Responsibilities
- Manage the CEO's schedule, strategic priorities, weekly planning cycle, and daily progress reviews
- Transform unstructured input into organized action items, assign owners, set deadlines, and escalate follow-ups as necessary
- Lead execution across multiple business units by aligning plans, resolving obstacles, and adapting quickly to changes
- Produce a weekly performance dashboard covering marketing, sales metrics, project timelines, risks, and upcoming steps
- Collaborate with operational leads and external partners to monitor deliverables and ensure accountability
- Coordinate activities across different time zones and teams, including on-island support and remote virtual assistants
- Handle limited communication with investors and clients, focusing on stakeholders rather than end users
Work Arrangement
Remote (Worldwide)
Team
Provides direct support to the CEO overseeing a diversified portfolio of three businesses: high-end vacation rental management in the Caribbean, residential insulation and home services, and real estate development in Boston
Team
Supports CEO across a 3-business portfolio: luxury Caribbean vacation rental asset management, home services/insulation, and Boston real estate development
