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About the role
Job TitleChief Executive Assistant
LocationRemote
Time ZoneUS Eastern (ET) preferred; must overlap core ET working hours
Role OverviewYou 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
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Own the CEO’s calendar, priorities, weekly planning rhythm, and daily execution check-ins
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Convert “brain dumps” into structured tasks, owners, deadlines, and follow-ups (with escalation when needed)
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Drive cross-business execution: unify plans, remove blockers, and keep momentum through rapid pivots
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Maintain a weekly portfolio scorecard (marketing, sales KPIs, project milestones, risks, next actions)
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Partner with key operators/partners (Ops, Sales, and Deal partners) to track commitments and accountability
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Coordinate across time zones and teams (including St. Martin ground support and remote VAs)
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Support light investor/client communication (owners/investors, not guests)
Required Qualifications
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Experience working as Chief of Staff / Senior Executive Assistant / Operations Partner roles supporting a founder or CEO
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Proven ability to run execution systems end-to-end (priorities → plans → tracking → completion)
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Comfort enforcing accountability with senior operators and partners; clear, confident follow-up style
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Strong project management skills (ClickUp, Asana, or equivalent) and KPI reporting discipline
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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.
Preferred Qualifications
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Experience supporting multi-business or portfolio operators
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Working knowledge of CRM + marketing ops workflows (email sequences, tagging, lead routing)
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Exposure to real estate development or home services operations
Tools & TechnologyClickUp/Asana, Google Workspace, Slack/Zoom, Airtable/Google Sheets, CRM (HubSpot/GoHighLevel/Salesforce or similar), Zapier/Make, AI tools for writing/automation (e.g., ChatGPT)
Please NOTE
It is crucial that you complete the application form in full. As part of the application process, you will be required to record a video. If your application is successful, you will receive an email confirming next steps—the video is the first step of the interview process. If you do not record a video, we will not be able to consider you for ANY open roles
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