Director, Tech Strategy & Operations

Oscar Health•New York, NY

6h•$218,592 - $286,902•Hybrid

About The Position

As a Director, Technology Strategy & Operations, you will be responsible for driving the overarching strategic direction and operational excellence for Oscar’s technology organization. This role serves as a primary advisor to technology leadership, influencing high-stakes decision-making and driving innovation through large-scale process improvements and strategic initiatives. The role works independently to oversee multi-year roadmaps and ensures alignment with enterprise-level goals. You will report into the Chief of Staff, Technology. 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

Requirements

Bachelor’s degree in a STEM field or 4+ years of commensurate work experience.
10+ years of professional experience in technology strategy, operations, or a related leadership role.
7+ years of experience building, coaching, and developing high-performing technical or operational teams.
Demonstrated expertise in using data (e.g., Excel, SQL) to influence complex organizational decisions and drive investments

Nice To Haves

Advanced Degree: Master’s degree (MBA or MS in a technical field) preferred
Industry Context: Deep expertise in the healthcare regulatory landscape (e.g., HIPAA) and experience in high-growth or public company environments
Methodologies: Process Improvement or Lean Six Sigma certification
Communication: Proven history of successfully briefing C-suite executives during high-pressure situations.

Responsibilities

Strategic Leadership: Orchestrate cross-functional collaboration at the executive level across Technology, Finance, and Product to architect and implement global technology strategies.
Operational Excellence: Establish and report on high-level Technology Operations KPIs and business-aligned metrics to executive leadership and the Board.
Roadmap & Governance: Direct the long-term evolution of technology architecture, overseeing multi-year roadmaps for tool evaluation, selection, and implementation.
Leadership Development: Lead and scale a high-performing organization of managers and individual contributors, focusing on mentorship and professional growth.
Crisis & Risk Management: Serve as a point of escalation for complex technical issues and proactively identify and mitigate organizational risks.
Compliance with all applicable laws and regulations.
Other duties as assigned.