Product Manager

Summary

Obie is an insurance technology company helping real estate investors and landlords obtain property insurance through advanced technology, real-time data, and agent partnerships. The company is seeking an experienced, hands-on Product Manager to own a product area end-to-end, shape strategy and roadmaps, collaborate with cross-functional teams, and turn complex technical problems into measurable customer and business outcomes.

Responsibilities

• 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. Bring experience with technically deep products, such as APIs, integrations, data pipelines, or Salesforce’y systems. You’ll happily dig into an API spec or sketch a workflow in Figma to understand what’s going on under the hood. Learn enough to ask good questions, spot constraints, and sequence the work - and notice when the UX still feels clunky
• You can work async: You don’t need someone hovering over your shoulder to move things forward. Own decisions as context shifts, and leave a trail your teammates can actually follow: research, decisions, metrics, and open questions that are easy to find and use. You can show who a written artifact or stakeholder conversation clarified a complex decision, resolved disagreement, or enabled others to act

Skills

• 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 can point to work you've owned through multiple iterations and explain what changed as you learned
• You've improved the flow, clarity, or quality or work reaching engineering and can show how you evaluated results after launch
• Bring experience with technically deep products, such as APIs, integrations, data pipelines, or Salesforce'y systems
• You'll happily dig into an API spec or sketch a workflow in Figma to understand what's going on under the hood
• You can show who a written artifact or stakeholder conversation clarified a complex decision, resolved disagreement, or enabled others to act
• Experience in insurance, insurtech, fintech, or another regulated environment; Salesforce, data products, carrier/partner integrations, or workflow-heavy B2B software; or balancing platform work with customer facing improvements
• Have you built a scrappy AI prototype, tinkered with an agent, or found a better way to show an engineer what you mean? We'd love to hear about it! These are help additions, not requirements

Qualifications

Must Haves

• 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 can point to work you've owned through multiple iterations and explain what changed as you learned
• You've improved the flow, clarity, or quality or work reaching engineering and can show how you evaluated results after launch
• Bring experience with technically deep products, such as APIs, integrations, data pipelines, or Salesforce'y systems
• You'll happily dig into an API spec or sketch a workflow in Figma to understand what's going on under the hood
• You can show who a written artifact or stakeholder conversation clarified a complex decision, resolved disagreement, or enabled others to act

Nice to Haves

• Experience in insurance, insurtech, fintech, or another regulated environment; Salesforce, data products, carrier/partner integrations, or workflow-heavy B2B software; or balancing platform work with customer facing improvements
• Have you built a scrappy AI prototype, tinkered with an agent, or found a better way to show an engineer what you mean? We'd love to hear about it! These are help additions, not requirements

Benefits

• Comprehensive health, dental, vision and life insurance
• Flexible paid time off
• Retirement savings plan with company match
• Chicago-based employees are hybrid, and expected to be in office on Tuesdays and Thursdays.