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
Skills Required
- 2+ years 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
- Ability to handle highly confidential matters with discretion and sound judgment
- Coordinate complex travel including private aviation, luxury accommodations, and ground transportation
- Interface with wellness, lifestyle, and service providers and oversee private events/reservations
- AI-forward mindset and willingness to leverage AI tools to improve productivity
- Genuine interest in health and wellness and familiarity with high-quality service environments
What We Do
The Calendar Group is a full-service staffing firm established in 2002, specializing in recruiting experienced support staff for high net worth individuals, family offices, busy executives, and their companies. They provide staffing solutions for both home and office environments.
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