Chief of Staff, Operations and Project Management

We're building a world of health around every individual , shaping a more connected, convenient and compassionate health experience.

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.

Key Responsibilities

1. Executive Enablement and Decision Support

Serve as a trusted advisor to the VP, providing insight, analysis, and recommendations on priorities, risks, and organisational effectiveness.

1. Operating Rhythm and Leadership Cadence

Design, implement, and continuously optimise 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.

1. Capacity, Budget, and Financial Management

Partner with HR on talent strategy, staffing, onboarding, headcount planning, and succession pipelines. Partner with HR and Finance to ensure balanced and predictable resource management and financial adherence.

1. Cross-Functional Orchestration

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.

1. Communication, Messaging & Executive Storytelling

Develop executive-level presentations, strategy documents, communications, and business narratives for internal and external audiences. Craft crisp messaging for product/program updates, leadership updates, operating model changes, and investment cases. Ensure consistent and high-quality communications across all levels of the organisation.

1. Program Leadership & Special Initiatives

Lead high-impact, VP-sponsored initiatives spanning but not limited to operational priorities, engagement initiatives, or change management initiatives. Manage confidential and sensitive initiatives that require executive discretion and precision. Maintain an escalation log and risk register, give the VP a short pre-brief on each item before leadership discussions, and track closure.

1. Talent, Culture, and Organisational Health

Serve as a culture champion , driving clarity, transparency, collaboration, and continuous improvement across the Client & Member Experience team. Monitor team morale, workload balance, role clarity, and leadership alignment.

1. Decision Support & Prioritisation

Triaging decisions, aligning stakeholders, and ensuring 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.

Required Qualifications

• 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 synthesise complexity.
• Proven ability to lead through influence in large, matrixed organisations.
• Strong analytical, problem-solving, and strategic planning skills.
• Experience with executive-level financials (budget, headcount, capacity models).

Preferred Qualifications

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

Leadership Competencies

• Executive Presence: Operates with discretion, maturity, and high trust.
• Strategic Thinking: Converts vision into clear plans, priorities, and measurable outcomes.
• Collaboration & Influence: Aligns multiple senior leaders and cross-functional teams.
• Operational Excellence: Obsessed with clarity, execution rigor, and predictable results.
• Communication Mastery: Elite storyteller capable of simplifying complex information.

Pay Range $100,000.00 - $231,540.00

Benefits This full-time position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial well-being of colleagues and their families. The benefits for this position include medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility.