Senior Manager, Office of the President

Hi, we're Oscar. We're hiring a Senior Manager, Office of the President to join our Corporate Strategy 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, Office of the President will report to the Chief of Staff to the President of Oscar Insurance and help translate organizational priorities into coordinated action and measurable results.

This role will serve as an execution-oriented partner responsible for operating key leadership cadences, program-managing selected cross-functional initiatives, and ensuring decisions are translated into clear plans, owners, milestones, and follow-through. The Senior Manager, Office of the President will work closely with leaders across Insurance, Operations, Finance, People, Technology, Strategy, and other enterprise functions to maintain organizational alignment and momentum.

You will report into the Senior Director, Corporate Strategy.

Work Location: 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. #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:

• Office of the President Operations
  • 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 associated with key management cycles, including goals and KPIs, financial planning, talent planning, and other enterprise processes.
  • Manage priority requests and critical operational coordination across the organization, ensuring you route work to the appropriate owners and complete it on time.
  • Translate leadership decisions into clear next steps, accountable owners, milestones, and communication plans.
  • Identify and anticipate 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.
  Cross-Functional Program Management
  • Partner with the Chief of Staff and business leaders to establish governance structures for selected strategic and operational initiatives.
  • Develop integrated program plans that define scope, milestones, owners, dependencies, decision points, risks, and success measures.
  • Program-manage selected initiatives from planning through implementation, ensuring teams remain aligned and accountable for results.
  • Facilitate working sessions and governance meetings, synthesize discussions, document decisions, and resolve outstanding issues.
  • Establish practical reporting mechanisms that give leaders visibility into progress, risks, dependencies, and decisions needed.
  • Define success criteria and operating metrics in partnership 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.
  Executive and Chief of Staff Support
  • Coordinate the development of executive-level presentations and decision materials, synthesizing inputs from multiple departments into clear, action-oriented narratives.
  • Develop meeting materials, analyses, and other content that support 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 help translate direction into coordinated action.
  • Maintain discretion and sound judgment when handling sensitive organizational, performance, and personnel information.
  • Comply with all applicable laws and regulations.
  • Perform other duties as assigned.

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.

Bonus points:

• Experience working 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.