Lead Director, Project Management Chief of Staff

CVS Health•Work At Home-Illinois, IL

2d•$100,000 - $231,540

About The Position

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. The role plans and manages 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 and requests to help the VP and organization operate with clarity, velocity, and impact.

Requirements

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, including 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, including budget, headcount, and capacity models.
Bachelor’s degree or equivalent experience required.

Nice To Haves

MBA or master’s degree.
Experience in healthcare, PBM, insurance, or financial services.

Responsibilities

Serve as a trusted advisor to the VP, providing insight, analysis, and recommendations on priorities, risks, and organizational effectiveness.
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.
Partner with HR on talent strategy, staffing, onboarding, headcount planning, and succession pipelines.
Partner with HR and Finance to support balanced, predictable resource management and financial adherence.
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.
Develop executive-level presentations, strategy documents, communications, and business narratives for internal and external audiences.
Craft messaging for product and program updates, leadership updates, operating model changes, and investment cases.
Ensure consistent, high-quality communications across all levels of the organization.
Lead high-impact, VP-sponsored initiatives, including operational, engagement, and change management initiatives.
Manage confidential and sensitive initiatives requiring executive discretion and precision.
Maintain an escalation log and risk register, provide the VP with short pre-briefs before leadership discussions, and track closure.
Champion a culture of clarity, transparency, collaboration, and continuous improvement across the Client & Member Experience team.
Monitor team morale, workload balance, role clarity, and leadership alignment.
Triage decisions, align stakeholders, and ensure 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.