Director, Pharmacy Operations Strategy & Integration

Hi, we're Oscar. We're hiring a Director, Pharmacy Operations Strategy & Integration to join our Pharmacy 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, Pharmacy Operations Strategy & Integration reports to the SVP, Pharmacy is responsible for shaping and executing Oscar's pharmacy operational excellence agenda for the Pharmacy Clinical Strategy and Operations area. This role translates strategic priorities into a coherent portfolio of operating-model improvements, cross-functional programs, vendor capabilities, and scalable workflows that advance affordability, health outcomes, and the member and provider experience. The Director serves as a connective leader across Pharmacy, Clinical, Product, Engineering, Finance, Actuarial, Concierge, Compliance, and PBM/vendor partners—aligning priorities, decisions, and execution to deliver measurable business impact. This role balances enterprise affordability, member and provider experience, regulatory compliance, operational quality, and long-term scalability as Oscar advances its pharmacy operating model.

You will report into the SVP, Pharmacy.

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: $180,504.00 - $236,911.00 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities:

• Set the pharmacy operational excellence strategy, operating rhythm, and execution model, ensuring priorities are aligned to Oscar's enterprise agenda, Pharmacy objectives, affordability goals, and member and provider outcomes.
• Lead high-priority pharmacy operational transformation initiatives from strategy through execution, including opportunity definition, roadmap development, operational readiness, launch planning, and sustained adoption.
• Serve as a primary operational partner across internal and external teams, translating pharmacy and PBM opportunities, member and provider needs, and frontline insights into clear priorities, decisions, and measurable outcomes.
• Stay aware of applicable PBM, pharmacy benefit, managed care, and healthcare regulatory requirements, interpreting the business need and communicating it clearly to internal and external partners so solutions are designed and implemented appropriately.
• Maintain deep understanding of the pharmacy and healthcare ecosystem, including payer economics, benefit and network dynamics, claims processes, formulary operations, prior authorization workflows, utilization patterns, vendor handoffs, and the drivers of affordability and experience.
• Partner with cross-functional internal stakeholders and external vendors to manage implementation plans, business reviews, strategic meetings, issue escalation, performance monitoring, and operational integration.
• Coordinate cross-functionally across Clinical, Pharmacy Operations, Product, Engineering, Finance, Actuarial, Concierge, Compliance, and vendor partners to align decision rights, dependencies, tradeoffs, and delivery plans for high-priority pharmacy initiatives.
• Serve as an internal consultant and apply an operational excellence lens to diagnose complex process, data, technology, and vendor friction points, then design practical end-to-end solutions that improve throughput, quality, affordability, and member/provider experience.
• Shape the end-to-end member and provider experience by partnering with Pharmacy, Clinical, Product, Engineering, Concierge, and vendor teams to identify friction points and translate insights into scalable, measurable improvements across pharmacy journeys.
• Lead governance and executive reporting for pharmacy operational excellence initiatives, synthesizing operational, member, provider, clinical, and financial data into clear priorities, recommendations, and accountability for senior leadership.
• Identify and manage implementation risks, dependencies, decisions, and change-management needs, ensuring stakeholders understand scope, impact, tradeoffs, and operational readiness requirements.
• Build repeatable operating playbooks, process standards, controls, and best practices that support a scalable PBM operating model, continuous improvement, and a coherent end-to-end pharmacy experience.
• Use independent judgment to resolve complex problems, evaluate variable factors, and determine the best course of action for technology-enabled process improvement and operational transformation.
• Support capacity planning, budget management, business-case development, and value realization measurement for PBM, vendor, and operational excellence initiatives.
• Ensure operational workflows, vendor capabilities, and program execution meet applicable regulatory, compliance, quality, and contractual requirements.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 10+ years of experience in healthcare, business operations, strategy and operations, product operations, or program leadership.
• 7+ years of Managed Care, PBM, pharmacy operations, clinical operations, or related healthcare payer experience.
• 5+ years leading large-scale, cross-functional strategy, operational transformation, or implementation initiatives from opportunity definition through launch and adoption.
• 5+ years partnering directly with cross-functional business, Product, Engineering, vendor, or operations teams to set priorities, define requirements, influence solutions, and deliver business outcomes.
• Experience interpreting regulatory, compliance, operational, or contractual business needs and translating them into actionable requirements for cross-functional partners.
• Experience with strategic planning, roadmapping, business analysis, operational readiness, change management, and translating priorities into executable cross-functional plans.
• Experience translating complex operational data and performance information into executive-level insights, recommendations, and governance materials.
• Experience managing budgets, capacity models, business cases, or financial performance for operational or transformation initiatives.

Bonus points:

• MBA, MPH, Master's degree in Business Administration or a related field preferred.
• Management consulting, internal strategy and operations, process engineering, Lean, Six Sigma, or similar structured problem-solving experience.
• Experience with PBM implementation, pharmacy benefit administration, claims adjudication, formulary operations, prior authorization, rebate/formulary systems, or healthcare data feeds.
• Experience working in a matrixed teams through enterprise transformation, implementation, or operational excellence work.