Personal Executive Assistant

Executive Personal Assistant
Location: Must be located in Lake Mary, FL or Big Sky, Montana (Hybrid | Travel Required)
Compensation Starting At: $90,000
Contract: 3-6 Month Contract | Intent to Convert to Permanent
Reports To: Chief Executive Officer / Confidential Executive Client

We are seeking an experienced and discreet Executive Personal Assistant to support a high-profile, confidential CEO client. This unique opportunity combines executive-level administrative responsibilities with personal support in a fast-paced, high-touch environment. The ideal candidate is polished, proactive, adaptable, and thrives in dynamic settings while handling sensitive matters with absolute professionalism and discretion.

This role blends corporate-level executive assistance with personal support, event coordination, and high-level travel management. You will serve as a trusted right hand to the executive, ensuring seamless execution of both business and personal priorities. The environment is fast-moving and ever-changing, making flexibility, anticipation of needs, and strong problem-solving skills essential for success.

This is a hybrid role based in Lake Mary, FL, with travel required for executive meetings, private events, seasonal stays, and business engagements, including travel to Montana.

Key Responsibilities

• Provide full executive and personal administrative support to a confidential CEO client in a fast-paced environment.
• Manage complex, high-volume calendars and daily priorities across multiple time zones using TimeTree or comparable scheduling systems.
• Coordinate domestic and international travel arrangements, logistics, and detailed itineraries.
• Handle personal errands, appointments, and lifestyle management tasks with the utmost discretion and professionalism.
• Coordinate logistics for meetings, corporate engagements, private functions, and high-profile events, including vendor management and on-site support.
• Draft, proofread, and manage executive correspondence, presentations, reports, and documents with exceptional attention to detail.
• Serve as a trusted liaison between the executive, internal teams, external partners, vendors, and VIP clientele.
• Maintain strict confidentiality regarding sensitive business and personal matters, including experience working under NDAs.
• Anticipate executive needs, proactively resolve issues, and ensure seamless execution of plans in a rapidly evolving environment.
• Support administrative projects, operational initiatives, and special assignments as needed.
• Maintain professionalism and composure in all interactions while representing the executive and organization positively.

Qualifications

• 5+ years of experience as an Executive Assistant, Personal Assistant, or Executive Administrative Assistant supporting C-level leadership or high-profile clients.
• Proven experience handling confidential information with discretion and professionalism, including working under NDAs.
• Strong communication, organizational, multitasking, and time management skills.
• Advanced proficiency in Microsoft Office Suite (Outlook, Word, Excel, PowerPoint).
• Highly adaptable and comfortable working in fast-paced, evolving environments.
• Strong attention to detail with the ability to anticipate needs and problem-solve independently.
• Valid driver's license and reliable transportation for errands and local support.
• Flexible availability for occasional evenings, weekends, and travel as needed.
• Startup company experience is highly preferred.
• Preferred backgrounds include real estate, luxury services, hospitality, event coordination, corporate, or professional services environments.
• Familiarity with tools such as TimeTree, CRM systems, or project management software is a plus.

Ideal Candidate Attributes

• Confidential & Trustworthy: Exercises discretion and integrity in handling sensitive information.
• Adaptable & Resourceful: Comfortable managing shifting priorities in fast-moving environments.
• Service-Oriented: Anticipates needs and consistently delivers high-level support.
• Professional & Polished: Maintains composure and professionalism in all settings.
• Self-Sufficient: Operates independently while maintaining excellent communication and follow-through.
• Startup Mentality: Comfortable wearing multiple hats and thriving in entrepreneurial environments.

Additional Details

• Contract Duration: 3-6 months with strong intent to convert to permanent.
• Travel: Approximately 20-50%; all business-related travel expenses are covered.
• Schedule: Hybrid with flexibility to support executive needs.
• Interview Process: Two-step interview process including Zoom and in-person interviews for local candidates.
• Location Requirement: Candidates must currently reside in the Greater Orlando / Lake Mary, FL area or Big Sky, Montana.
• Immediate Availability: Candidates with immediate travel availability are strongly preferred due to upcoming executive events and engagements.