Chief of Staff – Operations & Strategy Leader

CVS Health; Springfield (IL); On-site; USD 100,000 - 232,000; Full time

Job summary

CVS Health is seeking a Chief of Staff, Operations and Project Management to partner with the VP of Client & Member Experience and drive alignment, execution, and operational excellence across Caremark Product, Client Services, and Technology teams.

You will shape the operating model, lead cross-functional initiatives, develop executive-level communications, and manage capacity, budgets, and talent planning to ensure clarity, velocity, and impact across the organization.

Qualifications

• 10+ years of experience in technology strategy, product/program leadership and/or technology operations.

Responsibilities

• Provide executive enablement, insights, analysis, and recommendations on priorities, risks and organizational effectiveness.
• Design and optimize operating rhythm for the Client & Member Experience team.
• Lead preparation and follow-ups for leadership meetings, QBRs, MBRs, program reviews, special projects, and executive discussions.
• Manage capacity, budget, and headcount planning, and succession pipelines.
• Coordinate with HR on talent strategy and resource management to ensure financial adherence.
• Align priorities and dependencies across Product Management and Technology Operations.
• Unblock cross-team issues to increase predictability in execution across products and programs.
• Develop executive-level presentations, strategy documents, communications, and business narratives.
• Lead VP-sponsored initiatives spanning operational priorities and change management.
• Maintain escalation log and risk register; brief the VP before leadership discussions and track closures.
• Champion culture, monitor morale, workload balance, and leadership alignment.
• Prepare briefing materials, analysis, insights, and recommendations for complex decision-making.
• Represent the VP in key meetings when needed to drive continuity and alignment.

Skills

Executive leadership

Strategic planning

Cross-functional collaboration

Communication

Financial acumen

Problem solving

Education

MBA or master's degree

Bachelor’s degree or equivalent experience

Job description

CVS Health is seeking a Chief of Staff, Operations and Project Management to partner with the VP of Client & Member Experience and drive alignment, execution, and operational excellence across Caremark Product, Client Services, and Technology teams.

You will shape the operating model, lead cross-functional initiatives, develop executive-level communications, and manage capacity, budgets, and talent planning to ensure clarity, velocity, and impact across the organization.