Wrapbook

Director, Chief of Staff

Wrapbook

full-time

Posted on:

Location Type: Remote

Location: United States

Visit company website

Explore more

✨ AI Apply
Apply

Salary

💰 $148,400 - $240,900 per year

Job Level

Lead

About the role

  • 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
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
AIoperating systemsworkflowssynthesisdecision-makingplanninganalysiscross-functional initiativesoperating efficiencyrisk identification
Soft Skills
analytical skillsbusiness judgmentindependent thinkingcommunication skillshigh agencycuriositybias toward actionstakeholder alignmentambiguity navigationleadership facilitation