Personal Assistant

We are seeking a highly organized, proactive, and personable Personal Assistant to provide day-to-day support to a private individual based in Winter Park, Florida. The position can begin on a part-time basis, with the opportunity to evolve as the relationship and needs develop. This is a particularly appealing opportunity for someone looking for a flexible role that combines traditional personal assistance with a highly personable, relationship-driven working environment. The right individual will become a trusted and valued presence in the client’s day-to-day life — someone who keeps things organized and running smoothly, but is also warm, engaging, intuitive, and genuinely enjoys building a strong working relationship with the person they support. This is a hybrid/remote position; however, candidates must live locally in the Winter Park/Greater Orlando area and be readily available for in-person support as needed. Key Responsibilities Calendar, Appointments & Correspondence Manage personal and professional calendars, appointments, reminders, important dates, and deadlines. Manage email and correspondence, draft routine responses, organize mail, and flag matters requiring attention. Coordinate medical, dental, grooming, and other personal appointments. Travel & Personal Organization Coordinate flights, hotels, transportation, restaurants, activities, and detailed travel itineraries. Organize travel documents, passports, confirmations, luggage, packing/unpacking, and ensure travel essentials are stocked and ready. Maintain organized digital and physical files for important personal and travel documents. Home & Lifestyle Management Coordinate household staff, vendors, maintenance, repairs, deliveries, contractors, and service appointments. Handle personal errands, returns/exchanges, prescriptions, meal delivery services, and other day-to-day needs. Assist with personal shopping, wardrobe needs, dry cleaning, alterations, and preparation for trips and events. Vehicle Management Coordinate vehicle servicing, maintenance, detailing, and other automotive needs. Special Occasions & Gifting Keep track of birthdays, anniversaries, and other important occasions. Coordinate gifts, flowers, cards, and deliveries throughout the year. Ideal Candidate Highly organized, intelligent, resourceful, and proactive, with excellent follow-through. Warm, personable, engaging, and someone who naturally builds strong relationships. Strong written and verbal communication skills with a polished, professional demeanor. Discreet, trustworthy, and comfortable handling confidential and personal matters. Tech-savvy and comfortable managing calendars, email, travel, digital files, and online purchases. Flexible and willing to assist with a variety of needs as they arise. Prior experience supporting a private individual, family, family office, or UHNW household is preferred. Comfortable supporting a principal who is actively involved in philanthropic, charitable, and community organizations. Work Arrangement This is a hybrid/remote role based in Winter Park, Florida and can begin on a part-time basis. While many responsibilities can be handled remotely, the Personal Assistant must be local and available to provide hands-on support in Winter Park as needed. There is flexibility around how the position is structured initially, making this an excellent opportunity for the right individual to establish a strong working relationship with the principal and potentially grow the role over time. #J-18808-Ljbffr