Strategic Executive Assistant to the CEO & Board

Florida Blue; Jacksonville (FL); On-site; USD 75,000 - 115,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

Life insurance

Disability benefits

Retirement plan (employer match)

Paid time off

Holidays and well-being days

Job summary

Florida Blue is seeking an Executive Assistant to the CEO, a strategic partner in the Office of the CEO. You will anticipate needs, connect the dots across the enterprise, and safeguard the CEO’s time for priority decisions.

You will leverage AI tools to accelerate workflows and collaborate with the Chief of Staff and Board Services for a seamless, coordinated office. In this role, you’ll manage the CEO’s calendar, triage communications, and prepare briefing materials for Board engagements,

Qualifications

• 7+ years of progressively responsible experience supporting senior executives, ideally a CEO or C-suite leader.
• Proven ability to exercise judgment, handle confidential information and act independently.
• Advanced Microsoft Office skills and experience adopting new technology, including AI tools.
• Ability to anticipate needs, prioritize competing demands and use sound judgment for a senior executive.
• Project management experience coordinating multiple initiatives and deadlines.
• Ability to connect dots across the enterprise and make recommendations, not just observations.
• Willingness to work flexible hours and travel up to 10%, including board-related travel.
• Hands-on experience using AI tools, automation, or workflow technology to streamline executive support.
• Strong discretion, emotional intelligence and trust-building with leaders at all levels.
• Self-starter who raises issues and offers recommendations without prompting.
• Bachelor’s degree preferred or equivalent related work experience.

Responsibilities

• Act as a day-to-day operating partner to the CEO and the Office of the CEO, anticipating priorities and keeping the office proactive.
• Connect the dots across the enterprise and flag cross-functional impacts with recommendations.
• Prepare the CEO with a regular look ahead on decisions and risks.
• Manage the CEO's calendar as a strategic tool and protect focus time.
• Filter meeting requests, elevate discussions when needed, and ensure agendas and pre-reads are timely.
• Triage and manage the CEO's inbox; draft replies and summarize items for review.
• Draft, edit and proofread CEO correspondence in the CEO's voice.
• Use technology and AI tools to run the office and automate workflows while following confidentiality guidelines.
• Support Board and executive engagements and coordinate CEO travel.
• Coordinate with the Chief of Staff and Board Services to ensure coordinated communications and materials.
• Prepare briefing notes and open items for boards; raise conflicts early.
• Track commitments, deadlines and special projects; manage office operations and records.

Skills

Executive support

Discretion

Anticipation & prioritization

Project management

Analytical thinking

AI tools proficiency

Emotional intelligence

Self-motivation

Flexible & travel readiness

Judgment under pressure

Communication & coordination

Education

Bachelor’s degree or equivalent

Tools

Microsoft Office

AI tools / automation

Job description

Florida Blue is seeking an Executive Assistant to the CEO, a strategic partner in the Office of the CEO. You will anticipate needs, connect the dots across the enterprise, and safeguard the CEO’s time for priority decisions.

You will leverage AI tools to accelerate workflows and collaborate with the Chief of Staff and Board Services for a seamless, coordinated office. In this role, you’ll manage the CEO’s calendar, triage communications, and prepare briefing materials for Board engagements,