Executive Assistant- Remote

Private Principal / Fully Remote / Written Communication Location: Fully remote; open to candidates in any location

Schedule: Full−time, Monday to Friday,8:00 a.m. to 4:00 p.m. Atlantic Standard Time (AST)

Compensation: $___________ annually, commensurate with experience

Reports To: The Principal and the Executive Chief of Staff

Position Summary

Private Staff Group is conducting a confidential search on behalf of a private principal based in the Caribbean for a senior Executive Personal Assistant. This is a full-time, fully remote position that offers the flexibility to work from anywhere while providing hands‑on personal support directly to the Principal. The assistant receives tasks from the Principal and sees each one through to completion.

This is a unique role: all communication is conducted in writing, primarily via Telegram. The assistant will often receive tasks with limited information or direction and is trusted to independently find the best way to complete them, without the need for oversight or lengthy explanation. Discretion, privacy, and cybersecurity are paramount in every aspect of this role.

The Executive Chief of Staff leads staffing, property, legal, and household management, and oversees the assistant’s onboarding and administration. The assistant focuses on the Principal’s personal tasks.

Communication

The Principal communicates in writing, primarily via ______, and values short, clear updates throughout the day. The Executive Chief of Staff serves as the point of contact for any matters that require a phone call. Strong written communication is essential, and candidates who can convey a great deal in few words will thrive in this position.

Key Responsibilities

• Personal Purchasing: Sourcing and purchasing personal items, including international shipping and delivery logistics.
• Appointments and Bookings: Scheduling and confirming in-home appointments, services, and reservations, with clear written instructions.
• Personal Administration: Managing forms, applications, and personal documentation with agencies and institutions.
• Signatures: Preparing documents for e‑signature and coordinating notary services.
• Research and Recommendations: Gathering comparable quotes and presenting options with a clear recommendation.
• Follow-Through: Following up with vendors, providers, and deliveries until every task is complete.
• Daily Updates: Providing a brief written update each workday on completed items, progress, and next steps.
• Security and Confidentiality: Maintaining secure, organized records and handling all personal information with strict confidentiality and sound security practices.

Qualifications

• Education is highly valued for this role. An undergraduate degree is required , and a graduate degree or additional advanced education is strongly preferred.
• Eight to ten years of experience in the senior executive or personal assistant space, or in other private service sectors. Experience supporting ultra-high-net-worth principals or working within a private household is an asset, but not required.
• A history of long tenures with previous principals or employers, demonstrating loyalty, stability and trusted long-term relationships.
• A proven record of the highest level of privacy, discretion and confidentiality.
• A strong understanding of data privacy and cybersecurity best practices; familiarity with AI tools and AI privacy is an asset.
• Demonstrated success working remotely and independently.
• Comfortable with Telegram, secure email, e‑signature platforms, and shared documents.
• Sophisticated written English that is clear and concise. Spanish is a plus.
• Ability to work reliably on Atlantic Standard Time hours, with slight flexibility during the week as needed.

Character Profile

• Problem Solver: Resourceful and solution-oriented, with a talent for thinking outside the box.
• Sound Judgment: Anticipates the downstream impact of a task and raises it with the right person.
• Independent: Thrives when given a task with limited direction and takes it through to completion.
• Clear Communicator: Asks precise, well‑considered questions when something is unclear.
• Transparent: Provides honest, transparent updates, including alternatives when a task cannot be completed as planned.
• Absolute Discretion: Takes initiative while knowing when to seek approval.
• Proactive: Contributes from the very first week.
• Concise: Communicates in short, clear messages, favoring brevity over lengthy explanation.
• Results-driven: Delivers results and is trusted to choose their own methods without needing oversight.