CPT-11387 Executive & Personal Assistant Virtual Assistant

20four7VA is seeking offshore independent contractors to deliver remote services to clients worldwide, with a primary focus on developed markets such as the United States, the United Kingdom, Canada, and Australia.

The company is a family-run group of businesses operating across HR outsourcing, IT hardware distribution, software development, aviation, and investments.

The company is seeking a highly organized, discreet, proactive, and experienced Executive & Personal Assistant to support two principals who are a husband-and-wife team and both CEOs. Each principal manages multiple companies and frequently travels internationally for extended periods throughout the year.

This is a true right-hand support role covering both professional and personal responsibilities. The VA will manage calendars, inboxes, travel arrangements, communications, household logistics, and day-to-day coordination across multiple areas of the principals' lives.

The ideal candidate must be exceptionally trustworthy, detail-oriented, resourceful, and capable of anticipating needs before being asked. The candidate should be comfortable taking ownership of problems from start to finish and making sound decisions independently.

Discretion and confidentiality are essential, as the role involves sensitive business, financial, travel, household, and personal information.

The objective of each engagement is to assist the client in improving business efficiency, enhancing service delivery, or supporting operational functions through high-quality, task-specific services rendered by a qualified contractor.

Contractors will be required to provide services that align with the following client tasks:

• Manage personal and professional email accounts for both principals.
• Monitor multiple Gmail and Outlook/Office 365 inboxes.
• Triage incoming emails and aggressively filter information based on priority.
• Determine which messages require the principals' attention and handle, delegate, or route others appropriately.
• Draft email responses for review and approval before sending on behalf of the principals.
• Monitor and manage inbound phone calls.
• Screen callers and determine the appropriate follow-up or escalation.
• Maintain accurate follow-up records and ensure outstanding matters are addressed.
• Protect sensitive business, financial, and personal information at all times.

• Own and manage both principals' personal and professional calendars.
• Coordinate meetings across multiple businesses, teams, and time zones.
• Manage Google Calendar and Outlook calendars.
• Schedule, reschedule, and confirm meetings and appointments.
• Resolve scheduling conflicts proactively.
• Build appropriate buffers between meetings and activities.
• Ensure the principals have complete and accurate information before meetings and appointments.
• Protect the principals' time by prioritizing important commitments and minimizing unnecessary interruptions.

• Research, plan, and book complex domestic and international travel.
• Arrange:
  • Flights
  • Hotels
  • Ground transportation
  • Extended stays
  • Furnished accommodations
  • Local services
• Coordinate travel across multiple countries and time zones.
• Arrange month-long or extended international stays.
• Manage award travel using points and miles.
• Research and book award flights using:
  • Amex Membership Rewards
  • Capital One
  • Airline loyalty programs
  • Seats.aero
  • AwardTool
• Track points balances, elite statuses, airline benefits, and credit card benefits.
• Evaluate available redemption options and recommend the best travel solution.
• Coordinate group and family travel, including:
  • Multi-family vacations
  • Large vacation rentals
  • Group flights
  • Cruises
  • Charter events
  • WeTravel arrangements
• Manage logistics associated with establishing a temporary home base during extended international stays.
• Handle travel disruptions in real time, including:
  • Cancelled flights
  • Flight changes
  • Hotel issues
  • Transportation changes
  • Last-minute itinerary adjustments
• Take ownership of travel-related problems and resolve them without unnecessary escalation.

• Manage restaurant reservations, appointments, events, and experiences.
• Research and arrange premium or specialized services as needed.
• Coordinate household staff and recurring service providers.
• Manage relationships with:
  • Housekeepers
  • Private chefs / meal-prep providers
  • Handymen
  • Electricians
  • Plumbers
  • Dry cleaners
  • Automotive service providers
  • Other household vendors
• Research, compare, and vet service providers when new needs arise.
• Coordinate gifts, celebrations, special occasions, and personal errands.
• Maintain organized records of trusted vendors and service providers.
• Keep track of personal preferences, household information, and recurring arrangements.
• Ensure consistent quality and service across recurring household needs.

