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Job Post Details

Executive Personal Assistant
Charles MacPherson Associates Inc.
Toronto, ON
$85,000–$120,000 a year
Permanent, Full-time
Apply now

Job details

$85,000–$120,000 a year
Permanent, Full-time
Monday to Friday
Toronto, ON

Full job description

Executive Personal Assistant

Position Overview:

We are seeking an exceptionally capable, proactive, discreet, and polished Executive Personal

Assistant to provide comprehensive, high-level administrative, personal, and lifestyle support to

a prominent couple (with a primary focus on MR). The successful candidate will streamline daily

operations, manage complex schedules, oversee multiple property logistics, and handle

sensitive family office matters.

This is a core Monday through Friday role, 9:00 AM – 5:00 PM, with room for flexibility (working

remotely with regular visits to the main residence for mail, tasks, and in-person alignment

meetings). While the principals value work-life balance and do not expect weekend email

coverage, flexibility to handle occasional time-sensitive matters via phone is required. Absolute

discretion, strong organizational acumen, and an unwavering commitment to privacy are

paramount.

Key Responsibilities

●

Calendar & Schedule Management (Primary Focus: MR):

○

Manage and maintain complex daily calendars, prioritizing a high volume of

meeting requests, board commitments, mentorship requests, and speaking

engagements.

○

Coordinate closely with Mrs regarding shared commitments, respecting her

independent calendar management.

○

Proactively block out calendar time and maintain real-time updates to ensure

seamless alignment across all activities.

●

Travel & Logistics Optimization:

○

Coordinate end-to-end travel logistics for domestic and international trips,

including commercial flights, private aviation, luxury accommodations, ground

transportation/drivers, luggage handling, and detailed itineraries.

○

Manage travel logistics for family pets when traveling.

○

Track and optimize airline reward/frequent flyer points, NEXUS memberships,

and passport renewals.

●

Property & Estate Coordination:

○

Serve as the main point of contact and liaison for House Managers across

multiple global properties and the family cottage.

○

Review, maintain, and manage vendor, landscape, and service contracts;

schedule routine and seasonal maintenance (e.g., cottage septic/sewage

testing).

○

Oversee comprehensive insurance policies for all residential properties, vehicles,

boats, and new high-value acquisitions in coordination with outgoing support.

●

Mail, Financial & Professional Liaison:○

Conduct regular visits to the main residence to collect, monitor, open, and action

mail.

○

Maintain key relationships with accountants, lawyers, and financial brokers.

○

Assist with complex tax preparations, route invoices and bills to accounting, track

credit card accounts, and ensure timely tax/bill payments.

●

Foundation, Philanthropy & Art Collection Management:

○

Oversee and maintain inventory records for an extensive, high-value artwork

collection.

●

Events, Hospitality & On-Site Tasks:

○

Coordinate private home dinners and social gatherings, managing catering

vendors, guest lists, and RSVPs.

○

Participate in weekly virtual check-ins to review priorities/to-do lists and bi-weekly

in-person strategy meetings.

○

Complete key transition training with long-standing assistant to learn key contact

lists, preferences, and operational protocols.

Candidate Profile & Qualifications

●

Experience: 5+ years of experience as an Executive Personal Assistant, Family Office

Assistant, or Personal Assistant supporting high-net-worth individuals, executives, or

private families.

●

Discretion & Privacy: Absolute commitment to confidentiality and diplomacy. Must be

willing to sign a comprehensive Non-Disclosure Agreement (NDA).

●

Communication & Relationship Management: Exceptional written and verbal

communication skills. Ability to liaise professionally with high-profile contacts, board

members, legal/financial advisors, estate staff, and vendors.

●

Organizational Skills: Exceptional attention to detail, strong prioritization skills, and the

ability to anticipate needs and manage competing priorities with minimal supervision.

●

Travel & Identity Documents: Possess a valid passport, valid driver’s license with a

clean driving record.

●

Technical Proficiency: Comfortable utilizing digital calendar systems, travel booking

platforms, and administrative/spreadsheet software for record-keeping and tracking.

Pay: $85,000.00-$120,000.00 per year

Experience:

  • Executive assistant : 5 years (required)

Work Location: In person

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