Senior Personal/Executive Assistant

We are seeking an exceptional Senior Executive Assistant / Personal Assistant to support two highly successful entrepreneurs. This is a fast-paced, highly collaborative role working alongside an established executive support team and long-tenured staff. This role serves as the trusted operational backbone for both the professional and personal lives of the Principals. While you will support both founders directly, much of your day-to-day interaction will be with the executive team, ensuring priorities, projects, household operations, and personal matters move forward seamlessly. You will be the person who keeps every moving piece organized, anticipated, and executed with exceptional attention to detail. The position combines sophisticated executive/personal support with extensive personal assistant responsibilities. No two days are ever the same. One moment you may be coordinating executive meetings, tracking business initiatives, and preparing briefing materials; the next you may be organizing a family celebration, managing gifting, coordinating household vendors, arranging travel, handling personal appointments, or ensuring every detail of the Principals' day runs effortlessly. This role requires exceptional discretion, sound judgment, resourcefulness, and the ability to anticipate needs before they arise. Success comes from being comfortable with ambiguity, managing multiple priorities simultaneously, and approaching every responsibility—whether business or personal—with the same level of urgency, professionalism, and care. No task is too large or too small. Key Responsibilities Executive & Administrative Support Provide sophisticated executive and personal support to both Principals while partnering closely with the executive leadership team. Manage highly complex calendars, meetings, appointments, and ever-changing priorities. Prepare agendas, presentations, briefing materials, meeting notes, and follow-up action items. Support ongoing business initiatives by tracking projects, deadlines, deliverables, and cross-functional priorities. Serve as a liaison between the Principals, executives, advisors, vendors, household staff, and outside partners. Create and improve organizational systems, processes, and workflows that increase efficiency. Personal Assistant & Lifestyle Management Manage personal calendars, medical appointments, grooming appointments, family commitments, and daily logistics. Coordinate errands, personal shopping, returns, alterations, tailoring, and wardrobe needs. Coordinate dining reservations, entertainment, private events, and personal celebrations while managing preferences and VIP relationships. Draft personal correspondence, thank-you notes, invitations, and communications on behalf of the Principals. Gifting & Relationship Management Source, purchase, personalize, and coordinate thoughtful gifts for family, friends, employees, clients, and key business relationships. Maintain detailed spreadsheets and databases tracking birthdays, anniversaries, gift history, preferences, sizes, allergies, and important dates. Coordinate holiday gifting programs from planning through execution. Travel Coordination Coordinate domestic and international travel alongside a dedicated travel concierge. Prepare detailed itineraries including flights, accommodations, transportation, dining, activities, and confirmations. Manage travel documents, loyalty programs, packing logistics, and last-minute itinerary changes while proactively resolving travel disruptions. Household & Estate Coordination Coordinate the day-to-day operations of the Principals' residences by working closely with housekeepers, vendors, contractors, property managers, and household staff. Oversee maintenance, repairs, deliveries, mail, packages, household inventory, subscriptions, and seasonal household needs. Assist with family logistics, relocations, home projects, pet care, veterinary appointments, and other personal priorities. Special Projects Take ownership of a wide variety of personal and business-related projects, ensuring exceptional execution and follow-through. Coordinate with accountants, bookkeepers, and advisors regarding routine bill pay, reimbursements, and administrative matters. Step in wherever needed, recognizing that flexibility, initiative, and a service-first mindset are essential to success. Qualifications 10+ years of experience supporting founders, C-suite executives, entrepreneurs, family offices, or ultra-high-net-worth individuals as a Senior Executive Assistant and/or Personal Assistant. Significant experience balancing sophisticated executive support with extensive personal assistant responsibilities. Proven ability to manage highly complex calendars, travel, logistics, projects, and competing priorities in a fast-paced environment. Outstanding organizational and project management skills with exceptional attention to detail. Highly polished, professional, discreet, and confident with outstanding judgment and executive presence. Naturally proactive with the ability to anticipate needs several steps ahead. Exceptional written and verbal communication skills. Strong technology skills, including Google Workspace, Microsoft Office, Slack, Asana, Monday.com, ChatGPT, and other AI productivity tools. Resourceful, solutions-oriented, and comfortable working independently with minimal supervision. High emotional intelligence with the ability to build trusted relationships across all levels of an organization. Collaborative, adaptable, service-oriented, and genuinely enjoys making other people's lives easier. Flexible to work outside traditional business hours, including occasional evenings, weekends, and travel as needed. Valid driver's license and reliable transportation preferred. Compensation/Benefits Up to $150,000 base salary plus discretionary bonus depending on experience. Benefit package includes medical, dental, vision, Life/AD&D, 401K with company match, paid time off, and holidays. The Company is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability or veteran status #J-18808-Ljbffr Post Real Estate Group