Full-time

Chief of Staff at AI Startup Winnipeg

Posted by Jagger • June 06, 2026

📍 winnipeg, mb, Canada
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Description

Drive operational excellence as the Chief of Staff for a dynamic AI startup in Winnipeg. Collaborate closely with the Co-Founder to enhance productivity and implement AI-driven solutions.
This pivotal Chief of Staff role requires someone operationally minded and comfortable with strategic challenges. You'll take charge of projects, build automations, and prepare insightful reports for leadership. Your expertise with AI tools is essential in navigating and structuring ambiguous problems effectively.
Key Responsibilities:
• Own and drive projects to completion independently
• Build AI-driven workflows across sales and operations
• Prepare reports and performance insights for leadership
• Evaluate new vendors, tools, and technologies
• Support coordination across the US ad sales team
Requirements:
• 2-5 years in operational or strategic roles
• Deep experience with AI tools like Claude and ChatGPT
• Experience in startup or high-growth environments benefic...

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