Executive Assistant to CEO (Remote, US Eastern)

About the role

You will serve as the CEO’s command center, translating fast‑moving ideas into actionable plans across a portfolio of three businesses (luxury Caribbean rentals, home services, and Boston real‑estate development). This remote position requires you to keep operators accountable and ensure nothing slips through the cracks.

Key responsibilities

• Own the CEO’s calendar, priorities, weekly planning rhythm, and daily execution check‑ins.
• Convert “brain dumps” into structured tasks, assign owners, set deadlines, and manage follow‑ups with escalation when needed.
• Drive cross‑business execution by unifying plans, removing blockers, and maintaining momentum during rapid pivots.
• Maintain a weekly portfolio scorecard covering marketing, sales KPIs, project milestones, risks, and next actions.
• Partner with operators and partners (Ops, Sales, Deal partners) to track commitments and enforce accountability.
• Coordinate across time zones and teams, including St. Martin ground support and remote VAs.
• Support light investor and client communications (owners/investors, not guests).

Required profile

• Experience as a Chief of Staff, Senior Executive Assistant, or Operations Partner supporting a founder or CEO.
• Proven ability to run execution systems end‑to‑end (priorities → plans → tracking → completion).
• Comfort enforcing accountability with senior operators and partners; clear, confident follow‑up style.
• Prior remote‑work experience and fluency with remote collaboration tools (Slack, Zoom, Google Workspace, ClickUp/Asana).
• Preferably experience with US or UK‑based companies.

Required skills

• ClickUp or Asana
• Google Workspace
• Slack
• Zoom
• Airtable
• Google Sheets
• HubSpot, GoHighLevel or Salesforce (CRM)
• Zapier or Make
• AI writing/automation tools (e.g., ChatGPT)