Senior Security Engineer I, AI

Hi, we're Oscar. We're hiring a Senior Security AI Engineer 1 to join our Security Engineering team.

Oscar is the first health insurance company built around a full‑stack technology platform and a relentless focus on serving our members.

About The Role

As Senior AI Security Engineer, you will safeguard Oscar’s digital ecosystem and shape the secure deployment of artificial intelligence. You will collaborate across Data, Engineering, Privacy, HR, and Compliance to architect cutting‑edge security solutions and proactive guardrails that drive safe AI innovation, secure enterprise model adoption, and protect the business from emerging adversarial threats.

Work Location

Based in our New York City office, the position requires a hybrid work schedule with three days in‑office per week. Thursdays are a mandatory in‑office day for team meetings and events; the other two days are flexible.

Pay Transparency

Base pay: $163,944–$215,176 per year. You are also eligible for employee benefits, participation in Oscar’s unlimited vacation program, company equity grants, and annual performance bonuses.

Responsibilities

• Spearhead a secure AI data & model lifecycle: lead the development and implementation of a comprehensive AI security framework encompassing secure model adoption, training data pipelines, retrieval‑augmented generation (RAG) architectures, and fine‑tuning environments.
• Design and implement safer guardrails & contextual access: architect automated controls to mitigate risks such as prompt injection, model poisoning, data exfiltration, and insecure output handling while enforcing least‑privilege principles across LLMs and agentic workflows.
• Drive strategic AI security initiatives & threat modeling: lead proactive AI red‑team exercises and map adversarial tactics against industry frameworks like MITRE ATLAS and the OWASP Top 10 for LLMs.
• Measure and report on AI security initiatives: develop metrics and reporting frameworks to evaluate the impact and adoption of AI safety policies, providing actionable insights for executives and ensuring accountability to compliance and legal stakeholders.
• Champion AI security best practices and culture: partner cross‑functionally to establish secure‑by‑default blueprints, helping employees responsibly harness AI technologies and fostering a strong security‑first mindset.
• Other duties as assigned.

Requirements

• 4+ years of relevant experience in technical security engineering, application security, cloud security infrastructure, or software engineering with a distinct focus on data security or AI frameworks.

Bonus Points

• Proven experience evaluating LLM security postures, implementing alignment guardrails, and managing cloud security infrastructure (AWS/GCP IAM boundaries).
• Comfort and fluency with frontier AI technologies (e.g., Claude, Code, Codex) and an aptitude for rapid adoption of emerging tools.
• Experience communicating technical AI risk requirements and architectural implications clearly to non‑technical stakeholders, legal, and compliance teams.
• Ability to commit, review, and manage code independently across multiple enterprise repositories.
• Familiarity with health insurance data regulations (e.g., HIPAA) and their intersections with automated data usage and generative model architectures.
• Bachelor’s degree in a technical discipline (Computer Science, Data Science, Cybersecurity, or equivalent).

Equal Opportunity Employer

At Oscar, being an Equal Opportunity Employer means cultivating an environment where people can be their authentic selves and find belonging and support. We’re on a mission to change health care with diverse backgrounds and perspectives.

Artificial Intelligence (AI) Guidelines

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Reasonable Accommodation

Oscar applicants are considered solely based on qualifications, without regard to disability or accommodation needs. Applicants requiring reasonable accommodations during the application process should contact the Oscar Benefits Team ( ).

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