Chief of Staff to the CEO

About this role

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. 🚀

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. While the rest of the industry debates whether AI will change how companies work, we already did it. 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. 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.

Our CEO also serves as de facto Chief Product Officer. He lives inside the product, talks to customers daily, and his morning briefing comes from an AI agent, not a person. He's building the future of work software while simultaneously running the company on it. That's not hyperbole. It's Tuesday.

WHY THIS ROLE EXISTS

We're not hiring a Chief of Staff because it's time to "professionalize." We're hiring one because the most intense, most product-obsessed, most in-the-details CEO in SaaS needs a force multiplier who operates at his frequency.

Here's what separates this from every other COS role on the market: you will be the living proof that AI changes what one person can do. Not comfortable with AI. Not "leaning into" AI. Weaponized by it. You will personally operate at a level that would have required a team of ten three years ago. And then you'll walk into every function in this company and demand they do the same, starting from the question: why does this process exist in the first place?

This is the most leveraged non-CEO seat in a company that's setting the pace for the entire industry. If that doesn't get your blood moving, this isn't for you.

THE JOB

You are the connective tissue between the CEO and the rest of the company. Part operator, part strategist, part translator, part architect of a new way of working that the rest of the industry will eventually copy. You make the CEO faster, the leadership team more aligned, and the company more coherent in execution, at a scale that's only possible because you refuse to do anything the old way.

Operating System Design

Stand up the operating rhythms of a company in hypergrowth: weekly leadership syncs, monthly business reviews, quarterly planning, annual strategy. Define the formats, own the prep, drive the follow-through. Most companies have this. We don't. You build it, and you build it AI-first from day one: automated briefings, agent-driven prep, real-time synthesis. If a human is doing something a well-orchestrated agent could handle, you've failed.

AI Transformation Leadership

This is the defining mandate of the role. You are the CEO's partner in pushing every single function to ask: why do we do this at all? Not optimization. Not automation of the existing. Total reinvention from first principles. You will challenge leaders to decompose their workflows from scratch, identify what should be done by agents, what should be eliminated entirely, and what requires genuinely irreplaceable human judgment. ClickUp is leading an industry-wide shift in how companies operate. You are the internal engine making sure we stay years ahead of everyone else.

CEO Intelligence Layer

The CEO wants to be in the details of everything. Most advisors would tell him to zoom out. We're going the other direction: build AI-powered systems that make being in the details sustainable at scale. You decide what he sees, when, and in what format. You architect the filtering system that ensures signal over noise. 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.

Industry & Competitive Immersion

ClickUp's CEO doesn't follow industry trends. He sets them. 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. When he speaks publicly, he's three moves ahead of every other CEO on stage. That doesn't happen by accident. It happens because you built the system that makes it effortless.

Strategic Program Execution

The CEO generates priorities faster than any single function can absorb them. You intake those priorities, scope them, assign ownership, track progress, and ensure they land. You are the accountability layer between "Zeb said we should do X" and "X shipped." Not X is in progress. Shipped.

Board & Investor Operations

Own the preparation cycle for board meetings: narrative development, data assembly, materials review, dry runs. 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. You make that narrative tight, board-grade, and undeniable.

Cross-Functional Reinvention

Be the escalation point for work that sits between teams. But more importantly: be the person who walks into any function and asks "why does this process exist?" When the answer is "because it always has," you help them kill it and rebuild it from zero. You are the forcing function for first-principles thinking. Every function should be slightly uncomfortable with how much you're pushing them to rethink, and grateful a year later when they're operating at 10x their previous output.

Leadership Team C

Similar jobs

• Chief of Staff to the CEO — Nooks · San Francisco
• Chief of Staff to the CEO — Homevision · San Francisco
• Chief of Staff to CEO — Hike-medical · San Francisco, CA
• Chief of Staff to CEO — Employerdirecthealthcare · Dallas, Texas, United States
• Chief of Staff to Chief Executive Officer (CEO) — Accuweather · State College, PA
• Chief of Staff to the Chief Executive Officer — Agilityrobotics · Hybrid- Fremont, CA
• Chief of Staff, CEO — Handshake · San Francisco, CA
• Chief of Staff, CEO — Depthfirst · San Francisco