Executive Director, Chief of Staff - Caremark Medical Affairs

We’re building a world of health around every individual — shaping a more connected, convenient and compassionate health experience. At CVS Health®, you’ll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselves accountable and prioritize safety and quality in everything we do. Join us and be part of something bigger – helping to simplify health care one person, one family and one community at a time.

Position Summary Caremark Medical Affairs is dedicated to advancing clinical quality, customer success, and innovation for members, providers, and plan sponsors. Reporting to the SVP and Chief Medical Officer of Caremark, the Executive Director, Chief of Staff serves as a strategic partner to the CMO and Medical Affairs leadership team, helping translate priorities into action and drive organizational effectiveness.

This role will shape and execute the strategic agenda for Caremark Medical Affairs, ensuring alignment between long-term objectives and day-to-day operations. Working across leadership teams and enterprise partners, the Executive Director will advance key initiatives, address complex business challenges, prepare senior leaders for critical engagements, and strengthen operational performance across the function.

The position requires exceptional judgment, organizational savvy, and the ability to influence across a broad range of stakeholders without direct authority. Operating in a highly visible environment with accountability for business outcomes, the Executive Director serves as a key integrator, bringing together the right expertise to drive alignment, execution, and measurable results.

Job Responsibilities

• Strategic Planning & Integration: Partner with the SVP/CMO and Caremark Medical Affairs leadership team to shape and drive strategic priorities, the strategic roadmap, and alignment to broader enterprise priorities.

• Business Operations & Execution: Lead cross-functional initiatives from planning through execution, measurement, and follow-through, while identifying organizational and operational challenges and helping drive practical, sustainable solutions.

• Stakeholder Leadership & Influence: Build strong relationships across leadership teams, enterprise partners, and subject matter experts, and use influence and organizational intelligence to drive alignment across complex priorities and decisions.

• Financial Stewardship: Support management of Caremark Medical Affairs budget line items, including payroll and travel, with a focus on effective resource management.

• Executive Support & Communications:

• Develop executive-ready presentations, proposals, briefing materials, and other communications for senior leadership with a high degree of discretion, judgment, and confidentiality.

• Lead the management of leadership meeting cadence, including staff meetings, senior leader meetings, town halls, and other key forums, by setting agendas, ensuring content and presentation readiness, aligning speakers, and driving follow-through on decisions and action items.

Required Qualifications The candidate will have a strong work ethic, be a self-starter, and be able to be highly productive in a dynamic, collaborative environment. This position offers broad exposure to all aspects of the company’s business, as well as significant interaction with all the business leaders. The candidate will be expected to have the following key attributes:

• 10+ years of business leadership, Chief of Staff, strategy, operations, or related experience.

• Proven ability to lead complex, cross-functional initiatives and drive execution in a fast-paced environment.

• Strong strategic thinking, business judgment, and problem-solving skills, with the ability to translate insights into action.

• Exceptional written and verbal communication skills, including developing executive-level presentations and communications.

• Experience partnering with senior executives and influencing stakeholders across functions without direct authority.

• Ability to balance long-term strategic planning with operational execution and follow-through.

• Strong analytical capabilities with experience using data and insights to inform decisions and solve complex business challenges.

• Change leadership experience, bringing structure, alignment, and accountability to evolving priorities.

• AI and technology fluency, with a demonstrated ability to identify and leverage solutions that improve effectiveness, decision-making, and business outcomes.

Preferred Qualifications

• Experience developing, overseeing, and executing multi-functional strategic plans.

• Experience with multi-functional budget development, oversight, and reporting.

• Significant enterprise-wide program and project management experience.

• Prior leadership experience.

• PBM/PSS experience.

Education Bachelor’s Degree or equivalent work experience required.

Pay Range The typical pay range for this role is:

$131,500.00 - $303,195.00 This pay range represents the base hourly rate or base annual full-time salary for all positions in the job grade within which this position falls. The actual base salary offer will depend on a variety of factors including experience, education, geography and other relevant factors. This position is eligible for a CVS Health bonus, commission or short-term incentive program in addition to the base pay range listed above. This position also includes an award target in the company’s equity award program.

Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong.

Great benefits for great people

We take pride in offering a comprehensive and competitive mix of pay and benefits that reflects our commitment to our colleagues and their families.

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. Additional details about available benefits are provided during the application process and on Benefits Moments.

We anticipate the application window for this opening will close on: 10/01/2026

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.