We are looking for a highly organized Executive Assistant &amp; 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.<br><br>Responsibilities:<br>• Provide proactive administrative support to senior executives, ensuring schedules, priorities, and communications are managed efficiently.<br>• Coordinate complex calendars, arrange meetings, and prepare materials to support leadership decisions and day-to-day operations.<br>• Organize business travel, including itineraries, bookings, and related logistics, while anticipating changes and resolving scheduling conflicts.<br>• Prepare, review, and submit expense reports with accuracy and in accordance with internal policies and timelines.<br>• Oversee general office administration, including supplies, document handling, scanning, photocopying, and maintenance of organized records.<br>• Support meeting delivery through virtual platforms such as Cisco Webex Meetings and assist with room setup or technical coordination as needed.<br>• Maintain and update administrative information across business systems, including CRM and timekeeping or expense platforms such as Kronos, Concur, or ADP-related tools.<br>• 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.

<ul><li>Minimum 5 years of experience as an Executive Assistant, Office Manager, Operations Coordinator, or similar role</li><li>Experience supporting senior executives or business owners in a small, entrepreneurial environment</li><li>Advanced proficiency in Microsoft 365 (Outlook, Teams, SharePoint)</li><li>Working knowledge of AI tools such as ChatGPT, Claude, or Copilot</li><li>Comfort managing software platforms, user access, and administrative systems</li><li>Experience with vendors, facilities, office operations, and project coordination</li><li>Strong written and verbal communication skills</li><li>Excellent organization and attention to detail</li><li>Post-secondary education or equivalent experience</li><li>Experience in commercial real estate, design, professional services, or family-office environments is an asset</li></ul><p>The Ideal Candidate</p><p>You are someone who:</p><ul><li>Demonstrates strong judgment and discretion with confidential information</li><li>Works quickly and accurately while maintaining high professional standards</li><li>Asks thoughtful questions and moves forward independently</li><li>Anticipates needs rather than waiting for direction</li><li>Balances priorities across two principals and multiple business streams</li><li>Is curious, tech-savvy, and enthusiastic about AI and automation</li><li>Manages vendors confidently while maintaining strong relationships</li><li>Remains calm and effective in a fast-changing environment</li><li>Enjoys variety and takes pride in keeping operations running smoothly</li><li>Is proactive, resourceful, and committed to seeing tasks through to completion</li></ul><p>What Success Looks Like</p><p>Within the first year, the successful candidate will:</p><ul><li>Complete a structured onboarding and confidently manage established systems</li><li>Reduce operational demands on both principals through proactive support</li><li>Keep technology subscriptions, IT tickets, and vendor relationships organized and current</li><li>Ensure the office runs smoothly with minimal escalation</li><li>Support seamless onboarding so new employees are productive from day one</li><li>Become a trusted, go-to resource across the organization</li></ul><p>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.</p><p>Candidates must be comfortable working <strong>100% onsite in North Toronto</strong> and will be required to sign a confidentiality agreement.</p>

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