Chief of Staff to the CEO

About the Office of the CEO

The Office of the CEO works across Thumbtack’s most important company-wide priorities alongside the CEO, senior leadership team, and the leaders accountable for delivering them. It operates across organizational boundaries, with a close view of the strategy being set, the tradeoffs being made, and how decisions are being implemented. Deliberately small, the team creates leverage through judgment, access, and the ability to help the company move with greater clarity and speed.

About the role

As Chief of Staff to the CEO, you will be a second set of eyes on the whole business and close the gap between leadership decisions and organizational action. You will identify consequential questions, emerging risks, and conflicts across teams early, form a point of view, and ensure they are addressed by the right leaders. You will also help the company act on leadership decisions quickly, consistently, and with clear ownership. 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.

What you’ll do

• Translate senior leadership decisions into coordinated action by clarifying what was decided, identifying the teams affected, 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 that lack clear ownership, then ensure they are resolved 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 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.

In order to be successful, you must bring

• 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 a significant period of growth is a strong plus.
• Evidence of entrepreneurial ownership, whether as a founder, early-stage operator, or internal builder who has led an ambiguous, high-stakes mandate from definition through execution.
• A track record of driving complex, cross-functional initiatives to completion without relying on direct authority, title, or headcount.
• The 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 the ability to compress complexity into clear, actionable direction quickly.
• Exceptional organization, resilience, discretion, and follow-through, with the 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.

Expected salary ranges

• For candidates living in Ontario and British Columbia, the expected salary range for the role is currently $232,000 - $284,000.