Executive Assistant

Role Overview

Provides high-level, diversified, and confidential executive support to the Chief Information Officer of US Employer Technology (USET), serving as a trusted partner in the effective execution of leadership and organizational priorities. Exercises exceptional judgment, discretion, and organizational skill to manage complex calendars, meetings, travel, communications, correspondence, executive deliverables, and other critical business activities in a fast-paced environment.

Proactively anticipates needs, resolves routine and complex inquiries, and helps create clarity and coordination across the USET leadership team and broader organization. Partners closely with the Chief of Staff and other key stakeholders to facilitate seamless communication, strengthen executive operations, and support the execution of priorities, including light project management and cross-functional coordination. The role requires strong executive presence, adaptability, attention to detail, technology proficiency, and the ability to build effective relationships across all levels of the organization while handling highly confidential information with integrity and discretion.

Key Responsibilities

Executive Support

• Manage complex calendars, travel arrangements, and meeting logistics.
• Prepare briefing materials, agendas, and follow-up documentation for executive meetings.
• Handle confidential communications and correspondence with discretion.
• Serve as a liaison between CIO and internal/external stakeholders.

Project Coordination

• Partner with the Chief of Staff to track and follow up on key initiatives and deliverables.
• Support project planning, milestone tracking, and status reporting for strategic efforts.
• Coordinate cross-functional meetings and ensure timely documentation of action items.
• Assist in preparing presentations and dashboards for leadership reviews.

Operational Excellence

• Maintain and improve organizational systems for document management, scheduling, and communications.
• Identify opportunities to streamline workflows and enhance executive productivity.
• Leverage digital tools (e.g., Microsoft 365, Teams, SharePoint, project tracking platforms) to support daily operations.

Financial & Administrative Support

• Manage expense reports, invoices, purchase orders, and budget tracking activities.
• Coordinate vendor relationships and support contract and procurement processes as required.
• Ensure compliance with company policies related to travel, expenses, and records management.

Required Qualifications

• Minimum of 5 years of progressively responsible experience in executive administration, senior-level administrative support, or project coordination.
• Demonstrated success managing complex executive calendars and coordinating meetings with multiple senior-level stakeholders.
• Advanced skills in Microsoft Word, Outlook, PowerPoint, and Excel, with experience using Microsoft Teams, Zoom, Webex, or similar meeting platforms.
• Excellent written and verbal communication skills, with executive presence.
• Strong organization and prioritization skills, with the ability to work independently, manage competing demands, and remain effective under pressure.
• Proven ability to protect confidential information, use sound judgment, and build trusted relationships across a virtual or hybrid organization.
• Ability to troubleshoot routine technology issues and partner with technical support teams when needed.

Preferred Qualifications

• Experience supporting IT executives or working within a large, complex enterprise.
• Enthusiasm for Copilot and AI tools, and a willingness to keep building AI skills.
• Experience using Concur, SharePoint, Slido, or similar business tools.
• Demonstrated learning agility, resourcefulness, collaboration, and comfort navigating ambiguity.

If you will be working at home occasionally or permanently, the internet connection must be obtained through a cable broadband or fiber optic internet service provider with speeds of at least 10Mbps download/5Mbps upload.For this position, we anticipate offering an hourly rate of 33 - 49 USD / hourly, depending on relevant factors, including experience and geographic location.

This role is also anticipated to be eligible to participate in an annual bonus plan.

At The Cigna Group, you’ll enjoy a comprehensive range of benefits, with a focus on supporting your whole health. Starting on day one of your employment, you’ll be offered several health-related benefits including medical, vision, dental, and well-being and behavioral health programs. We also offer 401(k), company paid life insurance, tuition reimbursement, a minimum of 18 days of paid time off per year, paid holidays, and leaves of absence. For more details on our employee benefits programs, click here.

About The Cigna Group

Doing something meaningful starts with a simple decision, a commitment to changing lives. At The Cigna Group, we’re dedicated to improving the health and vitality of those we serve. Through our divisions Cigna Healthcare and Evernorth Health Services, we are committed to enhancing the lives of our clients, customers and patients. Join us in driving growth and improving lives.

Qualified applicants will be considered without regard to race, color, age, disability, sex, childbirth (including pregnancy) or related medical conditions including but not limited to lactation, sexual orientation, gender identity or expression, veteran or military status, religion, national origin, ancestry, marital or familial status, genetic information, status with regard to public assistance, citizenship status or any other characteristic protected by applicable equal employment opportunity laws.

If you need a reasonable accommodation to complete the online application process, please email [email protected] for assistance.  Please note that this email inbox is dedicated to accommodation requests only and cannot provide application updates or accept resumes.

The Cigna Group has a tobacco-free policy and reserves the right not to hire tobacco/nicotine users in states where that is legally permissible. Candidates in such states who use tobacco/nicotine will not be considered for employment unless they enter a qualifying smoking cessation program prior to the start of their employment. These states include: Alabama, Alaska, Arizona, Arkansas, Delaware, Florida, Georgia, Hawaii, Idaho, Iowa, Kansas, Maryland, Massachusetts, Michigan, Nebraska, Ohio, Pennsylvania, Texas, Utah, Vermont, and Washington State.

Qualified applicants with criminal histories will be considered for employment in a manner consistent with all federal, state and local ordinances.