100x Operator, Chief Of Staff

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

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 .

• 01

  Taste

  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.

• 02

  Judgment

  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.

• 03

  Speed 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.

• 04

  Ownership 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.