About this role

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 VAs)
Support light investor/client communication (owners/investors, not guests)

5+ years in Chief of Staff / Senior Executive Assistant / Operations Partner roles 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
Strong project management skills (ClickUp, Asana, or equivalent) and KPI reporting discipline
Non-negotiable: Prior remote work experience; fluent with remote collaboration tools (Slack, Zoom, Google Workspace, Asana/ClickUp or similar) and ideally experience working with US or UK-based companies—applications without this will not be considered.

Senior Executive Assistant

Key skills