Senior Executive Assistant – Remote (US Eastern)

About the role

You will serve as the CEO’s command center, translating fast‑moving ideas into structured plans across a portfolio of three businesses: luxury Caribbean vacation rentals, home services/insulation, and Boston real‑estate development. This remote position requires tight coordination, accountability enforcement, and rapid execution to keep all operators aligned.

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 operations, sales, and deal partners to track commitments and ensure accountability.
• Coordinate across time zones and teams, including St. Martin ground support and remote virtual assistants.
• 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 end‑to‑end execution systems (priorities → plans → tracking → completion).
• Comfort enforcing accountability with senior operators and partners; clear, confident follow‑up style.
• Strong project‑management background with tools such as ClickUp or Asana.
• Prior remote‑work experience and fluency with remote collaboration tools (Slack, Zoom, Google Workspace, ClickUp/Asana).
• Preferably experience with multi‑business or portfolio operators and exposure to real‑estate or home‑services operations.

Required skills

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