Lead Director – Project Management Chief of Staff

This is a fully remote position, open to applicants in Illinois.

📋 Description

• Act as a trusted advisor to the VP of Client & Member Experience, offering insights, analyses, and recommendations.

• Create, implement, and enhance the operational rhythm for the Client & Member Experience team.

• Lead the preparation and follow-ups for leadership meetings, QBRs, MBRs, program reviews, special projects, and executive discussions.

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

• Work alongside HR and Finance on resource management and financial compliance.

• Align priorities, resource distribution, and dependencies between Product Management and Technology Operations.

• Resolve cross-team challenges and establish predictability across products and programs.

• Develop executive presentations, strategic documents, communications, and business narratives.

• Generate messaging for product/program updates, leadership briefings, operational model changes, and investment proposals.

• Lead significant VP-sponsored initiatives and manage confidential and sensitive projects.

• Maintain an escalation log and risk register, inform the VP, and monitor issue resolution.

• Foster clarity, transparency, collaboration, and continuous improvement within the team.

• Monitor team morale, balance workloads, clarify roles, and ensure leadership alignment.

• Prioritize decisions, align stakeholders, and prepare analyses and recommendations.

• Represent the VP in key meetings when necessary.

⛳️ Requirements

• Over 10 years of experience in technology strategy, product/program leadership, and/or technology operations.

• Experience in supporting senior executives or leading cross-functional technology initiatives.

• Excellent written and verbal communication abilities with a talent for synthesizing complex information.

• Demonstrated capability to lead through influence in large, matrixed organizations.

• Strong analytical, problem-solving, and strategic planning abilities.

• Familiarity with executive-level financials (budgeting, headcount, capacity models).

• Bachelor's degree or equivalent experience is required.

• Preferred experience in healthcare, PBM, insurance, or financial services.

• An MBA or master’s degree is preferred.

🏝️ Benefits

• 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.

• Additional resources supporting physical, emotional, and financial well-being.