Insurance Program Analyst

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.

The Insurance Program Analyst will play a critical role in helping Obie build, manage, and optimize the insurance programs that drive our business.

Reporting to the Head of Rev Ops and Analytics, this role sits at the intersection of insurance, analytics, technology, and business strategy. You'll use data, SQL, AI, and business intelligence tools to understand product and portfolio performance, support product development and expansion, and help turn complex insurance questions into clear insights and action.

This is an opportunity for someone who enjoys getting into the details, solving problems, and seeing their work directly influence business decisions. The right person will bring strong technical skills, insurance curiosity, business judgment, and a willingness to take ownership from question through execution.

• Analyze insurance product and portfolio performance to identify trends, opportunities, and areas requiring attention.
• Support insurance product managers and program leaders with rate revisions, state expansion, product development, and other strategic initiatives.
• Conduct quantitative and qualitative analysis across products, states, customer segments, and other areas of the business to support profitable growth.
• Help translate portfolio performance into clear recommendations and actions.
• Build and maintain dashboards, reporting, and analytical tools using Sigma and other business intelligence platforms.
• Develop and refine metrics that help the Insurance Programs team understand product performance, operational efficiency, and business outcomes.
• Answer complex reporting, metric, and data questions for insurance stakeholders across the organization.
• Perform data quality checks, reconciliations, and validation to ensure teams can confidently make decisions using the data available to them.

• Use AI tools, including Claude, to improve analytical processes, build more effective tools and frameworks, and accelerate how insurance products are developed and brought to market.
• Partner with Product, Engineering, Data, and Insurance teams to identify opportunities to automate work, improve workflows, and create better decision-making tools.
• Bring curiosity and experimentation to how emerging technology can improve the way Obie operates.

• Work closely with Insurance Product Managers, Underwriting, Compliance, Data Engineers, Data Analysts, Distribution, and other business partners to solve complex problems.
• Translate technical analysis and business logic into clear, actionable insights for both technical and non-technical audiences.
• Serve as a trusted resource for insurance stakeholders seeking to better understand data, metrics, and performance.
• Help build a culture of data literacy and evidence-based decision-making across the Insurance organization.

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