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Product Manager

Obie

This Product Manager role focuses on solving complex technical problems within the real estate insurance space. You will own a specific product area end-to-end, translating messy workflows into functional products for customers and internal teams.

What you’d own

  • End-to-end ownership of a core product area
  • Technical systems including APIs, integrations, and data pipelines
  • Product roadmap, vision, and success metrics (KPIs)
  • Cross-functional collaboration with Design, Engineering, and QA

Who it’s for

A fit if you…

  • You have experience with technically deep products like APIs or complex B2B workflows.
  • You are comfortable making decisions with incomplete information and explaining trade-offs.
  • You enjoy 'getting your hands dirty' in technical specs and workflow mapping.

Not for you if…

  • You are seeking a people management or team lead role (this is an IC role).
  • You prefer high-level strategy over digging into messy, backend system improvements.
  • You require a perfectly defined roadmap or clear instructions before taking action.

Reading between the lines

  • The mention of 'messy, technically complex problems' and 'tangled workflows' suggests the product may have significant technical debt or legacy complexity.
  • The emphasis on 'making decisions with incomplete information' and 'not waiting for perfect evidence' implies a high degree of autonomy and a need for rapid decision-making.
  • The focus on 'removing avoidable process drag' suggests the team values efficiency over heavy, formal project management frameworks.

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Benefits

HealthDentalVisionRetirement MatchPTO
Full job description
Location: Remote (United States) Location Type: REMOTE Employment Type: {'label': 'SALARIED_FT', 'id': 'Salaried, full-time'} Compensation: [{'location': 'Remote (United States)', 'currency': 'USD', 'frequency': 'YEAR', 'rangeStart': 90000.0, 'rangeEnd': 130000.0, 'isRemote': True}] Department: Product {"company": " At Obie, we don\u2019t just insure properties \u2014 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\u2019t 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. ", "role": " Brief Summary of Role We\u2019re looking for an experienced, hands-on Product Manager who loves figuring out how things work and can\u2019t wait to make them better. You\u2019ll 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\u2019t need prior insurance experience; curiosity, ownership, and strong product judgement matter most. You\u2019ll 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 \u201ccould we\u2026?\u201d into a working first version. You\u2019ll think across customers, agents, internal teams, and interconnected systems. Initial ownership is open, with room to contribute access domains as priorities evolve. You\u2019re the person who asks, \u201cWhat does the data say?\u201d 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\u2019re curious beyond the current tools and playbook. If you find a smarter way to do something, you\u2019re eager to try it with the team and share what worked (and what didn\u2019t). What you'll Do You\u2019ll be a product owner: Take a problem from \u201cwe should\u2026\u201d 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\u2019ve owned through multiple iterations and explain what changed as you learned. You\u2019re 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\u2019re 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\u2019re mission first: You get stuff done. Help the team turn business priorities into clear work that\u2019s 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\u2019ve 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\u2019y systems. You\u2019ll happily dig into an API spec or sketch a workflow in Figma to understand what\u2019s 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\u2019t 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\u2019d 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 \u201ccool product problems.\u201d 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\u2019ll love it here. You\u2019ll join a growing PM team that wants your point of view. Bring the thing you\u2019re great at, learn from the people around you, and take ownership or work you can point to and say \u201cI helped build that.\u201d Found a better way to do it? Show us! You get to find out whether the thing you shipped actually helped. You\u2019ll 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\u2019ll work across multiple users, surfaces, and channels, connecting the dots between customer needs, partner constraints, and technical systems. If you\u2019re the kind of person who keeps asking \u201cwhy does it work that way?\u201d until you\u2019ve mapped it out, you\u2019ll have plenty to dig into here. We\u2019re 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\u2019re 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\u2019ll happily use a framework when it helps, but a beautifully organized board isn\u2019t 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\u2019ll help decide what\u2019s 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\u2019ll have partners and support, but you\u2019ll 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\u2019s 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\u2014just honest conversations about your skills and aspirations. To help you prepare, please familiarize yourself with these resources before moving forward: Our company\u2019s blog\u00a0 to learn more about the market we serve and the information our customers value. Check out our LinkedIn to see how people interact with our brand and product. Press and podcast features like Inc. 5000 , TechCrunch , Innovate State , Uncontested Investing Podcast , Insurtech Amplified Podcast Meet us and get to know Obie You'll first talk to\u00a0 Kara \u00a0on a 30-minute call to determine whether we\u2019re a good fit for one another. You\u2019ll 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. "}

Obie sells landlord insurance to real estate investors and property owners, replacing the usual broker-and-paperwork process with an online flow that quotes and binds a policy in minutes. Founded in 2017 and based in Chicago, it also distributes through an embedded channel, where proptech and fintech partners like Baselane and Kiavi surface Obie coverage inside their own lending and property management products. The company has raised a Series B and says it has placed over $20 billion in total coverage. For a product manager the interesting shape is two-sided: a direct self-serve experience plus a partner-facing API, with underwriting and insurance data work alongside both. Roles are typically listed as Chicago or remote in the US.

Financial Services & FintechReal Estate & PropTechParental leave

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