AI-Driven Chief of Staff & Operating System Architect

ClickUp USA; San Diego (CA); On-site; USD 180,000 - 320,000; Full time

Job summary

ClickUp USA is seeking a 100x AI operator and Chief of Staff to be the connective tissue between the CEO and the leadership team. You will build the systems that keep the CEO in the details while accelerating the entire organization, across every function and decision.

You’ll own the CEO operating system, drive AI transformation, and design an intelligence layer that surfaces critical context before questions arise. This is the most strategic COS role in a fast-growing SaaS company.

Qualifications

• No years-of-experience requirement (though you’ve likely done 6+ years in strategic ops, consulting, or a prior COS role)
• No degree required (MBA is fine but irrelevant if the work speaks)
• No resume needed
• Chief of Staff title is the role, not a stepping stone to COO
• Only criteria: Leverage + Reinvention. That’s it.

Responsibilities

• Own CEO operating system: cadence, intelligence, accountability, board/exec reviews.
• Lead AI transformation across every function and build scaled agent-driven systems.
• Architect the intelligence layer that surfaces what matters before the CEO asks.
• Run the system that makes the CEO’s vision land in every department, week by week.

Job description

ClickUp USA is seeking a 100x AI operator and Chief of Staff to be the connective tissue between the CEO and the leadership team. You will build the systems that keep the CEO in the details while accelerating the entire organization, across every function and decision.

You’ll own the CEO operating system, drive AI transformation, and design an intelligence layer that surfaces critical context before questions arise. This is the most strategic COS role in a fast-growing SaaS company.