Executive Assistant

Remote Raven Jamaica
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You will act as the right hand to a fast-moving CEO managing multiple businesses and a 45–50 person team. This environment is dynamic, ambiguous, and fast. You will not be given perfect instructions — you are expected to figure things out, move quickly, and execute with precision.

We are specifically looking for individuals with a Catalyst or Persuader profile—people who can build relationships fast, influence outcomes, and keep momentum in high-pressure environments.

If you need structure, predictability, or detailed instructions, this role will not work. If you thrive in motion, solve problems in real time, and keep things moving—this is a strong fit.   What You Will Do • Manage complex calendars across multiple businesses and stakeholders • Implement and optimize scheduling systems and automation • Attend meetings, capture decisions, and track execution • Drive follow-through on priorities, deadlines, and commitments • Support both business and occasional personal executive needs • Maintain organized systems, documentation, and knowledge bases • Use tools like Microsoft Office, HubSpot, OneNote, Adobe, and password vaults • Leverage AI tools (ChatGPT, Gemini) for efficiency and output • Act as a trusted operator who keeps pace with rapid decision-making

  Work Environment • Fully remote • High-speed, high-accountability culture • Minimal supervision — high trust • Constant change — priorities shift quickly

What to Expect You will work closely with a visionary, high-energy CEO who moves quickly and communicates briefly. Your role is to: • Stay grounded • Keep operations moving • Bring structure without slowing things down • Maintain momentum under pressure

  If you need predictability, this role will feel overwhelming. If you thrive in fast-moving environments and enjoy solving problems in real time, this role will suit you.