Product Manager

Chicago, IL
Product & Engineering /
Full-time /
About Obie

At Obie, we are shaking up landlord insurance, making it easily available for landlords and real estate investors both when and where they need it. With a focus on driving efficiency and innovation for our customers and within our team, we’re on the search for new talent that can take Obie to the next level.

At Obie, you’ll collaborate with a diverse team that embraces evidence-based decision making, learns from failure, accepts feedback, and is always prepared to make changes for the better. You’ll be expected to operate with flexibility and leverage your curiosity to drive innovation while collaborating with colleagues across teams and areas of expertise. Our ideal teammates are kind, passionate, committed to excellence and eager to nerd out over the best ways to make Obie even better.

Our Chicago based employees are hybrid, and expected to be in office on Tuesdays and Thursdays.

Brief summary of role

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 something 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:

    • 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 working to solve a number of technical product challenges in an otherwise antiquated industry. If you're into real estate investment, and insurance, you'll love helping build our product.
    • We're medium sized, so you'll be able to contribute efficiently and without bureaucracy. You'll quickly have responsibility over big areas of our product.
    • Our team has a wide range of experiences (Y Combinator graduates, Meta leads, landlords, startup veterans, Amazon engineers, etc) and are excited to learn from you, too.
    • We’ll work with you to ensure you’re growing in the ways that are important to you. We care a ton about your satisfaction and job happiness, and will do our best to prep you for whatever you're looking for in the future.
    • We work hard and also highly value a balanced work/life. We care about family and your life outside of Obie, and we’ll work to protect that.

Why you might not be excited about us:

    • We're growing but still relatively small (~90 people in the company now), so if you like more established companies, it's not (yet) the right time. You'll continue to help shape our company's culture.
    • Since we're a middle stage startup, projects and priorities may shift.
    • Our customers love us, and there's a lot we can improve. It's a great place to be, but means there's some jank. (Nothing too scary! 😃)
    • We can provide some close mentorship, but we’re mostly looking for someone who is already a leader.
    • You'll have a lot of responsibility and creativity over projects, however some of those projects may not be defined perfectly initially. You'll be expected to bring your own experience and perspective to help us do the right things, and raise flags if you think we should do things differently.
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:
- Our company’s blog to learn more about the space we’re working in and where we write about landlord insurance.
- Check out our Twitter and LinkedIn to get a glimpse of how people interact with our brand and product.
- Some posts with and about us around the web (Inc 5000, Business Insider, Best Places to Work, Financial Times)
- Podcast appearances (Legacy Leaders, Insurance Town, PropTechBuzz)

1. Meet us and learn about Obie
You'll first talk to Kara, Rebecca or Mary 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.

2. Meet the hiring manager
You'll get to have a 45 minute video interview with the hiring manager, Adam Tsouras. This discussion will be more technical in nature to ensure you have the skills needed to be successful in the role.

3. 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.

More About Obie

Founded in 2017, Obie is paving a new path in insurance for landlords and real estate investors. Obie’s goal is to fundamentally change how insurance is bought and sold  by building technology and insurance products that increase ease and accessibility for the 17 million residential real estate investors and landlords in the US. Obie offers a superior insurance experience, allowing real estate investors and landlords to obtain the right coverage where it’s most convenient for them, whether that means using our digital quote tools, working with independent agents, or finding us through our integrations with industry partners.

With over 6,000 active policy holders, and over $20 billion in coverage secured, Obie has still barely scratched the surface of its growth potential. That growth is supported by $39 million secured in funding, positioning it perfectly to continue revolutionizing the industry.

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
Health and wellness benefit
Equipment budget - everything you need to do your best work
Professional development support
Summer hours