Chief of Staff, Operations & Strategy

CVS Health; United States; Remote; USD 100,000 - 232,000; Full time

Benefits offered by this job

Medical, dental, and vision coverage

Paid time off

Retirement savings options

Wellness programs

Job summary

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

You will shape the operating model, coordinate cross-functional initiatives, and prepare executive communications to enable clear decisions and fast, high-impact delivery.

Qualifications

• 10+ years of experience in technology strategy, product/program leadership and/or technology operations.
• Experience supporting senior executives or leading cross-functional technology programs.
• Exceptional written and verbal communication skills with the ability to synthesize complexity.
• Proven ability to lead through influence in large, matrixed organizations.
• Strong analytical, problem-solving, and strategic planning skills.
• Experience with executive-level financials (budget, headcount, capacity models).

Responsibilities

• Executive Enablement and Decision Support: serve as trusted advisor to the VP with insights on priorities, risks and organizational effectiveness.
• Operating Rhythm and Leadership Cadence: design and optimize operating rhythm; lead prep for leadership meetings and reviews.
• Capacity, Budget, and Financial Management: partner with HR on talent strategy, staffing, onboarding, headcount planning, and succession pipelines; partner with HR and Finance on resource management and financial adherence.
• Cross-Functional Orchestration: align priorities and resources across Product Management and Technology Operations.
• Communication, Messaging & Executive Storytelling: develop executive-level presentations, strategy documents, communications, and business narratives.
• Program Leadership & Special Initiatives: lead VP-sponsored initiatives and manage confidential or sensitive projects.
• Talent, Culture, and Organizational Health: drive clarity, transparency, collaboration and continuous improvement across teams.

Skills

Technology strategy

Executive support

Cross-functional leadership

Financial planning

Communication

Healthcare familiarity

Education

MBA (preferred)

Bachelor’s degree or equivalent

Job description

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

You will shape the operating model, coordinate cross-functional initiatives, and prepare executive communications to enable clear decisions and fast, high-impact delivery.