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 Robust 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