Chief of Staff to the CEO

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ThumbtackHome services technology
Location: Remote, United StatesFull-TimeSenior
Salary287,000 - 351,000 USD per year
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Job Details

Experience
12+ years of experience
Required Skills
Artificial IntelligenceStrategyBusiness Operations

Requirements

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

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 persist until the appropriate leaders address them.
  • Identify duplicated work, conflicting roadmaps, and cross-functional problems without clear ownership, then ensure the right teams resolve them.
  • 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 so leaders have the context they need to act.
  • Lead a small number of CEO-priority efforts without a natural functional home, partnering with accountable leaders to move them through completion.
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287,000 - 351,000 USD per year
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