Product & Engineering Product Manager Chicago, IL​/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.

While Obie does offer fully remote opportunities for those outside of Chicagoland, we are only currently hiring in the following states: AZ, FL, GA, IL, IN, LA, MA, MI, MO, NH, NJ, NC, OH, PA, SC, SD, TN, TX, UT, WI

We’re looking for a Product Manager who thrives in a fast-moving, high-growth environment and loves solving complex, real-world problems. You don’t need prior real estate insurance experience - what matters most is curiosity, ownership, and a bias toward action.

In this role, you’ll own meaningful product areas end-to-end: deeply understanding the problem, aligning stakeholders on what “good” looks like, and partnering with Design and Engineering to ship iteratively with quality. You’ll bring strong systems thinking, and are capable of connecting dots across multiple user types, surfaces, and channels. You’ll balance customer empathy with decisive judgment, and you’re comfortable operating with imperfect information while keeping teams focused on outcomes.

You have a keen design sensibility - you notice when something feels off, and you can give constructive feedback that raises the bar for user experience. You’re also technically curious and data-driven, eager to dig into how systems work and use insights to guide decision‑making. Above all, your attitude sets the tone: you see roadblocks as design constraints and believe the team can figure things out together - quickly, thoughtfully, and with high standards.

• You’ll be a product owner: Assist in defining product vision, strategy and roadmap for various projects and always bring your own point of view for the entire end-to-end experience. You have a proven track record of owning a product’s life cycle through multiple iterations.
• You’re the best listener in the room: You’re never dogmatic about your views and understand how to listen to users and stakeholders.
• You get that product building is a team sport: With no shortage of product opportunities at Obie, you understand how to talk to every kind of role inside and outside of the product team and how to get the most out of people. You will be a promoter of great product amongst other cross functional teams at the company as you get people excited about complex problems and lead teams towards clear goals and outcomes.
• You’re mission first: You get stuff done and don’t let anything get in the way of moving the product forward. You have expert knowledge of product management principles, frameworks, and product best practices.
• You can get your hands dirty: You have a strong understanding of user experience and user research best practices, love diving into API specs, and can write user stories in your sleep. You have a familiarity with common tools of the trade, like Mixpanel, Confluence, and Fullstory. You understand tech debt and when it’s a good idea; you understand tech debt and when it’s a bad idea.
• You can work async: You are able to work independently and make decision with minimal supervision. You are able to demonstrate your excellent communication skills, including the ability to build relationships internally and externally. As such, you are happy writing documentation so that others can ramp up super easily and you’re never a single-source-of-failure. We’re still too small to have silos.
• Nice to have: You have experience building out products at scale in a Saas, Payments, or Insurtech environment. You can be a…