Obie is a venture-backed InsurTech focused on landlord and investor property insurance. Headquartered in Chicago, founded around 2018, licensed in all 50 states. The model is tech-enabled embedded insurance: Obie's quote engine is integrated into the checkout flow of major PropTech lenders (Kiavi, Visio Lending, MoFin) and platforms (Liberty Mutual's Comparion network). When you close a DSCR loan with Kiavi, Obie's quote is right there.
What Obie does well
Distribution. Obie wins customers at the moment of transaction. An investor closing a DSCR loan with a partner lender gets Obie's quote integrated into the closing process. No separate shopping, no separate forms, no separate carrier conversations. The convenience is real.
The technology stack is strong. The Knowledge Hub and Risk Map tools provide actual investor-relevant content. Obie has won HousingWire Tech100 three years in a row, ranked #350 on the 2025 Inc. 5000, and is rated #9 in insurance on that list. The Markel carrier partnership announced in 2025 expanded their underwriting capacity meaningfully.
For a tech-first investor who wants the insurance to feel like part of the lending stack rather than a separate vendor relationship, Obie delivers that experience.
Where Obie falls short
The direct-consumer experience is secondary to the partner channel. Obie is built to win business through PropTech integrations. Investors who find Obie directly (not through a lender) get a competent product but not the proactive advisory that a real broker provides.
Coverage breadth is residential investor only. No commercial property, no trucking, no specialty asset classes (mobile home parks, self-storage, hospitality). An investor who needs more than residential investor property has to maintain another agency relationship for the rest.
The Obie pricing through partner channels is not always the cheapest. The convenience of embedded insurance comes at a quote that often loses to a real broker shopping the same property across multiple carriers. Always worth comparing.
Naming confusion is a small but real friction: obie.com redirects to a hospitality company, and a customer trying to find Obie Insurance has to know to use obieinsurance.com.
Who Obie is best for
An investor closing a DSCR loan with Kiavi, Visio, or MoFin who wants the insurance integrated into the lending stack and values speed over price-shopping. A first-time investor who appreciates the embedded experience and does not yet know they are leaving money on the table by not comparing.
Who Obie is not best for
- Investors who want a real broker relationship and proactive renewal advisory.
- Investors with portfolios across multiple asset classes (commercial, multifamily, specialty).
- Investors who also need trucking or personal lines under the same agency.
- Investors who want to shop the policy across multiple carriers, not just Obie's program.
- Investors with non-standard properties (vacant, rehab, MHP, self-storage, mixed-use).
Common questions
What is Obie Insurance and who owns it?
Obie is a tech-enabled landlord and investor insurance platform headquartered in Chicago. It is a venture-backed InsurTech, founded around 2018. They are licensed in all 50 states and partner with major PropTech firms (Kiavi, Visio Lending, MoFin, Liberty Mutual's Comparion). They write through multiple carriers including a Markel partnership announced in 2025.
Is Obie the same as obie.com?
No. The obie.com domain redirects to a hospitality company called Obie Companies. Obie Insurance lives at obieinsurance.com. The naming overlap causes confusion at the front end. If you searched for Obie and ended up at a hospitality site, the right URL is obieinsurance.com.
Does Obie work with DSCR loans?
Yes, this is one of their strongest channels. Obie is embedded in Kiavi and Visio's lending platforms, which means investors closing DSCR loans through those lenders often get Obie offered as an integrated insurance option. The integration is convenient. The trade-off is that Obie's quote may not be the most competitive once you compare across multiple carriers.
What is Obie not good for?
Obie is built for the embedded transaction, not for an ongoing broker relationship. They cover residential investor property well but do not write commercial, trucking, mobile home parks, self-storage, or many specialty asset classes. For a portfolio investor with mixed asset types or anyone who wants a real broker advocate, Obie is not the right fit.
The bottom line
Obie is well built for what they target: embedded landlord insurance through PropTech lender platforms. If you are closing a DSCR loan with Kiavi or Visio and value the integrated experience, Obie is a legitimate option. If you want a broker who shops your account across 10+ carriers and handles your full insurance program, Obie is not designed for that role.