We are looking for a highly organized Executive Assistant & Office Manager to support senior leadership while keeping daily office operations running smoothly in Toronto, Ontario. This position combines executive-level coordination with hands-on administrative oversight, requiring strong judgement, discretion, and a service-focused approach. The successful candidate will manage competing priorities, maintain efficient workflows, and help create a detail-oriented and well-organized workplace environment.

Responsibilities:
• Provide proactive administrative support to senior executives, ensuring schedules, priorities, and communications are managed efficiently.
• Coordinate complex calendars, arrange meetings, and prepare materials to support leadership decisions and day-to-day operations.
• Organize business travel, including itineraries, bookings, and related logistics, while anticipating changes and resolving scheduling conflicts.
• Prepare, review, and submit expense reports with accuracy and in accordance with internal policies and timelines.
• Oversee general office administration, including supplies, document handling, scanning, photocopying, and maintenance of organized records.
• Support meeting delivery through virtual platforms such as Cisco Webex Meetings and assist with room setup or technical coordination as needed.
• Maintain and update administrative information across business systems, including CRM and timekeeping or expense platforms such as Kronos, Concur, or ADP-related tools.
• Act as a reliable point of contact for internal stakeholders, demonstrating strong attention to detail when working with C-suite leaders and cross-functional teams.

• Minimum 5 years of experience as an Executive Assistant, Office Manager, Operations Coordinator, or similar role
• Experience supporting senior executives or business owners in a small, entrepreneurial environment
• Advanced proficiency in Microsoft 365 (Outlook, Teams, SharePoint)
• Working knowledge of AI tools such as ChatGPT, Claude, or Copilot
• Comfort managing software platforms, user access, and administrative systems
• Experience with vendors, facilities, office operations, and project coordination
• Strong written and verbal communication skills
• Excellent organization and attention to detail
• Post-secondary education or equivalent experience
• Experience in commercial real estate, design, professional services, or family-office environments is an asset

The Ideal Candidate

You are someone who:

• Demonstrates strong judgment and discretion with confidential information
• Works quickly and accurately while maintaining high professional standards
• Asks thoughtful questions and moves forward independently
• Anticipates needs rather than waiting for direction
• Balances priorities across two principals and multiple business streams
• Is curious, tech-savvy, and enthusiastic about AI and automation
• Manages vendors confidently while maintaining strong relationships
• Remains calm and effective in a fast-changing environment
• Enjoys variety and takes pride in keeping operations running smoothly
• Is proactive, resourceful, and committed to seeing tasks through to completion

What Success Looks Like

Within the first year, the successful candidate will:

• Complete a structured onboarding and confidently manage established systems
• Reduce operational demands on both principals through proactive support
• Keep technology subscriptions, IT tickets, and vendor relationships organized and current
• Ensure the office runs smoothly with minimal escalation
• Support seamless onboarding so new employees are productive from day one
• Become a trusted, go-to resource across the organization

This is a unique opportunity for an experienced Executive Assistant and Office Manager to work at the centre of a dynamic entrepreneurial business. The role offers broad exposure, meaningful ownership, direct access to leadership, and the chance to help modernize operations through technology and AI.

Candidates must be comfortable working 100% onsite in North Toronto and will be required to sign a confidentiality agreement.

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