Senior Executive Assistant

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, a CVS Health company, is seeking an exceptionally organized and resourceful Executive Assistant to provide dedicated, high-level support to the VP of Digital. This is a critical role at the center of one of the most strategically important and fast-moving divisions within CVS Health - one that is shaping how millions of patients and members experience healthcare digitally. The ideal candidate is a proactive problem-solver who anticipates needs before they arise, thrives in a large enterprise environment, and operates with the discretion and polish befitting a Fortune 5 organization.

• Own and manage a complex, high-demand calendar for the VP of Digital, navigating competing priorities across product, engineering, operations, and enterprise leadership.
• Coordinate internal and external meetings with senior stakeholders across CVS Health, Caremark, and digital ecosystem partners.
• Prepare comprehensive briefing documents, agendas, and pre-read materials to ensure the VP is set up for success in every engagement.
• Exercise sound judgment in prioritizing, rescheduling, and protecting time to align with evolving business priorities.

• Act as a trusted extension of the VP, managing high-volume email and Teams communications with professionalism and speed.
• Draft executive-level communications, talking points, and correspondence for internal and external audiences including CVS Health senior leadership, vendor partners, and cross-functional teams.
• Facilitate information flow between the VP's office and direct reports, helping keep the Digital organization aligned and informed.

• Plan and coordinate domestic travel including flights, hotels, ground transportation, and detailed day-of itineraries.
• Support attendance at industry conferences, CVS Health enterprise events, and in-person leadership offsites.
• Manage expense reporting and timely reconciliation in compliance with CVS Health travel and expense policies.

• Track and follow up on action items, decisions, and deliverables emerging from leadership meetings and cross-functional initiatives.
• Support preparation of materials for Digital leadership reviews, OKR check-ins, and enterprise reporting cycles.
• Coordinate team rhythms including all‑hands meetings, town halls, and team events for the Digital organization.
• Partner with EAs and Chiefs of Staff across CVS Health to align on enterprise-wide initiatives and communications.
• Manage onboarding logistics for new members joining the Digital leadership team.

• 6+ years of experience supporting VP-level or above executives, preferably within a large enterprise, Fortune 500, or technology-driven organization.
• Exceptional organizational skills with the ability to manage multiple high-priority work streams simultaneously without losing attention to detail.
• Strong proficiency in Microsoft Office Suite (Outlook, Word, PowerPoint, Excel), Teams, and SharePoint.
• Outstanding written and verbal communication skills; able to represent the VP's voice with accuracy and professionalism.
• High degree of discretion and integrity when handling sensitive business and personnel information.
• Self-directed and comfortable operating independently in a hybrid/remote environment with minimal supervision.

• Experience supporting digital, technology, or product organizations within healthcare or a regulated enterprise environment.
• Familiarity with CVS Health or Caremark internal systems, processes, and organizational structure.
• Comfort with agile, fast-paced digital team rhythms including sprint reviews, OKR cycles, and roadmap planning.
• Experience with project tracking…