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

Solid 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