Chief of Staff - Canada

We are looking for a Chief of Staff to serve as the operational backbone and strategic partner to the GM of Canada. This high-trust, high-impact role involves driving revenue operations, supporting regional strategy, coordinating complex enterprise relationships, and ensuring smooth operations across the Canadian market.

Responsibilities:

• Partner with the GM of Canada on commercial strategy, revenue operations, and regional planning
• Own forecasting, pipeline hygiene, performance reporting, and capacity planning for the Canadian team
• Support the execution of complex, high-value deals and strategic customer relationships
• Join AE interviews and customer meetings, representing the GM when needed
• Manage complex calendars, projects, and coordination across teams and time zones
• Keep the team aligned with company processes, priorities, and commitments
• Identify and solve operational challenges before they escalate
• Build clear, repeatable processes that help the Canadian organization scale efficiently
• Use AI tools to automate workflows, streamline operations, and multiply your impact
• Handle sensitive matters with discretion and serve as a trusted partner across the organization

Requirements:

• Low ego, high ownership, and willing to take on any task
• Smart, structured, and pragmatic, with strong commercial instincts
• Exceptional communicator who can bring clarity to ambiguous, fast-moving situations
• Comfortable in front of customers and equally at home working in a spreadsheet or Salesforce dashboard
• Highly organized, detail-oriented, and skilled at managing multiple competing priorities
• Passionate about AI and excited to help build a category-defining company
• Based in Toronto and able to work closely with the GM and broader regional team
• Experienced in consulting, investment or private banking, revenue operations, or a GTM role within a high-growth startup
• Fluent in English, both written and spoken; French proficiency is strongly preferred

Benefits:

• Innovative culture
• Growth paths
• Learning & development support
• Social travel stipend
• Annual company offsite
• Co-working stipend