Executive Personal Assistant/Chief of Staff- Orlando, Florida

We are seeking an exceptional Executive Assistant / Chief of Staff to serve as a trusted right hand to a highly driven executive overseeing multiple businesses, organizations, and real estate interests. This is a high-level, hands-on role for someone who is highly organized, proactive, discreet, and capable of managing a fast-moving environment with numerous priorities. The ideal candidate will anticipate needs, solve problems independently, coordinate across multiple entities, and represent the executive with professionalism and sound judgment.

The position is based in Orlando, Florida, with extensive domestic and international travel required.

Responsibilities

• Serve as a trusted partner and central point of coordination across multiple businesses, organizations, and real estate.

• Manage a wide range of executive priorities, ensuring follow-through and accountability across all areas.

• Coordinate directly with executives, attorneys, accountants, household vendors, property managers, and other key professionals.

• Anticipate needs, identify potential issues, and proactively develop solutions.

• Manage complex logistics, scheduling, travel, correspondence, and day-to-day priorities.

• Draft correspondence, letters, reports, and other communications quickly and professionally.

• Take detailed notes and maintain highly organized records and files.

• Coordinate property-related issues and vendors across multiple states.

• Research and manage special projects, including identifying appropriate companies, vendors, and resources.

• Travel extensively with the executive, both domestically and internationally.

Qualifications

• Significant experience as an Executive Assistant, Personal Assistant, Chief of Staff, or similar high-level support role.

• Exceptional organizational, project management, and multitasking abilities.

• Excellent written and verbal communication skills.

• Strong computer and technology skills.

• Highly proactive, resourceful, and solutions-oriented.

• Excellent judgment and discretion; absolute confidentiality is essential.

• Energetic, driven, and comfortable working in a fast-paced environment.

• Willing and able to travel extensively, including internationally.

Salary: $100,000 - $150,000 per year