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Obie Revolutizes the Industry Through Embedded Insurance

What Obie Does


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. Designed to meet the needs of owners, lenders, agents, and property managers, Obie’s mission is to build technology and insurance products that drive efficiency and fundamentally change the way insurance is bought and sold.


The Current Landscape


Much of the residential real estate market still obtains insurance through a process that requires manually locating an agent, setting a meeting or call with that agent, followed by a waiting period of up to two weeks. Obie has set out to change the way we landlord insurance is bought and sold.


As the new standard in landlord insurance, Obie is redefining how long it takes to get coverage by introducing the industry’s first instantly bindable quote. The company is also reimagining where insurance can be obtained by introducing the first embedded distribution strategy for landlord insurance. Through this distribution strategy, Obie has been able to partner with over 75 proptech and fintech companies, offering a more simple, streamlined insurance experience for their customers.


Obie’s Birth Story


Obie was founded in 2017 by brother duo, Aaron and Ryan Letzeiser. Using their combined knowledge of the real estate industry and understanding real estate investing, the Letseizer brothers were able to identify a key pain point for real estate investors: getting the proper insurance. With the industry unable to meet real estate investors where they were, Aaron and Ryan founded Obie. After much exploration, including going through Y Combinator, Aaron and Ryan settled on a focus of providing insurance in an easy-to-obtain way, to investors owning single-family homes and 1–4 unit properties.


The Solution


The Obie instant quote process allows customers to obtain a quote in under 5 minutes. Investors can then bind and pay for their insurance policy instantly. Obie’s proprietary quote engine analyses over 1000 data points, allowing for a more accurate assessment of risk and more efficient underwriting. This analysis enables Obie to bring clients the best value in their policy, while also meeting the unique needs of each investor and their properties.


The company currently has three distinct distribution models for their product: digital and embedded solutions for partners, a direct-to-consumer website, as well as partnerships with independent insurance agents.


The company’s direct-to-consumer model allows real estate investors to obtain insurance directly through the Obie website, utilizing the Obie quote process to obtain an instant quote.


Obie’s digital and embedded solutions are offered through partners'’ platforms, enabling them to offer a streamlined, white-labeled insurance experience to their customers. A few of Obie’s over 75 industry partners include Baselane, Awning, and Marketplace Homes.


Lastly, Obie’s partnerships with independent insurance agents and brokerages across the country give unique access to Obie’s technology. These partnerships allow independent agents to provide a superior insurance experience to their customers by increasing efficiencies.


The Team Culture


Obie is based out of Chicago, with a combination of hybrid and remote workforce. The company has 85 employees across 22 states but has plans to continue expanding its workforce in 2023.


Having been named one of Inc Magazine’s Best Workplace 2023, as well as one of Built In’s Best Places to Work 2023, Obie plans to continue scaling employee programming and benefits, believing employee support and community has been key to their success and growth.



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