ClickUp is hiring
The force multiplier that keeps the CEO in every detail while making the entire leadership team faster.
$250K – $1Mtotal compensation
From the CEOWe’re executing on the 100x org.
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.
The standard
Not just “a good operator.” An Artisan is someone whose taste and judgment are so refined that they can orchestrate AI systems at hyperspeed while maintaining quality that lesser teams can’t achieve at any speed.
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.
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.
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.
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
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 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.
Sound like you?
The surface
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
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
The filter
The application
No resume. No cover letter. Record two short videos (Loom, Clip, or whatever you prefer) and show us the work.
Show us how you’ve created leverage for a CEO or senior leader using AI-native systems.
Walk us through it. What did you build? What does the CEO see vs. not see? How does the system keep them in the details without drowning them?
Show us how you’ve led a first-principles reinvention of a function or workflow.
What did you challenge? What did you kill? What did you rebuild? How did you push people past the discomfort of dismantling what they knew?
If you get it, you get it.
If this posting confuses you, it’s not for you.
Zeb Evans
Founder & CEO, ClickUp
Read the original post that started it all: May 21 on X
