Oscar Health Insurance Co

Staff AI Engineer

Oscar Health Insurance Co$198K — $260K *
Healthcare
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 7+ years of experience in software engineering, data science, or related fields with proven achievements.
  • 5+ years leading cross-functional or cross-company projects.
  • 5+ years improving quality through technical leadership.
  • 5+ years applying computer science principles in practical settings.
  • 5+ years establishing coding standards for maintainable code.
  • 5+ years mentoring junior engineers and leading technical teams.
  • Proficiency in Python programming.
  • Experience navigating complex, ambiguous problem-solving challenges.

Responsibilities

  • Lead the development and deployment of AI products from prototypes to production.
  • Collaborate with product, design, and business units to meet user needs and enhance metrics.
  • Experiment with AI models and tools, iterating based on user feedback.
  • Build full-stack applications and intelligent agents for healthcare automation.
  • Evaluate and integrate emerging AI technologies to maintain Oscar's innovative edge.
  • Contribute to the AI strategy and technological vision for Oscar.
  • Perform additional duties as assigned.

Benefits

  • Participation in Oscar's unlimited vacation program.
  • Company equity grants.
  • Annual performance bonuses.
Full Job Description
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

About Oscar Health Insurance Co

Oscar Health Insurance Co. is a technology-driven health insurance company founded in 2012 and headquartered in New York City. The company offers individual and family health insurance plans, as well as Medicare Advantage plans. Oscar Health Insurance Co. uses technology to simplify the health insurance experience for its customers, including a mobile app that allows customers to manage their health insurance policies and access telemedicine services. The company has raised over $1 billion in funding and is valued at over $5 billion.
Learn more about Oscar Health Insurance Co
Size
4,000 employees
Market Cap
$466 million
Industry
Founded
2012
NASDAQ

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