Product & Engineering Product Manager​/Remote

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.

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).

• 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. Bring people into decisions early, navigate disagreement, and create clarity that helps others execute with confidence. You’re happy to own the hard call, share the credit, and jump in when a fellow PM needs a hand. Making the team better is part of the fun.
• You’re mission first: You get stuff done. Help the team turn business priorities into clear work that’s ready to build, without getting stuck in planning limbo. Balance larger bets with smaller, high‑leverage improvements, remove avoidable process drag, and keep attention on outcomes. You’ve improved the flow, clarity, or quality or work reaching engineering and can show how you evaluated results after launch.
• You can get your hands dirty: Turn complex problems into clear, buildable work with Design and Engineering.…