Chief of Staff to the CEO

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 Cohesion

Monitor the health of the executive team's operating dynamic. Surface misalignment early. Facilitate resolution. This is a founder-led company moving at founder speed. That creates pressure. Your job is to ensure the leadership team channels that pressure into momentum, not friction.

Internal Communications & Narrative

ClickUp isn't just building a product. We're demonstrating a thesis about how companies will work for the next twenty years. The 100x org isn't a tagline, it's an operating model, and you own making sure the internal narrative matches the external ambition. Shape how the CEO communicates with the company. Draft all-hands talking points, org-wide memos, strategic context. Make every employee understand they're part of something that's reshaping their industry.

What You're Measured On

After one year:

• 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.

• ClickUp is cited externally as the case study for how a company actually operates in the AI era, and your work is a meaningful reason why.

Who Thrives Here

• You've operated at the right hand of a founder-CEO before, in a company with 500+ employees, ideally 1,000+. You know the difference between supporting a CEO and creating leverage for one.

• You've built operating cadences and structures, not inherited them.

• You have 6+ years in strategic operations, management consulting, or a prior Chief of Staff role. An MBA is fine but irrelevant if the work speaks for itself.

• You've managed people (3+ years). You know how to build a small, elite team and hold them to an unreasonable bar.

• You're fluent in pre-IPO dynamics: governance, compliance readiness, investor relations, board management.

• You are an AI power user, full stop. You've already rebuilt your own workflows around AI. You use agents, prompting, and automation daily to operate at a level that shocks people who work the old way. You can demonstrate this live in the interview. Talking about it doesn't count.

• You think from first principles. Your instinct when encountering a process isn't to optimize it. It's to ask whether it should exist at all. You've led teams through that kind of reinvention and have the scars and results to prove it.

• You default to writing things down. Memos, frameworks, decision docs. Clarity is a deliverable, not a nice-to-have.

• You move fast without being sloppy. You have taste. You know when 80% is enough and when perfection is the only option.

• You have high EQ and low ego. You make other people look brilliant and don't need the credit.

• You're energized by ambiguity. Paralysis isn't in your vocabulary.

Who Should Not Apply

• People who need stable, well-defined scope. The scope is "whatever the CEO needs to move faster." That changes weekly.

• People who see Chief of Staff as a stepping stone to COO. This is a discipline, not a rotation.

• People who "use ChatGPT sometimes." We need someone whose relationship with AI has fundamentally altered their professional output, not someone who's experimented.

• People who hear "why do we do this?" and feel threatened rather than lit up.

• People who optimize for consensus over velocity.

• People who haven't operated in high-growth tech or SaaS. We can't teach you the pattern recognition you need here.

Compensation & Details

• Reports to: CEO (Zeb Evans)

• Location: Remote (US), with regular travel to San Diego HQ

• Compensation: Competitive base + significant equity. ClickUp's comp philosophy rewards outsized leverage, and this role is definitionally about leverage. If you're the right person, the equity conversation will reflect that.

Why You'd Want This

Let's be direct: this might be the single highest-leverage non-founder role in SaaS right now.

You'll be at the center of the company that is defining how AI reshapes organizations, not theoretically, but in production, with 4,000+ agents and a CEO who refuses to accept that anything has to be done the way it was done before. You won't just watch this transformation. You'll be the person making it happen, function by function, process by process, assumption by assumption.

You'll see every decision before it's made. You'll have the CEO's ear and the exec team's trust. You'll challenge smart people to think harder about why they do what they do. You'll push an already-fast company to move at a speed the rest of the industry can't comprehend.

And in three years, when every company has a version of this role, you'll have been the person who defined what it looks like. That's the gig.

Equal Opportunity 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.

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Visa Sponsorship

Please note we are unable to sponsor or take over sponsorship of an employment visa for roles outside of engineering and product at this time. Sponsorship for engineering and product roles is not guaranteed, but is instead based on the business needs for that specific role at that time. Please reach out to the recruiter with any questions.

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AI Processing Notice

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