Obie

Come work for Obie!

Posted Yesterday

Hiring Remotely in United States

Remote

Entry level

Insurance • PropTech

Obie is an insurtech company, hyper-focused on driving value for the modern real estate investor and their partners.

The Role

Obie seeks passionate talent to innovate landlord insurance services, encouraging flexibility and creativity to improve customer experience and operational efficiency.

Summary Generated by Built In

About Obie:

At Obie, we are shaking up landlord insurance, making it easily available for landlords and real estate investors both when and where they need it. With a focus on driving efficiency and innovation for our customers and within our team, we’re on the search for new talent that can take Obie to the next level.

At Obie, you’ll collaborate with a diverse team that embraces evidence-based decision making, learns from failure, accepts feedback, and is always prepared to make changes for the better. You’ll be expected to operate with flexibility and leverage your curiosity to drive innovation while collaborating with colleagues across teams and areas of expertise. Our ideal teammates are kind, passionate, committed to excellence and eager to nerd out over the best ways to make Obie even better.

If you are interested in working at Obie but don't see a current position that fits your background, please apply and share what type of role you are interested in, and what skills you would bring to Obie.

Should we have an opportunity that matches your background and could be a fit, we will be sure to reach out!

More about Obie:

Founded in 2017, Obie is paving a new path in insurance for landlords and real estate investors. Obie’s goal is to fundamentally change how insurance is bought and sold by building technology and insurance products that increase ease and accessibility for the 17 million residential real estate investors and landlords in the US. Obie offers a superior insurance experience, allowing real estate investors and landlords to obtain the right coverage where it’s most convenient for them, whether that means using our digital quote tools, working with independent agents, or finding us through our integrations with industry partners.

With over 6,000 active policy holders, and over $20 billion in coverage secured, Obie has still barely scratched the surface of its growth potential. That growth is supported by $39 million secured in funding, positioning it perfectly to continue revolutionizing the industry.

Obie has you covered:

Being in the insurance industry, we understand the importance of comprehensive benefits for you and your family. These are just some of the benefits and perks we provide:

Competitive salary

Flexible time off with an encouraged minimum time away to support a healthy work-life balance

12 weeks of Paid Parental Leave

Great health, dental and vision coverage

Life Insurance

Flexible Spending & Health Savings Accounts

Stock Options

401k match

Pet Insurance Reimbursement

Health and wellness benefit

Equipment budget - everything you need to do your best work

Professional development support

Summer hours

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The Company

HQ: Chicago, IL

125 Employees

Year Founded: 2017

What We Do

Obie is the leading investment property insurance platform, providing landlords, real estate investors, and partners with instant quotes, tailored coverage, and an entirely digital experience. Backed by proprietary technology, Obie simplifies insurance so deals can close faster and investors can move forward with confidence. Whether they’re obtaining a quote in under 5 minutes on our website, via a partner platform, or through an independent agent partner, Obie has real estate investors covered.

Since 2017, Obie has been on a mission to simplify, streamline, and enhance landlord insurance for the 17 million real estate investors and landlords across the United States. With expert-backed coverage, intuitive tools, and embedded technology, Obie delivers fast, reliable insurance solutions designed to fit how real estate professionals work today. Instead of waiting weeks to satisfy insurance requirements or to find the right coverage on a rental, investors and landlords of 1-4 unit properties can obtain instantly bindable quotes thanks to the Obie instant quote process. This offering goes beyond Obie’s own web presence by integrating into partner websites, platforms, and processes. Obie is more than a pioneer; it is the only company to offer a truly seamless embedded insurance process to investors.

The Obie instant quote process leverages data enrichment, applying unique algorithms to up to 1,000 data points obtained through multiple databases. This methodology allows Obie to more accurately assess risk, making underwriting faster and more efficient. In doing so, Obie’s technology not only drives faster quote generation, but also ensures that each quote meets the distinct needs of each property and investor. The result is a superior customer experience that confirms Obie’s position as the leading digital provider of insurance for real estate investors.

With thousands of policyholders nationwide and $60 billion in coverage secured, Obie is already transforming how real estate investors protect their assets—and we’re just getting started. Backed by $39 million in funding from industry giants like Battery Ventures and Thomvest Ventures, we’re rapidly growing and continually adapting to meet the unique needs of our customers. Whether through our advanced digital tools, trusted agent network, or strategic partnerships, Obie sets a new standard in real estate investment insurance, ensuring those we serve move forward.

Why Work With Us

Joining our team means embracing a fast-moving environment driven by innovation, collaboration, and constant progress. We learn quickly, iterate often, embrace curiosity, and celebrate wins together. If you're passionate about driving change and eager to impact the real estate and insurance market, Obie is the place for you.