On behalf of our client, Robert Half is seeking an Executive Assistant based in Toronto, ON. This on-site position provides comprehensive support to two principals and ensures the smooth operation of the office environment. The role requires a proactive approach to executive support, office management, and oversight of daily technology and software functions.

• Coordinate schedules, travel arrangements, meetings, and correspondence for both principals, including personal and family administration.
• Manage document routing for signatures and organize logistics for events and charitable activities.
• Oversee office operations, including supplies, vendor relationships, telecom services, and team events.
• Facilitate onboarding and offboarding of staff, ensuring proper account and device setup using established checklists.
• Serve as the primary contact for IT issues, triaging requests to the managed IT vendor and maintaining a weekly review of open tickets.
• Administer software and AI subscriptions, monitor usage and renewals, and track monthly expenditures to remain within set limits.
• Supervise low-code automations and scheduled processes, ensuring adherence to existing documentation and runbooks.
• Maintain the internal IT Hub and standard operating procedure library to support ongoing operations.
• Provide one-on-one assistance to team members on software and AI tools, updating quick-start guides as needed.
• Handle operational projects delegated by the principals, such as sourcing vendors, obtaining quotes, and managing small purchases.

• Minimum of 3 years in an executive assistant, office manager, or operations coordination role.
• Demonstrated experience supporting senior leaders in a small business or entrepreneurial setting.
• Strong proficiency with Microsoft 365, including Outlook, Teams, and SharePoint, as well as familiarity with admin consoles.
• Experience managing AI tools such as ChatGPT, Claude, or Copilot, and overseeing related subscriptions.
• Vendor management skills, including accountability and follow-up on service delivery.
• Ability to prioritize tasks for multiple principals and maintain discretion in handling sensitive matters.
• Comfort with documented low-code systems; coding ability is not required.
• Strong organizational discipline, attention to detail, and the capacity to independently close tasks.

Robert Half is the world’s first and largest specialized talent solutions firm that connects highly qualified job seekers to opportunities at great companies. We offer contract, temporary and permanent placement solutions for finance and accounting, technology, marketing and creative, legal, and administrative and customer support roles.

Robert Half works to put you in the best position to succeed. We provide access to top jobs, competitive compensation and benefits, and free online training. Stay on top of every opportunity - whenever you choose - even on the go. Download the Robert Half app and get 1-tap apply, notifications of AI-matched jobs, and much more.

This job posting is for a current vacancy with our client.

Our specialized recruiting professionals apply their expertise and utilize our proprietary AI to find you great job matches faster.

Questions? Call your local office at 1.888.490.4154. All applicants applying for Canadian job openings must be authorized to work in Canada.

Only job postings for jobs located in Quebec appear in French.

© 2026 Robert Half. By clicking “Apply,” you’re agreeing to Robert Half’s Terms of Use and Privacy Notice.