Insurance Product & Data Analytics Insurance Data Analyst II Chicago, IL​/Remote

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. For this position, we are looking for someone located within Eastern or Central timezones.

We are seeking an individual to join the Data Analytics team se successful in this role will have data analytics experience, finance and accounting reporting skills, and experience in P&C insurance. Successful candidates will also have stellar interpersonal skills and be comfortable communicating both within the data analytics team and with leadership across the company.

• Perform daily data quality checks of all critical data sets and recommend required changes to the data (and potentially systems creating the data)
• Perform reconciliations between different critical data sets that contain similar data to identify and explain any discrepancies to VP of Finance
• Perform daily updates to our external reporting datasets to ensure data is accurate and complete
• Answer data quality/reconciliation questions from other departments and produce findings to the data team and inquiring party
• Lead data team automations, such as the implementation of data quality tools/automated data quality checks
• Assist with building simple dashboards/reporting within our Business Intelligence/Data Visualization tool
• Assist with the implementation of data quality tools/automated data quality checks

• 2+ years of experience in data analytics, or an adjacent field
• Familiarity with accounting principles and financial reporting required
• Insurance experience required
• Strong SQL experience required
• Python experience required
• Strong interpersonal and communication skills
• Strong time management skills and ability to manage competing priorities

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 Linked In to see how people interact with our brand and product.
• Meet us and get to know Obie. You’ll first talk to Skylar 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.
• Meet the hiring manager. Next, you’ll have a 45-minute video interview with the hiring manager, Sam Isken, to assess your technical skills for the role.
• Complete a Project Exercise. This role requires strong planning, collaboration, communication, and analytical skills, so we’ll ask you to complete a short exercise to flex those muscles. You can take your time and use the resources available. We’ll assess your problem-solving abilities, writing skills, empathy, demeanor, and how well you apply key data analytics principles. More details will come when you reach this step!
• 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.

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…