ComplexChaos
 is hiring a fractional

Chief of Staff

Added 

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 - Syndicated from 
Dover

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This is a Featured Job

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You’ll receive an update within 14 days
If the company is interested, we’ll intro the two of you directly

Weekly Commitment

10 - 20 hrs

Compensation Range

Unknown

Company Stage

Early-stage VC

Industry

AI

Location

Remote (US & Europe only)
moonlight ok
moonlight ok
convert full-time
convert full-time
equity offered
equity offered
hands-on needed
hands-on needed

Note: We've kept the name of the company private. If you'd like to know the company before requesting an intro, just email us at hello [at] fractionaljobs.io

The Role — What This Actually Is

This is a force-multiplier role for the CEO. You operate at the intersection of strategy, execution, and communication. One day you’re structuring a board narrative, the next you’re unblocking a cross-functional initiative, pressure-testing a go-to-market hypothesis, or turning chaos into a clean operating plan.

You are not a note-taker.
You are not an internal HR babysitter.
You are here to make the company move faster and think clearer.

What You’ll Do

  • Own the operating cadence
    • Drive weekly, monthly, and quarterly priorities
    • Turn messy strategy into executable plans
    • Track progress, surface risks early, and force decisions
  • Be the CEO’s strategic right hand
    • Prepare briefs, memos, and decision frameworks
    • Pressure-test ideas before they hit the team or the board
    • Act as a proxy in meetings when needed
  • Run cross-functional initiatives
    • Lead high-stakes, ambiguous projects end-to-end
    • Coordinate product, engineering, GTM, and external partners
    • Make sure things actually land—not just discussed
  • Interface with external stakeholders
    • Consulting partners, enterprise clients, investors, advisors
    • Translate between executive, technical, and commercial language
  • Be AI-native in execution
    • Use AI daily to synthesize information, draft materials, analyze data, and speed up decision-making
    • Continuously improve internal workflows using AI tools

Who This Is For

You are high-horsepower, low-ego, and comfortable operating in ambiguity. You like being close to power and accountability. You think in systems, not tasks.

Requirements (Non-Negotiable)

  • MBA from a strong program or equivalent demonstrated strategic rigor
  • Startup experience (early-stage preferred)
  • At least 1 year in a top-tier consulting environment
    (McKinsey, BCG, Bain, Accenture, Strategy&, Deloitte, etc.)
  • Prior experience as a Program Manager, Engagement Manager, or equivalent
  • Exposure to B2B software (SaaS, platforms, enterprise tools)
  • Daily, hands-on use of AI tools in your workflow (not theoretical interest)

Strong Plus

  • Experience working directly with founders or C-level executives
  • Familiarity with enterprise sales cycles or consulting-led GTM
  • Comfort operating across US and European business cultures
  • Ability to write clearly, think structurally, and push back respectfully

What Success Looks Like

  • The CEO’s calendar, decisions, and communications are sharper
  • The company ships faster with less internal friction
  • Strategic initiatives don’t drift—they land
  • Everyone knows what matters this quarter and why

Why This Role Is Interesting

  • Direct exposure to company-defining decisions
  • Real ownership, not performative “leadership”
  • Front-row seat to building a serious B2B company in the AI era

How to Apply

Note: This is a syndicated job post. Fractional Jobs found it on the web, but we are not working with the client directly, so we don't have control over or knowledge of the application process. To apply, click on the "View Application" button and follow the application's instructions. Let us know how it goes!


How to Get in Touch

Hit that "Request Intro" button below. Include any relevant links so we can get to know you better.

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If we think there's a fit, we'll reach out to schedule an intro call. Looking forward!

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