Senior Manager, Portfolio Strategy & Business Cycle Execution

Hi, we're Oscar. We're hiring a Senior Manager, Portfolio Strategy & Business Cycle Execution to join our Strategy and 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.

The Senior Manager, Portfolio Strategy & Business Cycle Execution drives the end‑to‑end orchestration of portfolio strategy within the enterprise business cycle for multiple markets. You'll ensure that you define, sequence, and finalize strategic decisions on time, enabling successful annual regulatory filings and downstream operational execution (e.g., OE and 1/1 readiness).

You will serve as the central integrator between strategy and execution, providing visibility, structure, and governance across portfolio planning, decision‑making, and cross‑functional dependencies.

You will report into the Senior Director, Project Management.

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.

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 bonus.

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.

• Own the portfolio strategy intake and intake governance process, capturing, vetting, and aligning all initiatives to enterprise priorities.
• Maintain the single source of truth for portfolio strategy, including initiative scope, status, and ownership.
• 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 you sequence and complete all critical strategy decisions 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, track, manage and elevate cross‑functional dependencies between strategy, filings, and operational execution.
• Ensure downstream teams (Product, Network, Finance, Tech, Ops, Compliance, etc.) have clear, timely 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.
• Compliance with all applicable laws and regulations.
• Other duties as assigned.

• 6+ years of experience in…