Remote Executive Personal Assistant to Private Principal

Schedule: Full-Time | Remote with flexibility to travel to the Principal when necessary
Compensation: $65–$85 per hour, depending on experience

Benefits

• Two weeks paid vacation

• Five paid personal/sick days

• Paid major holidays

• $500 per month health and wellness stipend

• Mileage reimbursement for approved business-related driving

Position Overview

A private principal with multiple residences is seeking an experienced, highly organized Executive Personal Assistant to provide comprehensive administrative and personal support. The Principal spends much of his time between Las Vegas and Florida and travels frequently.

This is a remote position with the flexibility and availability to travel to the Principal when necessary.

The ideal candidate is exceptionally proactive, financially detail-oriented, discreet, technologically savvy, and comfortable working with a high degree of autonomy. The Principal is looking for someone who can learn his preferences, handle routine matters independently, and recognize when something requires his attention.

This person should be highly responsive during reasonable working hours and possess the judgment and confidence to execute without requiring constant direction or approval. A natural curiosity about technology and willingness to utilize modern tools, including AI, to improve efficiency and organization would be highly valued.

Primary Responsibilities

Executive & Personal Support

• Manage the Principal's calendar, appointments, scheduling, and reminders

• Coordinate personal and business-related appointments and commitments

• Maintain organized records, documents, and important information

• Track deadlines and proactively manage time-sensitive matters

• Manage correspondence and administrative tasks as needed

• Anticipate upcoming needs and follow through without requiring frequent direction

• Serve as a trusted point person for day-to-day administrative and personal matters

Financial & Administrative Management

• Track and manage bills and recurring financial obligations

• Monitor real estate tax bills and other property-related expenses

• Maintain accurate financial records and documentation

• Assist with banking-related administrative matters

• Prepare and initiate wire transfers and payments at the Principal's direction and in accordance with established authorization procedures

• Maintain organized records of payments, transactions, and important financial documents

• Track important financial and administrative deadlines

• Communicate and coordinate with accountants, financial professionals, attorneys, and other advisors as requested

Property & Real Estate Administration

• Assist with the administrative oversight of multiple private residences

• Maintain organized property records and important documentation

• Track property taxes, insurance, recurring expenses, and important deadlines

• Coordinate appointments and services related to the residences as needed

• Maintain communication with property-related vendors and professionals

• Help ensure property matters are handled regardless of the Principal's location

Technology & AI Tools

• Comfortably utilize modern technology and digital tools to improve organization, research, communication, and productivity

• Have working familiarity with large language models and AI platforms such as ChatGPT/OpenAI, Claude, Gemini, Grok, or similar tools

• Use AI tools appropriately for research, drafting, organization, summarization, and administrative efficiencies

• Stay current with emerging technology that may help streamline the Principal's personal and administrative needs

• Exercise appropriate discretion when using technology or AI tools with confidential or sensitive information

Advanced AI expertise is not required; however, practical experience using AI tools and a genuine comfort with emerging technology are strongly preferred.

Organization & Special Projects

• Create efficient systems for records, documents, schedules, and recurring responsibilities

• Research and coordinate projects on behalf of the Principal

• Handle confidential and sensitive information with exceptional discretion

• Assist with special projects and changing priorities

• Follow projects through from initial request to completion

• Identify potential issues and proactively develop solutions

• Travel to the Principal as necessary to provide in-person support or assist with specific projects

Ideal Candidate

The ideal candidate is an experienced Executive Assistant, Executive Personal Assistant, or Family Office professional who is comfortable supporting a private principal with significant financial, administrative, and personal responsibilities.

This individual should be confident making appropriate day-to-day decisions independently rather than seeking approval for every detail. At the same time, they must have excellent judgment regarding matters that require the Principal's involvement.

The right person will be responsive, resourceful, highly organized, trustworthy, technologically current, and naturally proactive. They should be adaptable, comfortable learning new platforms and systems, and interested in utilizing modern technology to work more efficiently.

They should enjoy creating order, staying several steps ahead, and making a busy Principal's life easier.

Requirements

• Previous Executive Assistant, Executive Personal Assistant, Family Office, or comparable high-level private service experience

• Experience handling confidential financial and personal information

• Strong financial and administrative organizational skills

• Exceptional discretion and sound judgment

• Excellent written and verbal communication skills

• Highly organized with exceptional attention to detail

• Comfortable working independently with minimal supervision

• Tech-savvy and comfortable managing information digitally

• Working familiarity with AI and large language model platforms such as ChatGPT/OpenAI, Claude, Gemini, Grok, or similar tools preferred

• Comfortable learning and adopting new technology and digital platforms

• Ability to prioritize and manage multiple responsibilities simultaneously

• Responsive and accessible by text during agreed-upon working hours

• Ability and willingness to travel to the Principal when necessary

• Ability to maintain strict confidentiality

• Professional references and background screening required