Executive Personal Assistant with Flexiblity

A New York City-based family seeks an exceptional full-time Personal Assistant to provide high-touch support across family logistics, complex travel, children's schedules, household staff, and four residences. The role will be employed through the family's business and based between a Midtown office and the family's Upper East Side townhouse, while reporting primarily to the principals. This is a high-expectation role requiring a 24/7 service mentality, including responsiveness during travel, evenings, and weekends when needed. The ideal candidate is energetic, warm, highly intelligent, and proactive; anticipates what will suit the family; communicates clearly; and always has plans B and C ready. The successful hire will inherit strong existing systems and be expected to elevate them rather than rebuild them unnecessarily. Responsibilities include, but are not limited to: Provide comprehensive personal and family support, taking ownership of requests through completion Manage schedules and logistics for three children, including online schooling and a competitive tennis circuit Coordinate highly detailed commercial and private travel, exact preferences, points, pricing, and contingencies Open and prepare residences before family arrivals and ensure every property is fully ready Provide administrative oversight of four residences, including vendors, maintenance, inventories, and projects Coordinate a lean household team consisting of a full-time Housekeeper, live-in Nanny, and Driver Work fluidly between the family office and Upper East Side townhouse while maintaining seamless communication Maintain and elevate established Notion systems covering history, travel, vendors, residences, and art Respond promptly to requests, acknowledge communications, and remain available during off-hours and travel Anticipate needs, research options, secure value, and keep plans B and C ready for changing circumstances Requirements: Legally able to work within the United States Significant experience as a Personal Assistant supporting a private family or high-net-worth principals Strong New York City experience and comfort working in both a private home and finance-oriented office Exceptional complex-travel planning across commercial and private aviation, including points and value analysis Experience coordinating multiple residences, household staff, vendors, and property-readiness projects Highly capable managing multiple children's schedules, education, activities, and travel logistics Technologically proficient in a Mac-based environment and comfortable using Notion and shared systems Energetic, charismatic, warm, wholesome, and genuinely comfortable interacting with children Highly intelligent and proactive, with strong judgment and a solutions-oriented approach beyond box-checking Excellent communicator who acknowledges requests promptly and provides clear, concise updates Discreet, resilient, organized, and able to meet exacting standards while building lasting trust Schedule: Monday through Friday, 8:30 AM - 6:00 PM, with evening, weekend, and travel responsiveness as needed. Location(s): New York City; based between a Midtown office and Upper East Side townhouse, with travel as needed Benefits: Comprehensive, fully employer-paid benefits package; phone and computer provided #J-18808-Ljbffr Gilder Search Group