Chief of Staff (AI)

TL;DR

Chief of Staff (AI): Orchestrating the CEO's operating rhythm and driving an AI-native organizational transformation with an accent on first-principles workflow redesign and executive leverage. Focus on building AI-powered intelligence systems, managing board operations, and executing high-priority strategic programs in a hypergrowth SaaS environment.

Location: Remote (US), with regular travel to San Diego HQ

Salary: $175K – $275K

Company

ClickUp is an AI-native "everything app" for work, unifying tasks, docs, and chat to enable high-leverage organizations.

What you will do

• Design and implement AI-first operating rhythms (syncs, reviews, planning) to maximize CEO efficiency.
• Lead the AI transformation of all company functions, replacing legacy processes with agent-driven workflows.
• Architect an "intelligence layer" for the CEO to ensure sustainable access to critical company details.
• Manage board and investor operations, developing high-stakes narratives for a pre-IPO trajectory.
• Execute strategic programs, acting as the accountability layer between CEO priorities and shipment.
• Foster leadership team cohesion and refine internal communication and organizational narratives.

Requirements

• Must be based in the United States.
• 6+ years of experience in strategic operations, management consulting, or as a Chief of Staff.
• Proven track record as a right-hand to a founder-CEO in a company with 500-1,000+ employees.
• 3+ years of experience managing people and building elite teams.
• Expert-level AI power user capable of demonstrating AI-driven workflow automation.
• Deep familiarity with pre-IPO dynamics, governance, and investor relations.

Culture & Benefits

• Competitive base compensation and significant equity.
• Comprehensive US benefits including 401k, Health, Dental, and Vision insurance.
• Flexible paid time off and paid parental leave.
• Professional development and employee wellness stipends.
• High-leverage environment focused on first-principles thinking and extreme velocity.