100x Operator - Chief Operating Officer

ClickUp

1d•$500,000 - $1,000,000

About The Position

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

Requirements

AI fluency is expected and evaluated.
Ability to build and improve systems that make an entire company run at 100x speed.
Rigor to know when something is actually working versus when people are just going through the motions.
Refined taste and judgment to orchestrate AI systems at hyperspeed while maintaining quality.
Ability to identify which operational processes are driving results and which are theater.
Ability to make high-stakes calls about what to automate, what to kill, and where humans need to be in the loop.
Ability to operate AI systems like instruments: building accountability loops, automating reporting, creating self-healing processes.
Ability to own a surface end to end: systems, accountability, execution, quality.
Ability to build operational systems that scale a business.
Ability to build and iterate on AI agents that run operational cadences.
Ability to build workflows that handle pricing, reporting, planning, vendor management at scale.
Ability to build accountability systems that surface issues before they become a crisis.
Ability to create feedback loops for systems to learn and improve.
Ability to hold an absurdly high bar for operational excellence.
Ability to instantly know whether dashboard numbers are real or being gamed.
Ability to review an agent's output and know whether it actually moved the business or just produced activity.
Ability to hold people accountable and ensure people are holding agents accountable.
Direct reporting to the CEO.
Authority to redesign any process, kill any meeting, automate any workflow.
Access to every piece of company context for AI systems.
No years-of-experience requirement.
No degree required.
No resume needed.
Only criteria: Systems + Review.

Nice To Haves

Experience with AI-native operations.
Experience with a $4B company.
Experience with 3,000+ internal AI agents.

Responsibilities

Build and improve systems that make an entire company run at 100x speed.
Review operational processes to identify what is working versus what is theater.
Orchestrate AI systems at hyperspeed while maintaining quality.
Build accountability loops, automate reporting, and create self-healing processes.
Own the entire operational machine: systems, accountability, execution, quality.
Build operational systems that scale a business.
Build and iterate on AI agents that run operational cadences.
Build workflows that handle pricing, reporting, planning, vendor management at scale.
Build accountability systems that surface issues before they become a crisis.
Ensure systems get better every week by learning from data and feedback loops.
Hold an absurdly high bar for operational excellence.
Determine if dashboard numbers are real or being gamed.
Review agent output to determine if it moved the business or just produced activity.
Hold people accountable and ensure people are holding agents accountable.
Own pricing & packaging strategy and governance.
Own data, analytics, and BI (scorecard).
Own customer support & technical support operations.
Own business systems & internal AI infrastructure.
Own cross-functional PMO and strategic initiative execution.
Own operational planning cadence (AOP, QBRs, H1/H2 planning).
Own talent systems, org design, and performance management at scale.
Own vendor strategy and procurement.
Own pre-IPO operational readiness.
Own growth marketing.
Own the 100x org concept: ownership and implementation of the 100x organizational model.
Own merit-based rewards and compensation systems.
Own company-wide communications: all hands, town halls, org-wide visibility.
Be the judgment for AI systems and agents.
Be heavily in front of the company, acting as the operational face.
Operate any function or system (growth ops, customer ops, finance ops, people ops).
Run the machine that makes every department work.