Lifestyle Personal Assistant

Pocketbook Agency; Miami (FL); On-site; USD 120,000 - 160,000; Full time

Job summary

Pocketbook Agency is seeking an experienced Personal Assistant to support a high-profile family in Miami, handling day-to-day personal and lifestyle operations. The role requires discretion, proactive planning, and flawless execution of complex travel with minimal oversight.

Reporting to the principals, you will anticipate needs, coordinate private and international travel, events, and milestones, and reduce mental load through thoughtful, proactive support in a demanding, fast-paced environment.

Qualifications

• Significant experience supporting UHNW principals or families.
• Proven track record as a true Personal Assistant, handling high-touch logistics.
• Strong ability to anticipate needs and act proactively.
• Excellent communication and judgment under pressure.

Responsibilities

• Provide day-to-day personal and lifestyle support to the principals.
• Coordinate complex domestic and international travel, flights, hotels, and ground transport.
• Plan milestones such as birthdays, anniversaries, events and recurring travel.
• Coordinate travel and logistics while maintaining timelines.
• Maintain calendars, resolve conflicts, and follow up with vendors and stakeholders.
• Ensure seamless personal logistics with minimal direction.

Skills

UHNW support

Personal assistant experience

Travel logistics

Proactive mindset

Communication skills

Discretion

Job description

High-profile entrepreneurial family is seeking an experienced Personal Assistant to support their day-to-day personal and lifestyle operations. Reporting directly to the principals, this is a high-touch role for someone who is exceptionally proactive, organized, discreet, and comfortable managing complex logistics with minimal oversight.

The ideal candidate is someone who naturally stays ahead of the principals, creates structure in a fast-moving environment, and takes ownership without needing to be asked. Calm under pressure, highly resourceful, and focused on reducing the principals’ mental load through thoughtful, proactive support.

Key Responsibilities

• Provide day-to-day personal and lifestyle support to the principals
• Manage complex domestic and international travel, including private/commercial flights, hotels, ground transportation, and multi-stop itineraries
• Anticipate and proactively plan for birthdays, anniversaries, recurring travel, events, and other personal milestones
• Coordinate travel and logistics
• Monitor calendars, identify potential conflicts, and proactively resolve issuesMaintain consistent follow-up with the principals, vendors, and other stakeholders to keep decisions and logistics moving
• Ensure personal logistics are executed seamlessly, often without detailed direction

Ideal Candidate

• Significant experience supporting UHNW and/or high-profile principals and families
• Prior experience in a true Personal Assistant capacity required
• Strong background managing complex, high-touch travel and lifestyle logistics
• Highly proactive with a natural ability to anticipate needs and think several steps ahead
• Strong communicator with excellent follow-through and sound judgment
• Comfortable supporting a dynamic lifestyle with evolving priorities and occasional needs outside traditional business hours
• Familiarity with luxury service standards and high-profile event logistics preferred

Compensation

$140k

Location

Miami

Schedule

24/7 mindset required