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