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Chief of Staff – Executive Assistant, AI

Remote · Canada Full-time

Job Description:

  • Translate CEO/Board vision into clear company priorities, OKRs, and execution plans.
  • Drive cross-functional initiatives, process improvements, and systems that support growth.
  • Prepare CEO for board, investor, and client engagements; manage executive meetings and follow-ups.
  • Provide research, data, and analysis to inform strategic decisions.
  • Act as liaison between CEO, leadership team, and wider organization.
  • Lead high-impact initiatives (new market entry, acquisitions, organizational scaling).
  • Run and facilitate executive leadership meetings, ensuring follow-through.
  • Track key metrics, projects, and accountability against company goals.
  • Draft CEO communications (internal and external).
  • Coordinate investor and board materials.
  • Identify bottlenecks and resolve cross-departmental issues.
  • Drive “CEO-only” projects to completion without constant oversight.
  • Serve as an early warning system for risks or gaps in execution.

Requirements:

  • 7–12+ years’ experience supporting CEOs/Founders in entrepreneurial, fast-scaling small and medium size, award winning companies
  • Worked for a 100-300 staff company during their growth curve ideally twice, for 3-5+ years (candidates)
  • Comfortable managing and facilitating executive director board-level meetings, notes, materials, investors, VVIPs, and confidential projects, while also handling calendar, travel
  • Deep business understanding of D2C/eCommerce/digital marketing/digital marketplace models/online training courses/digital coaching apps
  • Passionate about one or more sports, health, wellness, fitness, supplements, at an advanced level like a biohacker.

Benefits: Apply To this Job

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