Product Manager

Obie; Chicago (IL); Hybrid; USD 120,000 - 160,000; Full time

Job summary

Obie is seeking an experienced Product Manager to own a meaningful product area from concept to delivery. You will collaborate across Engineering, Design, and Business teams to turn complex problems into usable solutions, even without prior insurance experience.

A curious, proactive mindset and strong product judgement are essential. You will think across customers, agents, and internal systems, defining strategy, roadmaps, and KPIs while prioritizing based on evidence and impact.

Qualifications

• Experience with technically deep products such as APIs, integrations, data pipelines, or Salesforce systems.
• Curiosity, ownership, and strong product judgement.
• Ability to explain tradeoffs and make decisions with incomplete information.

Responsibilities

• Own a meaningful product area end-to-end, shaping vision, strategy, and roadmap.
• Gather customer insight and data, weigh options, and prioritize work.
• Collaborate with Engineering, Design, and Business partners.
• Turn business priorities into clear, buildable work; measure outcomes.
• Work with Design and Engineering to sketch workflows and understand constraints.
• Document decisions and maintain traces for async work.

Skills

Customer insights

Cross-functional collaboration

Data-driven decision making

Product strategy

Tools

Salesforce

Figma

Job description

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. 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.
  
• Nice to have: 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.

Why you might be excited about us

• Insurance might not be the first thing that comes to mind when you think “cool product problems.” Take a look under the hood. There are tangled workflows to simplify, systems to connect, and plenty of chances to make something people will be genuinely relieved to use. If you like solving hard problems where the work actually matters, you’ll love it here.
  
• You’ll join a growing PM team that wants your point of view. Bring the thing you’re great at, learn from the people