Lead Director – Project Management Chief of Staff

CVS Health Careers

. Serve as a trusted advisor to the VP of Client & Member Experience, providing insight, analysis, and recommendations .

Posted 11/9/2026full-timeRemote • Illinois • United StatesSenior💰 $100,000 - $231,540 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in technology strategy and product leadership, with a strong focus on executive communication, analytical problem-solving, and cross-functional collaboration. Proven ability to manage high-impact initiatives and align resources effectively within matrixed organizations.

Highest-signal resume keywords

Technology StrategyProduct LeadershipExecutive CommunicationAnalytical Problem-SolvingCross-Functional Collaboration

ATS Keywords

Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills

Technology OperationsStrategic PlanningBudget ManagementCapacity ModelingResource Management

Soft Skills

Influence LeadershipSynthesis of ComplexityTeam CollaborationDecision TriageStakeholder Alignment

Certifications & Qualifications

Bachelor's DegreeMBA

Industry Keywords

HealthcarePBMInsuranceFinancial Services

About the role

Key responsibilities & impact

Serve as a trusted advisor to the VP of Client & Member Experience, providing insight, analysis, and recommendations
Design, implement, and 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 on resource management and financial adherence
Align priorities, resource allocation, and dependencies across Product Management and Technology Operations
Unblock cross-team issues and create predictability across products and programs
Develop executive presentations, strategy documents, communications, and business narratives
Craft messaging for product/program updates, leadership updates, operating model changes, and investment cases
Lead high-impact VP-sponsored initiatives and manage confidential, sensitive initiatives
Maintain an escalation log and risk register, brief the VP, and track closure
Drive clarity, transparency, collaboration, and continuous improvement across the team
Monitor team morale, workload balance, role clarity, and leadership alignment
Triage decisions, align stakeholders, and prepare analysis and recommendations
Represent the VP in key meetings when needed

Requirements

What you’ll need

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

Benefits

Comp & perks

CVS Health bonus, commission or short-term incentive program
Equity award program
Medical coverage
Dental coverage
Vision coverage
Paid time off
Retirement savings options
Wellness programs
Other resources supporting physical, emotional, and financial well-being