Director, Chief of Staff
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Job Description
Director, Chief of Staff at Wrapbook, partnering with the CEO to drive strategic initiatives. Focusing on AI integration and operational efficiency across the organization.
Responsibilities:
- 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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