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.

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