Staff AI Engineer

Join Oscar's AI team as a Staff AI Engineer, where you'll take end-to-end ownership of high-impact projects, build and launch transformative AI-powered products, and collaborate with a world-class team of engineers and business leaders. You'll have the autonomy to identify opportunities, experiment with the latest AI models and techniques, and deliver solutions that streamline operations and improve the healthcare experience for millions.

• 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.

• 5+ years of experience with practical application of CS concepts within their team
• 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
• Experience solving complex, ambiguous problems
• 5+ years of experience leading technical teams including mentoring and training more junior engineers
• Experience designing and analyzing experiments or evaluations
• Experience or an interest in prototyping full-stack applications
• 5+ years of experience setting and enforcing the standard for writing stable, correct, and maintainable code
• Strong Python programming skills
• 5+ years of experience leading technical contributions, improving the quality of what your teams create
• Experience with the healthcare industry. Familiarity with automation of legal and financial processes
• 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
• Experience with compliance and privacy requirements