Clickup

Chief of Staff to the CEO

United States · Exec

Sponsorship not specifiedDetected 11 days ago

RESTAgentic AICadenceLeadershipCommunication

About the role

Join us and help redefine what's possible. 🚀 CHIEF OF STAFF TO THE CEO CLICKUP | SAN DIEGO, CA (REMOTE ELIGIBLE, US) THE COMPANY ClickUp is the everything app for work, and we're rewriting the rules of how companies operate. $300M+ ARR.
Pre-IPO. ~1,000 employees and 4,000+ AI agents running as one workforce.
We restructured around what our CEO calls the "100x org": fewer people, radically higher leverage per person, AI agents embedded at every layer of execution.

build AI-powered systems that make being in the details sustainable at scale.
You build the intelligence infrastructure so he shows up to every conversation, investor meeting, product review, and customer call as the most informed person in the room.
Your job is to build the information loops, agent-powered and human-curated, that keep him embedded in the landscape: competitive moves, market shifts, emerging technology, customer signal, analyst takes.
This company is on a path to IPO and the story we tell the board isn't just about numbers, it's about why we're building the defining company of the AI era.
That creates pressure.
ClickUp isn't just building a product.

You will personally operate at a level that would have required a team of ten three years ago.
You are the connective tissue between the CEO and the rest of the company.
You are an AI power user, full stop.
You can demonstrate this live in the interview.
You know when 80% is enough and when perfection is the only option.
You have high EQ and low ego.

There is a functioning CEO office running on AI-native systems and cadence that would be impossible to replicate manually.
People outside ClickUp ask how it works.
CEO's calendar reflects a deliberate shift toward product, external, and strategic time, while simultaneously being more in the details than before, not less.
At least 3 functions have undergone first-principles workflow redesign with measurable results: fewer people doing more, agents handling what used to be grunt work, leaders freed to think instead of operate.
The leadership team is more aligned, less bottlenecked, and permanently rewired to question why before asking how.
Board prep runs on rails.
The board narrative positions ClickUp as the defining AI-era company, because it is.
At least 3 major cross-functional initiatives shipped that would have otherwise stalled or died.

Stand up the operating rhythms of a company in hypergrowth: weekly leadership syncs, monthly business reviews, quarterly planning, annual strategy.

weekly leadership syncs, monthly business reviews, quarterly planning, annual strategy.
Define the formats, own the prep, drive the follow-through.
Most companies have this.
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. 🚀
CLICKUP | SAN DIEGO, CA (REMOTE ELIGIBLE, US)
ClickUp is the everything app for work, and we're rewriting the rules of how companies operate. $300M+ ARR.
While the rest of the industry debates whether AI will change how companies work, we already did it.
The Wall Street Journal, Forbes, and every major tech outlet covered it.
Not because it was controversial, but because nobody else had the conviction to actually do it.

Employer
ClickUp is an Equal Opportunity Employer, and qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, or national origin.
Visa Sponsorshi
ClickUp collects and processes personal data in accordance with applicable data protection laws.

This listing is sourced directly from Clickup's careers page and normalized into a canonical job model.