Executive Personal Assistant

Location: Central Toronto| In-person, private home office

Compensation: $130,000+ CAD + benefits

Vacation: 3 weeks uninterrupted annually (Yes, actually uninterrupted)

Environment: High-performance | High autonomy | Fast-paced

Reporting Structure: Dual-reporting line. Reports to the Residence Manager on household operations, the renovation project, and the local move. Reports directly to the Principal on personal files, calendar, and private correspondence.

About the Role

We are seeking an exceptional Executive Personal Assistant to serve as the trusted right hand, strategic gatekeeper, and administrative engine for a dynamic business leader and philanthropist.

This is a high-trust, high-accountability role for a master organizer who looks at chaos and sees an opportunity to alphabetize it. Currently, the Principal is undertaking a full build-out of a new residence and a local relocation within Toronto. Working as a critical gear in a dedicated private office team, you will collaborate closely with the Collections Manager and the Residence Manager to ensure priorities are managed efficiently and commitments are executed seamlessly.

Because the Principal is deeply involved in philanthropy, a background or strong interest in the arts is highly valued. You should possess the rare ability to switch effortlessly between tracking a drywall budget, organizing a corporate calendar, and appreciating the delicate handling required for valuable collections.

Key Responsibilities

Direct Support to the Principal

• Calendar Tetris: Masterfully manage an ever-changing calendar, balancing corporate real estate development (CEO duties), philanthropic commitments, and personal life across multiple time zones.
• Inbox Triage: Monitor folders and draft general correspondence on the Principal’s behalf, acting as a polite but firm gatekeeper who knows exactly what deserves an hour, a minute, or a delete.
• Private File Mastery: Directly manage, organize, and protect the Principal's highly confidential personal files, digital documents, and private correspondence with absolute discretion.

Estate Operations & Project Support (Reporting to the Residence Manager)

• Renovation Air Traffic Control: Coordinate the ongoing residential build project by tracking timelines, deliverables, construction milestones, and the army of vendors making it happen.

• Budget Tracking: Manage project expenditures, invoices, and contracts (using QuickBooks) to ensure the renovation is as financially sound as it is beautiful.
• The Local Move: Mastermind the physical relocation across town, orchestrating movers, logistics, and packing schedules so seamlessly that the Principal barely notices the change of address.
• Collections Collaboration: Partner with the Collections Manager to coordinate logistics, documentation, and the safe transport/installation of fine art and specialized assets during the build and move.

Personal & Household Administration

• Life Logistics: Coordinate personal appointments, gallery viewings, private dinner reservations, and family logistics.
• Property Manuals: Co-author and update existing residence manuals with the Residence Manager, turning institutional knowledge into clear, repeatable processes.

Who You Are

• The Background: 5+ years supporting a senior executive, entrepreneur, or UHNW principal as an EA or PA. A personal or professional alignment with the arts or creative industries is highly preferred.
• The Tech: Advanced with Microsoft Office and Google Workspace; QuickBooks experience is a strong asset.
• The Mindset: Borderline obsessive attention to detail with strong budget-tracking capabilities. You don't panic; you pivot.
• The Communication: Polished, articulate, and entirely comfortable representing the Principal to high-profile stakeholders, gallery directors, and contractors alike.
• The Style: Operates with minimal supervision and a massive amount of accountability to both reporting lines. Maintains composure, perspective, and a healthy sense of humour.