Staff AI Engineer

About the role

Staff Applied AI Engineer

Oscar is a health insurance company built on a full stack technology platform. Founded in 2012, our mission is to deliver care that feels like having a doctor in the family. We are currently seeking a Staff Applied AI Engineer to join our AI team and help build transformative products for millions of members. This role is based in our New York City office, operating on a hybrid schedule with three days in the office per week. Thursdays are fixed for in-office collaboration, while the remaining days offer flexibility.

The position reports to the Sr. Director, AI. The base salary range is $198,720 to $260,820 per year, accompanied by benefits, equity, an unlimited vacation policy, and performance bonuses.

You will take ownership of high-impact AI initiatives, guiding ideas from conception to deployed production systems. The work involves conceiving, building, and launching generative AI solutions that address real challenges across the healthcare ecosystem. Collaboration will occur with product, design, and business teams to align on user needs and key metrics. You will have the autonomy to identify opportunities, experiment with advanced AI methods, and deliver solutions that improve operations, patient experiences, and business outcomes.

Primary Responsibilities

• Lead the design, development, and deployment of AI driven features, moving from initial exploration to robust production systems.
• Partner with cross functional teams to deeply understand problems and deliver solutions that meaningfully impact members and providers.
• Conduct rapid experimentation with large language models, retrieval systems, and agentic workflows, using data and feedback to guide decisions.
• Build and scale full stack applications and intelligent agents that automate complex insurance processes.
• Monitor the evolving AI landscape and evaluate emerging technologies to maintain Oscar's leadership in healthcare innovation.
• Contribute to the technical vision and long term AI strategy for the company.
• Mentor engineers and help establish best practices for scalable, reliable AI systems.

Core Qualifications

• Over seven years of professional experience in software engineering or data science, with a record of impactful delivery.
• More than five years of experience leading cross team deliverables under pressure.
• Demonstrated ability to improve code quality, reliability, and maintainability within engineering teams.
• Consistent application of core computer science concepts in day to day work.
• A history of setting and enforcing standards for stable, correct, and maintainable codebases.
• Experience mentoring junior engineers through review, guidance, and feedback.
• Strong Python skills for data processing and application logic.
• Comfort with poorly defined problems and ambiguous scopes.
• Ability to design and analyze experiments that measure product and model performance.
• Interest in connecting prototypes to production services and user flows.

Additional Desired Experience

• Familiarity with healthcare specific constraints, including claims or clinical data.
• Formal education in mathematics, statistics, data science, or a related technical field.
• Knowledge of natural language processing, neural networks, transformers, and modern AI frameworks.
• Experience with containerization, orchestration, and full stack development tools.
• An experimental mindset, including comfort with hypothesis testing and result interpretation.

Tools and Skills

Python, Docker, Kubernetes, React, Golang, LLMs, RAG, and agentic workflows.

Final Notes

Please confirm details on the official application page. We encourage candidates who resonate with this work to apply and help us reimagine the healthcare experience through technology.

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Requirements

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Practical notes

This role is based in our New York City office, operating on a hybrid schedule with three days in the office per week. Thursdays are fixed for in-office collaboration, while the remaining days offer flexibility to support focus and work-life balance. The position reports to the Sr. Director, AI, and you will be expected to not only execute at a very high level but also to contribute to shaping the long-term technical vision and AI strategy for the company.