Chief of Staff, Operations & Strategy — Executive Partner

CVS Health; Illinois; Hybrid; USD 100,000 - 232,000; Full time

Benefits offered by this job

Bonus eligibility

Equity award

Comprehensive benefits

Job summary

CVS Health in the United States is seeking a Chief of Staff for Operations and Project Management to partner with the VP of Client & Member Experience, enabling alignment and execution across Caremark's Product, Client Services, and Technology teams.

You will shape operating rhythms, lead cross-functional initiatives, manage budgets and talent planning, and drive executive storytelling and change initiatives to ensure clarity, velocity, and impact.

Qualifications

• 10+ years of 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: advise on priorities, risks, and organizational effectiveness.
• Operating Rhythm and Leadership Cadence: design and optimize leadership meeting rhythms and reviews.
• Capacity, Budget, and Financial Management: coordinate talent strategy, staffing, headcount, and finances.
• Cross-Functional Orchestration: align Product Management and Technology Operations, remove blockers.
• Communication, Messaging & Executive Storytelling: create presentations and strategic updates for executives.
• Program Leadership & Special Initiatives: lead VP-sponsored initiatives and manage confidential projects.
• Talent, Culture, and Organizational Health: foster clarity, collaboration, and engagement.
• Decision Support & Prioritization: prepare briefings and recommendations for key decisions.

Skills

10+ yrs tech strategy

Executive support

Clear communication

Influence in matrix orgs

Analytical thinking

Budget & headcount finance

Education

MBA or master’s degree preferred

Bachelor’s degree or equivalent experience

Job description

CVS Health in the United States is seeking a Chief of Staff for Operations and Project Management to partner with the VP of Client & Member Experience, enabling alignment and execution across Caremark's Product, Client Services, and Technology teams.

You will shape operating rhythms, lead cross-functional initiatives, manage budgets and talent planning, and drive executive storytelling and change initiatives to ensure clarity, velocity, and impact.