Insurance Product & Data Analytics Data Analyst 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.

We are seeking an analytics individual to join the growing Revenue Operations (Rev Ops) and Analytics department’s Business Insights team se successful in this role will have a good mix of technical skills (SQL, python, data visualization, AI), business acumen, and insurance or financial services knowledge.

Strong ownership abilities and interpersonal skills are critical for the individual in this role. At the same time, they will be a team player who is comfortable collaborating within the analytics team and across departments, from individual stakeholders to executives. The person in this role must be a doer who can strategize through problems, have the flexibility to adapt to whatever is most critical, and have the technical skills and discipline to execute.

• Develop hypotheses to understand the state of the business, such as drivers of growth or stagnation
• Build and maintain dashboards / reports within our Business Intelligence / Data Visualization tool Sigma
• Align and support various analytics, metrics, data, and reporting needs at Obie across various departments like Growth & Channel Distribution, Product & Engineering, Insurance, Finance & Accounting, and the Executive team in collaboration with Data Engineers, Insurance Product Analysts, and Operations Analysts
• Support financial budgeting, forecasting, and tracking
• Perform data quality checks and reconciliations to datasets as needed
• Serve as a trusted advisor to all stakeholders of data, answering reporting, metric, and data questions, and facilitating a culture of data literacy and data-driven decision making

• Experience in data analytics or business analytics with strong SQL abilities
• Knowledge and interest in insurance
• Ability to drive initiatives start to end and manage competing priorities
• Ability to dive deep into the data and details while synthesizing the bigger picture for stakeholders
• Strong interpersonal, communication, and leadership skills
• Team player attitude with the desire to drive impact at a fast growing company

• Experience in insurance, financial services, or similar
• Experience with another analytics tool like python, R, or similar
• Experience working with AI (We use Claude), github, and dbt
• Experience in strategy, operations and analytics, GTM analytics, financial forecasting, consulting, or similar

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 Kara on a 30-minute call to determine whether we’re a good fit for one another.…