Chief of Staff – CEO

This is a fully remote position, open to applicants in United States, +2 more countries.

📋 Description

• Convert decisions made by senior leadership into coordinated actions by clarifying those decisions, identifying the teams impacted, sequencing communication, and monitoring execution.

• Identify critical questions, organizational limitations, and potential risks early on, ensuring that the appropriate leaders address them.

• Detect duplicated efforts, conflicting roadmaps, and cross-functional issues without clear ownership, then ensure resolution by the relevant teams.

• Take ownership of and continuously enhance the operating rhythm of the senior leadership team, which includes priority reviews, decision-making processes, and tracking commitments.

• Enhance the quality and flow of information between the CEO and other stakeholders.

• Spearhead a select number of CEO-priority initiatives that lack a natural functional home, collaborating with accountable leaders until completion.

⛳️ Requirements

• Over 12 years of experience in operations, business operations, strategy, general management, or a chief of staff role within high-growth technology settings.

• Previous experience as a chief of staff to a CEO, leading an integration or organizational transformation, or scaling operations during significant growth is highly advantageous.

• Demonstrated entrepreneurial ownership as a founder, early-stage operator, or internal builder who has navigated an ambiguous, high-stakes mandate from definition to execution.

• Proven track record of successfully driving complex, cross-functional initiatives to completion without relying on direct authority, title, or headcount.

• Possess credibility, sound judgment, a low ego, and the ability to operate as an intellectual peer to senior executives.

• Capable of forming and articulating a clear point of view, challenging the CEO, and delivering difficult messages directly.

• Exceptional written and verbal communication skills.

• Outstanding organizational skills, resilience, discretion, and follow-through.

• Ability to create structure in the midst of ambiguity and shifting priorities.

• Proficient in utilizing AI in personal work.

• Well-developed perspective on how AI should transform the operations of a company like Thumbtack.

🏝️ Benefits

• Remote work options available.

• Commitment to being an equal opportunity workplace.

• Provision of reasonable accommodations for individuals with disabilities.

• Consideration of qualified applicants with arrest and conviction records, in accordance with applicable law.