Hi, we're Oscar. We're hiring a Director, Tech Business Operations to join our Technology team.
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 in 2012 to create the kind of health insurance company we would want for ourselves-one that behaves like a doctor in the family.
About the role:
As a Director, Tech Business 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 a Head of Tech Strategy & Operations.
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: $218,592.00 - $286,902.00 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.
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.
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
Bonus points:
- 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.