Wrapbook

Wrapbook is a smart, intuitive platform that makes production payroll and accounting easier, faster, and more secure.

Director, Chief of Staff

Chief of StaffChief of StaffFull TimeRemoteTeam 51-200H1B No SponsorCompany SiteLinkedIn

Location

United States

Posted

3 days ago

Salary

$148.4K - $240.9K / year

Bachelor Degree7 yrs expEnglish

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.

Job 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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