Senior Manager, Portfolio Strategy & Business Cycle Execution

Oscar Health•Atlanta, GA

2d•Remote

About The Position

Oscar is hiring a Senior Manager, Portfolio Strategy & Business Cycle Execution to join their Strategy and Operations team. Oscar is a health insurance company built on a technology platform focused on serving its members. The Senior Manager will drive the end-to-end orchestration of portfolio strategy within the enterprise business cycle for multiple markets. This role ensures strategic decisions are defined, sequenced, and finalized on time, enabling successful annual regulatory filings and downstream operational execution. The position serves as a central integrator between strategy and execution, providing visibility, structure, and governance across portfolio planning, decision-making, and cross-functional dependencies. The role reports into the Senior Director, Project Management.

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.

Nice To Haves

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

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 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, 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.