Hi, we're Oscar. We're hiring a Senior Data Scientist, AI Enablement to join our Data Team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role

Oscar's data team is focused on pushing our understanding of the complex landscape of the healthcare and insurance business. Insurance companies sit on a trove of data that is both broad and deep—spanning financial claims, clinical medical records, and rich product interaction data from our members.

As a Senior Data Scientist for AI Enablement, you will sit at the intersection of data science, data engineering, and artificial intelligence. You will be responsible for designing, building, and maintaining AI-powered analytical systems and pipelines that empower our internal stakeholders to self-serve their data needs. This is a builder-focused role: the ideal candidate is a data scientist with a strong engineering background (or vice versa) who is energized by turning ambiguous workflows into well-engineered, LLM-augmented data tools and automated insights.

You will act as a foundational driver for AI Enablement for Data. You will be expected to operate with a high degree of independence, taking projects from initial conception to launch. While you will own these workflows end-to-end, you won’t be building in a silo. This is a highly cross-functional position where you will partner closely with a talented group of AI engineers, software engineers, data scientists, and business stakeholders to bring scalable, production-ready solutions to life.

You will report into the Director, Data Science.

Work Location: This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $163,944 - $215,176.50 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants, and annual performance bonuses.

Responsibilities

Lead the design, development, and deployment of AI-driven self-serve analytics products, from zero-to-one prototypes to robust production systems.
Rapidly experiment with new models, techniques, and tools, selecting approaches based on measured quality, reliability, performance, and cost.
Establish evaluations and monitoring for analytical accuracy, generated queries, and AI-generated insights, including how systems handle ambiguous questions and unsupported conclusions.
Collaborate cross-functionally with AI engineers, software engineers, and business leaders to deeply understand user needs and seamlessly integrate your data workflows into broader software applications.
Help shape Oscar’s technical direction and roadmap for AI-enabled analytics.
Compliance with all applicable laws and regulations.
Other duties as assigned.

Requirements

4+ years of industry or other quantitative technical fields (which may include academia).
3+ years of experience working with SQL and Python to query, manipulate, and analyze data
2+ years of experience with LLMs, prompt engineering, and GenAI concepts, with a track record of applying them to practical use cases.
Experience building data models, using more advanced analytics methods, statistical modeling, and/or data processing
Experience designing, building, and maintaining production data pipelines or systems, applying software engineering best practices such as version control, code review, and testing
Experience acting as a primary driver of technical projects, operating independently to scope and deliver solutions from end-to-end.

Bonus points

Experience integrating advanced agentic workflows into analytical tools and automated pipelines.