Product Manager

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 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.

What you'll do

• 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 pseudo-designer - Figma is your playground but you aren’t really sure what that auto layout button does. You can work your way around basic databases and maybe even issue a few SQL queries if you are feeling spicy. You’ve taken a stab at founding your own company or startup.

Why you might be excited about us

• We're building products in an industry that’s overdue for modernization - real estate investing + insurance is full of complex workflows, real constraints, and high-stakes decisions. If you like solving hard problems where the work actually matters, you’ll love it here.
  
• Our team is medium sized, so you can contribute without bureaucracy and quickly take responsibility over meaningful parts of the product. The people around you bring a wide range of experience (Y Combinator, big tech, startup veterans, landlords, etc.), and we genuinely like learning from each other.
  
• We're also a great fit if you’re data-curious and technically fluent - not in a “go write the code” way, but in the “I want to understand how this works, what the data says, and what tradeoffs we’re making” way. You’ll work closely with engineers, dig into specs, and help guide decisions with both customer empathy and real-world constraints.
  
• You'll get to work on a platform with multiple surfaces, channels, and user types (internal teams, partners, and customers), which means you’ll be challenged to think like a generalist systems PM: connect dots, understand tradeoffs, and help the team make smart decisions quickly.
  
• We move fast, but we care a lot about doing things well. You’ll have real ownership, and your judgment will matter - especially in the details. If you have strong product taste and enjoy partnering with design (or you’re “design-adjacent” and like giving thoughtful UX feedback), you’ll have a lot of room to raise the bar.
  
• Finally, we work hard - and we protect balance. We care about family and life outside of Obie, and we’ll do our best to make sure you can do your best work without burning out.

Why you might not be excited about us

• You  want a company where every problem is already solved by process. We’ve grown up a lot and have stronger planning, delivery, and operating rhythms than we used to - but some situations will still require judgment, collaboration, and figuring things out with imperfect inputs.
  
• You prefer “pure discovery” with minimal operational complexity. Insurance is a real-world, regulated domain. Even in a hardened product, work often includes edge cases, compliance considerations, partner constraints, and rollout / change-management details.
  
• You only enjoy greenfield building. A meaningful portion of the work is improving, scaling, and evolving existing systems and experiences (the unsexy work that makes a product great), not always launching something brand new.
  
• You want decisions to be made for you up front. You’ll usually have clear goals and support, but you’ll still be expected to ask good questions, surface tradeoffs, and help clarify the “why” and “what” as we go.
  
• You’re not comfortable getting feedback early. We move best when we share drafts, test assumptions, and iterate in the open - if you prefer to work in isolation until something is “perfect,” it may feel uncomfortable.
  
• You want a role that’s only leadership or only execution. This role can flex: you can grow as a strong individual contributor with mentorship and support, and over time take on broader leadership as you’re ready - without needing to come in as the loudest voice in the room on day one.

When applying, be sure to include your favorite emoji (🫒🎊⛸️🦞) so we know that you’re a real human, who also loves emojis.

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:

• Our company’s blog 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

1. 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.
2. Meet the hiring manager
   Next, you'll have a 45-minute video interview with the hiring manager, Adam Tsouras, to assess your technical skills for the role.
3. 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!
4. 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 leading the future of real estate investment protection, securing over $25 billion in coverage for thousands of policyholders nationwide. Backed by $39 million in funding and recognized as a top workplace by Built In and Inc., we’re committed to driving progress for our customers and team. Through advanced digital tools, a trusted agent network, and strategic partnerships, Obie provides real estate investors the insurance coverage they need to move forward confidently.

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.