AI strategy and execution define this Chief of Staff position, based full time in the office in Montreal or Toronto, Canada. Partner directly with the founder. This senior founding leadership role supports a rapidly scaling, founder-led AI product company. You will shape strategy, lead cross-functional initiatives, and build systems for growth. The position combines business operations, financial judgment, hiring, and commercial expansion. Key Responsibilities:

Partner with the founder on strategy, growth, and execution Lead strategic and cross-functional company initiatives Translate goals into priorities, plans, and measurable results Build scalable processes, systems, and organisational infrastructure Own forecasting, financial modelling, and operating metrics Requirements:

Two to three years in top-tier management consulting Two to six years in Chief of Staff or business operations Experience with high-growth, venture-backed technology companies Strong commercial and financial judgment, including modelling experience Practical AI, automation, coding, or programming experience Bring analytical ability, ownership, and founder-level judgment to build the company’s next stage of AI growth.

📌 Chief of Staff AI Strategy (Winnipeg)
🏢 Savannah Search
📍 Winnipeg