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

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

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.

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

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

Interested? Send your resume to: [email protected]