Job Description

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.