Executive Assistant - Rewards

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.

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.

Responsibilities

• 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 work streams; 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 operating rhythm work
• Comfort working across complex stakeholder networks and navigating competing priorities
• Interest in improving systems, workflows, and how teams communicate and execute

Education

High School/GED required, Bachelor's degree preferred

Anticipa…