Chief Executive Assistant
Core
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).
Role type
Chief Executive Assistant (CEO Command Center)
Builds
Execution systems, weekly portfolio scorecards, and cross-business operational plans.
Domain
Multi-business operations (Real Estate, Home Services, Vacation Rentals)
Deliverable
production ML models | product features | dashboards & analysis | research | client delivery | infrastructure | physical/clinical work
Required skills
Calendar management, execution system design, cross-functional coordination, KPI reporting, project management, remote collaboration tool proficiency, accountability enforcement
Preferred skills
Multi-business portfolio support, CRM/marketing ops workflows, real estate development operations
Technologies
ClickUp, Asana, Google Workspace, Slack, Zoom, Airtable, HubSpot, GoHighLevel, Salesforce, Zapier, Make
Responsibilities
Own CEO's calendar and weekly planning rhythm; convert ideas into structured tasks and deadlines; drive cross-business execution and remove blockers; maintain weekly portfolio scorecard; partner with operators to track commitments; coordinate across time zones and teams; support light investor/client communication
Seniority
Senior, hands-on IC
