Chief Of Staff Jobs

About The Position

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.

Benefits

• Medical coverage
• Dental coverage
• Vision coverage
• Paid time off
• Retirement savings options
• Wellness programs
• CVS Health bonus, commission, or short-term incentive program eligibility
• Eligibility for an award target in the company’s equity award program