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 around you, and take ownership or work you can point to and say “I helped build that.” Found a better way to do it? Show us!
- You get to find out whether the thing you shipped actually helped. You’ll connect customer insight to business value, define what success looks like, and use results to guide the next iteration. We value someone who can make a sound call without waiting for perfect information.
- You’ll work across multiple users, surfaces, and channels, connecting the dots between customer needs, partner constraints, and technical systems. If you’re the kind of person who keeps asking “why does it work that way?” until you’ve mapped it out, you’ll have plenty to dig into here.
- We’re curious about what Product and Engineering can build when we figure out the problem together earlier. Maybe a working prototype gets an idea across better than another page of requirements. Maybe AI helps us test it sooner. If that gets you excited, bring your experiments. No AI portfolio required; we’re interested in learning what actually helps.
Why you might not be excited about us
- You're looking for immediate people management or team-lead scope. This is a hands-on IC role. Previous management experience is welcome, but the work here is owning product problems and outcomes, not managing a team.
- Your favorite part of product is adding another process. We’ll happily use a framework when it helps, but a beautifully organized board isn’t the same as making something better for a customer. We care about what the process helps us do.
- You want to hand off the big idea and skip the messy details - or have someone hand you a fully baked plan. You’ll help decide what’s worth building and stay close enough to the work to make it happen!
- You want decisions made for you up front or perfect evidence before moving forward. You’ll have partners and support, but you’ll be expected to seek relevant input, explain tradeoffs, and make timely calls as context evolves.
- You only get excited about shiny new features. Some of the most satisfying wins here will be fixing a stubborn workflow or making an integration behave. You should enjoy improving the machinery as much as the experience it powers.
- You prefer to disappear until the big reveal. We like seeing the rough draft, asking questions, and making it better together. Bring ambition and a strong POV - and be ready to change your mind. There’s plenty to own without competing for credit.
Interview Process
At Obie, transparency is core to our interview process. We focus on open communication and a positive experience; no trick questions—just honest conversations about your skills and aspirations. To help you prepare, please familiarize yourself with these resources before moving forward:
- Meet us and get to know Obie
You'll first talk to Kara on a 30-minute call to determine whether we’re a good fit for one another. You’ll learn more about Obie and have the chance to ask about our company, team, culture, and product. - Meet the hiring manager
Next, you'll have a 45 minute video interview with the hiring manager, Adam Tsouras, to assess your technical skills. - Complete a Project Exercise
This role requires strong planning, collaboration, and communication skills, so we'll also present you with a short exercise to complete to provide you a chance to flex those muscles. You will be able to complete this exercise on your own time, so please be thorough and use the resources available to you. We'll be looking to see your problem solving abilities, writing and communication skills, empathy, general demeanor, and ability to leverage key product management strategies. More on this when you get there! - Meet the Team
Since you'll be joining a close-knit team, we'll ask you to meet other people in the company so we get to know each other a bit better
Moving Forward with Obie
Obie is a leading insurance platform for real estate investors, combining proprietary technology with a modern insurance experience to simplify Home and Landlord insurance. Today, we serve customers nationwide through direct digital experiences, a growing network of insurance agents, and strategic partnerships with lenders, property management platforms, and real estate technology companies.
As part of The Baldwin Group, one of the nation's leading insurance distribution platforms and a USA TODAY Top Workplace, we're combining the agility of a fast-growing technology company with the scale, resources, and career opportunities of a larger organization as we shape the future of investment property insurance.
Obie has you Covered
Being in the insurance industry, we understand the importance of comprehensive benefits for you and your family. These are just some of the benefits and perks we provide:
- Comprehensive health, dental, vision and life insurance
- Flexible paid time off
- Retirement savings plan with company match
Obie values transparency and data driven decision making, enabling us to have a consistent and equitable approach to compensation. We are informed by a benchmarking tool which provides real time compensation data allowing us to regularly check our salary ranges against other venture backed companies and startups within our industry. We've provided the full base salary range for this role below, but please note that we typically target the mid point of the salary range to allow room for growth within the role. Your salary is dependent upon many factors, including years of relevant experience, expertise, etc.
During your first interview, you can expect to have an open conversation with your recruiter regarding your compensation expectations.
The pay range for this role is:
90,000 - 130,000 USD per year (Remote (United States))
Click here for some insight into our culture!
The Baldwin Group will not accept unsolicited resumes from any source other than directly from a candidate who applies on our career site. Any unsolicited resumes sent to The Baldwin Group, including unsolicited resumes sent via any source from an Agency, will not be considered and are not subject to any fees for any placement resulting from the receipt of an unsolicited resume.
