Executive Assistant / Chief of Staff / Special Projects Manager

Job Description

Job Description : Executive Assistant / Chief of Staff / Special Projects Manager

About WHL / Company Profile

World Health Labs (Barbados) Inc is an innovative management company with operating companies in a variety of industries including healthcare.

WHL Barbados is looking for an ambitious EA / Chief of Staff / Special Projects Manager 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 a minimum of one (potentially multiple) PA(s) who are in-market where the CEO is located while primarily focussing on supporting in execution CEO’s personal matters as opposed to projection planning and business matters.

Role Details

Role Title

Executive Assistant / Chief of Staff / Special Projects Manager

Function

Corporate

Department

Executive Office

Type of Position

Full time

Location

The CEO would prefer to find an EA who travels with him to Como for ~6 months and Miami for ~4 months per year. The CEO may consider candidates who will either live in Miami year round or Como, Italy year round.

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 / Chief of Staff / Special Projects Manager will administer and manage many simultaneous work streams that require advanced organisational skills and a high level of job ownership and creativity. The successful candidate will provide a full scope of support to the CEO. Candidate success will be based on the ability to manage the chaos, reduce / eliminate the time the CEO must spend on any admin activities and add as much structure as possible.

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 potentially AirBnB / Property Management. If the CEO and the EA are not in the same timezone, the CEO will expect the EA to match his hours and be on call at all times.

• Only Candidates who are willing to travel 11 months of the year will be considered for this role

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

EA functions

Travel

Calendar

Short and long term accommodations

Screen requests of the CEO

Note taking at important meetings

Family Birthday reminders

Non-work (example health) appointment managing

Residency Management

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

Electronic and physical filing and records management

Liasing with PA(s) to ensure projects get executed; appropriate documents are sent to you. Potential management of PAs

Budgeting / oversight of department financial records

Following the CEOs email to understand the CEO’s evolving schedule without the CEO updating you

Other functions :

Filling in for PA roles from time to time which may include cleaning, cooking, etc

Building systems and processes so the department functions more favourably

Increasing revenue in AirBnBs and other rental properties. Property management

Planning, managing, oversight, potential execution of complex family trips with guests arriving from multiple countries

Managing insurance claims

Complex healthcare management including research on supplements, peptides, etc

Add structure and organization to unstructured / unorganized projects

Create scalable manuals and documentation

Must have experience managing others

Researching new topics and navigating bureaucracy in areas where you haven’t worked before

Hiring / Firing

Training

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

Reporting Structure

This role will report to the CEO. This role will be working as part of a developing team which may evolve.

Critical Accountabilities

Experience thriving in both virtual and physical settings

Experience extrapolating significant amounts of records / information and presenting them to the CEO in writing and verbally so that he can understand this information and make decisions in and as short amount of time as possible.

Consistently communicating with the CEO in an organized, concise fashion so that priorities are managed.

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

Attendance during business meetings, note taking and both documenting and following up on action items. Accurately record, update and distribute Meeting Minutes

Schedule all travel (flights (including shipping the bike / Hotel / Drivers) for the CEO. This includes financial analysis, rewards management and making predictions / taking action without direct  instruction from the CEO based on following the CEO’s email.

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. Longevity Management

The Principal is personally invested in longevity and has a number of resources that relies on supplements, peptides, training and nutrition. These resources are often evolving so frequent management is required.

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.

Requirements

Executive Support