---
title: 'Chief of Staff to the CEO at Thumbtack'
canonical: 'https://feeny.ai/job/chief-of-staff-to-the-ceo-thumbtack-ontario-smzsvc1rr024'
type: 'job'
last_seen: '2026-10-15'
---

# Chief of Staff to the CEO at Thumbtack

- **Company:** Thumbtack
- **Location:** Ontario, Canada
- **Employment:** full-time
- **Work type:** remote
- **Posted:** 2026-10-08
- **Last confirmed live:** 2026-10-15
- **Apply:** https://jobs.ashbyhq.com/thumbtack/5e63219a-4949-44d5-b15e-a2657bc85ac3

## Job 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 Ontario and British Columbia, the expected salary range for the role is currently $232,000 - $284,000.

Actual offered salaries will vary and will be based on various factors, such as calibrated job level, qualifications, skills, competencies, and proficiency for the role. Thumbtack embraces diversity. We are proud to be an equal opportunity workplace and do not discriminate on the basis of sex, race, color, age, pregnancy, sexual orientation, gender identity or expression, religion, national origin, ancestry, citizenship, marital status, military or veteran status, genetic information, disability status, or any other characteristic protected by federal, provincial, state, or local law. We also will consider for employment qualified applicants with arrest and conviction records, consistent with applicable law. Thumbtack is committed to working with and providing reasonable accommodation to individuals with disabilities. If you would like to request a reasonable accommodation for a medical condition or disability during any part of the application process, please contact: recruitingops@thumbtack.com. For information about how Thumbtack collects, uses, and shares personal information about job applicants, please see our [Job Applicant Privacy Policy](https://www.thumbtack.com/job-applicant-privacy-policy). We put as much craftsmanship into candidate safety as we do into the hiring experience itself. While scammers may try to impersonate our team, we’ll never ask you for money, banking info, or SSNs during hiring. [Check out our blueprint on how to spot the fakes.](https://careers.thumbtack.com/recruiting-scams)

## About Thumbtack

## Company Overview
- **One-liner**: Thumbtack is a technology platform that connects homeowners with local service professionals for home repairs, maintenance, and improvements, while providing AI-powered tools and guidance.
- **Entity Type**: Private (Series E, $774.4M total funding)
- **Headquarters**: San Francisco, California, United States
- **Founded**: 2008
- **Founders**: Marco Zappacosta, Jonathan Swanson, Sander Daniels

## Core Business
- **Primary industry/industries**: Home Services Marketplace, Software Development
- **Target customers**: B2C (homeowners) and B2B (local service professionals, SMBs)
- **Mission or purpose statement**: To help millions of people confidently care for and improve their homes, while empowering local professionals to turn their talents into thriving businesses.

## Products & Services
- **Thumbtack Platform**: A mobile app and website where homeowners can find, compare, and book local pros for home services across 500+ project categories. Includes personalized guidance, AI tools, and a best-in-class hiring experience.
- **Pro Tools**: A suite of business management tools for the 300,000+ local service businesses on the platform, helping them find profitable jobs, manage bookings, and grow their operations.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed (last reported valuation of $1.7B in 2021 per secondary market data)
- **Key Metric**: Annual Revenue of $300M (LinkedIn estimate); Total Funding of $774.4M
- **Notable Investors/Partners**: Sequoia Capital, Tiger Global Management, Javelin Venture Partners, Baillie Gifford, CapitalG
- **Growth Signals**: Over 12 million 5-star projects completed; 90 million+ projects started on the platform; 1,109 employees (+17.2% YoY); operates in 13 countries; acquired Setter (2020); the home services industry is less than 10% penetrated online, representing a $600B market opportunity.

## Competitive Advantages
- **Scale and Trust**: With over 12 million 5-star reviews and 300,000+ pros, Thumbtack has built a trusted, nationwide network that is difficult for new entrants to replicate.
- **Data and AI Moat**: The company is investing heavily in AI-native tools (e.g., AI-powered Marketing Analytics Agent) to improve matching, personalization, and operational efficiency for both homeowners and pros.
- **Dual-Sided Network Effects**: More homeowners attract more pros, and better pro tools attract more homeowners, creating a self-reinforcing growth loop.

## Strategic Focus
- **AI-First Transformation**: Thumbtack is rethinking workflows across the company, reducing repetitive tasks, and exploring how AI can improve day-to-day operations for both employees and users.
- **Expanding the "Home Care" Ecosystem**: Moving beyond a simple marketplace to become a comprehensive home care platform that provides guidance, AI tools, and a seamless hiring experience.
- **Virtual-First Talent Strategy**: Building a distributed workforce across the U.S., Canada, and the Philippines to access top talent while maintaining in-person connection through offsites and events.

## Why Work Here
- **Culture**: 94% of employees rate Thumbtack a great place to work. The company emphasizes a "virtual-first, not virtual-only" model, offering flexibility with opportunities for in-person connection.
- **Benefits**: $1,000 USD remote work support stipend (paid semi-annually), professional coaching via BetterUp, mental health resources from Modern Health and Therify, 12 weeks paid parental leave for all parents (birthing parents get 8 additional weeks), generous fertility benefits, flexible PTO, and 18 companywide holidays including a week-long end-of-year shutdown.
- **Engineering Culture**: Strong focus on data and AI, with engineers working at the intersection of these fields to solve real business problems. The company is "nimble enough to ensure your work is making an impact."
- **Remote Policy**: Virtual-first, with the ability to work from anywhere in the United States, Ontario/British Columbia (Canada), or the Philippines.
- **Employee Rating**: 4.1/5.0 on LinkedIn (682 reviews), with high marks for Work-Life Balance (4.2) and Culture (4.0).

## Sources
1. [thumbtack.com](https://www.thumbtack.com/about)
2. [careers.thumbtack.com](https://careers.thumbtack.com/)
3. [linkedin.com](https://www.linkedin.com/company/thumbtack-inc.)
4. [jobs.ashbyhq.com](https://jobs.ashbyhq.com/thumbtack)
5. [careers.thumbtack.com/jobs](https://careers.thumbtack.com/jobs)

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