Role Overview:

The Executive Assistant is the operational engine behind the Chief of Staff to The Cigna Group's Executive Leadership Team (ELT). The Chief of Staff designs and runs the ELT management process: the cadence of ELT forums, strategy sessions, business performance reviews and Senior Leadership Team (SLT) meetings through which the enterprise sets direction and makes decisions. This role takes ownership of the logistics that make that process run, including securing ELT time, coordinating agendas and materials across a network of senior executive assistants, and managing the Chief of Staff's own calendar.

This is not a traditional single-executive support role. Much of the work gets done through influence rather than authority. The Executive Assistant partners daily with the executive assistants who manage ELT and SLT calendars and agendas, and must be comfortable negotiating for time on crowded calendars, holding firm on deadlines, and pushing respectfully to keep the ELT agenda moving. The ideal candidate is confident, polished and discreet, operates with a high degree of autonomy, and anticipates what the Chief of Staff needs before being asked.

Key Responsibilities:

ELT management process and forum logistics

·       Own end-to-end logistics for recurring ELT forums, as well as ad hoc ELT sessions, including scheduling, rooms, virtual access, catering and attendee management.

·       Maintain the rolling ELT meeting calendar and forward-looking forum plan in partnership with the ELT Operations team, tracking which topics are slotted into which meetings and flagging conflicts, gaps and slippage early.

·       Run the materials timeline for every ELT session: set and communicate pre-read deadlines to topic owners, follow up on late content, and distribute materials to ELT members, as needed.

·       Coordinate presenters and guest attendees for ELT and SLT agenda topics, including invitations, run-of-show timing, virtual access details and pre-meeting preparation holds.

·       Plan and execute logistics for larger-format sessions such as ELT offsites and onsites, SLT meetings, and enterprise milestone events and rehearsals, partnering with events, communications, corporate real estate and technology teams.

·       Keep ELT management process artifacts organized and current, including forum charters, meeting plans, agenda archives, distribution lists, and SharePoint and Teams sites.

Executive stakeholder and EA network management

·       Build strong, trusted working relationships with the executive assistants and chiefs of staff who support ELT and SLT members, serving as the primary point of contact for ELT scheduling and logistics requests from the Chief of Staff's office.

·       Negotiate for time on highly constrained executive calendars by proposing options, holding firm on priorities, and escalating tactfully when ELT process milestones are at risk.

·       Push, with respect and diplomacy, to secure commitments, materials and responses on deadline, representing the Chief of Staff's priorities with confidence and without needing day-to-day direction.

·       Serve as a professional, discreet and credible representative of the Chief of Staff's office with senior leaders at every level.

Chief of Staff calendar and time management

·       Manage the Chief of Staff's complex, fast-moving calendar end to end: triage and respond to invitations, resolve conflicts, and reshuffle quickly when ELT priorities shift.

·       Protect time for preparation, focus work and follow-through around major ELT milestones, and ensure the Chief of Staff walks into each meeting with the right materials and context.

·       Schedule and maintain recurring cadences, including 1:1s with direct reports and cross-functional partners, team meetings, and chief-of-staff network meetings.

·       Provide a weekly look-ahead that highlights key meetings, deadlines, preparation needs and conflicts requiring a decision.

Communications and follow-through

·       Draft and send correspondence on the Chief of Staff's behalf, including meeting invitations, agenda notes, materials reminders and follow-up emails to executive audiences.

·       Monitor the Chief of Staff's inbox for time-sensitive ELT requests, route items to the right team member, and track open loops to closure.

·       Prepare and format agendas, trackers, meeting materials and presentations in Word, Excel and PowerPoint.

·       Use Copilot and other AI tools to accelerate agenda drafting, meeting summaries, action tracking and scheduling.

Administrative and operational support

·       Manage travel arrangements and expense reporting (e.g., Concur) for the Chief of Staff, and coordinate travel logistics for offsites and in-person sessions.

·       Coordinate onboarding and offboarding logistics for the Chief of Staff's team, and maintain distribution lists, Teams channels and SharePoint access.

·       Handle confidential and pre-decisional information, including strategy, organizational and financial materials, with complete discretion.

·       Secure help desk and technology support as needed, and resolve logistical issues in real time with sound judgment.

Qualifications:

·       5+ years of progressively responsible executive assistant experience, including substantial time supporting ELT or SLT team members, or their chiefs of staff.

·       Proven ability to influence without authority, and to hold peer executive assistants and senior stakeholders to deadlines with tact and confidence.

·       Exceptional calendar management across multiple executives and competing priorities, with the composure to handle constant change.

·       Enthusiasm for Copilot and AI tools, and a willingness to keep building AI skills.

·       Expert skills in Microsoft 365 (Outlook, Teams, Word, Excel, PowerPoint, SharePoint) and meeting platforms (Teams, Webex, Zoom).

·       Excellent written and verbal communication skills, with executive presence.

·       Impeccable organizational skills, attention to detail and follow-through.

·       High degree of integrity, discretion and judgment with highly confidential information.

·       Ability to work independently in a fast-paced environment with shifting priorities, and a proactive, solutions-oriented mindset.

Preferred Competencies:

·       Organizational and political savvy

·       Influencing and relationship building

·       Proactive anticipation and drive for results

·       Managing ambiguity and complexity

·       Resourcefulness

·       Discretion and trustworthiness

·       Learning agility

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.