Executive & Personal Assistant, Virtual Assistant

This is a fully remote position, open to applicants anywhere in the world.

📋 Description

• Oversee personal and professional email accounts for both principals.

• Monitor and prioritize multiple Gmail and Outlook/Office 365 inboxes.

• Prepare email drafts for review and approval.

• Manage inbound phone calls, screen callers, and track follow-ups.

• Take charge of both principals' personal and professional calendars.

• Arrange meetings across various businesses, teams, and time zones.

• Schedule, reschedule, and confirm meetings and appointments.

• Research, plan, and book intricate domestic and international travel.

• Organize flights, hotels, ground transportation, extended stays, furnished accommodations, and local services.

• Handle award travel utilizing points and miles.

• Coordinate group and family travel, including vacations, rentals, flights, cruises, charter events, and WeTravel arrangements.

• Address travel disruptions and itinerary changes in real-time.

• Manage restaurant reservations, appointments, events, experiences, household staff, and service providers.

• Research, compare, and evaluate vendors.

• Organize gifts, celebrations, special occasions, and personal errands.

• Collaborate with executive, operations, IT, and creative teams.

• Oversee tasks and operational activities using HighLevel CRM and shared tools.

• Monitor outstanding tasks and deadlines across multiple companies.

• Present well-researched options with their differences, advantages, disadvantages, costs, and recommendations.

• Research solutions independently before escalating issues.

• Document workflows and establish repeatable processes and standard operating procedures.

⛳️ Requirements

• At least 3 years of experience supporting executives, business owners, high-net-worth individuals, or families as an Executive Assistant, Personal Assistant, or Estate/Household Manager.

• Proven experience managing complex executive calendars and schedules.

• Strong background in handling domestic and international travel arrangements.

• Experience in booking intricate international itineraries.

• Solid understanding of points, miles, transfer partners, and travel rewards programs.

• Excellent written and verbal communication skills in English.

• Strong professional phone presence.

• Exceptional discretion, judgment, and confidentiality.

• Willingness and ability to sign an NDA and manage sensitive information.

• Strong problem-solving abilities and capacity to independently research solutions.

• Ability to anticipate needs and take initiative without waiting for direction.

• Outstanding organizational and time-management capabilities.

• Ability to juggle multiple priorities across two CEOs and various businesses.

• Keen attention to detail and commitment to follow-through.

• Ability to work during fixed U.S. Eastern business hours.

• Reliable high-speed internet and a professional, quiet workspace.

• Capability to work independently while maintaining consistent communication.

• Preferred: experience assisting high-net-worth individuals or families.

• Preferred: experience in family office settings.

• Preferred: background in providing international extended-travel executive support.

• Preferred: experience as a travel agent or in professional travel planning.

• Preferred: advanced knowledge of award travel and loyalty programs.

• Preferred: familiarity with luxury travel, fine dining, premium hotels, and high-end experiences.

• Preferred: experience in project management; certification is a plus.

• Preferred: experience with AI tools and workflow automation.

• Preferred: experience with Canva or other creative/design tools.

• Preferred: coordination of household staff and service providers.

• Preferred: experience supporting multiple businesses or business owners simultaneously.

• Proficiency with Gmail, Outlook, Microsoft Office 365, Google Calendar, Outlook Calendar, Microsoft Teams, HighLevel CRM, shared task-management tools, airline and hotel booking platforms, Seats.aero, AwardTool, Amex Membership Rewards, Capital One, airline loyalty programs, WeTravel, Google Workspace, Microsoft Office, AI productivity tools, workflow automation platforms, and Canva (preferred).

• 40 contracted hours per week, Monday through Friday.

• English language preference with Level A–B, native or near-native proficiency.

• Willingness to work as an independent contractor under a Master Services Agreement and Statement of Work.

🏝️ Benefits

• Competitive compensation rates.

• Weekly payment schedule.

• Various open positions available.

• Free training and upskilling opportunities.

• Ongoing support and guidance.

• A vibrant community always ready to assist you.