Personal Assistant Toronto, ON
Position Overview: 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.
Candidate Profile: You are a high energy, hands-on, and adaptable professional who exercises excellent judgment in a fast-paced environment. Strong written and verbal communication skills are vital, alongside a robust service mindset and the ability to operate comfortably in a primarily English-speaking, North American environment. You have a background that blends high-level executive support with the ability to manage personal and lifestyle logistics seamlessly. The ideal candidate is active and comfortable participating in sports or outdoor activities as needed.
Primary 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
Performs additional duties as assigned by the Principal
Applicant Qualities:
Strong Executive Assistant or Personal Assistant experience
Educated at a top-tier U.S. university (Ivy League or equivalent preferred); a finance-related major is highly advantageous
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
Some understanding of Asian—particularly Chinese—culture is an asset (No Mandarin is required; fluent English is sufficient)
Excellent communication, interpersonal, and relationship-building skills
Must be a confident, experienced driver with a clean driving record
Must maintain privacy and confidentiality at all times, exercising diplomacy and strict discretion
Must be legally entitled to work in Canada or the United States
Personal Assistant • Toronto, ON, ca
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