A highly successful entrepreneur, real estate owner, and trusted professional is seeking an exceptional Personal Assistant / Estate & Household Manager to serve as a trusted right hand in both personal and business matters. This is a unique opportunity for a highly organized, resourceful, and proactive professional who thrives in a fast-paced, ever-changing environment. The successful candidate will oversee the day-to-day management of multiple residences, coordinate personal and business affairs, manage household operations, and ensure every detail is handled with professionalism, discretion, and efficiency. This role extends far beyond traditional administrative support. The ideal candidate is someone who anticipates needs, solves problems before they arise, and is comfortable managing everything from executive scheduling and real estate projects to household staff, vendors, travel logistics, charitable initiatives, and special projects. No task is too small or too large. The successful candidate will become a trusted partner responsible for helping manage a demanding lifestyle while maintaining the highest level of confidentiality, organization, and service. Responsibilities: Executive & Personal Support Manage complex calendars, appointments, meetings, and travel arrangements Coordinate personal and business scheduling across multiple priorities Monitor and manage email correspondence and important communications Prepare reports, spreadsheets, presentations, and project updates Conduct research and proactively solve problems Estate & Household Management Oversee the day-to-day operations of multiple residences Coordinate architects, designers, contractors, vendors, and service providers Supervise household staff, including housekeepers and additional support personnel Manage household inventories, maintenance schedules, and ongoing projects Coordinate furniture purchases, deliveries, installations, and home organization Ensure each residence operates efficiently and according to owner preferences Project & Lifestyle Management Coordinate real estate-related projects and renovations Manage charitable and philanthropic initiatives Schedule personal appointments, errands, and lifestyle services Track action items and ensure timely completion of ongoing projects Build and maintain relationships with vendors, contractors, and trusted service providers Handle confidential personal and business matters with absolute discretion Provide occasional evening and weekend support as needed Perform additional duties as assigned Requirements: 3+ years of experience as a Personal Assistant, Executive Assistant, Estate Manager, Household Manager, Family Office Assistant, Lifestyle Manager, Chief of Staff, or similar high-level support role Experience supporting executives, entrepreneurs, high-net-worth, or ultra-high-net-worth individuals strongly preferred Exceptional organizational and project management skills Ability to anticipate needs and work proactively with minimal supervision Outstanding communication and interpersonal abilities Strong multitasking and prioritization skills High level of professionalism, discretion, and confidentiality Comfortable managing multiple residences, vendors, contractors, and household staff Tech-savvy with proficiency in Microsoft Office, Google Workspace, spreadsheets, and digital organization tools Ability to thrive in a fast-paced, ever-changing environment Flexible schedule with occasional evenings and weekends as needed