Personal Assistant

Diamond Group • Full-time • Toronto, Ontario, Canada • USD $ 150k / year • 2d ago

We are seeking a highly organized, proactive and systems oriented Personal/Family Assistant to support a busy family and oversee the smooth operation of two residential properties located in Calgary and Toronto.

Schedule: Monday - Friday, 9:00 am -5:00 pm with flexibility as required.

Compensation: Up to $150,000 Gross Annual Salary (Commensurate with experience) + Benefits Package + 4 Weeks Paid Vacation

Responsibilities:

Household & Property Operations Management: Coordinate and supervise day-to-day operations for multiple residences (Toronto & Calgary), including staff oversight, maintenance scheduling, vendor sourcing, contractor coordination, and execution of preventive and seasonal home maintenance plans.
Administrative & Financial Oversight: Manage household administration such as permits, renewals, property taxes, payroll coordination, expense reimbursements and liaison with accountants and payroll providers.
Pet Care Coordination: Oversee all administrative and logistical aspects of pet care, including veterinary appointments, grooming, travel documentation, insurance claims, medication schedules, boarding arrangements, and municipal licensing.
Travel, Calendar & Logistics Management: Integrate complex family and professional calendars, identify scheduling conflicts, and manage end-to-end travel logistics (flights, ground transport, accommodations, pet-in-cabin arrangements, and disruption claims).
Personal, Family & Professional Support: Provide comprehensive personal assistance including medical and personal appointments, children's school administration and extracurricular coordination, event planning, ticket and activity management, professional hosting, gifting, and tracking of tax and compliance deadline, and Vehicle Management.
Vehicle & Asset Management: Track, schedule, and coordinate routine maintenance, insurance, registrations, and seasonal servicing for multiple vehicles across locations.

Requirements:

Excellent time management skills, Able to prioritize and manage time accordingly. Strong administrative and technical skills, Digital fluency in MS office suite, word, excel, zoom/teams. Willingness to learn new systems. Great at project management, organizing, planning and implementing. Highly administrative and detail oriented,