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EnterpretPosted 1 month ago

[Founder's Office] Chief of Staff to the CEO

HybridNew York, United States

Full TimeSenior LevelSmallAnalytics Software

Job Summary

Partner directly with the CEO and founding team as a trusted sounding board and proxy, representing leadership in rooms they cannot attend and turning founder intent into scoped workstreams with clear owners and timelines. Protect the CEO's focus by prioritizing attention and handling non-critical tasks, while preparing for board meetings, investor conversations, and high-stakes decisions. Own finance-adjacent operating work including vendor decisions, budget tracking, and cash-conscious prioritization, and run the company's operating rhythm across leadership meetings and weekly business reviews. Take messy operational projects independently across people, process, finance, and vendor workflows, and build analyses and narratives for strategy memos and investor materials. Operate AI-natively to research, draft, and automate work, and take first sales calls to learn the ICP and build conviction on growing ARR. Step in as temporary owner on highest-priority cross-functional problems collaborating across Sales, Marketing, Customer Success, Product, and Engineering.

Required Qualifications

  • 5+ years in a high-agency role, such as startup operating, management consulting, investment banking, venture capital, or strategy/business operations, where you owned ambiguous, high-stakes work end to end
  • Strong analytical and data fluency, comfortable in spreadsheets, building models, and reasoning from data, and AI-native in how you work, using modern AI tools to move faster and go deeper
  • Sharp written and verbal communication: you can write a crisp memo one day and represent the CEO in the room the next
  • Commercially minded and energized by customers, willing to take sales calls, learn the product cold, and build conviction directly from the market
  • A track record of collaborating across functions and earning trust without relying on formal authority
  • High ownership, sound judgment with sensitive information, and genuinely energized by startup ambiguity and variety, where no two weeks look the same

Desired Qualifications

  • Early-stage startup operating experience is strongly preferred
  • ex-founder experience is a strong plus
  • A track record of growing your own mandate: you've walked into an undefined problem and walked out with a system, a decision, or an outcome the team now relies on
  • Energized by building culture through rituals, operating cadence, communication, and follow-through

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