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ComplexChaos · 1 day ago

Chief of Staff (Interim/Fractional)

Florida, USA

Full-time

Hybrid

Mid, Senior Level

1+ years exp

ComplexChaos is a venture-backed, early-stage B2B software company seeking a Chief of Staff to act as a force-multiplier for the CEO. The role involves structuring board narratives, unblocking initiatives, and turning chaos into executable plans while interfacing with various stakeholders.

Computer Software

Responsibilities

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

Qualification

MBAStartup experienceConsulting experienceB2B software exposureAI tools proficiencyProgram Manager experienceClear writingStructural thinkingRespectful pushback