Chief of Staff to the CEO

ClickUp

11d•$175,000 - $275,000•Remote

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. 🚀 The Chief of Staff to the CEO is 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. This role makes 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. This is the most leveraged non-CEO seat in a company that's setting the pace for the entire industry.

Requirements

Operated at the right hand of a founder-CEO before, in a company with 500+ employees, ideally 1,000+.
Built operating cadences and structures, not inherited them.
6+ years in strategic operations, management consulting, or a prior Chief of Staff role.
Managed people (3+ years).
Fluent in pre-IPO dynamics: governance, compliance readiness, investor relations, board management.
AI power user, full stop. Have already rebuilt own workflows around AI. Use agents, prompting, and automation daily to operate at a level that shocks people who work the old way. Can demonstrate this live in the interview.
Think from first principles. Instinct when encountering a process isn't to optimize it. It's to ask whether it should exist at all. Have led teams through that kind of reinvention and have the scars and results to prove it.
Default to writing things down. Memos, frameworks, decision docs. Clarity is a deliverable, not a nice-to-have.
Move fast without being sloppy. Have taste. Know when 80% is enough and when perfection is the only option.
High EQ and low ego. Make other people look brilliant and don't need the credit.
Energized by ambiguity. Paralysis isn't in your vocabulary.

Nice To Haves

MBA is fine but irrelevant if the work speaks for itself.

Responsibilities

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. Build it AI-first from day one: automated briefings, agent-driven prep, real-time synthesis.
Partner with the CEO in pushing every single function to ask: why do we do this at all? 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.
Build AI-powered systems that make being in the details sustainable at scale. Decide what the CEO sees, when, and in what format. Architect the filtering system that ensures signal over noise. Build the intelligence infrastructure so the CEO shows up to every conversation, investor meeting, product review, and customer call as the most informed person in the room.
Build the information loops, agent-powered and human-curated, that keep the CEO embedded in the landscape: competitive moves, market shifts, emerging technology, customer signal, analyst takes.
Intake CEO-generated priorities, scope them, assign ownership, track progress, and ensure they land. Be the accountability layer between 'Zeb said we should do X' and 'X shipped.'
Own the preparation cycle for board meetings: narrative development, data assembly, materials review, dry runs. Ensure the story told to the board positions ClickUp as the defining company of the AI era.
Be the escalation point for work that sits between teams. Ask 'why does this process exist?' When the answer is 'because it always has,' help teams kill it and rebuild it from zero.
Monitor the health of the executive team's operating dynamic. Surface misalignment early. Facilitate resolution.
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.