Executive Personal Assistant, UHNW Principal Family Office, Naples

And Simple ApS; Naples (FL); Hybrid; USD 120,000 - 180,000; Full time

Benefits offered by this job

Comprehensive Healthcare

Discretionary Bonus

Job summary

And Simple ApS is seeking an Executive Personal Assistant to support a UHNW entrepreneurial principal in Naples, FL, in a hybrid arrangement. The role requires strategic thinking, discretion, and polished communication as you manage calendars, travel, and high-trust tasks.

You will draft correspondence, optimize processes with AI, coordinate property management, and oversee complex schedules with meticulous attention to detail. Bachelor's degree and 5+ years in similar environments are expected.

Qualifications

• Bachelor’s degree required.
• 5+ years supporting a high-net-worth principal or family office.
• Strong written and verbal communication skills.
• Proficient with Microsoft Office; comfortable using AI to improve processes.
• Ability to run projects from start to finish and handle sensitive information.

Responsibilities

• Manage calendar, travel, meetings, and information flow for the principal.
• Draft correspondence and plan reservations for meals and events.
• Coordinate domestic and international travel with detailed itineraries.
• Oversee multiple properties and household staff in Naples.
• Handle personal tasks, errands, registrations, and expenses.
• Lead ad hoc projects with discretion and strategic thinking.

Skills

Communication

Project management

Discretion

Emotional intelligence

Organizational skills

Ambiguity handling

High touch service

Microsoft Office

AI literacy

Multitasking

Education

Bachelor’s degree

Tools

Microsoft Office Suite

AI tools

Job description

Right-hand EPA to a serial entrepreneur principal with a family office: calendar, domestic and international travel, meeting prep and holistic life support.

Executive Personal Assistant to UHNW Entrepreneurial Principal/Family Office, Naples Florida, Hybrid

About the Job:

Trusted Partner & Strategic Support

Act as a thought partner and sounding board, offering perspective, feedback, and quiet counsel when needed.

Anticipate needs and proactively solve problems with little intervention.

Prepare the principal for meetings and conversations with context and background information.

Time, Energy & Focus Management

Manage a complex and fluid calendar with an understanding of priorities and relationships, personally and professionally

Protect the principal’s time by thoughtfully filtering requests and creating space for strategic thinking.

Coordinate domestic and international travel, personal and professional including detailed itineraries.

Communication & Relationship Management

Serve as a warm liaison between the principal, with internal and external stakeholders.

Draft and manage correspondence on the CEO’s behalf, ensuring tone, values, and intent are consistently reflected.

Prioritize emails/inbox and craft responses on his behalf

Plan reservations for lunches/dinners

Manage multiple properties and the household staff in Naples

Handle personal work, run errands, car and boat registrations, insurance, expenses

Other ad hoc projects, as needed.

Information Flow & Follow-Through

Distill information into clear, actionable insights.

Track commitments, decisions, and follow-ups to ensure accountability.

About You

Bachelor’s degree required.

At least 5 years of experience supporting a HNW principal preferably in the finance/family office space

Strong written and verbal communication skills

High proficiency with Microsoft Office Suite; daily experience with general AI and an interest in improving processes using AI

Ability to run projects from start to finish

Experience managing multiple properties a PLUS

Handle highly sensitive information with absolute discretion.

High emotional intelligence and sound judgement.

You thrive in ambiguity and are energized by anticipating needs rather than reacting to them.

You are highly organized, detail-oriented, and capable of managing multiple priorities personally and professionally.

You communicate with warmth, clarity, and confidence You bring polish and presence, while remaining grounded and approachable with a “high touch” service mentality.

Base Salary, Discretionary Bonus, Comprehensive Healthcare