United States onlyAt 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
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.
What you'll Do
- Design, build, and maintain end-to-end data pipelines from source systems to user-facing analytics.
- Develop modeled warehouse tables using the Data Vault 2.0 framework.
- Translate business needs into technical solutions by collaborating with analysts, product managers, and leadership.
- Build and maintain ad-hoc and temporary data solutions to keep teams unblocked.
- Champion data quality and governance, including defining key metrics, building glossaries, and documenting data lineage.
- Work within Obie’s current stack—and help us evolve it—with tools like AWS, PostgreSQL, Python, SQL, dbt, and orchestration platforms.
What you'll Bring
- 7+ years of experience in data engineering or analytics, ideally in Property & Casualty insurance.
- Strong experience with SQL, scripting in Python (and optionally JavaScript/TypeScript), and querying SQL-based systems.
- Deep familiarity with AWS cloud services, especially S3 and managed databases.
- Experience with cloud data warehouses, orchestration tools, and modern data modeling practices.
- Excellent technical writing and documentation skills.
- Ability to work independently and deliver on complex projects with minimal guidance.
- Strong communication skills and comfort working in a matrixed, cross-functional environment.
Why Obie?
- Real ownership. This role is pivotal to our growth—your work will directly impact internal teams and external customers.
- Speed + stability. We move fast, and we’re backed by $39M in funding and $25B+ in insured property.
- Startup pace, solid support. You’ll get the autonomy of a startup with the mentorship and tools to thrive.
- Culture that ships. We believe in high standards, meaningful work, and showing up—for each other, and in our code.
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.
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 including 12 week Paid Parental Leave
- Retirement savings plan with company match
- Equity participation opportunities
- Monthly stipends to support a healthy lifestyle and learning and development opportunities
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.
