Chief of Staff to the CEO (Remote) at Thumbtack

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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.

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.

Benefits & Perks

Health & Wellness

Health Insurance

Medical coverage is part of Thumbtack's benefits package, which the company notes varies by location.

Dental Insurance

Dental coverage includes a PPO plan option.

Vision Insurance

Life Insurance

Life insurance includes AD&D coverage, and supplemental life insurance is also available.

Disability Insurance

Coverage includes both short-term and long-term disability insurance.

Health Savings Account (HSA)

Flexible Spending Account (FSA)

Mental Health Benefits

Through Modern Health, employees and their dependents get 12 coaching sessions and 12 therapy sessions a year plus on-demand group sessions. Therify adds access to multicultural and diverse therapists.

Employee Assistance Program

Thumbtack's employee assistance program is delivered through Modern Health and supports mental health and well-being.

Financial

401(k) / Retirement Plan

Thumbtack's retirement plan includes both traditional and Roth 401(k) options.

Pay Transparency

Most Thumbtack job postings publish salary ranges, with US roles priced across three geographic pay tiers.

Equity / RSUs

Time Off

Paid Holidays

Employees get 18 companywide holidays, including a week-long end-of-year company shutdown.

Company Shutdown Days

The whole company takes a week-long shutdown at the end of each year, counted within its companywide holidays.

Flexible Schedule

Thumbtack works asynchronously across time zones but expects employees to be available during core synchronous collaboration hours of 9 a.m. to 3 p.m. PT.

Bereavement Leave

Remote & Equipment

Internet Stipend

Thumbtack reimburses wifi and cell phone expenses for employees in North America.

Company Offsites / Retreats

Every role includes travel to in-person gatherings: service and support staff 1-2 times a year, corporate individual contributors and managers 2-3 times, and leaders 4-6 times.

WFA Allowance (Days/Year)

Employees may work internationally for up to 60 days per country per calendar year, with no more than 15 consecutive days outside the Americas.

Family & Care

Parental Leave

In the US and Canada, all parents receive up to 12 weeks of 100% paid parental leave and birthing parents receive 8 additional weeks, for 20 weeks in total. Birthing parents in the Philippines receive 105 days of paid parental leave.

Fertility Benefits

Thumbtack offers fertility and family-forming benefits as part of its support for growing families.

Professional Growth

Learning & Development Budget

Employees receive a $1,000 USD ($1,400 CAD; PHP 46,600) annual stipend, paid semi-annually, for professional development, conferences and self-care. BetterUp professional coaching is also available.

Culture & Perks

Employee Resource Groups

Thumbtack runs ERGs in North America and the Philippines, including a Parents ERG and an Immigrants ERG.

Employee Recognition Awards

Thumbtack's Values Awards recognize employees who embody the company values, with prizes for winners.

Team Events & Social Budget

Employees connect through more than 30 Local Communities across the U.S., Canada and the Philippines.

Employee Product Discount

Frequently Asked Questions

Which countries does Thumbtack hire in?

Thumbtack's careers site says it hires for virtual roles in the US, Canada and the Philippines. In Canada, its people work from Ontario and British Columbia.

Can I work from another country for a while?

Yes, within limits. Thumbtack's virtual-first page asks employees to limit stays to 60 days per country per calendar year, and to spend no more than 15 calendar days in a row outside of the Americas.

How much travel does a Thumbtack role involve?

Travel is required for every role. The careers FAQ says service and support professionals travel 1 to 2 times per year, corporate individual contributors and managers 2 to 3 times per year, and leaders 4 to 6 times per year. Another section of the same site says 1 to 2 events for individual contributors and 3 to 6 for managers, so confirm the expectation for your specific role during interviews.

What benefits does Thumbtack highlight?

Thumbtack's careers site lists a remote work stipend of $1,000 USD a year (with local equivalents in Canada and the Philippines), paid semi-annually, for professional development, conferences and self-care. It also lists flexible PTO with 18 companywide holidays, including a week-long end-of-year shutdown; 20 weeks of 100% paid parental leave for birthing parents in the US and Canada (12 weeks for all parents), and 105 days for birthing parents in the Philippines; Modern Health coaching and therapy sessions for employees and dependents, plus Therify and BetterUp coaching; and a quarterly stipend in Thumbtack Bucks to book a pro. Benefits vary by location.

Does pay at Thumbtack depend on where I live?

Yes. Thumbtack's US job postings use three geographic pay tiers: the first covers the SF Bay Area, San Jose, New York City and Seattle; the second covers Austin, DC, California, Massachusetts, New Jersey and Washington; the third covers the rest of the US. US and Canadian postings include a salary range, so you can see the pay for a role before you apply.

What should I know about Thumbtack's hiring process?

Thumbtack's postings note that the company uses AI tools to support resume screening. Its recruiting team says it will only contact active candidates from verified company accounts and name@thumbtack.com email addresses, and the careers site keeps a dedicated page on recruiting scams, so treat outreach from any other address with suspicion.