Senior Executive Assistant – Remote (US ET)

About the role

We are seeking a Senior Executive Assistant to serve as the CEO’s command centre across a portfolio of three businesses – luxury Caribbean vacation rentals, home services/insulation, and Boston real‑estate development. This fully remote role supports the CEO in translating fast‑moving ideas into clear plans, ensuring execution and accountability.

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 follow‑ups, escalating 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 accountability.
• Coordinate across time zones and teams, including St. Martin ground support and remote VAs.
• Support light investor and client communications.

Required profile

• 5+ years experience in Chief of Staff, Senior Executive Assistant or Operations Partner roles 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.
• Strong project‑management and KPI‑reporting discipline.
• Prior remote‑work experience and fluency with remote collaboration tools.

Required skills

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