• Work closely with the principals' existing executive, operations, IT, and creative teams.
• Communicate and coordinate through Microsoft Teams and other approved systems.
• Manage tasks, follow-ups, and operational activities through HighLevel CRM and shared tools.
• Monitor outstanding tasks and ensure deadlines are met.
• Coordinate information between multiple companies and internal teams.
• When presenting decisions or options to the principals, provide 2–3 well-researched choices, including:
  • Key differences
  • Advantages and disadvantages
  • Relevant costs or considerations
  • Recommended option
• Research solutions independently before escalating issues.
• Document recurring workflows and develop repeatable processes.
• Turn routine tasks into organized systems and standard operating procedures.

Each engagement is based on a defined scope of work and is governed by an independent contractor agreement. Services must be performed professionally, with adherence to any timelines, guidelines, and deliverables agreed upon in writing.

The Contractor must demonstrate proficiency in the following, depending on the Client’s requirements:

• Minimum of 3 years of experience supporting executives, business owners, high-net-worth individuals, or families as an Executive Assistant, Personal Assistant, or Estate/Household Manager.
• Demonstrated experience managing complex executive calendars and schedules.
• Strong experience handling domestic and international travel arrangements.
• Experience booking complex international itineraries.
• Hands-on experience with airline loyalty programs and award travel is highly preferred.
• Strong understanding of points, miles, transfer partners, and travel rewards programs.
• Excellent written and spoken English communication skills.
• Strong professional phone presence.
• Exceptional discretion, judgment, and confidentiality.
• Willingness and ability to sign an NDA and handle sensitive information.
• Strong problem-solving skills and the ability to independently research solutions.
• Ability to anticipate needs and take initiative without waiting for instructions.
• Exceptional organizational and time-management skills.
• Ability to manage multiple priorities across two busy CEOs and multiple businesses.
• Strong attention to detail and follow-through.
• Ability to work fixed U.S. Eastern business hours.
• Reliable high-speed internet and a professional, quiet work environment.
• Ability to work independently while maintaining consistent communication with the principals and internal team.

• Experience supporting high-net-worth individuals or families.
• Experience working in a family office environment.
• Experience supporting executives who travel internationally for extended periods.
• Travel agent or professional travel planning background.
• Advanced knowledge of award travel and loyalty programs.
• Familiarity with luxury travel, fine dining, premium hotels, and high-end experiences.
• Experience with project management.
• Project management certification is a plus.
• Experience with AI tools and workflow automation.
• Canva or other creative/design experience.
• Experience coordinating household staff and service providers.
• Experience supporting multiple businesses or business owners simultaneously.

• REQUIRED SERVICE: Business Support
• REQUESTED EXPERIENCE TIER LEVEL: Junior, Senior, and Advanced Level
• Contracted Hours per Week: 40 hours/week
• Daily Working Time: U.S. Business Hours – Fixed Schedule (TBD)
• Scheduled Working Days: Monday-Friday
• REPORTING TO/POC: To Be Determined
• Number of VAs: 1
• GENDER PREFERENCE: None
• LANGUAGES SPOKEN/PREFERENCE: English
• ACCENT PREFERENCE: Level A–B (Native or Near-Native English Proficiency)
• REGION PREFERENCES: Any

• Contracted Hours per Week: 40 Hours
• Scheduled Working Days: Monday through Friday (unless otherwise mutually agreed in writing)
• Daily Working Time: U.S. Business Hours – Fixed Schedule (TBD)

Note: The Company will make reasonable efforts to align the Assigned VA’s schedule with the Client’s preferred hours as set forth above. However, availability may vary based on time zones, capacity, and the contracted hours set in this SOW. Any changes must be mutually agreed to in writing through a revised SOW.

• Contractors will operate under a Master Services Agreement and a Statement of Work
• This is not an offer of employment; contractors are not employees of 20four7VA or any client
• All compensation is processed through 20four7VA according to the terms of the engagement