Executive Assistant to the CEO

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

Benefits offered by this job

Health Insurance (CareFirst)

Dental & Vision Insurance

Disability Insurance

Life Insurance

401(k) with up to 4% company match

15 personal days

Job summary

Stouffer Legal in Naples, FL seeks an Executive Assistant to the CEO to provide comprehensive administrative and personal support, ensuring the CEO’s day-to-day operations run smoothly, confidentially, and efficiently.

You will manage calendars, emails, travel between Maryland and Florida, prepare agendas, take notes, liaise with staff and vendors, and handle personal tasks with discretion. This is a full-time, long-term role with strong benefits.

Qualifications

• Must demonstrate strong organizational habits and attention to detail.
• Ability to manage sensitive information with discretion.
• Comfort with routine, processes, and steady workflow.

Responsibilities

• Provide comprehensive administrative support to the CEO, including calendar management and email organization.
• Prepare, organize, and maintain all files and records for business and personal needs.
• Coordinate travel logistics across Maryland and Florida and prepare itineraries.
• Schedule meetings, create agendas, take notes, and ensure follow-ups.
• Manage personal errands and vendor relationships to maintain an organized home life.

Skills

Detail-oriented

Organized

Systematic

Patient

Discretion

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.

Coordinate complex travel, including:

• Booking and managing all domestic travel arrangements between Maryland and Florida, and occasional other destinations.
• Preparing detailed travel itineraries and packing lists, ensuring nothing is missed.
• Traveling with the CEO as needed to ensure seamless transitions and support.

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 depending on experience with a track to increase salary.
• Health Insurance (CareFirst) – 50% company-paid
• Dental & Vision Insurance available
• 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