Lifestyle Personal Assistant

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 ResponsibilitiesProvide day-to-day personal and lifestyle support to the principalsManage complex domestic and international travel, including private/commercial flights, hotels, ground transportation, and multi-stop itinerariesAnticipate and proactively plan for birthdays, anniversaries, recurring travel, events, and other personal milestonesCoordinate travel and logisticsMonitor calendars, identify potential conflicts, and proactively resolve issuesMaintain consistent follow-up with the principals, vendors, and other stakeholders to keep decisions and logistics movingEnsure personal logistics are executed seamlessly, often without detailed directionIdeal CandidateSignificant experience supporting UHNW and/or high-profile principals and familiesPrior experience in a true Personal Assistant capacity requiredStrong background managing complex, high-touch travel and lifestyle logisticsHighly proactive with a natural ability to anticipate needs and think several steps aheadStrong communicator with excellent follow-through and sound judgmentComfortable supporting a dynamic lifestyle with evolving priorities and occasional needs outside traditional business hoursFamiliarity with luxury service standards and high-profile event logistics preferredValid passport requiredCompensation: $140kLocation: MiamiSchedule: 24/7 mindset requiredPocketbook Agency is acting solely as a recruiting and placement firm for this position and is not the employer of record for this role unless otherwise explicitly stated. All hiring decisions, compensation, benefits, and employment terms are determined by the client employer. By applying, you acknowledge that submission of an application does not guarantee placement or employment.Pocketbook Agency is an equal opportunity recruiting firm and does not discriminate in its recruiting, screening, or placement practices based on race, color, religion, sex, gender identity, sexual orientation, national origin, age, disability, veteran status, or any other protected characteristic under applicable law.