Strategic Executive Assistant to CEO

Stouffer Legal; Naples (FL); On-site; USD 90,000 - 115,000; Full time

Benefits offered by this job

Health Insurance (CareFirst) - 50%

Dental & Vision Insurance

Short-Term & Long-Term Disability - %

Life Insurance - 100% company-paid

401(k) with 4% match

15 personal days

Job summary

Stouffer Legal is seeking an Executive Assistant to the CEO in Naples, FL. This full-time role supports day-to-day operations, personal and professional tasks, and confidential executive-level scheduling.

You will manage calendars, organize emails, prepare files, coordinate household and personal tasks, and handle meeting logistics with discretion and care. The position requires reliability, process orientation, and a proactive mindset.

Qualifications

• Must have at least 5 years of experience.
• Must have valid driver’s license.
• Dress code required.

Responsibilities

• Provide comprehensive administrative support for CEO, including calendar management and email organization.
• Prepare, organize, and maintain personal and business files and records.
• Oversee personal tasks such as food prep, housekeeping coordination, and travel-ready wardrobe.
• Schedule meetings, prepare agendas, take notes, and ensure follow-ups are completed.
• Liaise with internal staff and external contacts with discretion and professionalism.

Skills

Calendar management

Email organization

Note taking

Administrative support

Personal support

Vendor management

Discretion

Organized

Education

5+ years experience

Job description

Stouffer Legal is seeking an Executive Assistant to the CEO in Naples, FL. This full-time role supports day-to-day operations, personal and professional tasks, and confidential executive-level scheduling.

You will manage calendars, organize emails, prepare files, coordinate household and personal tasks, and handle meeting logistics with discretion and care. The position requires reliability, process orientation, and a proactive mindset.