Executive Administrative Assistant

GuideWell; Jacksonville (FL); On-site; USD 44,000 - 72,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

Life insurance

Disability coverage

Retirement plan

PTO

Holidays

Wellness program

Job summary

GuideWell in Jacksonville, FL is seeking an Executive Administrative Assistant to provide advanced administrative support to an executive leader and staff. You will manage complex calendars, coordinate conferences and prepare executive-ready materials such as presentations and reports.

You will also handle monthly time and expense reporting, filing systems, and special projects while upholding confidentiality and professional standards across all interactions.

Qualifications

• 5+ years diversified administrative experience.
• Advanced proficiency with Microsoft 365 including Outlook, Word, Excel, PowerPoint and Teams.
• Ability to produce executive-ready materials in SharePoint, OneDrive and the Microsoft 365 suite accurately and on short timelines.
• Experience leveraging organizational skills to support management team and client needs, focusing on execution, accuracy and efficiency.
• Must be able to work flexible hours/schedule to meet business needs.
• Demonstrated experience using AI integrated with the Microsoft suite to solve business problems and improve efficiency.
• Working knowledge of Claude Desktop and Claude Projects to support executive workflows.
• Sound judgment in the responsible use of AI, including protecting confidential information and validating AI-generated output.

Responsibilities

• Provide advanced, diversified, confidential administrative support for the executive leader and staff.
• Receive, screen and handle correspondence, including confidential matters.
• Coordinate conferences and meetings with complex calendar management and logistics.
• Prepare high-quality materials such as presentations, spreadsheets and reports.
• Manage expense reports, budget and administrative compliance.
• Create and maintain filing and organization systems.
• Maintain knowledge of organizational policies and resources.
• Participate in special projects as needed.
• Interact professionally with internal and external stakeholders.
• Anticipate executive needs and resolve operational challenges.

Skills

Administrative experience

Communication

Confidentiality

AI-assisted workflows

Financial acumen

Calendar management

Problem solving

Education

High school diploma or GED

Tools

Microsoft 365

Outlook

Word

Excel

PowerPoint

Teams

SharePoint

OneDrive

Claude Desktop

Claude Projects

Job description

Job Summary

The Executive Administrative Assistant provides advanced administrative support for an executive leader and staff and is responsible for managing complex calendars, coordinating conferences and meetings, and preparing high-quality materials such as presentations, spreadsheets, and reports. Additionally, this role involves processing monthly time and expense reporting, maintaining filing and organization systems, and completing special projects as needed. Possess excellent communication and organizational skills, with the ability to interact effectively with individuals at all levels within and outside of the Company in a professional and confidential manner.

Key Responsibilities

• Provide advanced, diversified and confidential administrative support for the executive leader and staff.


• Receive, screen and handle correspondence, much of which is confidential or sensitive in nature.


• Coordinate conferences and meetings and perform complex calendar management including managing and communicating all meeting logistics and agendas to involved parties.


• Compose and proofread correspondence and produce high-quality materials such as presentations, spreadsheets and reports.


• Manage expense reports, budget 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 effectively with individuals at all levels within and outside of the Company in a professional and confidential manner.


• Anticipate executive needs and proactively resolve operational challenges.

Key Requirements

• 5+ years 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 produce executive-ready materials in SharePoint, OneDrive and the Microsoft 365 suite accurately and on short timelines.


• Experience leveraging organizational skills to support management team and client needs, focusing on execution, accuracy and efficiency.


• Must be able to work flexible hours/schedule to meet business needs.


• Demonstrated experience using AI integrated with the Microsoft suite, to solve business problems and improve efficiency (for example, summarizing email and meeting content, drafting correspondence, analyzing data in Excel and building presentations).


• Working knowledge of Claude Desktop, including effective prompting and the use of Claude Projects to support executive workflows.


• Sound judgment in the responsible use of AI, including protecting confidential information and validating AI-generated output for accuracy of names, numbers and dates.


• Working financial acumen, including the ability to read, reconcile and summarize budgets, expense reports and financial data, and to support timely and accurate time and expense processing.

Preferred Requirements

• Advanced Microsoft 365 skills, including Excel (PivotTables, XLOOKUP, advanced formulas, Power Query and basic financial modeling), PowerPoint materials suitable for CEO and board audiences, long-form Word documents, and SharePoint and Teams site management.


• Demonstrated use of AI integrated with the Microsoft suite to solve operational problems, such as consolidating inbox, calendar and meeting information into daily briefings and turning raw data into executive summaries.


• Strong financial acumen, including budget tracking, variance analysis, expense and invoice review, and preparing concise financial summaries for executive review.


• Advanced proficiency with Claude Desktop, including creating and managing Claude Projects (custom instructions and knowledge files), building and maintaining skills for repeatable work such as briefings and formatted documents, and using connectors to Microsoft 365 for email, calendar and SharePoint content.


• Skilled in prompt and context engineering, with disciplined practice of verifying AI output before it reaches an executive.


• Ability to document, share and coach others on AI practices, including maintaining a library of reusable prompts and skills for the team.

Required Education

• High school diploma or GED

Preferred Licenses and Certifications

• Microsoft Office Specialist: Expert (Microsoft 365 Apps)

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.

Hourly Pay Range

$32 - $52

Typical Hourly Pay Range

$32 - $40

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.