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.
While Obie does offer fully remote opportunities for those outside of Chicagoland, we are only currently hiring in the following states: AZ, FL, GA, IL, IN, LA, MA, MI, MO, NH, NJ, NC, OH, PA, SC, SD, TN, TX, UT, WI
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Brief Summary of Role**
We’re looking for a Senior Data Engineer to join our growing data analytics team and help build the systems that power data-driven decisions across Obie. You’ll own end-to-end pipelines, shape how data flows through the organization, and collaborate with stakeholders across teams—especially within our Insurance division.
This is a high-impact role for someone who thrives on technical depth, cross-functional collaboration, and the chance to leave things better than they found them.
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What you'll Do**
What you'll Bring
Why Obie?
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
Intro Chat (30 min.)
A conversation with Kara or Skylar to get to know you—and let you get to know Obie.
Hiring Manager Interview (45 min.)
A deeper technical discussion with Curtis Jackson, focused on your experience and how you approach data challenges.
Take-Home Exercise
You’ll complete a short project using Python and SQL, working with realistic data from our world of real estate insurance. Our tech stack includes AWS S3 and PostgreSQL, so familiarity there will help.
Team Interview (1 hour)
You’ll meet a few members of the team to talk through your approach and explore how we’d work together.
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.
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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:
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.
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The pay range for this role is:**
105,000 - 175,000 USD per year(US)