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.

About the role:

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.

Work Location: This is a remote position, open to candidates who reside in:
Atlanta, Georgia. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $134,136 - $176,053 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonus.

Responsibilities:

• 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 escalate 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

Requirements:

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

Core Competencies

• Strategic Orchestration - Connects strategy to execution across a complex portfolio
• Decision Discipline - Drives clarity, accountability, and timeliness in decision-making
• Systems Thinking - Understands upstream/downstream impacts and interdependencies
• Execution Rigor - Brings structure, governance, and predictability to delivery
• Influence & Communication - Effectively engages stakeholders at all levels

Bonus points:

• Experience working within a…