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Chief of Staff AI Strategy

Savannah Search Ltd

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.

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Vacancy posted 16 hours ago
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