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We are seeking a highly capable, proactive Strategic Executive Assistant to serve as a trusted right-hand partner to the President/COO across multiple business entities. This is a high-impact role that goes well beyond traditional executive support. The ideal candidate will play an integral role in executive operations, project management, internal communications, and cross-departmental coordination. This position supports leadership across five affiliated companies spanning financial services, development, hospitality, management services, and marketing. The Strategic Assistant will help optimize executive time, drive strategic initiatives forward, and ensure seamless communication and follow-through across teams.
Job Responsibility:
Partner closely with the President/COO to manage priorities, deadlines, and key initiatives
Manage complex, multi-entity calendars and high-volume communications
Prepare briefing materials, executive summaries, and meeting documentation
Track action items and ensure timely follow-up across departments
Conduct research and compile data to support business decisions
Support operational initiatives and cross-functional projects
Monitor timelines, deliverables, and workflow efficiency
Collaborate with accounting, HR, property management, and operations teams
Help implement and improve systems, processes, and internal coordination
Oversee daily administrative functions including scheduling, expense management, and document organization
Maintain records, files, and internal communications across multiple entities
Ensure consistent follow-up and closed communication loops
Handle occasional personal scheduling and time-sensitive matters with discretion
Requirements:
5+ years of experience in executive support, operations, or project management (C-level support preferred)
Exceptional organizational and prioritization skills
Strong written and verbal communication abilities
High level of discretion, emotional intelligence, and professionalism
Detail-oriented with the ability to manage competing priorities
Proficiency in Microsoft 365 (Excel, Word, PowerPoint) and other business applications
Ability to travel occasionally and maintain schedule flexibility