Senior Manager, Office of the President

Oscar Health•New York, NY

4d•$149,040 - $195,615•Hybrid

About The Position

Oscar is hiring a Senior Manager, Office of the President to join its Corporate Strategy Team. The role translates organizational priorities into coordinated action and measurable results. Reporting to the Senior Director, Corporate Strategy, the Senior Manager partners with the Chief of Staff to the President of Oscar Insurance and leaders across Insurance, Operations, Finance, People, Technology, Strategy, and other enterprise functions. The role operates leadership cadences, program-manages selected cross-functional initiatives, and ensures decisions become clear plans with owners, milestones, and follow-through. It also supports executive decision-making through presentations, analyses, meeting materials, and coordination of executive priorities. The position is based in Oscar’s New York City office and follows a hybrid schedule requiring three in-office days per week. Thursday is a required office day; the other two office days are flexible. The stated base pay is $149,040–$195,615 per year, with eligibility for employee benefits, the unlimited vacation program, and annual performance bonuses.

Requirements

6+ years of experience in program management, project management, business operations, or a related operational role.
4+ years of experience directly managing complex projects involving multiple functions and senior stakeholders.
Strong project-management or operational experience in health insurance, healthcare, or another complex and highly regulated industry.
Demonstrated ability to build governance structures, integrated work plans, operating cadences, and executive-ready status reporting.
Experience coordinating executive-level presentations that distill complex business challenges, cross-functional inputs, and decisions into clear actions.
Strong written and verbal communication skills, including the ability to work effectively with senior leaders and influence without direct authority.
Demonstrated ability to manage competing priorities, anticipate obstacles, maintain attention to detail, and drive consistent follow-through.
Comfort using data and performance indicators to assess progress, identify issues, and support decision-making.
Bachelor’s degree or commensurate professional experience.

Nice To Haves

Experience within a Chief of Staff, executive operations, business operations, transformation, or enterprise program-management function.
Experience in health insurance or healthcare operations.
Experience leading large-scale cross-functional initiatives.
Experience in change management, process improvement, or operating-model implementation.
Experience supporting recurring business or performance reviews, including executive presentation development.
Familiarity with financial planning, KPI management, talent processes, or other enterprise management cycles.
Project or program management certification.

Responsibilities

Own the day-to-day operating rhythm of the Office of the President, including leadership-team agendas, meeting preparation, materials, decisions, action items, and follow-through.
Coordinate recurring organizational governance and performance-management cadences, including monthly business reviews and other leadership reviews.
Coordinate inputs and deliverables for management cycles, including goals and KPIs, financial planning, talent planning, and other enterprise processes.
Manage priority requests and critical operational coordination, routing work to appropriate owners and ensuring timely completion.
Translate leadership decisions into next steps, accountable owners, milestones, and communication plans.
Identify blockers, dependencies, and emerging issues; manage escalations and bring matters requiring leadership attention to the Chief of Staff.
Coordinate with Finance, People, Technology, Strategy, Communications, and other partners to maintain alignment across shared priorities and deliverables.
Support culture, communications, organizational-engagement activities, and external engagements led by the Office of the President.
Partner with the Chief of Staff and business leaders to establish governance structures for selected strategic and operational initiatives.
Develop integrated program plans defining scope, milestones, owners, dependencies, decision points, risks, and success measures.
Program-manage selected initiatives from planning through implementation, maintaining alignment and accountability for results.
Facilitate working sessions and governance meetings, synthesize discussions, document decisions, and resolve outstanding issues.
Establish reporting mechanisms that give leaders visibility into progress, risks, dependencies, and decisions needed.
Define success criteria and operating metrics with initiative owners; use available data to identify execution gaps and support corrective actions.
Build reusable workflows and operating processes that improve consistency and coordination.
Support change-management and process-improvement efforts required to implement new plans.
Coordinate executive-level presentations and decision materials, synthesizing cross-departmental input into clear, action-oriented narratives.
Develop meeting materials, analyses, and other content supporting the Chief of Staff’s work with the President and executive leadership team.
Provide targeted execution support for executive-team priorities, including research, material preparation, documentation, and follow-through.
Participate in selected executive and cross-functional discussions to build context, capture implications, and translate direction into coordinated action.
Maintain discretion and sound judgment when handling sensitive organizational, performance, and personnel information.
Comply with applicable laws and regulations.
Perform other duties as assigned.