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 (Montreal)
🏢 Savannah Search
📍 Montreal