Join the Pack

Ready to shake up the insurance industry? Let's talk.

Ready to shake up the insurance industry? Come play with us.

Apply today

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Obie shares its name with a beloved four-legged friend of our cofounder. You don’t have to be a dog lover to apply, but we embrace Obie’s earnest, playful, and determined spirit and apply it to everything we do.

The legs we stand on

Do Good.

Everything we do is rooted in respect. Respect for our customers, our team, and ourselves. We strive to be empathetic, helpful, and trustworthy.

Be Curious.

No question is a dumb one. Obies love tackling new problems, thinking outside of the box, and pursuing big ideas to grow through.

Play fair.

We built our product on honesty and transparency. We ask all Obies to work with integrity and to pursue a diverse and inclusive atmosphere.

Stay flexible.

Life happens. Whether it’s a work project that requires creative problem solving or a family emergency that takes you away from work — we know how to prioritize what matters.

Your wellness, our priority

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, and vision offerings
• Paid parental leave
• 401K match
• Flexible PTO  
• Life insurance
• Commuter benefit plan


• Pet insurance reimbursement
• Stock options
• Flexible Spending Accounts
• Health Savings Accounts
• Continuing education & professional development


• Summer hours
• Remote & hybrid work options
• Parent coaching & return to work support
• Dog friendly office
• On-site gym (Chicago location)

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.

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Fetch the career of your dreams


Come Work for Obie!

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Chicago, IL
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Licensed P&C Insurance Sales Agent

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Chicago, IL; Sarasota, FL / Remote (Canada/US)
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Insurance Customer Success Rep

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Chicago, IL; Sarasota, FL / Remote (Canada/US)
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Senior Software Engineer

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Chicago, IL / Remote (Canada/US)
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Lead Quality Assurance Specialist

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Chicago, IL / Remote (Canada/US)
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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.