Chief of Staff + AI

Chief of Staff alongside the CEO Founder of a High-Growth D2C Digital Marketplace (USA, Remote). I’m leading an executive search for a $100MM+ high-growth D2C digital marketplace, on a clear path to $500MM+ revenue in the next few years. With a proven COO and CMO already in place, this Chief of Staff role is designed to amplify the CEO and SLT - optimizing time, focus, decision-making, and execution across the Senior Leadership Team.

You operate seamlessly between strategy and action: trusted partner, gatekeeper, sounding board, and execution lead for the CEO’s most sensitive priorities.

You’re also AI-native and tech-savvy, using tools like ChatGPT, ideally Claude Code, Cursor, Anti-Gravity or similar daily at an intermediate–advanced level and certainly come from that type of company environment eg AI native or early adopters as this business aims to become AI first (where appropriate).

Core Responsibilities

• Translate CEO & Board vision into priorities, OKRs, and execution plans
  

• Drive cross-functional initiatives and operating cadence
  

• Prepare CEO for board, investor, and key stakeholder engagements
  

• Provide research, analysis, and decision support
  

• Act as communication bridge across the executive team
  

• Lead high-impact special projects (scale, M&A, market entry)
  

• Run executive and SLT meetings with clear follow-through
  

• Track priorities, metrics, and accountability
  

• Draft CEO communications (internal & external)
  

• Coordinate board and investor materials
  

• Resolve cross-functional blockers
  

• Own “CEO-only” initiatives end-to-end
  

• Surface risks early and proactively close gaps
  

Your Profile

• 7–12+ years supporting CEOs/Founders in fast-scaling SMBs
  

• Experience scaling a 100–300 person company (ideally more than once)
  

• Board-level confidence: meetings, materials, investors, confidentiality
  

• Strong D2C customer acquisition and retention, eCommerce, performance advertising and digital marketplace understanding and experience of those GTM and TOMs
  

• Passion for eLearning, online training, sporting goods, health, wellness, fitness, or biohacking could be a good culture fit
  

• USA-based, fully remote