Find Your Place At Obie

Unlock your potential with a career at Obie

Unlock your potential with a career at Obie

Apply today

Join our Award-Winning workplace

We’re honored to be recognized as a leading company in both tech and insurance.

Our culture

We embrace evidence, learn from failures, accept criticism, and are always prepared to change our opinions. This creates a culture and environment where everyone—regardless of their role, background, gender, or opinion—can feel comfortable speaking up and being understood.

We want all Obians to feel seen, and valued, making space for everyone to contribute to the team.

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How we work

We work as one unified team to set a new standard in landlord insurance. In our hybrid nationally-distributed workforce, employees located in Chicago, IL and Lakewood Ranch, FL have the unique opportunity to experience in-office collaboration weekly, while connecting with remote employees nationwide.

We believe the keys to connecting our many fully remote team members are transparent communication, investing in team-building, and celebrating milestones together. Obie does this through the intentional use of Slack and virtual meeting time, as well as virtual social events and celebrations.

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Our values

Our values guide how we treat our customers, our teammates, and ourselves. We prioritize doing good, being curious, playing fair, and staying flexible.

Do Good.

From the insurance process, to employee well-being, we’re committed to leaving things better than we found them.

Be Curious.

We never stop challenging ourselves to ask hard questions and explore new possibilities.

Play Fair.

We value all respectful opinions, giving opportunity for all voices to be heard.

Stay Flexible.

We adapt as we learn, working collaboratively to introduce new ideas and solutions.

Our benefits

At Obie, we know life isn’t always a walk in the park. This is why we provide flexible and supportive benefits to make life easier where we can.

Here's how we take care of our team:

Medical, Dental, Life, Vision

401(k) Matching

Pet Insurance

Paid Parental Leave

Hotel Discounts

Telehealth

Flexible Time Off

L&D Stipend

Wellness Stipend

Benefit Support Tools

Job opportunities

Join the team

Be part of the team that's changing the landlord insurance process.

Diversity and inclusion make us stronger

We believe everyone has something unique to offer — and to that point, we welcome anyone to apply. Where in the world you work from doesn’t matter to us as much as the value you are adding to the team, both as a person and in your area of expertise.

We embrace evidence, learn from failures, accept criticism, and are always prepared to change our opinions. We believe this leads to a culture and environment where everyone — regardless of their role, background, gender, or opinion — can feel comfortable speaking up and being understood.

View open roles

Risk

Customer Success Representative II

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Chicago, IL / Remote (Canada/US)
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Full-time
Multi-Family

Client Services Executive II

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Chicago, IL / Remote (US)
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Full-time
Growth

Growth Marketing Manager

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Chicago, IL / Remote (Canada/US)
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Full-time
Growth

Marketing Manager (Generalist)

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Chicago, IL / Remote (Canada/US)
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Full-time
General

Come Work for Obie!

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Chicago, IL
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Full-time

Transparency in Coverage - BCBSIL Machine Readable Files

This link leads to the machine-readable files that are made available in response to the federal Transparency in Coverage Rule and includes negotiated service rates and out-of-network allowed amounts between health plans and healthcare providers. The machine-readable files are formatted to allow researchers, regulators, and application developers to more easily access and analyze data.