Chief Executive Assistant

Remote, South Africa

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Job Title Chief Executive Assistant

Location Remote

Time Zone US Eastern (ET) preferred; must overlap core ET working hours

Role Overview You are the CEO’s command center and execution integrator across a 3-business portfolio (luxury Caribbean vacation rental asset management, home services/insulation, and Boston real estate development). You translate fast-moving ideas into clear plans, systems, and follow-through—keeping operators accountable so nothing slips.

Key Responsibilities

Own the CEO’s calendar, priorities, weekly planning rhythm, and daily execution check-ins

Convert “brain dumps” into structured tasks, owners, deadlines, and follow-ups (with escalation when needed)

Drive cross-business execution: unify plans, remove blockers, and keep momentum through rapid pivots

Maintain a weekly portfolio scorecard (marketing, sales KPIs, project milestones, risks, next actions)

Partner with key operators/partners (Ops, Sales, and Deal partners) to track commitments and accountability

Coordinate across time zones and teams (including St. Martin ground support and remote...