Thumbtack is a U.S. marketplace and SaaS company that helps homeowners find and hire local professionals for repairs, maintenance, remodeling, and other home projects. Customers can describe what they need, compare providers across trades, review ratings and cost estimates, and communicate through the platform. Thumbtack also offers professionals software, resources, community support, and tools for managing leads and reviews. Its consumer and pro experiences are supported by practical project guidance, cost information, and home maintenance planning.
Chief of Staff to the CEO at Thumbtack
Partner with Thumbtack’s CEO to turn leadership decisions into coordinated action. Strengthen company-wide operating rhythms and resolve cross-functional priorities at this home services marketplace.
Canada
Philippines
United States$287,000 – $413,000 / year
RemoteFull-timeLeadEnglish RequiredChief of StaffDescription
- Turn senior leadership decisions into coordinated action by clarifying outcomes, engaging affected teams, sequencing communication, and tracking follow-through
- Raise consequential questions, organizational constraints, and emerging risks early so the appropriate leaders can address them
- Find duplicated work, conflicting roadmaps, and cross-functional issues without clear owners, then guide them to resolution by the right teams
- Run and continuously improve the senior leadership team’s operating cadence, including priority reviews, decision-making, and commitment tracking
- Strengthen the quality and flow of information to and from the CEO
- Drive a small portfolio of CEO-priority initiatives without a natural functional home, working with accountable leaders through completion
Requirements
- Bring at least 12 years of experience in operations, business operations, strategy, general management, or a chief of staff role in high-growth technology environments
- Experience serving as a CEO’s chief of staff, leading an integration or organizational transformation, or scaling operations through substantial growth is a strong advantage
- Show entrepreneurial ownership as a founder, early-stage operator, or internal builder who has taken an ambiguous, high-stakes mandate from definition through execution
- Demonstrate success delivering complex cross-functional initiatives without relying on direct authority, title, or headcount
- Bring credibility, sound judgment, humility, and the ability to engage senior executives as an intellectual peer
- Form and advocate a clear point of view, challenge the CEO when needed, and deliver difficult messages directly
- Communicate exceptionally well in writing and conversation
- Show exceptional organization, resilience, discretion, and follow-through
- Create structure in ambiguous situations and as priorities change
- Use AI fluently in your own work
- Have a well-developed view of how AI should change the way a company like Thumbtack operates
Benefits
- Remote work
- Equal opportunity workplace
- Reasonable accommodation for people with disabilities
- Qualified applicants with arrest or conviction records are considered in accordance with applicable law