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, DC, FL, GA, IL, IN, LA, MA, MI, MO, NH, NJ, NY, NC, OH, OR, PA, SC, SD, TN, TX, UT, WI

Brief Summary of Role

We are seeking an individual to join the growing data analytics team at Obie. Those successful in this role will have a mix of business, analytical, and technical skills with depth in technical / data engineering skills. Those successful will also be comfortable communicating with a wide range of individuals in understanding business requirements with respect to data.

Although reporting within the broader Insurance team, we work in a matrixed environment. The ability to collaborate and build trust with customers within and outside the Insurance team is important. This role will require the skill to complete intermediate tasks with minimal guidance from your leader.

What you'll Do

• Build, test, deploy, and manage end-to-end data pipelines from various sources to end user consumable data extracts
• Do the above using Obie’s current technologies and introducing new technologies as needed
• Build modeled data warehouse tables using the Data Vault 2.0 and Activity Schema models
• Work with business end users and analysts to understand the data requirements needed in the final data extracts; build and maintain temporary ad-hoc solutions when required
• Use data quality solutions, tools, and capabilities to improve business value of the data
• Assist with the creation of business glossaries and data dictionaries, including (1) defining key metrics and dimensions used to evaluate the business and (2) maintenance of data metadata and lineage

What you'll Bring

• 7+ years of experience in data analytics / engineering, ideally within the Property and Casualty insurance industry
• Experience using SQL and Python
• Experience querying, analyzing, and developing within SQL databases
• Experience using cloud data warehouses, data orchestration tools, and data modeling tools
• Experience using and developing within AWS
• Technical writing skills
• Ability to meet deadlines and manage competing demands

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

1. 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.
2. Meet the hiring manager
   Next, you'll have a 45-minute video interview with the hiring manager, Jeff White, to assess your technical skills for the role.
3. Complete a Project Exercise
   This role requires strong planning, collaboration, and leadership skills, so we’ll ask you to complete a short exercise. We use technology beyond spreadsheets to access, organize, and analyze our data. Our two primary languages for data analysis are Python and SQL. Our primary data stores are AWS S3 Object Storage and PostgreSQL databases hosted in AWS. The exercise will evaluate your Python and SQL skills applied to a real life insurance problem. More details will come when you reach this step!
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

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:

• 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

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.