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. Executive Calendar & Schedule Management 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. Communication & Stakeholder Liaison 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. Travel & Logistics 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. Project & Operational Support 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. Required 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 workstreams 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. Preferred Qualifications 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 tools such as Asana, Jira, or Microsoft Planner. Bachelor's degree in Business Administration, Communications, or a related field. Anticipated Weekly Hours 40 Time Type Full time Pay Range The typical pay range for this role is: $22.59 - $53.95. 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. 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: 06/06/2026. Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws. #J-18808-Ljbffr Hispanic Alliance for Career Enhancement