Executive Assistant

WHAT ARE WE LOOKING FOR?

We are looking for an office administrative assistant / personal assistant to the company's CEO, to work directly with the Chief of Staff. This hybrid role combines administrative, personal, and logistical responsibilities, working directly with the Chief of Staff to ensure the CEO's business and personal life run seamlessly. Duties will include the following :

• Running personal & office errands and completing personal shopping and gifting, as well as, high volume shipping
• Overseeing packaging and shipping of personal shopping items, including coordination and communication with the client and shipping company
• Booking and arranging travel, transport, and accommodation, including hotel bookings, personal preferences, and detailed rider requirements to ensure seamless accommodations
• Providing administrative support to corporate office and CEO, via instructions from Chief of Staff, and managing and prioritizing communication on behalf of the CEO — including email, calendar, calls, and messaging — acting as a thoughtful and effective gatekeeper when appropriate
• Assisting the Chief of Staff in overseeing the completion of house maintenance and other projects as they arise; communicate with contractors, vendors, etc.
• Scheduling personal, medical, business and other appointments
• Assisting with simple IT issues (phone settings, computer functions, etc.)
• Assist with property / villa rentals for our clients, including light property management, overseeing of house staff, and prepping homes for client arrivals
• Additional general administrative duties for the corporate office, as well as, Personal Assistant duties upon request with a constant need for overriding flexibility and desire to exceed all expectations
• Proactively anticipate needs before they arise; approach tasks with a forward-thinking, solution-oriented mindset
• Comfortable managing frequent ad-hoc requests across both personal and professional contexts — often with minimal notice or evolving expectations
• Coordinate high-touch gifting and VIP moments for clients or associates, including research, procurement, and white-glove delivery
• Maintain and regularly update inventories related to gifts, tech, household needs, and travel essentials
• Manage confidential information with the highest level of discretion and professionalism — including sensitive legal, financial, and medical matters
• Demonstrate strong intuition and the ability to read a room or situation to anticipate shifting needs and priorities
• Be diligent in documenting preferences, confirming details, and maintaining institutional knowledge for future reference
• Approach all responsibilities with a service-oriented mindset — whether executing complex travel or handling more routine personal tasks
• Able to support a high-performing, high-profile executive with professionalism, flexibility, and emotional intelligence

YOU MUST

Possess an understanding of high sense of urgency tasks and pay close attention to detail

Be able to work in a high-stress environment and work quickly and efficiently through assigned tasks

Have excellent organizational and problem-solving skills, with an "above and beyond" attitude

Have good written and spoken communication skills with the ability to work in an extremely fast-paced / multitasking environment

Set high standards for yourself and your work

Be self-motivated, proactive, and have an ability to think and work independently while managing multiple tasks

Be detail-oriented with meticulous organization, task management, and communication skills

Able to remain calm under pressure during hectic and stressful times

Own a car and be willing to run errands and coordinate tasks around town

Enjoy being around dogs and be able to assist with CEO's dog as needed (very pet-friendly environment)

WHO ARE YOU?

Background in Travel or Hospitality strongly preferred!

A true go-getter and "make it happen" kind of person

Think fast on your feet; able to multi-task under pressure

Proficient in both Mac and PC systems and programs including Microsoft Office Suite

Utmost discretion in all aspects of the job where integrity, accountability, and loyalty are paramount

Willingness to work long hours, overtime as needed and accessibility on weekends and evenings as needed

Real Estate License a plus!

This role may not be the right fit for candidates who :

• Prefer narrowly defined responsibilities or require frequent supervision
• Seek a traditional 9–5 environment with predictable routines
• Are uncomfortable adapting to rapidly changing priorities or high-performance expectations
• PLEASE, NO PHONE CALLS