letzeiser. “This funding supports the future of embedded insurance, as we expand our partnerships across industries and offer additional insurance products to clients.”

Having secured over $20B in total coverage, Obie has already attracted over 75 partners in proptech and fintech, including Baselane, Awning, and Marketplace Homes as embedded partners. With the embedded product seamlessly integrating into partner platforms, value is added by offering comprehensive insurance coverage, powered by Obie, all directly within their platform or preferred digital channel. Through the Obie product, partners can also ensure their insurance specifications are met, such as meeting unique insurance loan requirements.

With over 18M real estate investors across the United States, Obie’s unique distribution strategy positions the company to continue growing in a market still largely served by legacy insurance carriers. Having seen 300% growth over the past two years, Obie is proving that modern real estate investors are adopting new, easier ways to obtain insurance that align with other digitized proptech and fintech solutions.

“Despite the recent volatility in the real estate and insurtech markets, we believe Obie’s approach to growth—namely, by using an API-first approach and embedding their technology within their large ecosystem partners—is the right one for this market, and the company’s recent success demonstrates this,” said Michael Brown, a Battery general partner and Obie board member. “We’re excited to recommit to Obie and continue to help the company scale.”

After raising $10.7 million in their Series A funding round closed in 2021, this new round of funding brings the total equity raised to date to $39 million.

About Obie

Obie is an insurance technology company, hyper-focused on driving value for the modern real estate investor and the partners they work with every day. Whether you are an owner, lender, agent, or property manager, Obie’s mission is to build technology and insurance products that drive efficiency and fundamentally change the way insurance is bought and sold. Learn more at