About this opportunity
ClickUp USA lists this 100x Operator, Chief Of Staff opportunity in san diego, California. Review the employer’s description below for duties, qualifications and application requirements.
Job description
The force multiplier that keeps the CEO in every detail while making the entire leadership team faster.
I’m looking for a 100x AI operator and Chief of Staff to be the connective tissue between me and the rest of the company. One person who builds the systems that keep me in the details of everything while simultaneously making the entire leadership team faster, more aligned, and permanently rewired to question why before asking how.
We call this person an Artisan .
01Taste
They know what a well-running CEO office looks like before it exists. They can look at 10 processes touching the CEO and immediately identify which 2 are creating leverage and which 8 are wasting his time.
02Judgment
They know what the CEO needs to see, when, and in what format. They understand the business deeply enough to filter signal from noise and architect the intelligence layer that makes being in every detail sustainable at scale.
03Speed of orchestration
They don’t just “support the CEO.” They operate AI systems like instruments: automated briefings, agent-driven prep, real-time synthesis. If a human is doing something a well-orchestrated agent could handle, they’ve failed.
04Ownership breadth
An Artisan owns a surface end to end. Not “the scheduling part” or “the board prep part.” The WHOLE CEO operating system: cadence, intelligence, accountability, narrative. Fewer people means fewer handoffs. Fewer handoffs means the company moves faster.
The bar
The only two things that matter
01 Leverage
Can you make a founder-CEO 10x faster while keeping him more in the details?
Not “manage the calendar.” BUILD and ITERATE on the SYSTEM. AI-native operating rhythms. Agent-powered intelligence loops that surface what matters before he asks. Accountability chains that ensure “Zeb said do X” becomes “X shipped,” not “X is in progress.” Systems that turn one CEO into a presence in every function, every decision, every product detail, without burning out or losing depth.
Can you walk into any function and ask “why does this exist?”
Can you look at a team’s workflow and know instantly whether it was designed from first principles or inherited from 2019? Can you decompose a process from scratch and identify what should be done by agents, what should be eliminated entirely, and what requires genuinely irreplaceable human judgment? Your conviction IS the transformation engine. You push every leader to rethink why before asking how. The entire AI transformation of this company runs through you.
The surface
What you may own
CEO operating system: weekly syncs, monthly business reviews, quarterly planning, annual strategy
AI transformation leadership across every function
CEO intelligence layer: competitive, market, customer, and internal signal
Strategic program execution and cross-functional accountability
Board and investor operations, narrative development, and IPO readiness
Leadership team cohesion and alignment
Internal communications: all-hands narrative, org-wide memos, strategic context
Cross-functional reinvention: first-principles workflow redesign across teams
Industry and competitive immersion systems
You build the systems that make the CEO and the entire leadership team move at 100x speed. You are the judgment; the agents are the execution. You’ll be in every room that matters: board meetings, leadership forums, product reviews, investor conversations. This isn’t a back-office role. You’re the operational brain behind how the CEO runs.
The opportunity
Why this is the highest-leverage non-founder seat in SaaS
$4B
company scale you’ll operate at the center of
4,000+
AI agents already running as one workforce
$500K+
ClickUp is a $4B company with 4,000+ internal AI agents running. Our product IS the convergence of context, meaning you have total context on everything happening in the company, available to your AI systems.
We’re building a 100x software framework where you can operate as the CEO’s force multiplier across literally every function. You’re not running one department. You’re running the system that makes the CEO’s vision land in every department, every week.
You’ll have
Direct reporting to the CEO (me). No layers. No politics.
Visibility into every decision before it’s made.
Authority to challenge any process, kill any meeting, redesign any workflow.
Access to every piece of company context for your AI systems.
The most interesting AI-native Chief of Staff challenge that exists right now.
The filter
No gates.
Only signal.
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.
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Worksite address
san diego, CA, 92189, US
Who can apply
Review the original listing for work authorization, qualifications and employer requirements.