Hi, we're Oscar. We're hiring a Director, Tech Strategy & 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, 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.

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.

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At Oscar, being an Equal Opportunity Employer means more than upholding discrimination-free hiring practices. It means that we cultivate an environment where people can be their most authentic selves and find both belonging and support. We're on a mission to change health care -- an experience made whole by our unique backgrounds and perspectives.

Pay Transparency: Final offer amounts, within the base pay set forth above, are determined by factors including your relevant skills, education, and experience. Full-time employees are eligible for benefits including: medical, dental, and vision benefits, 11 paid holidays, paid sick time, paid parental leave, 401(k) plan participation, life and disability insurance, and paid wellness time and reimbursements.

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Reasonable Accommodation: Oscar applicants are considered solely based on their qualifications, without regard to applicant’s disability or need for accommodation. Any Oscar applicant who requires reasonable accommodations during the application process should contact the Oscar Benefits Team (accommodations@hioscar.com) to make the need for an accommodation known.

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