100x Operator - Chief Operating Officer

At ClickUp, we're building the future of work: the first truly converged AI workspace unifying tasks, docs, chat, calendar, and enterprise search, all supercharged by context-driven AI. We are an AI-native company. Every team member is expected to leverage AI daily, and we evaluate AI fluency as part of our hiring process. Join us and help redefine what's possible. 🚀

FROM ZEB EVANS, CEO

WE'RE EXECUTING ON THE 100X ORG.

I'm looking for a 100x AI operator and COO to own the operational backbone that makes ClickUp scale. One person who builds, and improves the systems that make an entire company run at 100x speed, and reviews everything with the rigor to know when something is actually working versus when people are just going through the motions.

We call this person an Artisan.

WHAT IS AN ARTISAN?

An Artisan is 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.

Taste: They know what a well-running system looks like before it exists. They can look at 10 operational processes and immediately identify which 2 are actually driving results and which 8 are theater.

Judgment: They know what to build, not just how. They understand the business deeply enough to make high-stakes calls about what to automate, what to kill, and where humans still need to be in the loop.

Speed of orchestration: They don't just "implement tools." They operate AI systems like instruments: building accountability loops, automating reporting, creating self-healing processes.

Ownership breadth: An Artisan owns a surface end to end. Not "the ops part" or "the analytics part." The WHOLE operational machine: systems, accountability, execution, quality. Fewer people means fewer handoffs. Fewer handoffs means the company moves faster.

THE ONLY TWO THINGS THAT MATTER

01: Systems - Can you build operational systems that scale a business?

Not "implement a new tool." BUILD and ITERATE on the SYSTEM. AI agents that run operational cadences. Workflows that handle pricing, reporting, planning, vendor management at scale. Accountability systems that surface when something is off BEFORE it becomes a crisis. Systems that get better every week because they learn from the data and the feedback loop YOU create.

02: Review - Can you hold an absurdly high bar for operational excellence?

Can you look at a dashboard and know instantly whether the numbers are real or whether someone is gaming the metric? Can you review an agent's output and know whether it actually moved the business or just produced activity? Your judgment IS the quality bar. You hold PEOPLE accountable. And you ensure people are holding AGENTS accountable. The entire accountability chain runs through you.

WHAT YOU MAY OWN

• Pricing & packaging strategy and governance

• Data, analytics, and BI (you own the scorecard)

• Customer support & technical support operations

• Business systems & internal AI infrastructure

• Cross-functional PMO and strategic initiative execution

• Operational planning cadence (AOP, QBRs, H1/H2 planning)

• Talent systems, org design, and performance management at scale

• Vendor strategy and procurement

• Pre-IPO operational readiness

• Growth marketing

• 100x org concept: ownership and implementation of the 100x organizational model

• Merit-based rewards and compensation systems

• Company-wide communications: all hands, town halls, org-wide visibility

You build systems that run all of this. You are the judgment. The agents and the teams are the execution. This is what an AI-native COO looks like.

You'll be heavily in front of the company. All hands, leadership forums, accountability reviews. This isn't a back-office role. You're the operational face of how we run.

WHY THIS IS THE BEST OPERATIONS JOB ON EARTH

ClickUp is a $4B company with 3,000+ internal AI agents already running. Our product IS the convergence of context. 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 literally ANY function, ANY system. Growth ops, customer ops, finance ops, people ops, all of it. The operational surface area is massive. You're not running one department. You're running the machine that makes EVERY department work.

You'll have:

• Direct reporting to the CEO (me). No layers. No politics.

• Authority to redesign any process, kill any meeting, automate any workflow

• Access to every piece of company context for your AI systems

• $1M comp growth path

• The most interesting AI-native operations challenge that exists right now

No gates. Only signal.

• No years-of-experience requirement

• No degree required

• No resume needed

• COO title is the role (this isn't a stepping stone)

• Only criteria: Systems + Review. That's it.

HOW TO APPLY

No resume. No cover letter. Record two short videos (Loom, Clip, or whatever you prefer) and show us the work.

Video 1: Show us an operational system you built that scales a business function. Walk us through it. What does it take in? What does it output? How does it hold people accountable without you manually chasing them?

Video 2: Show us how you handle accountability when output quality drops. How do you know something is off? What do you do about it? How do you make sure the system (or the person) doesn't repeat the failure?

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 https://x.com/DJ_CURFEW/status/2057522382315929802

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