Lead Director, Project Management

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

📋 Description

• Act as a trusted advisor to the VP, delivering insights, analyses, and recommendations regarding priorities, risks, and organizational effectiveness.

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

• Oversee the preparation and follow-ups for leadership meetings, Quarterly Business Reviews (QBRs), Monthly Business Reviews (MBRs), program evaluations, special projects, and executive discussions.

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

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

• Ensure alignment of priorities, resource allocation, and dependencies across Product Management and Technology Operations.

• Resolve cross-team issues and establish predictability in product and program execution.

• Develop presentations for executives, strategy documents, communications, and business narratives.

• Create messaging for product/program updates, leadership communications, operating model modifications, and investment proposals.

• Spearhead high-impact, VP-sponsored operational, engagement, and change management initiatives.

• Oversee confidential and sensitive initiatives that necessitate executive discretion.

• Maintain an escalation log and risk register, brief the VP prior to leadership discussions, and monitor issue resolution.

• Cultivate clarity, transparency, collaboration, and continuous improvement as a culture champion.

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

• Prioritize decisions, align stakeholders, and direct the VP’s focus on high-leverage activities.

• Prepare briefing materials, analyses, insights, and recommendations for complex decision-making.

• Represent the VP in key meetings as necessary.

⛳️ Requirements

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

• Proven experience supporting senior executives or managing cross-functional technology programs.

• Outstanding written and verbal communication skills with the ability to distill complex information.

• Demonstrated ability to lead through influence within large, matrixed organizations.

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

• Familiarity with executive-level financials, including budgets, headcount, and capacity models.

• Bachelor’s degree or equivalent experience is required.

• Experience in healthcare, Pharmacy Benefit Management (PBM), insurance, or financial services is preferred.

• An MBA or master’s degree is preferred.

• Possess executive presence, discretion, maturity, and high trust.

• Strategic thinking abilities to translate vision into clear plans, priorities, and measurable outcomes.

• Ability to collaborate and influence among senior leaders and cross-functional teams.

• Commitment to operational excellence and execution rigor.

• Proficient in advanced executive storytelling and communication skills.

🏝️ Benefits

• Medical coverage

• Dental coverage

• Vision coverage

• Paid time off

• Retirement savings options

• Wellness programs

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

• CVS Health bonus, commission or short-term incentive program

• Equity award program