Chief of Staff - Canada

This is a high trust, high impact role for someone who combines sharp strategic thinking with hands-on execution. As Chief of Staff, you’ll serve as the operational backbone and strategic partner to the GM of Canada - driving revenue operations, supporting regional strategy, coordinating complex enterprise relationships, and ensuring nothing slips as we scale across the Canadian market.

Responsibilities:

• Partner directly 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.
• An 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
• Social travel
• Annual company offsite
• Co-working