Chief of Staff – CEO

Thumbtack

. Translate senior leadership decisions into coordinated action by clarifying decisions, identifying affected teams, sequencing communication, and tracking execution .

Posted 10/8/2026full-timeRemote • United States, Canada, PhilippinesLead💰 $287,000 - $413,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in driving complex, cross-functional initiatives and improving operational efficiency in high-growth technology environments. Possesses strong leadership capabilities, exceptional communication skills, and the ability to navigate ambiguity while influencing senior executives.

Highest-signal resume keywords

12+ Years Experience In OperationsChief Of Staff ExperienceDriving Cross-Functional InitiativesExceptional Written And Verbal CommunicationFluency Using AI

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills

Business OperationsStrategy DevelopmentOrganizational TransformationIntegration LeadershipOperational Scaling

Soft Skills

CredibilityJudgmentResilienceDiscretionFollow-Through

Industry Keywords

High-Growth TechnologyCEO PrioritiesDecision-MakingCommitment TrackingAmbiguity Management

About the role

Key responsibilities & impact

Translate senior leadership decisions into coordinated action by clarifying decisions, identifying affected teams, sequencing communication, and tracking execution
Surface consequential questions, organizational constraints, and emerging risks early, and ensure appropriate leaders address them
Identify duplicated work, conflicting roadmaps, and cross-functional problems lacking clear ownership, then ensure resolution by the right teams
Own and continually improve the senior leadership team’s operating rhythm, including priority reviews, decision-making, and commitment tracking
Improve the quality and flow of information to and from the CEO
Lead a small number of CEO-priority efforts without a natural functional home, partnering with accountable leaders through completion

Requirements

What you’ll need

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 significant growth is a strong plus
Entrepreneurial ownership as a founder, early-stage operator, or internal builder who has led an ambiguous, high-stakes mandate from definition through execution
Track record of driving complex, cross-functional initiatives to completion without relying on direct authority, title, or headcount
Credibility, judgment, low ego, and ability to operate as an intellectual peer to senior executives
Ability to form and press a clear point of view, challenge the CEO, and deliver difficult messages directly
Exceptional written and verbal communication
Exceptional organization, resilience, discretion, and follow-through
Ability to create structure amid ambiguity and changing priorities
Fluency using AI in personal work
Well-developed perspective on how AI should change the way a company like Thumbtack operates

Benefits

Comp & perks

Remote work
Equal opportunity workplace
Reasonable accommodation for individuals with disabilities
Consideration of qualified applicants with arrest and conviction records consistent with applicable law