Director, Pharmacy Operations & PBM Strategy

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 build the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

Reporting directly to the SVP of Pharmacy, the Director of Pharmacy Operations Strategy & Integration shapes and executes Oscar's pharmacy operational excellence agenda across Clinical Strategy and Operations. In this key connective leadership role, you will bridge Pharmacy, Clinical, Product, Engineering, Finance, Actuarial, Member Concierge, Compliance, and PBM/vendor partners. You will translate enterprise priorities into a coherent portfolio of operating-model improvements, PBM vendor integrations, scalable workflows, and affordability initiatives that elevate health outcomes and the member/provider experience.

Key Responsibilities

• Pharmacy Operational Strategy & Governance: Set the operational excellence agenda, operating rhythm, and execution model for Pharmacy, aligning priorities with enterprise affordability goals and clinical outcomes.
• Large-Scale Transformation Leadership: Own high-priority pharmacy operational transformation initiatives end-to-end—from opportunity definition and roadmap development to operational readiness, launch, and sustained adoption.
• Cross-Functional & PBM Integration: Serve as the connective tissue across internal functions (Product, Engineering, Finance, Actuarial, Concierge, Legal) and external PBM/vendor partners to align decision rights, manage dependencies, and resolve operational friction.
• PBM & Managed Care Domain Ownership: Apply deep knowledge of managed care, payer economics, claims adjudication, formulary operations, prior authorization workflows, and rebate systems to streamline end-to-end pharmacy processes.
• Regulatory & Compliance Alignment: Interpret applicable PBM, pharmacy benefit administration, and managed care regulations, translating compliance rules into actionable workflows and controls.
• Member & Provider Experience Optimization: Diagnose process and technology bottlenecks across pharmacy journeys, designing scalable solutions that improve throughput, affordability, and user satisfaction.
• Executive Reporting & Business Case Development: Synthesize operational, clinical, and financial data into executive briefs, managing capacity models, budgets, and value realization metrics for leadership governance.
• Playbook & Control Development: Build repeatable operating playbooks, standard operating procedures (SOPs), and operational controls that support a scalable PBM operating model.

Requirements

Experience & Background

• 10+ years of progressive experience in healthcare, business operations, strategy and operations, product operations, or program leadership.
• 7+ years of direct experience within Managed Care, Pharmacy Benefit Management (PBM), pharmacy operations, clinical operations, or healthcare payer environments.
• 5+ years leading large-scale, cross-functional strategy, operational transformation, or implementation initiatives from concept through adoption.
• 5+ years partnering directly with cross-functional business, Product, Engineering, and external vendor teams to set requirements and deliver business outcomes.
• Data & Regulatory Fluency: Demonstrated ability to translate healthcare regulatory requirements into operational specifications and present complex operational/financial data to executive audiences.
• Financial & Operational Management: Experience managing operational budgets, capacity models, business cases, and ROI frameworks for large-scale transformation efforts.

Preferred Qualifications

• Master’s degree in Business Administration (MBA), Public Health (MPH), or a related healthcare leadership discipline.
• Management consulting background or formal training in structured problem-solving (e.g., Lean, Six Sigma, Process Engineering).
• Direct hands-on experience with PBM implementations, claims adjudication engines, prior authorization software, or healthcare data feeds.
• Proven success leading teams through enterprise transformations in a matrixed organization.

Total Rewards & Benefits

• Compensation & Equity: Competitive base salary of $162,453.60 – $213,220.35 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 time.
• Comprehensive Healthcare: Choice of premium medical, dental, and vision health plans, plus life and disability insurance.
• Family & Financial Well-Being: Paid parental leave, 401(k) retirement savings plan with match, and health/wellness reimbursements.