Chief of Staff - Canada

About the role

This is a high trust, high impact role for someone who combines sharp strategic thinking with hands-on execution. As Chief of Staff, you will serve as the operational backbone and strategic partner to the GM of Canada, owning the end to end management of revenue operations and commercial execution. You will drive regional strategy, coordinate complex enterprise relationships, and ensure flawless execution across the Canadian market with extreme ownership and low ego. The role demands comfort with ambiguity and the ability to step in wherever the business needs you, handling everything from forecasting to sensitive stakeholder conversations. You will be responsible for building clear, repeatable processes that allow the team to scale efficiently while leveraging AI to multiply your impact. You will own forecasting, pipeline hygiene, performance reporting, and capacity planning, ensuring nothing slips as we scale. You will support the execution of complex, high-value deals and strategic customer relationships, representing the GM in meetings and interviews when required.

Key facts

What you'll do

Partner directly with the GM of Canada on commercial strategy, revenue operations, and regional planning to define and execute the go to market approach for the region.

Own forecasting, pipeline hygiene, performance reporting, and capacity planning for the Canadian team, using data and AI tools to maintain accuracy and visibility.

Support the execution of complex, high value deals and strategic customer relationships, coordinating across teams to ensure smooth progression and risk mitigation.

Join AE interviews and customer meetings, representing the GM when needed and providing strategic input into positioning and commercial decisions.

Manage complex calendars, projects, and coordination across teams and time zones, ensuring seamless collaboration between functions.

Keep the team aligned with company processes, priorities, and commitments, enforcing standards while enabling fast execution.

Identify and solve operational challenges before they escalate, applying structured problem solving to remove blockers for the team.

Build clear, repeatable processes that help the Canadian organization scale efficiently, documenting workflows and best practices for adoption.

Use AI tools to automate workflows, streamline operations, and multiply your impact across reporting, planning, and communications.

Handle sensitive matters with discretion and serve as a trusted partner across the organization, maintaining confidentiality and providing sound counsel.

Requirements

Low ego, high ownership, and willing to take on any task, regardless of size or perceived ownership.

Smart, structured, and pragmatic, with strong commercial instincts and the ability to translate strategy into execution.

An exceptional communicator who can bring clarity to ambiguous, fast moving situations and make decisions with incomplete information.

Comfortable in front of customers and equally at home working in a spreadsheet or Salesforce dashboard, with a strong attention to detail.

Highly organized, detail oriented, and skilled at managing multiple competing priorities in a dynamic environment.

Passionate about AI and excited to help build a category defining company that is transforming how people interact with technology.

Based in Toronto and able to work closely with the GM and broader regional team, requiring proximity to support rapid decision making.

Experienced in consulting, investment or private banking, revenue operations, or a GTM role within a high growth startup, bringing relevant domain expertise.

Fluent in English, both written and spoken; French proficiency is a strong asset for engaging with a broader set of stakeholders.

Practical notes

This role is full time based in Toronto with no specified travel requirements, visa sponsorship details, or deadlines outlined in the provided source material. You will work closely with the leadership team to drive results in a fast moving, AI first environment that prioritizes impact over hierarchy. The successful candidate will thrive in a setting where autonomy, ownership, and rapid execution are expected on a daily basis.