Product Manager, Obie
$90-125k
More information about location
Insurance for landlords and real estate investors
Job no longer available
Insurance for landlords and real estate investors
101-200 employees
Job no longer available
$90-125k
More information about location
101-200 employees
Company mission
To provide a simple, affordable, and transparent insurance experience for landlords and real estate investors.
Role
Who you are
- 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
- 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 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’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
- If you like solving hard problems where the work actually matters, you’ll love it here
- 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
What the job involves
- 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 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 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
- 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
- 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
- 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
Application process
- When applying, be sure to include your favorite emoji (🫒🎊⛸️🦞) so we know that you’re a real human, who also loves emojis
- 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
- 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 for the role
- 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
- During your first interview, you can expect to have an open conversation with your recruiter regarding your compensation expectations
Our take
Obie is transforming how landlords across the US access insurance for their properties. Through its tech-driven platform, landlords can easily get instant quotes, connect with the right insurance provider, and secure coverage - all without the hassle of paperwork or complicated processes. The company insures over $25M in properties across all 50 states, offering a simple and affordable alternative to traditional insurance.
Focusing on small-to-medium-sized rental properties, Obie addresses the challenges landlords face with poor pricing and inadequate coverage. By leveraging technology, the company provides customized, industry-best rates and a straightforward online experience.
With strong funding to its name and its acquisition by leading insurance brokerage The Baldwin Group, Obie is well-positioned for continued growth under new ownership, planning to reshape the future of landlord insurance.
Steph
Company Specialist at Welcome to the Jungle
Insights
26% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
May 2023
$25.5m
SERIES B
May 2021
$10.7m
SERIES A
Total funding: $39.2m
Company benefits
- Medical, Dental, Life, Vision
- 401(k) Matching
- Pet Insurance
- Paid Parental Leave
- Hotel Discounts
- Telehealth
- Flexible Time Off
- L&D Stipend
- Wellness Stipend
- Benefit Support Tools
Company HQ
West Loop, Chicago, IL
Leadership
Ryan Letzeiser
(Co-Founder & CEO)They studied at Clemson University before working as a Real Estate Investment Analyst, and becoming an Investment Associate at Hudson Capital Investments. They joined MAC Properties in March 2015 as a Managing Member in 2015, before co-founding Obie in July 2018.
Salary benchmarks
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