Seeking an exceptional Personal Assistant to support a retired (for now) entrepreneur managing a full family life, personal projects, travel, and future professional pursuits. This is not a traditional PA role. The right person provides structure, memory, and external regulation-not just scheduling. You build systems, document everything, anticipate needs, and offer thoughtful pushback when priorities drift or schedules overload. You enjoy ownership, accountability, and long-term partnership.

Responsibilities

• Manage calendars, appointments, and logistics across personal, family, and professional life
• Run weekly check-ins to review priorities, open loops, and follow-ups
• Help create and protect weekly structure around family, health, and important goals
• Prepare notes for appointments and meetings; ensure follow-through
• Maintain organized, documented systems for tasks, records, and processes
• Arrange domestic and international travel and manage loyalty programs
• Handle light admin, insurance claims, mail, and occasional errands
• Coordinate vendors, household needs, family events, and gifting
• Maintain a running database of lifestyle ideas (date nights, trips, experiences)
• Act as a proactive partner and occasional sounding board

Ideal Background

• Experience as a PA, EA, Chief of Staff, or similar senior support role
• Strong systems thinking, organization, and judgment
• Comfort with Google Workspace and modern tools (Notion/Airtable/task systems/AI)
• Ability to manage ambiguity and evolving scope
• Discreet, reliable, and comfortable offering respectful pushback
• Some flexibility for occasional evenings or travel-related needs
• Valid driver's license and reliable transportation

This role is a long-term partnership, not a checklist job. There is room for growth in this opportunity. The right person will find it meaningful and engaging; the wrong person will find it ambiguous.