Chief of Staff (AI)

Location: Toronto, Canada; remote role prioritizing candidates based in Toronto

Company

AI research and product company developing voice, audio, creative, and conversational AI platforms for consumers and businesses.

What you will do

• 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 organization.
• Support complex enterprise deals, strategic customer relationships, AE interviews, and customer meetings.
• Coordinate calendars, projects, priorities, and commitments across teams and time zones.
• Identify operational challenges, build scalable processes, and improve execution across the region.
• Use AI tools to automate workflows and handle sensitive matters with discretion.

Requirements

• Based in Toronto and able to work closely with the GM and regional team.
• Fluent written and spoken English required.
• Experience in consulting, investment or private banking, revenue operations, or a go-to-market role at a high-growth startup.
• Strong commercial judgment, communication, organization, and prioritization skills.
• Comfort working with customers, spreadsheets, and Salesforce dashboards.
• Low-ego, high-ownership approach with enthusiasm for AI.

Nice to have

• French proficiency is strongly preferred.

Culture & Benefits

• High-velocity environment with autonomous teams and minimal bureaucracy.
• AI-first culture focused on experimentation, impact, and excellence.
• Annual discretionary professional development stipend.
• Annual social travel stipend and company offsite.
• Monthly co-working stipend for employees outside main hubs.
• Meaningful ownership and equity opportunity with direct access to senior leadership.