Executive Assistant to the CEO

The Executive Assistant to the CEO is a strategic, high-judgment member of the Office of the CEO. This role goes well beyond calendar and logistics. It helps run the CEO's office: anticipating what is coming, connecting the dots across the enterprise, protecting and directing the CEO's time and attention toward what matters most, and making sure the CEO is prepared for colleagues, the Board and external partners. The role uses modern technology, including AI tools, to run the office with speed, efficiency, accuracy and consistency, and works as a close partner to the Chief of Staff and the Office of the CEO team.

Who We Are Looking For:
We are looking for a dynamic, curious and highly capable partner who moves at the pace of a fast-moving CEO. You will anticipate needs, spot where the dots need to be connected, use sound judgment about where the CEO's time is best spent, and keep colleagues, leaders and Board members well served and well informed. You are comfortable using AI tools to automate routine work and sharpen drafts, which frees your time for the judgment calls only a trusted partner can make. You bring discretion, composure under pressure and genuine care for the experience of the people who work with the CEO.

Key Responsibilities
Strategic partnership and anticipation  
•    Act as a day-to-day operating partner to the CEO and the Office of the CEO: anticipate priorities, manage the flow of work, and keep the office running proactively rather than reactively.
•    Connect the dots across the enterprise. Recognize when a conversation, decision, deadline or risk in one area affects another, and flag it to the CEO and Chief of Staff with a recommendation, not just a heads-up.
•    Prepare the CEO with a regular look ahead: what is coming, what needs a decision, and what is at risk.
Time and priorities  
•    Manage the CEO's calendar as a strategic tool. Use judgment to prioritize, protect focus time and decide where the CEO's time and presence matter most.
•    Filter meeting requests: accept those that are needed, decline or pass on others, and elevate to the Chief of Staff anything that needs a discussion.
•    Make sure each meeting has the right people, preparation and purpose, and that agendas and pre-reads reach participants in time.
Inbox and communications  
•    Triage and manage the CEO's inbox and incoming requests, many confidential or sensitive. Draft replies for the CEO’s review, route and prioritize the rest, and summarize what needs the CEO’s attention.
•    Pull out items that need a conversation, especially speaking invitations and requests for the CEO's endorsement or presence, and review them with the Chief of Staff before they go to the CEO.
•    Working closely with the dedicated communications resource, draft, edit and proofread CEO correspondence in the CEO's voice, in plain and clear language, for CEO review. 
Technology and AI  
•    Use technology and AI tools to run the office: build and improve workflows, templates, trackers and knowledge systems; automate routine tasks; and share what works with the Office of the CEO team.
•    Follow GuideWell's guidelines for handling confidential, Board and protected information in any tool.
Colleague and Board experience  
•    Support the experience of colleagues and Board members in their interactions with the CEO. Prepare the CEO for Board and executive engagements and coordinate the CEO's own participation and travel.
•    Stay closely attuned to the CEO's meetings with the Board Chair: know the timing, who needs to know about it, and what the CEO will need beforehand.
•    Partner closely with the Board Services leader, who owns the Board calendar, portal and logistics. Stay connected on Board schedules and on the CEO's review of Board materials so the CEO's time is set aside when it is needed.
•    Work as part of a tight team with the Chief of Staff, the Chief of Staff's executive assistant, and the dedicated communications resource, so that the CEO and Board members experience one coordinated office.
The CEO’s other board service  
•    Proactively manage the CEO’s service on other boards. Keep a long-range view of meeting cycles, committee meetings and key dates, and protect time well in advance, including around the GuideWell Board calendar.
•    Own the preparation timeline for those boards: track material deadlines and pre-reads, prepare the CEO with briefing notes and open items, and raise conflicts and risks early.
•    Work hand in hand with the dedicated communications resource on remarks, talking points and written materials for those boards, so the CEO’s materials are consistent, polished and on time.
•    Follow-through and office operations  
•    Track commitments and follow up with leaders and departments on assignments, decisions and deadlines. Bring forward what is slipping before it becomes a problem.
•    Complete or lead special projects, and manage office operations including budget, time and expense reporting, and filing and records systems.
•    Interact with individuals at all levels inside and outside the Company, including Board members, with professionalism, discretion and strict confidentiality

What Success Looks Like:
•    The CEO arrives at every meeting on time and prepared.
•    The CEO's calendar reflects his stated priorities, with protected time for strategy and for people.
•    Routine work runs with little CEO involvement, and the office is measurably faster because of the workflows and tools this person builds.
•    Commitments made by or to the CEO are tracked and closed on time.
•    The CEO's other board commitments are planned well ahead, and materials are ready before deadlines.

Key Requirements: 
•    7+ years of progressively responsible experience supporting senior executives, ideally a CEO or C-suite leader.
•    Track record of exercising judgment, handling confidential information and acting independently.
•    Advanced Microsoft Office skills (Outlook, Word, Excel, PowerPoint, Teams) and experience with adopting new technology, including AI tools.
•    Ability to anticipate needs, prioritize competing demands and use sound judgment on behalf of a senior executive.
•    Project management experience, with the ability to plan, coordinate and drive multiple initiatives and deadlines to completion across teams.
•    Ability to connect the dots across the enterprise, recognizing how developments in one area affect another and bringing forward recommendations, not just observations.
•    Ability to work flexible hours to meet business needs, including occasional evenings.
•    Ability to travel as required, 10% or less, including Board-related travel.
•    Hands-on experience using AI tools, automation or workflow technology to streamline executive support.
•    Exceptional discretion, emotional intelligence and the ability to build trust and influence with leaders at every level.
•    Self-starter who raises issues and offers recommendations without being asked.
•    Bachelor’s degree preferred or equivalent related work experience.

Preferred:
•    Experience supporting a CEO or Board of Directors, including Board meeting preparation and communications.
•    Experience in healthcare, insurance or another regulated and complex enterprise.
•    Strong business writing and editing skills, including writing in plain, clear language and in another person’s voice.

General Physical Demands
Sedentary work: Exerting up to 10 pounds of force occasionally to move objects. Jobs are sedentary if traversing activities are required only occasionally. 

What We Offer: 
As a Florida Blue employee, you will be at the heart of GuideWell’s vision – to lead the nation in transforming health through compassionate, connected, and technology-enabled care that delivers personalized value and empowered living. 

To support your wellbeing, comprehensive benefits are offered. As an employee, you will have access to: 
 

• Medical, dental, vision, life and global travel health insurance;
• Income protection benefits: life insurance, short- and long-term disability programs;
• Leave programs to support personal circumstances;
• Retirement Savings Plan including employer match;
• Paid time off, volunteer time off, 10 holidays and 2 well-being days;
• Additional voluntary benefits available; and
• A comprehensive wellness program

Employee benefits are designed to align with federal and state employment laws. Benefits may vary based on the state in which work is performed. Benefits for intern, part-time and seasonal employees may differ.

To support your financial wellbeing, we offer competitive pay as well as opportunities for incentive or commission compensation. We also conduct regular annual reviews with pay for performance considerations for base pay increases. 

Final pay will be determined with consideration of market competitiveness, internal equity, and the job-related knowledge, skills, training, and experience you bring.

We are an Equal Employment Opportunity employer committed to cultivating a work experience where everyone feels like they belong and can perform at their best in pursuit of our mission. All qualified applicants will receive consideration for employment.