Executive Leadership Support • Provide high-level, comprehensive administrative support to the CEO and three Regional Presidents • Act as a trusted partner to executive leadership, anticipating needs and resolving issues proactively • Handle sensitive and confidential matters with the utmost discretion and sound judgment Calendar & Priority Management • Manage extremely complex and dynamic calendars across multiple executives and time zones • Strategically prioritize meetings, travel, and commitments to align with business objectives • Prepare executives with agendas, materials, and relevant background information in advance Travel Coordination • Independently arrange and manage complex domestic and international travel • Create detailed travel itineraries including flights, accommodations, transportation, and schedules • Serve as the primary contact for travel changes or issues before and during trips Event Planning & Coordination • Lead coordination of executive-level meetings, board meetings, leadership retreats, regional events, and company-wide functions • Oversee event logistics including venue selection, catering, audiovisual needs, materials preparation, and post-event follow-up • Collaborate with internal teams and external vendors to ensure seamless execution Email & Executive Communications • Manage and prioritize executive inboxes using independent judgment • Draft, edit, and respond to high-level correspondence on behalf of executives • Serve as a liaison between executives and internal and external stakeholders Administrative & Strategic Support • Track action items, projects, and deliverables on behalf of executive leadership • Prepare reports, presentations, and briefing materials as requested • Process expenses, assist with budget tracking, and maintain organized records • Support special initiatives and cross-functional projects as assigned Qualifications Required • 10–15+ years of experience providing executive-level administrative support, ideally to a CEO and senior leadership team • Demonstrated experience supporting multiple executives simultaneously • Proven expertise in calendar management, travel coordination, and executive event planning • Exceptional organizational, communication, and time-management skills • High level of professionalism, discretion, emotional intelligence, and sound judgment • Advanced proficiency in Microsoft 365 (Outlook, Teams, Word, Excel, PowerPoint) Preferred • Experience in a multi-regional or matrixed organization • Experience supporting board meetings and executive leadership events • Familiarity with expense management, CRM, and travel booking platforms • Ability to work flexible hours to support executive schedules Core Competencies • Executive presence and strategic thinking • Anticipation of needs and proactive problem-solving • Attention to detail with the ability to operate independently • Stakeholder and relationship management • Adaptability in a high-growth or fast-paced environment

5+ years executive/administrative support experience

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Winter Park, FL
remote
Permanent
90000 - 95000 USD / Yearly
Executive Leadership Support • Provide high-level, comprehensive administrative support to the CEO and three Regional Presidents • Act as a trusted partner to executive leadership, anticipating needs and resolving issues proactively • Handle sensitive and confidential matters with the utmost discretion and sound judgment Calendar & Priority Management • Manage extremely complex and dynamic calendars across multiple executives and time zones • Strategically prioritize meetings, travel, and commitments to align with business objectives • Prepare executives with agendas, materials, and relevant background information in advance Travel Coordination • Independently arrange and manage complex domestic and international travel • Create detailed travel itineraries including flights, accommodations, transportation, and schedules • Serve as the primary contact for travel changes or issues before and during trips Event Planning & Coordination • Lead coordination of executive-level meetings, board meetings, leadership retreats, regional events, and company-wide functions • Oversee event logistics including venue selection, catering, audiovisual needs, materials preparation, and post-event follow-up • Collaborate with internal teams and external vendors to ensure seamless execution Email & Executive Communications • Manage and prioritize executive inboxes using independent judgment • Draft, edit, and respond to high-level correspondence on behalf of executives • Serve as a liaison between executives and internal and external stakeholders Administrative & Strategic Support • Track action items, projects, and deliverables on behalf of executive leadership • Prepare reports, presentations, and briefing materials as requested • Process expenses, assist with budget tracking, and maintain organized records • Support special initiatives and cross-functional projects as assigned Qualifications Required • 10–15+ years of experience providing executive-level administrative support, ideally to a CEO and senior leadership team • Demonstrated experience supporting multiple executives simultaneously • Proven expertise in calendar management, travel coordination, and executive event planning • Exceptional organizational, communication, and time-management skills • High level of professionalism, discretion, emotional intelligence, and sound judgment • Advanced proficiency in Microsoft 365 (Outlook, Teams, Word, Excel, PowerPoint) Preferred • Experience in a multi-regional or matrixed organization • Experience supporting board meetings and executive leadership events • Familiarity with expense management, CRM, and travel booking platforms • Ability to work flexible hours to support executive schedules Core Competencies • Executive presence and strategic thinking • Anticipation of needs and proactive problem-solving • Attention to detail with the ability to operate independently • Stakeholder and relationship management • Adaptability in a high-growth or fast-paced environment
2026-02-20T00:00:00Z

Executive Assistant Job in Winter Park, FL | Robert Half