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

Job Description

Job Description

Executive Assistant to the CEO - Multi-State Law Firm

About Us

Our growing, multi-state estate planning and elder law firm is dedicated to serving clients with excellence, reliability, and trust. As our CEO continues to expand the firm’s reach, we are seeking an exceptional Executive Assistant to become the steady, organized force behind a visionary leader.

This role is not just about scheduling. It's about bringing order, structure, and trusted personal support to the CEO’s busy professional and personal life. If you love creating seamless systems, caring for details, and helping someone achieve their best by handling everything behind the scenes, this is the opportunity for you.

Your Role

As Executive Assistant, you will be the CEO’s right hand - ensuring day-to-day operations flow smoothly, details never fall through the cracks, and the CEO can focus on leading, growing, and serving clients. This role includes significant administrative, organizational, and personal support functions.

You will:

Provide comprehensive administrative support, including:

• Proactive calendar management for both business and personal events.
• Daily email organization, responding to routine messages, and drafting clear communications.
• Preparing, organizing, and maintaining all personal and business files and records.

Manage daily personal support tasks, including:

• Overseeing food prep and light meal planning in coordination with household staff or local vendors.
• Coordinating light household tasks to keep the home environment tidy and welcoming.
• Keeping clothing organized, clean, and ready for travel or events.

Handle scheduling and meeting logistics, including:

• Setting up meetings, preparing agendas, and confirming details in advance.
• Taking accurate notes and ensuring follow-ups are completed.
• Liaising with internal staff and external contacts professionally and discreetly.

Support personal errands and needs, such as:

• Managing vendor relationships for household tasks.
• Running occasional personal errands to keep daily life organized and stress-free.

Rapid communication via text is preferred, with weekly planning meetings to review and confirm tasks and schedules. You will be acting as a steady, trusted liaison for the CEO, handling tasks with utmost confidentiality and care. This is a career-track role.

About You

The ideal candidate is naturally:

• Detail-Oriented & Systematic: You thrive on bringing order to chaos, enjoy repetitive tasks, and never let small details slip through.
• Patient & Consistent: You prefer steady work and enjoy following proven processes, even when things change fast around you.
• Supportive & Service-Minded: You take pride in anticipating needs before they’re asked for and love helping someone succeed.
• Low Ego, High Integrity: You handle sensitive information with discretion and loyalty.
• Organized & Dependable: You get satisfaction from completing checklists, maintaining routines, and knowing everything is in its place.

Position Details

• Location: Naples, FL
• Schedule: Full-time M-F 8:30 to 5:30; flexibility required for after-hours or pre-planned weekend needs.

Compensation & Benefits

• Salary range: $90,000-115,000 plus performance bonus.
• Health Insurance (CareFirst) - 50% company-paid
• Dental & Vision Insurance
• Short-Term & Long-Term Disability Insurance - 100% company-paid
• Life Insurance - 100% company-paid
• 401(k) with up to 4% company match (no vesting period)
• 15 personal days starting year one, with increases based on tenure

Requirements

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

Why Join US

• Be part of a firm that values excellence, service, and trust.
• Work directly with an inspiring leader - your contribution will make a daily impact.
• Enjoy the satisfaction of bringing calm, order, and support to a fast-paced, purpose-driven business.
• Grow in a stable, long-term position where your loyalty and care are genuinely appreciated.

Company Description

Company Description

Join our dynamic team and become a part of an organization that values its clients and employees alike. We offer competitive compensation, comprehensive benefits, and opportunities for professional growth within the firm.