Staff AI Engineer

Oscar Health•New York, NY

3d•$198,720 - $260,820•Hybrid

About The Position

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, Business Enablement 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 business leaders, 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 and move the needle for Oscar and our members.

Requirements

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

Nice To Haves

Experience with the healthcare industry.
Familiarity with automation of legal and financial processes.
Experience with compliance and privacy requirements.
Degree in math, statistics, data science, or engineering.
Our ideal candidate is a product manager with an engineering background, an engineer with a product 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

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.