# Chief of Staff to the CEO at Thumbtack

Thumbtack is hiring a Chief of Staff to the CEO for a remote role open to applicants in Canada. It pays $232k-$284k a year and Level rates it Little AI ●○○○; you can [apply on Level](https://jobsbylevel.com/go/979ce5ac-ed17-49f7-9c56-a490308e6baf).

AI Level 1, AI centrality 24 out of 100. Remote (Remote, Ontario).

## Details

- Company: [Thumbtack](https://jobsbylevel.com/companies/thumbtack)
- AI level: AI Level 1 (score 24 out of 100)
- Location: Remote (Remote, Ontario)
- Salary: $232k-$284k
- Posted: October 8, 2026
- Apply: https://jobsbylevel.com/go/979ce5ac-ed17-49f7-9c56-a490308e6baf

## Description

Thumbtack helps millions of people confidently care for their homes. Thumbtack is the one app you need to take care of and improve your home — from personalized guidance to AI tools and a best-in-class hiring experience. Every day in every county of the U.S., people turn to Thumbtack to complete urgent repairs, seasonal maintenance and bigger improvements. We help homeowners know which projects to do, when to do them and who to hire from our growing community of 300,000 local service businesses. If making an impact inspires you, join us. Imagine what we’ll build together. 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

The description is cut here. Read the full offer: https://jobsbylevel.com/jobs/chief-of-staff-to-the-ceo-at-thumbtack-a8e0b1

Source: https://jobsbylevel.com/jobs/chief-of-staff-to-the-ceo-at-thumbtack-a8e0b1

## Cite this page

Level. https://jobsbylevel.com/jobs/chief-of-staff-to-the-ceo-at-thumbtack-a8e0b1.

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