2021 Year in Review

2021 was anything but normal. For the world, as we entered the second year of the COVID-19 pandemic, and for Obie, as we grew and expanded both our team and our product. Our mission from day one has always been to provide a fast, transparent, and affordable way to buy landlord insurance. To that end, we want to be as honest and open as possible with our customers, our employees, our partners, and our investors. Join us as we reflect on our progress this past year. 

Our product

This year was an exciting year of growth for Obie. We kicked off the year by closing on our $10.5 million Series A funding, led by Michael Brown and Battery Ventures and followed by Thomvest Ventures and a host of previous investors including Funders Club, Second Century Ventures, and Metaprop.

And from the business side, our growth was exponential. We wrote over $13 million in premium – an increase of 100% from 2020 and an increase of 1,200% from 2019.

As our product grew, so did our brand name. In Q4 of 2021, there was a 480% YoY increase in search volume around Obie and our product. More and more customers are choosing Obie, telling their networks about us, and renewing their policies. In fact, our renewal rate has never been higher, with 95% of customers choosing to stay with Obie for their insurance needs.

Customer satisfaction is one of our main goals. And although customers can get instant quotes through our website without ever having to talk to anyone, our team goes the extra mile to provide exceptional customer service.

We’ve received nearly five stars across the board. Frank C. summed up  the Obie experience well: “What a fantastic experience! A real person  answered the phone. I called back with questions 4 times and all 4 times Alex answered the phone and answered my questions thoroughly. Thank you, Obie Insurance!”

Our partnerships

What a year for partnerships! We are thankful for every single person and partner who has spent time reviewing our product, brainstorming ideas, and inspiring us to do bigger things.

In the past year, we’re pleased to have announced partnerships with:

        •Doorvest

        •Belong

        •Fractional

        •NestEgg

In 2021, our partners have helped us insure roughly $200 million in property. We choose these partners carefully, to ensure that they support not only our own goals, but our customers’ as well. These partnerships — from property management tools to investment platforms — make it easier than ever for landlords and investors to obtain instant insurance. 

Stay tuned for more partnership announcements coming in 2022!

Our team

Last, but definitely not least, are the talented group of individuals whose passion and hard work make Obie what it is today.

In the past year, we are proud to say we added 29 employees and created 13 new roles. We’ve added team members to every department: from a Channel Operations Manager to a Chief Risk Officer to a Content Marketing Manager and much more. 

At the beginning of the year, we were a small group of 12 people working from our office in Chicago, from an RV traveling the country, and from a handful of several other cities. Now, we’re a global company with 46 employees in 16 states and 2 countries.

As our team grows, so does our capacity for recognizing the talent of our team members. In October we rolled out our Top Dog program – an employee appreciation program that comes with both bragging rights and fun prizes. 

And because we work hard, we’ve got to play hard too, which is why we’ve launched the Obie Fun Committee to plan fun team-wide activities. To date, we’ve hosted Digital Drinks, Spooky Sips, trivia, a gingerbread house building competition, and holiday-themed Family Feud. 

Our team represents an incredible group of diverse and talented individuals and we can’t wait to continue celebrating them and their work.

Looking ahead 

As the fastest growing landlord insurance platform in the market, we finished 2021 strong, setting the stage for a successful and busy 2022.

We are only at the beginning of Obie's journey. You can expect to see new and exciting partnerships with companies and platforms who are the bedrock of the landlord space. And, you can expect technology that continues to improve the insurance experience with a growing team that puts clients at the forefront of everything we do (after all, half of us are landlords ourselves). We’re on track for our best year yet and can’t wait to show you what we have planned.