Executive Assistant

The Calendar Group; Orlando (FL); On-site; USD 80,000 - 120,000; Full time

Job summary

The Calendar Group in Orlando seeks an exceptional Executive Assistant / Chief of Staff to support a high‑velocity executive overseeing business, real estate, ministry, and faith‑based initiatives. Based in Orlando with extensive domestic and international travel, you will coordinate across multiple entities with discretion and professionalism.

The role demands outstanding organizational and communication skills, proactive problem solving, and the ability to manage a fast-moving environment with

Qualifications

• Significant experience supporting executives at high level.
• Exceptional organizational, project management, and multitasking abilities.
• Excellent written and verbal communication skills.
• Strong computer and technology skills.
• Highly proactive, resourceful, and solutions-oriented.

Responsibilities

• Serve as a trusted partner and central point of coordination across multiple businesses and real estate.
• Manage a wide range of executive priorities with accountability across all areas.
• Coordinate with executives, attorneys, accountants, vendors, and property managers.
• Anticipate needs and proactively develop solutions.
• Coordinate meetings, travel, correspondence, and follow-up for ministry and faith-based initiatives.
• Draft correspondence, reports, and communications quickly and professionally.
• Take notes and maintain highly organized records and files.
• Coordinate property-related issues and vendors across states.
• Research and manage special projects and identify resources.
• Travel extensively with the executive domestically and internationally.

Skills

Executive support

Organizational skills

Communication skills

Travel readiness

Discretion

Tech proficiency

Tools

Computer proficiency

Job description

We are seeking an exceptional Executive Assistant / Chief of Staff to serve as a trusted right hand to a highly driven executive. The executive’s work spans business, real estate, ministry, and faith-based organizations. This role will coordinate across those interests and communicate with a wide range of senior leaders and external partners. 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.
• Coordinate meetings, travel, correspondence, and follow-up related to the executive’s ministry and faith-based initiatives.
• 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.