Personal Assistant

About the role

We are seeking an experienced Personal Assistant with an Ivy-League undergraduate degree to support a dynamic, travel-intensive lifestyle. The principal currently has one assistant in place and is looking to add a second to provide comprehensive support for both business and family-related matters.

Responsibilities

• Support a dynamic, travel-intensive lifestyle, providing seamless on-the-go assistance to the principal
• Coordinate and manage complex schedules, aligning directly with the principal's calendar and lifestyle needs
• Facilitate extensive travel planning and booking across Canada, the United States, and internationally
• Assist with both family and business-related matters, ensuring a balance between personal lifestyle management and corporate coordination
• Collaborate effectively with the existing assistant to ensure all operational and domestic needs are met
• Run personal and professional errands, maintaining high efficiency and attention to detail
• Help facilitate lifestyle activities, including participation in sports or outdoor activities as required
• Maintain active communication and manage local relationships or contractors as needed
• Research, compile solutions, and manage projects for principal approval
• Perform additional duties as assigned by the principal

Requirements

• Strong Executive Assistant or Personal Assistant experience
• Financial services, wealth management, or family office experience
• Professional background in finance, investment, private wealth, family office, consulting, or a major North American bank (client-facing or relationship management roles are a strong plus)
• Educated at a top-tier U.S. university (Ivy League or equivalent preferred); a finance-related major is highly advantageous
• Deep familiarity with U.S. culture, business environments, and lifestyle; familiarity with the Toronto financial market is a plus
• Some understanding of Asian—particularly Chinese—culture is an asset (No Mandarin is required; fluent English is sufficient)
• Must be a confident, experienced driver with a clean driving record
• Must maintain privacy and confidentiality at all times, exercising diplomacy and strict discretion

Skills

• Strong driving skills
• Interest in sports and outdoor activities
• Excellent communication, interpersonal, and relationship-building skills