A serial entrepreneurial UHNW principal with a family office who also sits on multiple boards is seeking an exceptional Executive Personal Assistant to serve as a true “right hand”. This is not a traditional administrative role, but a relational, and trust-based partnership designed to amplify the principal’s’ effectiveness, personally and professionally. The ideal candidate has worked for a HNW busy principal, looking at their lives holistically with many moving parts. You will act as a stabilizing force, thoughtful gatekeeper, and intuitive collaborator, someone who understands not only what needs to be done, but how and when to do it to help take as much off the principal’s plate as possible.

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.
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• Base Salary, Discretionary Bonus, Comprehensive Healthcare