Skip to content
ClickUpClickUpCalifornia

Chief of Staff to the CEO

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.

175k – 275k/yr
Remote8+ YOEBusiness Operations

About the role

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.

Skills

AI Agentsai transformationoperating cadencesboard preparationStrategic PlanningCross-Functional Leadershipinternal communicationsworkflow redesignfirst principles thinkingexecutive facilitationCompetitive Analysisnarrative development

Similar roles

Business Operations jobs
Trail of Bits

Technical Chief of Staff

Trail of BitsUnited States

Act as the CEO's right-hand person driving strategic initiatives, managing workflow and communications, leading planning, and ensuring execution across the organization. Requires 8+ years of engineering experience plus a strong desire to transition into business leadership.

175k – 250k/yr
Remote8+ YOEBusiness Operations
Ambience Healthcare

Chief of Staff, Care Transformation & Customer Enablement

Ambience HealthcareSan Francisco, CA

Operates Care Transformation team infrastructure, builds enablement systems bridging Marketing and customer-facing teams, owns OKRs, dashboards, and operating rhythms. Requires 5-8 years in strategy/ops or enablement at high-growth B2B, healthcare familiarity, and operational rigor.

175k – 233k/yr
Remote5+ YOEBusiness Operations
EliseAI

Chief of Staff to the CXO

EliseAINew York, NY

Acts as force multiplier for CXO, driving execution across customer operations, influencing product via customer insights, and building scalable processes in a fast-growing AI startup. Requires entrepreneurial ownership and comfort in technical environments.

175k – 250k/yr
On-siteBusiness Operations
EliseAI

Chief of Staff to the CSO

EliseAINew York, NY

Acts as force multiplier for CSO, driving strategic initiatives, planning, new verticals, and partnerships. Requires 5+ years in strategy consulting/IB/startups, strong analytics, financial modeling, and execution in high-growth environment.

175k – 250k/yr
On-site5+ YOEBusiness Operations
Permitflow

Chief of Staff

PermitflowNew York, NY

Act as CEO's primary thought partner and operational extension, driving strategic projects, holding executive accountability, and serving as a cross-functional force multiplier at a high-growth AI startup.

180k – 230k/yr
Hybrid4+ YOEBusiness Operations