Executive Assistant - Total Rewards

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. Role overview This Executive Assistant role is a force-multiplier for Total Rewards leadership—creating clarity, momentum, and a reliable operating rhythm across a fast-moving portfolio. The right candidate will anticipate needs, protect time for the highest-impact work, elevate the organization, and ensure leaders and stakeholders experience a high-trust, well-coordinated partnership. Success in this role comes from strong judgment, crisp communication, proactive follow-through, and a steady commitment to confidentiality and discretion in a complex, matrixed environment.

Executive & operational enablement Own complex calendars for 3 senior leaders, making smart trade-offs to optimize focus time, meeting flow, and decision-making Proactively prepare leaders for meetings with pre-reads, context, key questions, and tight briefing notes Coordinate travel, logistics, onsite events, and process and submit expense reports as needed with accuracy and timeliness Maintain a real-time pulse on commitments, priorities, and emerging conflicts; surface risks early and propose options Operating rhythm, coordination, and follow-through Track action items, deliverables, and follow-ups across leadership meetings and key workstreams; assist with follow-through and drive on-time outcomes Support preparation for leadership meetings, business reviews, and enterprise forums (agendas, materials, attendee coordination, notes/action capture when needed) Enable clear team communications and organizational transparency through consistent updates, reminders, and shared documentation Support onboarding of new leaders and team members by coordinating logistics, scheduling ongoing key meetings and meet and greets, and oversee completion of “first 30 days” essentials Stakeholder & relationship management Serve as a primary point of contact on behalf of supported leaders, responding with professionalism, responsiveness, and sound judgment Partner seamlessly with other Executive Assistants, Chiefs of Staff, HR colleagues, and cross-functional teams to coordinate dependencies and unblock work Handle sensitive information with discretion, care, and integrity Process excellence & continuous improvement Identify and implement practical improvements that simplify workflows, increase clarity, and reduce friction for leaders and stakeholders Use Microsoft 365 tools (Outlook, Teams, SharePoint, PowerPoint, Excel) to assist leaders in organizing information, maintaining systems, and supporting crisp execution Leverage emerging technology and productivity tools (e.g., Copilot) to streamline recurring work (drafting, summarizing meeting notes, action tracking), improve meeting readiness, and increase consistency—while protecting confidentiality and using sound judgment Contribute to small projects or operational initiatives across the Talent portfolio as needed Requirements 3+ years supporting senior leaders (VP+) in a large, matrixed organization Strong planning, influencing and prioritization skills, with the ability to manage multiple leaders and shifting priorities without losing details High judgment and executive maturity—able to handle sensitive information and situations with discretion and calm Strong written and verbal communication skills; able to draft clear notes, updates, and meeting materials Advanced proficiency with Microsoft 365 tools (Outlook, Teams, SharePoint, PowerPoint, Excel) Preferences Experience supporting HR/Total Rewards, talent, transformation, or enterprise