Hi, we're Oscar. We're hiring a Senior Portfolio Manager to join our Strategy & Business Cycle Execution 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 Senior Manager, Portfolio Strategy & Business Cycle Execution is responsible for driving the end-to-end orchestration of portfolio strategy within the enterprise business cycle for multiple markets. This role ensures that strategic decisions are defined, sequenced, and finalized on time and enables successful annual regulatory filings and downstream operational execution (e.g., OE and 1/1 readiness).

This individual serves as the central integrator between strategy and execution, providing visibility, structure, and governance across portfolio planning, and cross-functional dependencies.

You will report into the Senior Director, Project Management.

Work Location: This position is based in our New York 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: $149,040 - $195,615 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Own the portfolio strategy intake and intake governance process, ensuring all initiatives are captured, vetted, and aligned to enterprise priorities
• Maintain the single source of truth for portfolio strategy, including initiative scope, and status
• Lead portfolio planning and prioritization in partnership with local markets and cross-functional business partners, balancing enterprise goals, regulatory requirements, and capacity constraints
• Develop and manage the portfolio roadmap, ensuring alignment to filing timelines and broader enterprise milestones

• Establish and manage the decision calendar, ensuring all critical strategy decisions are sequenced and completed on time
• Drive on-time decision-making by partnering with leadership and escalating risks to timelines or clarity
• Ensure alignment of all strategy decisions to regulatory filing timelines, enterprise planning cycles, and downstream execution milestones
• Embed governance through stage gates and leadership forums to close decisions upstream and reduce downstream disruption

• Identify, manage and escalate cross-functional dependencies between strategy, filings, and operational execution
• Ensure downstream teams (Product, Network, Finance, Tech, Ops, Compliance, etc.) have clear, inputs to execute
• Proactively mitigate risks related to late decisions, fragmented inputs, or misaligned timelines
• Partner with execution teams to ensure strategy is actionable, sequenced, and implementation-ready

• Facilitate feasibility assessments for new initiatives, evaluating operational, technical, and regulatory complexity
• Partner with cross-functional teams to define what it takes to implement (resourcing, systems, timelines, risks)
• Ensure strategic initiatives are grounded in realistic execution plans and constraints
• Support trade-off decisions by providing clear visibility into effort, dependencies, and impact

• Own and continuously refine the intake and prioritization framework
• Drive clarity on what gets worked, when, and why, ensuring alignment to enterprise strategy and capacity
• Maintain and communicate roadmap updates, trade-offs, and changes to stakeholders
• Ensure transparency across leadership on portfolio progress, risks, and decision status

Requirements:

• 6+ years of experience in program management, portfolio management, or strategy operations in a complex, cross-functional environment
• Experience managing large-scale, interdependent initiatives tied to critical timelines (e.g., regulatory, product launches, or enterprise transformations)
• Experience in governance, roadmap planning, and executive-level communication
• Drive decision-making and influence senior stakeholders
• Experience with dependency management across Product, Technology, Operations, and Compliance

Bonus points:

• Experience working within a scaling organization
• BA/BS Degree
• Masters in Business Administration or healthcare related field(s)

Travel required:

• If outside NY, 10%.