Service League jobs

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

Pay: $100,000.00-$185,000.00 per year

Education:

• Bachelor's Degree (required)

Experience:

• Personal Assistant: 5 years (required)

Licence/Certification:

• Full G license and Vehicle (required)

Willingness to travel:

• 75% (required)

Work Location: In person