Insurance and Risk Management for Landlords

Product Manager

$90k - $150k
Job Type
3+ years
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About the role

About Obie

Obie is an insurance technology company, hyper-focused on driving value for the modern real estate investor and the partners they work with every day. Whether an owner, lender, agent, or property manager, Obie’s mission is to build technology and insurance products that drive efficiency and fundamentally change the way insurance is bought and sold.

As the industry leader in embedded and instant insurance products, Obie was recently honored as Business Insurance Best Places to Work and one of Inc Magazine's Fastest Growing Companies for 2022. Obie is one of a small number of companies that are both a Y-Combinator and NAR REACH accelerator alum. 

To date, Obie has raised $13.7 million from leading proptech investors including Battery Ventures, Thomvest Ventures, MetaProp, Second Century Ventures, and Funders Club. The company has two offices, one in Chicago, IL and the other in Sarasota, FL, but also offers employees the option to work remotely.

Obie is looking for a passionate, talented Product Manager to join our growing Product team and help lead product vision across various departments. We are a Chicago-based, venture-backed startup at the heart of the the Insurtech movement that is shaping the way landlord insurance is provided.

Applicant must be based in the US or Canada.

About the Job

First and foremost, we're looking for people who are excited about what we're doing—you don't need to know anything about real estate insurance, but should be excited to learn.  More than a specific set of skills, we're looking for someone that (1) has the talent/experience/drive/work ethic to drive your own work (2) understands that good employees do what you tell them to do, great employees tell you what they need to do. This role will encourage you to use creativity to help the team solve problems and delight our customers. 

The most important characteristic for a Product Manager joining our team is your attitude. We want you to join because you don't see roadblocks, you see opportunities to be at your best. You know that somehow, you and the rest of our team can figure anything out.

What You'll Do:

  • Be a product owner: Drive product vision, strategy and roadmap for various projects and always bring your own point of view for the entire end-to-end experience.
  • 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: You understand how to talk to every kind of role on a 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 can work async: You will be able to work independently and make decisions with minimal supervision. You also will be able to demonstrate your excellent communication skills, including the ability to build relationships internally and externally.

What You'll Bring:

  • Proven track record of owning a product’s life cycle through multiple iterations.
  • Expert knowledge of product management principles, frameworks, and product best practices.
  • Expert-level ability to think through complex user flows and wireframes in tandem with the design team.
  • Strong understanding of user experience and user research best practices.
  • Strong communication skills. You can get people excited about any complex problem and can lead teams towards clear goals and outcomes.
  • You love diving into API specs and can write user stories in your sleep.
  • Nice to have: experience building out products at scale in a Saas, Payments, or Insurtech environment.
  • Nice to have: basic (or better) experience with modern software development frameworks (JS, Python, etc.).
  • Nice to have: you can be a pseudo-designer - Figma is your playground but you aren’t really sure what that auto layout button does.
  • Nice to have: you can work your way around basic databases and maybe even issue a few SQL queries if you are feeling spicy.
  • Nice to have: you’ve taken a stab at founding your own company or startup.

Interview Process

We want you at your best, and won't be giving you any gotcha-style questions - we aren't like that. We want to get to know you, hear about what you're interested in, and learn about what you hope to do in the future.

You should familiarize yourself with these resources before continuing:

a. Our company’s blog) to learn more about the space we’re working in, where we write about landlord insurance.

b. Check out our Twitter and LinkedIn to get a glimpse of how people interact with our brand and product.

c. Some posts with and about us around the web (Commercial Observer, Estate Innovation, Geek Estate Blog, Business Wire))

d. Podcast appearances: (The Ryan Hanley Show, REM #22)

  1. Meet us and learn about Obie

You'll first talk to Kara, Rebecca, and/or Adam) on a 30 minute call; you won't need to prepare anything in advance. The goal of this conversation is to get to know you and mutually explore if we might be a good fit for each other. You'll learn more about Obie and have a chance to ask any questions about our company, team, culture, and product.

  1. 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.

  1. 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 demeanour, and ability to leverage key product management strategies. More on this when you get there!

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:

Competitive salary

Flexible time off with an encouraged minimum time away to support a healthy work-life balance

12 weeks of Paid Parental Leave

Great health, dental and vision coverage

Life Insurance

Flexible Spending & Health Savings Accounts

Stock Options

401k match

Pet Insurance Reimbursement

Equipment budget - everything you need to do your best work

Professional development support

Company off-sites to support team development (as COVID allows)

Summer hours

Why you should join Obie

Obie is the fastest, easiest, and most transparent way for landlords to get insurance!

Team Size:94
Location:Chicago, IL
Aaron Letzeiser
Aaron Letzeiser
Ryan Letzeiser
Ryan Letzeiser