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About the role

  • Chief of Staff translating Thumbtack CEO decisions into company-wide action. Improving executive operating rhythms, cross-functional execution, and information flow.

Responsibilities

  • Translate senior leadership decisions into coordinated action by clarifying decisions, identifying affected teams, sequencing communication, and tracking execution
  • Surface consequential questions, organizational constraints, and emerging risks early, and ensure appropriate leaders address them
  • Identify duplicated work, conflicting roadmaps, and cross-functional problems lacking clear ownership, then ensure resolution by the right teams
  • Own and continually improve the senior leadership team’s operating rhythm, including priority reviews, decision-making, and commitment tracking
  • Improve the quality and flow of information to and from the CEO
  • Lead a small number of CEO-priority efforts without a natural functional home through completion, partnering with accountable leaders

Requirements

  • 12+ years of experience across operations, business operations, strategy, general management, or a chief of staff function in high-growth technology environments
  • Prior experience as a CEO’s chief of staff, leading an integration or organizational transformation, or scaling operations through significant growth is a strong plus
  • Evidence of entrepreneurial ownership as a founder, early-stage operator, or internal builder who has led an ambiguous, high-stakes mandate from definition through execution
  • Track record of driving complex, cross-functional initiatives to completion without relying on direct authority, title, or headcount
  • Credibility, judgment, low ego, and ability to operate as an intellectual peer to senior executives, challenge the CEO, and deliver difficult messages directly
  • Exceptional written and verbal communication
  • Exceptional organization, resilience, discretion, and follow-through; ability to create structure amid ambiguity and changing priorities
  • Fluency using AI in your own work and a well-developed perspective on how AI should change the way a company like Thumbtack operates

Job type

Full Time

Experience level

Lead

Salary

CA$232,000 - CA$284,000 per year

Degree requirement

No Education Requirement

Location requirements

RemoteCanada

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