Staff AI Engineer

Hi, we’re Oscar. We’re hiring a Staff Applied AI Engineer to join our AI team.

Oscar is the first health insurance company built around a full stack technology platform and a 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

Join Oscar’s AI team to build and launch transformative AI-powered products that redefine the healthcare experience for millions. As an Applied AI Engineer, you’ll take end-to-end ownership of high-impact projects—conceiving, prototyping, and deploying generative AI solutions that solve real-world problems across the healthcare ecosystem.You’ll work alongside a world-class team of engineers and data scientists, rapidly iterating on ideas and shipping production-ready applications that drive measurable business and user outcomes. You’ll have the autonomy to identify opportunities, experiment with the latest AI models and techniques, and deliver solutions that streamline operations, improve patient experiences, and move the needle for Oscar and our members.

You will report to the Sr. Director, AI.

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: $198,720 - $260,820 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 products and features, from zero-to-one prototypes to robust production systems.
• Collaborate cross-functionally with product, design, and business teams to deeply understand user needs and deliver solutions that move key metrics.
• Rapidly experiment with new models, techniques, and tools (including LLMs, RAG, and agentic workflows), iterating based on data and user feedback.
• Build and scale full-stack applications and intelligent agents that automate complex healthcare workflows and deliver seamless user experiences.
• Stay on the cutting edge of the AI ecosystem, evaluating and integrating emerging technologies to keep Oscar at the forefront of healthcare innovation.
• Contribute to Oscar’s AI strategy and technical vision, helping shape the future of healthcare through technology.
• Other duties as assigned.

Qualifications

• 7+ years of professional experience in software engineering, data science, or a related field, with a track record of impactful accomplishments
• 5+ years of experience as a leader of cross-pod or cross-company deliverables
• 5+ years of experience leading technical contributions, improving the quality of what your teams create
• 5+ years of experience with practical application of CS concepts within their team.
• 5+ years of experience setting and enforcing the standard for writing stable, correct, and maintainable code
• 5+ years of experience leading technical teams including mentoring and training more junior engineers.
• Strong Python programming skills
• Experience solving complex, ambiguous problems
• Experience designing and analyzing experiments or evaluations
• Experience or an interest in prototyping full-stack applications

Bonus Points

• Experience with the healthcare industry. Familiarity with claims or clinical data.
• Degree in math, statistics, data science, or engineering.
• Our ideal candidate is a data scientist with an engineering background, an engineer with a data science background, or a founder-type who combines product thinking, rapid prototyping, and hands-on coding to deliver real-world impact.
• Experience with NLP, neural networks, transformers, and modern AI frameworks.
• Knowledge of containerization and deployment tools (e.g., Docker, Kubernetes) or full-stack development (e.g., React, Golang).
• Experimental mindset: comfort with testing hypotheses and iterating on failures

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At Oscar, being an Equal Opportunity Employer means more than upholding discrimination-free hiring practices. It …