Lead Director, Project Management Chief of Staff Remote (anywhere in Illinois)

We’re building a world of health around every individual — shaping a more connected, convenient and compassionate health experience. At CVS Health®, you’ll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselves accountable and prioritize safety and quality in everything we do. Join us and be part of something bigger – helping to simplify health care one person, one family and one community at a time.

The Chief of Staff, Operations and Project Management serves as the strategic partner and operational lead for the VP of Client & Member Experience, enabling alignment, execution, and operational excellence across Caremark’s Product and Client Services teams.

This role will plan and manage the Client & Member Experience team operating model within the Caremark Digital, Data and Analytics, and Technology team — spanning Product Management, User Experience, Operations Management, Strategic Planning, and Project Portfolio Management. The Chief of Staff drives operational norms, cross-functional collaboration, and special projects/requests. This ensures that the VP and the organization operate at maximum clarity, velocity, and impact.

Key Responsibilities

1. Executive Enablement and Decision Support

• Serve as a trusted advisor to the VP, providing insight, analysis, and recommendations on priorities, risks, and organizational effectiveness.

1. Operating Rhythm and Leadership Cadence

• Design, implement, and continuously optimize the 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.

1. Capacity, Budget, and Financial Management

• Partner with HR on talent strategy, staffing, onboarding, headcount planning, and succession pipelines

•Partner with HR and Finance to ensure balanced and predictable resource management and financial adherence.

1. Cross-Functional Orchestration

• Ensure alignment on priorities, resource allocation, and dependencies across Product Management and Technology Operations.
• Unblock cross-team issues and create predictability in execution across products and programs.

1. Communication, Messaging & Executive Storytelling

• Develop executive-level presentations, strategy documents, communications, and business narratives for internal and external audiences.
• Craft crisp messaging for product/program updates, leadership updates, operating model changes, and investment cases.
• Ensure consistent and high-quality communications across all levels of the organization.

1. Program Leadership & Special Initiatives

• Lead high-impact, VP-sponsored initiatives spanning but not limited to operational priorities, engagement initiatives, or change management initiatives.
• Manage confidential and sensitive initiatives that require executive discretion and precision.
• Maintain an escalation log and risk register, give the VP a short pre-brief on each item before leadership discussions, and track closure

1. Talent, Culture, and Organizational Health

• Serve as a culture champion — driving clarity, transparency, collaboration, and continuous improvement across the Client & Member Experience team.

•Monitor team morale, workload balance, role clarity, and leadership alignment.

1. Decision Support & Prioritization

• Triaging decisions, aligning stakeholders, and ensuring the VP focuses on the highest-leverage activities.
• Prepare briefing materials, analysis, insights, and recommendations for complex decision-making.
• Represent the VP in key meetings when needed to drive continuity and alignment.

Required 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)

Preferred Qualifications

• MBA or master’s degree preferred, Bachelor’s degree or equivalent experience required
• Experience in healthcare, PBM, insurance, or financial services.

Leadership Competencies

• Executive Presence: Operates with discretion, maturity, and high trust.
• Strategic Thinking: Converts vision into clear plans, priorities, and measurable outcomes.
• Collaboration & Influence: Aligns multiple senior leaders and cross-functional teams.
• Operational Excellence: Obsessed with clarity, execution rigor, and predictable results.
• Communication Mastery: Elite storyteller capable of simplifying complex information.

Pay Range

The typical pay range for this role is:

$100,000.00 - $231,540.00

This pay range represents the base hourly rate or base annual full-time salary for all positions in the job grade within which this position falls. The actual base salary offer will depend on a variety of factors including experience, education, geography and other relevant factors. This position is eligible for a CVS Health bonus, commission or short-term incentive program in addition to the base pay range listed above. This position also includes an award target in the company’s equity award program.

Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong.

Great benefits for great people

We take pride in offering a comprehensive and competitive mix of pay and benefits that reflects our commitment to our colleagues and their families.

This full‑time position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial well‑being of colleagues and their families. The benefits for this position include medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility.

Additional details about available benefits are provided during the application process and on Benefits Moments.

We anticipate the application window for this opening will close on: 12/31/2026

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.