Executive Assistant Winemaker Jobs in Boca Raton, FL

We are seeking an experienced, polished, and highly intuitive Personal & Lifestyle Assistant to become a trusted extension of an Ultra High Net Worth Principal. This is a true principal support role—not an estate or house management position.

The successful candidate will provide seamless lifestyle support across the principal's residences and while traveling, ensuring every aspect of their day-to-day life is thoughtfully organized and effortlessly executed.

This role is centered around anticipating needs, delivering exceptional service, and creating an effortless lifestyle experience with the highest level of discretion and professionalism.

Working closely alongside the Executive Assistant team and household staff, this individual will focus on supporting the principal—not managing the household. The ideal candidate thrives in dynamic environments, is exceptionally adaptable, and enjoys providing concierge-level service wherever the principal may be.

Travel is an essential component of this position. The successful candidate should expect to travel approximately 12–16 weeks per year, sometimes for extended periods, providing the same level of thoughtful support whether at a private residence, aboard private transportation, or abroad.

Household & Lifestyle Coordination

• Assist with the daily rhythm of the household, ensuring all activities are coordinated smoothly around the principal’s schedule
• Serve as a liaison between household staff and the administrative team to ensure seamless communication and execution
• Serve as a liaison with household staff and senior housekeepers across all properties and regions to ensure preferences, inventory, service standards, and household readiness are consistently maintained
• Work closely with the Executive Housekeeper to maintain exceptional household operations and service standards
• Help With final walkthroughs of properties prior to departure to ensure all spaces are secure and no personal belongings are left behind

• Comfortably operate within a highly collaborative administrative and household team environment where flexibility, communication, and shared support are essential
  

Personal Concierge Support

• Manage personal errands, specialty purchases, collections, and deliveries with efficiency and discretion
• Coordinate appointments, events, reservations, and concierge requests as needed
• Handle high-end shopping and sourcing for apparel, shoes, gifts, home items, liquor, yacht supplies, and specialty requests
• Research and present thoughtful, high-quality options and recommendations aligned with the principal’s preferences
• Maintain strong relationships with preferred restaurants, vendors, and luxury service providers globally
• Coordinate grooming, tailoring, and alteration appointments
• Maintain working knowledge of luxury apparel, designer brands, fabrics, garment care, and wardrobe maintenance to support high-end shopping, tailoring, packing, and presentation needs
• Ensure all confirmed personal bookings and logistics are communicated to the Executive Assistant team for calendar integration and scheduling continuity
• Anticipate day-to-day needs before they are expressed, ensuring personal items, consumables, and preferences are consistently prepared and maintained
• Provide thoughtful personal assistance and lifestyle support to the principal, partner, and family members as needed while traveling or in residence
• Assist with hospitality support and event coordination as needed

Travel & Departure Logistics

• Support travel preparation and departure-day logistics with a calm, organized, and solutions-oriented presence
• Travel alongside the principal as needed to provide seamless personal assistance, hospitality support, and travel coordination across changing locations and schedules
• Organize, label, tag, and track luggage for travel
• Ensure all personal effects are accounted for prior to departure, including sports equipment, jewelry, accessories, golf clubs, fishing gear, and travel essentials
• Coordinate airport transfers and transportation logistics, including transportation to and from private aviation terminals and FBOs
• Maintain awareness of the location and transport of personal belongings across all properties
• Be willing and available to travel, sometimes on short notice, including to properties in the Dominican Republic, Lake Geneva, and London
• Provide calendar management and travel logistics support as needed in partnership with the Executive Assistant team

Inventory & Property Readiness

• Maintain working knowledge of the location and organization of the principal’s personal belongings across all properties
• Coordinate with the Executive Assistant team and household staff to maintain accurate inventory systems and overall property readiness
• Assist in maintaining formal inventory systems for personal items, travel essentials, and household assets
• Manage wine inventory and in-home bar organization according to the principal’s preferences
• Coordinate wine selection and cellar management alongside the Executive Assistant team

Qualifications

• Prior experience directly supporting an Ultra High Net Worth individual or family is required.

• Experience traveling with and supporting a principal in a highly personalized service capacity is strongly preferred.

• Exceptional organizational skills with meticulous attention to detail.

• Ability to anticipate needs and think several steps ahead.

• Comfortable working in fast-paced, ever-changing environments.

• Outstanding communication and interpersonal skills.

• Calm, polished, and solutions-oriented under pressure.

• Strong discretion and ability to manage confidential information.

• Comfortable with frequent domestic and international travel.

• Valid passport with the ability to travel internationally.

• Spanish language skills are a plus.

Ideal Background
We recognize exceptional candidates come from a variety of luxury service environments. We are particularly interested in professionals with backgrounds such as:

• Personal or Lifestyle Assistant

• Traveling Executive Assistant

• Butler

• Interior Yacht Steward or Stewardess

• Luxury Hospitality or VIP Guest Services

• Wardrobe Manager or Valet

• Private Aviation Concierge

• Family Office Lifestyle Support

Candidates whose careers have focused on direct principal support, luxury hospitality, and personalized service are strongly preferred over traditional estate or property management backgrounds.

The Ideal Candidate
You are naturally service-oriented and genuinely enjoy making someone else's life run effortlessly. You notice the details others miss, anticipate needs before they're expressed, and take pride in delivering exceptional support with warmth, discretion, and professionalism.

You thrive in changing environments, enjoy traveling, and are energized by variety rather than routine. You are equally comfortable coordinating a last-minute international trip, preparing a wardrobe for travel, sourcing a hard-to-find item, or quietly ensuring every detail has been considered before the principal even asks.

Above all, you understand that true luxury service is proactive, personalized, and seamless—and you take pride in being the person who makes that happen.