Executive Administrative Assistant

GuideWell • Jacksonville, FL

11d

About The Position

The Executive Administrative Assistant provides advanced, diversified, and confidential administrative support to an executive leader and staff. The role manages complex calendars, coordinates conferences and meetings, communicates meeting logistics and agendas, and prepares executive-ready presentations, spreadsheets, reports, and correspondence. It also involves processing time and expense reports, supporting budgets and administrative compliance, and maintaining computer and paper filing and organization systems.

The successful candidate uses strong communication and organizational skills to work professionally and confidentially with people at all levels inside and outside the Company. The role requires sound judgment, accuracy, and efficiency, along with the ability to anticipate executive needs and proactively resolve operational challenges. The position also uses AI tools to support executive workflows while protecting confidential information and verifying generated content.

Requirements

• At least 5 years of diversified administrative experience, including one or more years of progressively responsible experience.
• Advanced proficiency with Microsoft 365, including Outlook, Word, Excel, PowerPoint, and Teams.
• Ability to accurately produce executive-ready materials in SharePoint, OneDrive, and Microsoft 365 on short timelines.
• Experience using organizational skills to support management team and client needs, with a focus on execution, accuracy, and efficiency.
• Ability to work flexible hours or a flexible schedule to meet business needs.
• Demonstrated experience using AI integrated with Microsoft tools to solve business problems and improve efficiency.
• Working knowledge of Claude Desktop, including effective prompting and use of Claude Projects to support executive workflows.
• Sound judgment in responsible AI use, including protecting confidential information and validating generated names, numbers, and dates.
• Working financial acumen, including the ability to read, reconcile, and summarize budgets, expense reports, and financial data, and support timely and accurate time and expense processing.
• High school diploma or GED.

Nice To Haves

• Advanced Microsoft 365 skills, including Excel PivotTables, XLOOKUP, advanced formulas, Power Query, and basic financial modeling.
• Ability to create PowerPoint materials suitable for CEO and board audiences, long-form Word documents, and manage SharePoint and Teams sites.
• Demonstrated use of AI integrated with Microsoft tools to consolidate inbox, calendar, and meeting information into briefings and turn raw data into executive summaries.
• Strong financial acumen, including budget tracking, variance analysis, expense and invoice review, and preparation of concise financial summaries for executive review.
• Advanced proficiency with Claude Desktop, including creating and managing Claude Projects, maintaining skills for repeatable work, and using Microsoft 365 connectors.
• Skill in prompt and context engineering, with disciplined verification of AI output before it reaches an executive.
• Ability to document and share AI practices and coach others, including maintaining a library of reusable prompts and skills.
• Microsoft Office Specialist: Expert (Microsoft 365 Apps) certification.

Responsibilities

• Provide advanced, diversified, and confidential administrative support for the executive leader and staff.
• Receive, screen, and handle correspondence, including confidential or sensitive material.
• Coordinate conferences and meetings and manage complex calendars, meeting logistics, and agendas.
• Compose and proofread correspondence and produce high-quality presentations, spreadsheets, and reports.
• Manage expense reports, budgets, and administrative compliance.
• Create and maintain computer- and paper-based filing and organization systems.
• Maintain knowledge of organization policies, procedures, and resources.
• Complete or participate in special projects as needed.
• Interact professionally and confidentially with individuals at all levels within and outside the Company.
• Anticipate executive needs and proactively resolve operational challenges.
• Use AI tools responsibly to support business and executive workflows, validating output and protecting confidential information.

Benefits

• Medical, dental, vision, life, and global travel health insurance.
• Short- and long-term disability programs.
• Leave programs to support personal circumstances.
• Retirement Savings Plan with employer match.
• Paid time off, volunteer time off, 10 holidays, and 2 well-being days.
• Additional voluntary benefits.
• Comprehensive wellness program.
• Competitive pay and opportunities for incentive or commission compensation.
• Regular annual reviews with pay-for-performance considerations for base pay increases.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: High school or GED