Note: The job is a remote job and is open to candidates in USA. Obie is an insurance technology company helping real estate investors and landlords obtain property insurance through advanced technology, data, agents, and partners. The Insurance Program Analyst will analyze and optimize insurance program performance, build dashboards and analytical tools, support product and portfolio decisions, and use SQL, AI, and business intelligence to generate actionable insights.

Responsibilities

• 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

Skills

• 1–3 years of experience in an analytics, insurance, underwriting, product, or related role within the property insurance industry
• Understanding of insurance product principles and the factors that influence product and portfolio performance
• Interest in using data to solve business problems and support profitable growth
• Experience using SQL to analyze and work with data
• Experience with data visualization and business intelligence tools; Sigma experience is a plus
• Ability to conduct quantitative and qualitative analysis and turn findings into clear business recommendations
• Curiosity and enthusiasm for using AI and emerging technology to improve how work gets done
• Ability to explain complex business logic and analytical findings to both technical and non-technical audiences
• Strong ownership mindset with the ability to move from identifying a problem to helping drive a solution
• Comfortable working across teams and with stakeholders at all levels of the organization
• Detail-oriented with the ability to manage competing priorities and maintain a high standard of quality
• Are naturally curious and enjoy figuring out how things work
• Don't stop at identifying a problem—you want to help solve it
• Can move comfortably between detailed analysis and big-picture business questions
• Enjoy collaborating with people who have different areas of expertise
• Are comfortable with ambiguity and willing to learn as the business evolves
• Use data to challenge assumptions while applying sound business judgment
• Care about the quality of your work and take pride in making the people around you more effective
• Experience with or knowledge of surplus lines insurance is strongly preferred

Benefits

• Our Chicago based employees are hybrid, and expected to be in office on Tuesdays and Thursdays.
• Comprehensive health, dental, vision and life insurance
• Flexible paid time off
• Retirement savings plan with company match

Company Overview