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About the Role

Seeking an experienced Personal Assistant 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. This position is full-time with a highly flexible schedule that aligns with the principal’s needs and travel itinerary. Frequent domestic (Canada/U.S.) and international travel will be required, an updated passport is necessary. Driving is an important aspect of this position, looking for experienced drivers.

Responsibilities

Provide seamless on-the-go assistance for a dynamic, travel-intensive lifestyle.
Coordinate and manage complex schedules aligned with the principal's calendar and lifestyle.
Facilitate extensive domestic and international travel planning and booking.
Assist with family and business matters, balancing personal lifestyle management and corporate coordination.
Collaborate with the existing assistant to meet operational and domestic needs.
Run personal and professional errands with high efficiency and attention to detail.
Facilitate lifestyle activities, including participation in sports or outdoor activities.
Maintain active communication and manage local relationships or contractors.
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.
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.
Deep familiarity with U.S. culture, business environments, and lifestyle.
Familiarity with the Toronto financial market is a plus.
Understanding of Asian, particularly Chinese, culture is an asset.
Confident, experienced driver with a clean driving record.
Ability to maintain privacy and confidentiality, exercising diplomacy and strict discretion.
Legally entitled to work in Canada or the United States.
Updated passport.

Skills

High energy
Hands-on approach
Adaptability
Excellent judgment
Strong written communication
Strong verbal communication
Robust service mindset
Comfortable operating in a primarily English-speaking, North American environment
Ability to blend high-level executive support with seamless personal and lifestyle logistics management
Active and comfortable participating in sports or outdoor activities
Excellent interpersonal skills
Relationship-building skills
Diplomacy
Strict discretion

Location

Toronto, ON
Frequent domestic travel (Canada/U.S.)
Frequent international travel

Work Type

Full-time
Highly flexible schedule

Education Level

Top-tier U.S. university education (Ivy League or equivalent preferred)
Finance-related major highly advantageous