Product Manager

The posting, as Obie wrote it

At Obie, we don’t just insure properties — we ensure progress. With advanced technology, real-time data, and a vast network of agents and partners, we help real estate investors and landlords get insurance coverage whenever and wherever they need it. Thousands of owners nationwide trust us to be the insurance experts, so they don’t have to be.

Joining our team means embracing a fast-moving environment driven by innovation, collaboration, and constant progress. We learn quickly, iterate often, 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.

Our Chicago based employees are hybrid, and expected to be in office on Tuesdays and Thursdays.

Brief Summary of Role
We’re looking for an experienced, hands-on Product Manager who loves figuring out how things work and can’t wait to make them better. You’ll join our growing team as an individual contributor, turning messy, technically complex problems into solutions and products that people actually use - and checking that they made a difference! You don’t need prior insurance experience; curiosity, ownership, and strong product judgement matter most.

You’ll own a meaningful product area end-to-end: bring your own point of view, get clear on why it matters to customers and the business, and build it with Design and Engineering. You enjoy turning “could we…?” into a working first version. You’ll think across customers, agents, internal teams, and interconnected systems. Initial ownership is open, with room to contribute access domains as priorities evolve.

You’re the person who asks, “What does the data say?” and then goes looking, talking to customers and teammates along the way. You can explain tradeoffs, make timely decisions with incomplete information, and follow through on results after launch. You’re curious beyond the current tools and playbook. If you find a smarter way to do something, you’re eager to try it with the team and share what worked (and what didn’t).

What you'll Do

• You’ll be a product owner: Take a problem from “we should…” to shipped, used, and improved. The backlog is a part of the job, not the finish line. Shape the vision, strategy, and roadmap for your area, define KPIs and success upfront, and use business and customer evidence to prioritize. You can point to work you’ve owned through multiple iterations and explain what changed as you learned.
• You’re the best listener in the room: Seek out customer insight, relevant data, and cross-functional input without treating every request as a requirement. Weigh options, make tradeoffs visible, and explain both what you recommend and what you choose not to do. You know which decisions need a deeper dive and which need a sensible call so the team can keep building.
• You get that product building is a team sport: Build trust across Engineering, Design, Technical Project Management, QA, operations, and business partners.

[…]
e on this when you get there!

• Meet the Team

Since you'll be joining a close-knit team, we'll ask you to meet other people in the company so we get to know each other a bit better

Moving Forward with Obie
Obie is a leading insurance platform for real estate investors, combining proprietary technology with a modern insurance experience to simplify Home and Landlord insurance. Today, we serve customers nationwide through direct digital experiences, a growing network of insurance agents, and strategic partnerships with lenders, property management platforms, and real estate technology companies.

As part of The Baldwin Group, one of the nation's leading insurance distribution platforms and a USA TODAY Top Workplace, we're combining the agility of a fast-growing technology company with the scale, resources, and career opportunities of a larger organization as we shape the future of investment property insurance.

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:

• Comprehensive health, dental, vision and life insurance
• Flexible paid time off
• Retirement savings plan with company match

Obie values transparency and data driven decision making, enabling us to have a consistent and equitable approach to compensation. We are informed by a benchmarking tool which provides real time compensation data allowing us to regularly check our salary ranges against other venture backed companies and startups within our industry. We've provided the full base salary range for this role below, but please note that we typically target the mid point of the salary range to allow room for growth within the role. Your salary is dependent upon many factors, including years of relevant experience, expertise, etc.

During your first interview, you can expect to have an open conversation with your recruiter regarding your compensation expectations.