Director, Chief of Staff

Job Description:

• Use AI as a core operating tool — not a supplement.
• Own and evolve the CEO's AI-powered operating system.
• Build and maintain agentic workflows that extend the CEO's and SLT's leverage.
• Be a force multiplier for the company's AI adoption: model best practices, share what works, and help the broader organization develop fluency with AI tools and workflows.
• Stay on the frontier. Continuously evaluate new AI tools, techniques, and capabilities — and translate what's relevant into practical leverage for the CEO and leadership team.
• Develop a deep understanding of Wrapbook’s business, priorities, and operating model.
• Synthesize information from across the company, escalating the most urgent items to the CEO and creating clear recommendations.
• Help shape and clarify company-level strategy and priorities.
• Proactively identify risks, gaps, and opportunities.
• Leverage AI and emerging tools to increase executive and company-wide leverage - improving synthesis, decision-making speed, and operating efficiency.
• Own and lead high-priority, cross-functional initiatives from scoping through execution.
• Align stakeholders, clarify decision-making, remove blockers and ensure follow-through.
• Step into ambiguous areas and create structure where needed.
• Own company-level planning and communication processes (annual planning, OKRs, MBRs, All Hands).
• Design and facilitate leadership meetings that drive clear decisions and accountability.
• Continuously improve operating rhythms and cross-team coordination.

Requirements:

• 7+ years of experience in a high-performance environment (consulting, banking, operating role, etc.).
• A systems-level thinker who leverages AI as a force multiplier in planning, analysis, and executive workflows.
• Demonstrated experience owning complex, cross-functional initiatives.
• Strong analytical skills and business judgment.
• Ability to form independent points of view and make clear recommendations.
• Excellent, executive-level written and verbal communication skills.
• High agency, curiosity, and a bias toward action.
• Comfort working directly with senior leaders and navigating ambiguity.

Benefits:

• Unlimited Paid Time Off
• Work from anywhere in Canada and USA
• Health and Dental benefits
• Up to $1,500 USD/ $2,025 CAD towards IT set up for your home
• Up to 2% matching RRSP / 401K
• Learning and Development opportunities
• Up to $50 USD/ $67.50 CAD towards Internet/Cell phone service

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