Director of Analytics Engineering - GCP, dbt & AI

Oscar is the first health insurance company built around a full-stack technology platform and a relentless focus on serving our members. We started Oscar to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

Reporting directly to the VP of Data, the Director of Analytics Engineering sets the enterprise strategy for trusted, governed, and reusable data products across Oscar Health. Leading a multi-team organization of analytics engineering managers and senior technical individual contributors, you will drive enterprise-wide transformation of data practices, semantic layers, and cloud platforms. You will establish production-grade engineering standards that accelerate self-service analytics, ensure strict data lineage and governance, and provide the clean foundation required to power business operations and responsible AI/ML applications.

Key Responsibilities

• Analytics Engineering Strategy & Delivery: Own and execute the enterprise analytics engineering operating plan, building scalable strategies that make reliable, reusable data products accessible across the company.
• Enterprise Data Transformation & Semantic Layer: Build and govern the enterprise transformation layer (dbt, Looker) to ensure data quality, clear lineage, standardized metrics, and secure, role-based access.
• Production Standards & Observability: Establish production-grade software engineering practices, testing protocols, data observability standards, and incident response procedures for core data products.
• Multi-Team Leadership & Talent Development: Recruit, mentor, and lead a high-performing organization of analytics engineering managers and senior technical talent, defining career growth paths and organizational structure.
• Executive Alignment & Governance: Partner with business, engineering, and executive stakeholders to align data investments, communicate risks, and report on operating metrics during quarterly business reviews.
• Self-Service & AI Enablement: Expand company-wide self-service analytics adoption while structuring governed data layers to feed downstream machine learning models and Generative AI applications.
• Operational Metrics & Cost Optimization: Measure and continuously improve data trust, pipeline reliability, delivery velocity, query performance, and cloud data platform spending efficiency.

Requirements

Executive Data Leadership & Technical Depth

• 10+ years of progressive experience in analytics engineering, data engineering, or quantitative technical architecture.
• 5+ years of direct leadership experience managing multi-team data or engineering organizations, including developing engineering managers and senior individual contributors.
• Enterprise Data Transformation: Proven track record of leading complex, cross-functional data transformation initiatives at scale across multiple teams or departments.
• Technical Stack Mastery: Advanced expertise in SQL, dimensional modeling, modern data architecture, cloud data warehouses (Google Cloud Platform / BigQuery, Snowflake, or Redshift), transformation tools (dbt), semantic layers, and BI tools (Looker).
• Data Governance & Lifecycle Management: Deep hands-on experience with data quality frameworks, metadata management, lineage, data product ownership, and lifecycle practices.
• AI & Analytics Enablement: Demonstrated experience preparing governed data models specifically designed to support analytics, machine learning, and Generative AI workflows.
• Executive Communication: Exceptional ability to translate complex data architecture into clear strategic narratives for executive and non-technical stakeholders.

Location & Logistics

• Ability to work a hybrid schedule out of Oscar's New York City, NY headquarters (3 days in-office per week, with required in-office presence on Thursdays).

Preferred Qualifications

• Direct domain experience within healthcare, health insurance, managed care, or other strictly regulated data environments (HIPAA compliance).
• Hands-on experience scaling dbt Mesh, enterprise semantic layers, or automated data observability platforms (e.g., Monte Carlo, Datadog Data Observability).

Total Rewards & Benefits

• Compensation & Equity: Competitive base salary of $198,720 – $260,820 USD + annual performance bonus + company equity grants.
• Time Off & Flexibility: Participation in Oscar's Unlimited Vacation Program, 11 paid holidays, paid sick time, and paid wellness reimbursements.
• Comprehensive Healthcare: Premium medical, dental, and vision insurance options, plus life and disability coverage.
• Family & Financial Support: Paid parental leave, 401(k) retirement savings plan with match, and wellness reimbursements.