Executive Personal Assistant- Miami, FL in Miami, Florida at The Calendar Group

Our client is seeking a highly capable Executive Personal Assistant to support the Founder/CEO of an AI-first e-commerce technology firm with family office operations. This role works closely with and reports to the Chief of Staff, operating across both business and personal capacities. The ideal candidate is proactive, resourceful, and outcome-oriented, with a strong ability to anticipate needs, solve problems independently, and execute at a high level.

This individual should have a strong sense of discretion, excellent judgment, and a polished, service-oriented approach. A genuine interest in health and wellness and familiarity with high-quality service environments are important. An AI-forward mindset with a willingness to leverage tools to improve efficiency is highly valued.

Key Responsibilities

• Coordinate complex travel on short notice, including private aviation, luxury accommodations, and ground transportation
• Prepare materials, briefings, and documents
• Manage personal logistics including appointments, errands, and time-sensitive requests
• Oversee dining, reservations, private events, and venue coordination
• Interface with wellness, lifestyle, and service providers
• Support both business and household-related needs as required
• Conduct research and provide recommendations across a range of topics
• Assist with social coordination and strategic introductions within private networks
• Track priorities and ensure seamless follow-through.
• Act as a representative on behalf of the principals when needed.
• Handle highly confidential matters with discretion and sound judgment
• Leverage AI tools to enhance productivity and workflow efficiency

Qualifications

• 2+ years of experience supporting a Founder/CEO, UHNW individual, or private family
• Based in Miami, FL
• Valid driver’s license and comfortable driving as needed
• Passport-ready with flexibility for international travel on short notice
• Highly organized with strong communication and problem-solving skills
• Comfortable in a fast-paced, ever-changing environment

Compensation: $90,000-$100,000 base, with discretionary bonus and medical benefits

Schedule: Monday-Friday with flexibility for evenings and weekends as needed