Chief of Staff | Williamsburg, NY · $150,000–$200,000 - 2374

Chief of Staff | Brooklyn, NY · $150,000–$200,000

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About the Role This is not a traditional Executive Assistant role — it's a seat at the table. You'll work directly alongside a CEO running multiple fast-growing companies across healthcare, operations, and new ventures, acting as his right hand across all of them. This role demands judgment, speed, and discretion: you won't be micromanaged, you'll be expected to think, decide, and execute.

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Key Responsibilities

Decision Support & CEO Representation

• Attend meetings and calls on behalf of the CEO when needed
• Deliver clear summaries with actionable Yes / No / Wait recommendations
• Flag risks, gaps, and misalignment before they become problems
• Ensure decisions convert into real execution

Research, Strategy & AI Intelligence

• Conduct deep research across AI tools, healthcare operations, vendors, and competitive landscape
• Use AI tools to accelerate research, synthesis, and writing
• Translate complexity into short, clear, actionable write-ups

Recruiting & Talent Gatekeeping

• Screen high volumes of resumes and identify only top-tier candidates
• Run first-round interviews and assess judgment, intelligence, and culture fit
• Bring the CEO only the candidates worth his time

Executive Communication

• Draft emails, messages, and summaries in the CEO's voice
• Handle follow-ups with internal and external stakeholders
• Prepare briefs, agendas, and talking points ahead of meetings

Execution & Follow-Through

• Track commitments across meetings, teams, and companies
• Assign owners and deadlines — then follow up relentlessly
• Prevent dropped balls across a multi-venture portfolio

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Qualifications

• Background as a Chief of Staff, senior Executive Assistant, consultant, or operations lead
• Proven ability to support a CEO or senior executive at a high level
• Strong research, analytical, and summarization skills
• Experience screening candidates and running interviews
• Excellent written and verbal communication
• High integrity, discretion, and reliability
• Healthcare experience is a plus, not required

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Interested? Send your resume to: [email protected]