Chief of Staff to the CEO (Founder's Office) (New York)

• Partner directly with our CEO and founding team as a true extension of the CEO: a trusted sounding board and proxy who represents them in rooms they can’t be in, makes calls on their behalf, and turns founder intent into scoped workstreams with clear owners, timelines, and follow-through
• Protect and prioritize the CEO’s focus by deciding what needs their attention and quietly handling what doesn’t, while preparing them for board meetings, investor conversations, and high-stakes decisions
• Own finance‑adjacent operating work, including vendor decisions, budget tracking, cash‑conscious prioritization, and analyses that help the CEO make sharper calls
• Run the company’s operating rhythm across leadership meetings, weekly business reviews, and planning cycles, setting agendas, surfacing the right data, and tracking every decision to close
• Take messy operational projects off the CEO’s plate and run them independently across people, process, finance, and vendor workflows
• Build the analyses and narratives that move decisions forward: first‑draft strategy memos, board and investor materials, and company‑wide communications, grounded in first- and third‑party data
• Operate AI‑natively by using modern AI tooling to research, draft, model, and automate the work, and help the leadership team adopt AI‑enabled ways of working as we scale
• Take first sales calls and earn real commercial reps by learning our ICP, their pain points, and where Enterpret wins, so you can build conviction on the question that runs the business: how do we grow ARR?
• Step in as temporary owner on the highest‑priority cross‑functional problems, collaborating across Sales, Marketing, Customer Success, Product, and Engineering wherever there’s a gap between strategy and execution

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 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

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

Early‑stage startup operating experience is strongly preferred; ex‑founder experience is a strong plus

High ownership, sound judgment with sensitive information, and genuinely energized by startup ambiguity and variety, where no two weeks look the same

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

Sharp written and verbal communication: you can write a crisp memo one day and represent the CEO in the room the next

A track record of collaborating across functions and earning trust without relying on formal authority