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Salary: CAD 232,000 - 284,000 / annual
Thumbtack is a marketplace platform that helps millions of homeowners care for their homes by connecting them with local service professionals. The company operates across the U.S. with a community of 300,000+ service businesses and provides personalized guidance, AI tools, and a hiring experience for home projects.
The Office of the CEO works across Thumbtack's most important company-wide priorities alongside the CEO and senior leadership team. As Chief of Staff to the CEO, you will serve as a second set of eyes on the whole business, closing the gap between leadership decisions and organizational action.
Key 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 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 how priorities are reviewed, decisions are made, and commitments are tracked
- Improve the quality and flow of information to and from the CEO so leaders have necessary context
- Lead a small number of CEO-priority efforts without a natural functional home, partnering with accountable leaders
This is neither an administrative role nor the owner of company strategy. You will sharpen and pressure-test the senior leadership team's direction while improving how the company acts on it.
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 ambiguous, high-stakes mandates 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 well-developed perspective on how AI should change the way a company like Thumbtack operates
