Executive Assistant

Job Description

Job Description : Executive Assistant and Special Projects Manager

About WHL / Company Profile

World Health Labs (Barbados) Inc is an international management solutions provider under contract to provide healthcare services.  In addition, the management company operates in additional industries and is in the process of expanding into additional industries.

WHL Barbados is looking for an ambitious EA who is accustomed to unconventional work hours in a high paced environment. The CEO works 7 days per week - typically across each of Central European Time and Eastern Standard Time for six months per year. (The CEO spends his time between Italy (~6 months per year) Miami (~4 months per year) and Canada / other (~2 months per year).  The CEO is quite demanding, expects the EA to match his timezone as much as possible and focus on reducing the amount of time the CEO must spend working on or thinking about administrative tasks.This role is for an EA who is at the peak of their powers. This EA will manage multiple PAs who are in-market where the CEO is located while primarily focusing on the CEO’s personal matters vs business matters.

Role Details

Role Title

Executive Assistant and Special Projects Manager

Function

Corporate

Department

Executive Office

Type of Position

Full time employment or Contract

Location

Virtual / Work from Anywhere (Must be flexible to work over multiple time zones).

Candidates who are based in Milan, Como area or other parts of Europe and can be onsite while the Principal is in Italy or who are based in Miami area may be prioritized.

Candidates who are willing to relocate throughout the year and spend ~6 months of the year in Italy and ~4 months of the year in Miami while the Principal is in-market may be prioritized.

Role Summary

In this challenging role, the Executive Assistant and Special Projects Manager will administer and manage multiple simultaneous work streams that require advanced organisational skills and a high level of job ownership. The successful candidate will provide a full scope of support to the CEO.

Support for the CEO’s demanding schedule will require unique requests and work across multiple time zones,  depending on travel (Europe, US and Canada), requiring non-traditional working hours. The role includes managing a team of in-market Personal Assistants and AirBnB / Property Management.

Roles and Responsibilities may include but are not limited to the following :

Booking short and long term accommodations and / or sourcing leasing out owned real estate

Subcontracting tasks to drivers, personal assistants or other support staff in other markets

Managing the CEOs medical records, days in each country, family commitments and other important documents

Keeping the CEO organized

Financial and qualitative negotiations

Financial analysis and record keeping

Hiring / firing

Documenting processes

Holding daily calls with PAs to keep them organized

Purchasing groceries, clothing, fitness accessories, etc on behalf of the CEO

Sourcing new PAs

Training, supporting, managing and developing PAs to be the best they can be

Constant improvement and optimization : always looking for new ways to make the Executive Office work.

Reporting Structure

This role will report to the International Finance Executive, Chief of Staff and / or the  CEO.

This role will be working as part of a developing team which may evolve.

Critical Accountabilities

Coordinating and sourcing temporary PA support when the CEO is travelling and / or nannies when family is visiting.

Attendance during business meetings, produce reports and client facing presentations. Accurately record, update and distribute Meeting Minutes

Schedule all travel (flights (including shipping the bike / Hotel / Drivers) for the CEO

Managing personal medical records for the CEO in various International locations

Managing personal correspondence and real estate for the CEO

Update and Maintain internal database and contacts to ensure accuracy

Extensive vendor sourcing / management and tracking of invoices

Proactive anticipation of CEO’s needs

Track and Maintain various forms and receipts

Track and submit expenses for reimbursement and manage evolving policies for PA expense submission

Daily updating of Executive Office Processes, Policies, Key Contacts, etc

Keeping important information and documents organised electronically

Maintaining a high degree of discretion and confidentiality

Performs miscellaneous job-related duties as assigned

Potentially sourcing and scheduling business development opportunities

Managing the PA team. The PA Team’s Key Responsibilities are as follows :

1. Wellness & Lifestyle Management

Meal Preparation & Nutrition : The Principal follows a strict meal plan which includes weighing food, preparing nutrition needs for on-bike / during workouts and other intricacies. Most meals are prepared 24 hours in advance with the exception of breakfast and other unique circumstances. .

Maintain a clean and organized kitchen, ensuring all ingredients and supplies are stocked and groceries available. Some grocery shopping typically is required 5+ days per week due to having fresh ingredients / evolving needs. Some meals / ingredients will be prepared using batching to reduce time.

Bike Maintenance & Gear Prep : Support daily bike rides by cleaning and maintaining Principal’s bicycle and potentially taking the bike to the mechanic and / or procuring new parts, ensuring it’s in top condition. Keep all cycling gear (helmets, shoes, hydration, etc.) clean by hand washing and well organized to reduce the Principal’s time looking for gear and ready for use. There is a component to the job to prepare on-bike nutrition. In some cases the PA may be in the car supporting the Principal’s cycling workouts for safety, mechanical and nutritional reasons.

2. Health record management - principal has healthcare providers in 4+ countries. Managing health records to ensure information isn’t fragmented but is consolidated is a must

other health support - the Principal has regular physio, massage, chiro, etc appointments. The PA will be responsible for sourcing, negotiating, managing, booking, ensuring bills are paid, etc

& errands

Personal & Transportation Support

Provide personal transportation for errands, appointments, and small weekend trips.

Grocery and personal shopping , ensuring all purchases align with preferences and needs.

Track and receive deliveries and online purchases , ensuring all packages arrive as expected.

Run miscellaneous personal errands efficiently and proactively.

3. Guest Management & Hospitality

Prepare the home for guest visits , ensuring a clean, welcoming, and organized environment.

Greet and assist guests, offering refreshments and ensuring they are comfortable.

Coordinate accommodations or itineraries for out-of-town guests when needed.

Handle any special requests or hospitality-related needs, maintaining professionalism and discretion .

4. Schedule & Logistics Coordination

Calendar Management : Work with logistics teams and executives across Principal’s companies to ensure his calendar is accurate and up to date. Generally speaking, the Principal books all of his own commitments and does not like to outsource the decisions of when to book appointments, however, all appointments which the Principal asks you to book (flights, doctor, physio, cycling, other, etc) will need to immediately be updated in the Principal’s calendar to avoid double booking.

Schedule and confirm appointments, personal engagements, and business meetings.

Proactively identify and resolve scheduling conflicts to maintain a smooth daily routine.

5. Household Maintenance & Vendor Management

Perform regular household cleaning and upkeep , ensuring the home is well-maintained at all times.

Handle minor maintenance tasks or coordinate with landlords, repair services, and vendors when needed.

Ensure all household supplies are stocked and organized.

Supervise and manage any scheduled home maintenance, cleaning services, or special projects.

Property Research, Scouting and Sourcing

6. Digital & Administrative Tasks

Track ongoing projects and assigned tasks , ensuring they are completed efficiently.

Requirements

Executive Support