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.

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.

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• 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.

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.

• 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.

Bachelor’s Degree or equivalent work experience required.

The typical pay range for this role is: