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Salary: USD 287,000 - 413,000 / annual
Thumbtack is a home services marketplace that helps millions of homeowners confidently care for their homes through personalized guidance, AI tools, and access to a network of 300,000 local service businesses.
As Chief of Staff to the CEO, you will serve as a second set of eyes on the entire business, closing the gap between leadership decisions and organizational execution. Operating across organizational boundaries with close visibility into strategy, tradeoffs, and implementation, you will work alongside the CEO and senior leadership team to drive company-wide priorities.
Key responsibilities include:
- Translating senior leadership decisions into coordinated action by clarifying decisions, identifying affected teams, sequencing communication, and tracking execution
- Surfacing consequential questions, organizational constraints, and emerging risks early, and ensuring appropriate leaders address them
- Identifying duplicated work, conflicting roadmaps, and cross-functional problems lacking clear ownership, then ensuring resolution by the right teams
- Owning and continuously improving the senior leadership team's operating rhythm, including how priorities are reviewed, decisions are made, and commitments are tracked
- Improving the quality and flow of information to and from the CEO so leaders have necessary context
- Leading a small number of CEO-priority efforts without a natural functional home, partnering with accountable leaders to completion
This is neither an administrative role nor a strategy-ownership position. You will sharpen and pressure-test the senior leadership team's direction while improving organizational execution.
REQUIREMENTS:
- 12+ years of experience across operations, business operations, strategy, general management, or 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, 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
- Exceptional written and verbal communication with ability to compress complexity into clear, actionable direction quickly
- Exceptional organization, resilience, discretion, and follow-through with 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
