# Chief of Staff to the CEO

**Company:** [ClickUp](https://hotfix.jobs/companies/clickup)
**Location:** Remote
**Role:** Business Operations
**Salary:** $175k – $275k/yr
**Experience:** 8+ years
**Skills:** AI Agents, ai transformation, operating cadences, board preparation, Strategic Planning, Cross-Functional Leadership, internal communications, workflow redesign, first principles thinking, executive facilitation, Competitive Analysis, narrative development
**Posted:** 2026-07-11

> Serve as force multiplier to the founder-CEO of AI-native ClickUp, designing AI-first operating systems, driving company-wide workflow reinvention from first principles, building CEO intelligence infrastructure, executing strategic priorities, and preparing board/IPO narratives. Requires prior right-hand experience to a founder-CEO at 500+ employee scale with deep AI fluency.

## Job Description

## Operating System Design
- Stand up operating rhythms: weekly leadership syncs, monthly business reviews, quarterly planning, annual strategy.
- Define formats, own prep, drive follow-through.
- Build AI-first from day one: automated briefings, agent-driven prep, real-time synthesis.
- Ensure no human does what a well-orchestrated agent could handle.

## AI Transformation Leadership
- Partner with CEO to push every function to reinvent workflows from first principles.
- Challenge leaders to decompose workflows: identify agent tasks, eliminate unnecessary work, retain irreplaceable human judgment.
- Drive total reinvention across the company to maintain years-ahead lead in AI-native operations.

## CEO Intelligence Layer
- Architect AI-powered systems for CEO to stay in details at scale.
- Decide what CEO sees, when, and in what format.
- Build filtering and intelligence infrastructure for maximum signal in every conversation, meeting, and review.

## Industry & Competitive Immersion
- Build information loops (agent-powered and human-curated) on competitive moves, market shifts, emerging tech, customer signals, analyst takes.
- Ensure CEO is three moves ahead in public speaking and strategy.

## Strategic Program Execution
- Intake CEO priorities, scope them, assign ownership, track progress, ensure completion ("shipped," not "in progress").

## Board & Investor Operations
- Own board meeting preparation: narrative development, data assembly, materials, dry runs.
- Craft IPO-path narrative positioning ClickUp as the defining AI-era company.

## Cross-Functional Reinvention
- Serve as escalation point for inter-team work.
- Challenge any function with "why does this process exist?"; kill legacy processes and rebuild from zero using first-principles.
- Act as forcing function for 10x output gains.

## Leadership Team Cohesion
- Monitor executive team dynamics, surface misalignment, facilitate resolution.
- Channel founder-speed pressure into momentum.

## Internal Communications & Narrative
- Shape CEO communications: all-hands talking points, org-wide memos, strategic context.
- Ensure internal narrative aligns with external ambition around the 100x org operating model.

## Requirements
- Operated at the right hand of a founder-CEO in a 500+ employee company (ideally 1,000+).
- Built operating cadences and structures from scratch.
- Deep AI fluency and ability to weaponize AI for 10x leverage (evaluated in hiring).
- Experience driving first-principles reinvention and cross-functional transformation.
- Strong in strategy, operations, communications, and executive facilitation.

## Nice-to-Haves
- Background that enables operating at CEO frequency with product obsession and detail-orientation.
- Track record of measurable 10x productivity gains through AI and process redesign.

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