Director, Technical Program Management

Hi, we're Oscar. We're hiring a Director, Technical Program Management to join our Tech Strategy & Operations 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:

The Director, Technical Program Management is a systems thinker who blends operational excellence with a deep understanding of the product development lifecycle to bridge the gap between strategy and tactical execution. This role is responsible for designing, building, and leading the operating model for cross-functional program execution across Technology teams, including Product, Engineering, Design, and Data. This individual owns the entire project lifecycle, from the "mobilization" phase of taking initial concepts and transforming them into organized workstreams with defined requirements and aligned resources, through to the ongoing tracking, execution, and final completion of critical business initiatives. They ensure rigorous dependency tracking and high delivery standards across a complex, matrixed organization, measured through successful outcome achievement.

You will report into the Head of Tech Strategy & Ops.

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: $198,720.00 - $260,820.00 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program company equity grants and annual performance bonuses.

Responsibilities:

• Project Mobilization & Kickoff: Partner with stakeholders to take initial project ideas and define the foundational structure, including outlining requirements, lining up cross-functional resources, and leading project kickoffs.
• Program Orchestration: Lead the day-to-day execution of large-scale, cross-functional programs, ensuring work remains aligned with strategic business goals.
• Dependency, Risk & Resource Alignment: Identify, track and resolve cross-functional dependencies, ensuring that the right people are lined up at the right time to prevent bottlenecks.
• Delivery Standards & Governance: Drive adoption of consistent project management best practices, ensuring a "single source of truth" for program health and documentation.
• Stakeholder Transparency: Facilitate stakeholder forums and cadences to provide real-time visibility into program health, risks, and blockers.
• Operating Model Design: Develop and refine the PMO operating model, including planning cadences, status reporting, and risk mitigation frameworks.
• Continuous Improvement & Coaching: Coach stakeholders and project leads on processes that drive focus and measurable impact, fostering a culture of high-quality delivery.
• Compliance & Administration: Maintain compliance with all applicable laws and regulations and perform other duties as assigned.

Requirements:

• Experience: 8+ years of experience specifically in program management, project operations or product management.
• Leadership: 3+ years in a leadership role managing complex delivery environments.
• Execution Expertise: Proven success in scaling delivery processes within a technology environment featuring complex internal stakeholder groups.
• Operational Precision: Highly proficient in designing "right-weight" processes for project definition and internal enablement.
• Influence: Demonstrated ability to influence cross-functional teams and drive adoption of new operational standards.
• Education: Bachelor’s degree or 4 years of commensurate experience.

Bonus points:

• Technical Background: Experience managing technical or system implementations specifically.
• Delivery Mindset: A metrics-driven approach focused on guiding partners toward "zero defects" in delivery.
• Domain Knowledge: Understanding of ticketing systems and project management software administration.

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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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