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 • Canada, Philippines, United StatesLead💰 CA$232,000 - CA$284,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive experience in operations and strategy within high-growth technology environments, with a strong focus on leading cross-functional initiatives and improving organizational effectiveness. Proven ability to communicate effectively with senior leadership and drive complex projects to completion in ambiguous settings.

Highest-signal resume keywords

12+ Years Experience In OperationsChief Of Staff ExperienceCross-Functional Initiative LeadershipExceptional Written And Verbal CommunicationFluency In AI Applications

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Operations ManagementBusiness StrategyOrganizational TransformationProject ManagementDecision-MakingCommitment TrackingIntegration LeadershipConflict ResolutionAmbiguity ManagementExecution Tracking

Soft Skills

CredibilityJudgmentResilienceDiscretionFollow-Through

Industry Keywords

High-Growth TechnologyCEO PrioritiesOrganizational ConstraintsEmerging RisksEntrepreneurial Ownership

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 through completion, partnering with accountable leaders

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
Evidence of 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, 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 your own work and a well-developed perspective on how AI should change the way a company like Thumbtack operates