Chief of Staff – CEO

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

📋 Description

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

• Highlight significant questions, organizational limitations, and emerging risks early on, ensuring that relevant leaders address them appropriately.

• Detect instances of duplicated efforts, conflicting roadmaps, and cross-functional issues that lack clear ownership, and facilitate their resolution by the appropriate teams.

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

• Enhance the quality and flow of information exchanged with the CEO.

• Lead a select few CEO-priority initiatives that do not have a designated functional area until their completion, collaborating with accountable leaders.

⛳️ 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 CEO’s chief of staff, leading an integration or organizational transformation, or successfully scaling operations during significant growth is a strong advantage.

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

• Proven ability to drive complex, cross-functional initiatives to completion without depending on direct authority, title, or headcount.

• Possess credibility, sound judgment, a low ego, and the capability to act as an intellectual peer to senior executives, challenge the CEO, and communicate difficult messages directly.

• Outstanding written and verbal communication skills.

• Exceptional organizational skills, resilience, discretion, and follow-through; adept at creating structure amidst ambiguity and shifting priorities.

• Proficient in utilizing AI in your own work and possess a well-formed perspective on how AI should influence the operations of a company like Thumbtack.

🏝️ Benefits

• Competitive salary and performance-based bonuses.

• Comprehensive health, dental, and vision insurance plans.

• Flexible work hours and remote work opportunities.

• Professional development and continuous learning opportunities.

• A vibrant company culture that promotes diversity and inclusion.