Technology Company Obie Launches to Reinvent the Investment Property Insurance Process, Saving Landlords and Real Estate Investors as Much as 30%

Company debuts the first instant quote platform for landlords; now offers coverage in all 50 states

Obie closes $10.7 million Series A, led by Battery Ventures

Obie unveiled its new insurance offering targeting landlords and investment property owners. Its innovative technology and approach means Obie’s policyholders can save up to 25-30% off their existing insurance premiums. (Photo: Business Wire)

CHICAGO--()--Launching today, emerging InsurTech innovator Obie unveiled its new insurance offering, specifically targeting landlords and investment property owners. Obie’s instant quote platform for landlords, the first of its kind, delivers the coverage these small businesses need through a dramatically improved, data-rich process. The company’s innovative technology and approach means Obie’s policyholders can save up to 25-30% off their existing insurance premiums. Starting today, Obie’s property and casualty insurance is now available in all 50 states.

Additionally, Obie disclosed that it has raised $10.7 million in Series A funding to fuel rapid growth. The round was led by global investment firm Battery Ventures, with General Partner Michael Brown joining Obie’s board of directors. Thomvest Ventures (the investment management firm of the Thomson family) also joined the round, in addition to previous investors Funders Club, MetaProp, and Second Century Ventures. Funding comes as Obie has secured insurance for over $3 billion in property over the past year.

“The number of small, hobbyist landlords and property investors is growing at an impressive rate, yet nothing exists in this space to provide them with the quality insurance coverage they need to safeguard their investments,” said Brown. “When we saw what the Obie team had built, we were immediately struck by how their technology didn’t just slap a band-aid on traditional approaches to insurance coverage; it brings intelligence and simplicity to the process to match each policy application to the ideal carrier for respective risk factors. This results in a win for all parties.”

Better Options for Rapidly Growing Market Segment

Obie was created to provide a simple, affordable, and transparent insurance experience for clients and their investment properties, with a particular focus on the 11 million small-to-medium size apartment landlords who own single family rentals and/or larger apartment buildings. Based on their work in real-estate private equity and insurance, Obie co-founders Aaron and Ryan Letzeiser recognized that despite being the largest class of real estate investors in the U.S, this group is significantly underserved. They are too small for larger brokerage houses, while the smaller, independent insurance agencies are generalists with only limited carrier partners that specialize in this type of risk. As a result, landlords get bad pricing and limited coverage, after enduring a lengthy and antiquated application process.

Obie remedies this by offering a consumer-friendly approach that matches the expectations of the digital world. The company replaces an opaque, email-based insurance acquisition process, where landlords are forced to fill out PDFs and spreadsheets before waiting more than a week to even receive a quote, with a short online questionnaire. Landlords and property investors then can get the coverage that fits their specific needs in less than five minutes.

“The impact of insurance premiums on real estate investors’ bottom line and the overall value of the asset is significant, yet the process of securing proper coverage has always been a bit of a black hole,” said Obie Co-Founder and COO Aaron Letzeiser. “Obie changes this. We built technology that makes securing insurance the least of a landlord’s worries. Now purchasing insurance is quick, easy, and extremely cost efficient, and with Battery’s support we can scale even faster to meet the needs of this growing market.”

Leveraging Technology to Reinvent Insurance

When landlords and property investors come to Obie, the platform walks them through a short series of questions and provides an instant quote that, once accepted, can be immediately underwritten. Obie is able to do this by extracting a few key data points from client responses, which its technology then enriches with dozens of public and privately available data points to eliminate the constant back-and-forth that normally occurs between a real-estate investor and an insurance agent. Obie’s platform analyzes over 50 novel and unique underwriting data points, which include things like the proximity of the landlord to the property, as this is often a great indicator of proactive and preventative maintenance as well as attentiveness to tenant issues.

Once Obie runs its analysis, the platform uses a proprietary algorithm to match an application to carriers based on the risk-appetite profiles that carriers have at any given point in time. For example, this could include things like writing properties in hurricane zones or excluding those that don’t want to write any policies this quarter for properties built before 1980. By targeting carriers accordingly, Obie is able to deliver the right level of coverage for a dramatically lower cost than other brokerages, which is particularly important for landlords who have been hit by rent uncertainty amid the COVID-19 pandemic.

“I had been using the same brokerage for years, but by managing my portfolio on Obie, I was able to easily request new quotes that saved me more than I ever would have expected on my existing premium-- something my old brokerage wasn’t able to do,” said Doug Hirsh, an Obie customer. “That kind of instant savings substantially increases IRR and cash-on-cash returns. Using Obie has been a no-brainer. I couldn’t be happier with the entire experience and level of coverage.”

To use Obie to make sure that you’re covered and your investment is protected, go to

About Obie

Obie is on a mission to provide a simple, affordable, and transparent experience for clients and their investment properties. Its technology guarantees industry-best rates for the property and casualty plans that are right for clients, ensuring that they, and their investments, are protected. Obie is now available to landlords and property investors in all 50 states. Learn more at


For Editorial Contact:
Amber Moore
GMK Communications for Obie

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For Editorial Contact:
Amber Moore
GMK Communications for Obie