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Obie is a fast-growing insurtech platform that simplifies property insurance for real estate investors and landlords nationwide. The company has secured over $25 billion in coverage for thousands of policyholders and is backed by $39 million in funding.
You'll join as a hands-on Product Manager, owning a meaningful product area end-to-end. This is an individual contributor role focused on turning complex, technically challenging problems into solutions that customers actually use. You'll work across a growing PM team, Design, Engineering, and business partners to shape vision, strategy, and roadmap for your area.
Key responsibilities include:
- Taking problems from conception through shipping, usage, and iterative improvement
- Defining KPIs and success metrics upfront; using business and customer evidence to prioritize
- Seeking customer insight and data without treating every request as a requirement; making tradeoffs visible
- Building trust across Engineering, Design, Technical Project Management, QA, operations, and business partners
- Turning complex problems into clear, buildable work; diving into technical specs and workflows to understand constraints
- Working asynchronously with clear documentation: research, decisions, metrics, and open questions that teammates can follow
- Balancing larger strategic bets with smaller, high-leverage improvements; removing process drag
- Evaluating results after launch and iterating based on what you learn
You don't need prior insurance experience. What matters most is curiosity, ownership, and strong product judgment. You're comfortable with technically deep products (APIs, integrations, data pipelines, workflow-heavy B2B systems) and can ask good questions, spot constraints, and sequence work. You're equally at home sketching in Figma or reviewing an API spec.
The role is based in Chicago with hybrid expectations (in-office Tuesdays and Thursdays), though remote options may be available.
Requirements:
- Demonstrated experience owning products through multiple iterations with measurable outcomes
- Ability to work with incomplete information, make timely decisions, and follow through on results
- Strong cross-functional collaboration skills; comfort navigating disagreement and creating clarity
- Experience with technically complex products (APIs, integrations, data pipelines, Salesforce-like systems, or workflow-heavy B2B software)
- Ability to work independently and asynchronously with clear documentation
- Curiosity and willingness to learn; comfort with regulated environments is a plus
Nice-to-have experience: insurance, insurtech, fintech, or other regulated industries; Salesforce or carrier/partner integrations; platform work balanced with customer-facing improvements; prototyping with AI or agents.
