Personal Assistant to Chief Executive Officer (Greenwich)

Private Personal Assistant to Founder

Greenwich CT

In-Person 5 days a week with flex

10am - 6pm

Salary up to 250K DOE plus Benefits

We are seeking an exceptionally loyal, experienced, polished, and hands-on Private Personal Assistant to support a dynamic UHNW Founder/Entrepreneur in the Greenwich Connecticut,

The ideal candidate is someone who genuinely enjoys being of service, is naturally caring, thoughtful, patient, and attentive, and takes tremendous pride in making another person's life easier, more comfortable, and exceptionally well organized. This person must be mature, discreet and highly confidential. We are looking for someone who is calm, poised, humble, exceptionally respectful, compassionate, and kind. Someone with quiet confidence, excellent instincts, and absolutely no ego. This individual should be comfortable working behind the scenes, never need to be the center of attention, and possess the emotional intelligence to anticipate needs before being asked.

This is a true hands-on, do-anything Personal Assistant position. No task should ever feel too small or beneath this person. Whether managing complicated travel, attending appointments, organizing technology, running errands, or ensuring the principal is comfortable and well taken care of, everything should be approached with patience, care, and professionalism. Confidentiality and discretion is of the utmost importance.

Having the ability to work on iPhone, Mac, and with Microsoft Office (specifically calendaring) is essential. Someone resourceful who can independently solve problems and make things happen.

Above all, we are seeking a career Personal Assistant who is truly of service, values loyalty and longevity, and is not looking to use this opportunity as a steppingstone into another industry or career.

Key Responsibilities

• Calendar & Scheduling: Manage an ever-changing personal schedule, working closely with the office administrative team to coordinate business meetings, personal commitments, and appointments. Prepare daily schedules and materials.

• Personal & Lifestyle Support: Thoughtfully oversee the principal's daily needs, routines, appointments, and logistics, ensuring everything runs smoothly and comfortably.

• Wellness & Fitness Coordination: Schedule, wellness, and fitness appointments, communicate with professionals, and accompany the principal to select appointments as needed.

• Technology Support: Manage and troubleshoot computers, iPhones, iPads, email, calendars, contacts, applications, and digital files. Assist with purchasing, setting up, and organizing devices.

• Complex Travel: Coordinate domestic and international travel, including private aviation, luxury hotels, transportation, and detailed itineraries. Anticipate changes and maintain contingency plans.

• Wardrobe & Organization: Oversee wardrobe and closet management, clothing purchases, and packing and unpacking for travel.

• Administrative Support: Prepare, print, scan, and organize documents; attend select meetings and appointments to take notes and manage follow-ups. Be comfortable working with business professionals in a corporate environment. Will be responsible for working alongside the business office to schedule and coordinate logistics for business meetings, zooms, and in person gatherings.

• Events & Entertaining: Coordinate private dinners, social gatherings, and special events, including transportation logistics.

• Errands & Gifting: Handle extensive personal errands, shopping, thoughtful gifting, returns, and daily requests for the principal and his partner.

• Team Coordination: Work closely with security, drivers, office teams, and vendors to ensure seamless support.

• Contacts & Expenses: Maintain an extensive VIP contact database and reconcile expenses related to travel, transportation, clothing, and entertainment.

• Trusted Liaison: Represent the principal and his partner with warmth, professionalism, discretion, and exceptional judgment.

Qualifications & Personal Attributes

Minimum 7–10 years of experience as a Private Personal Assistant supporting a founder, entrepreneur, or UHNW principal.

Extremely tech-savvy with exceptional computer skills. Must be comfortable troubleshooting devices, managing digital information, and solving technology-related problems independently.

Naturally caring, compassionate, patient, and attentive, with a genuine desire to make someone's life easier.

Absolutely no ego. Happy to do anything and everything, from the most complex arrangements to the simplest personal tasks.

Calm, poised, controlled, and emotionally intelligent, particularly when navigating last-minute changes or sensitive situations.

Exceptionally respectful, discreet, humble, and thoughtful, with an understanding of the importance of dignity and patience when supporting older adults.

Highly organized, meticulous, proactive, and resourceful, with outstanding follow-through.

Excellent written and verbal communication skills and the ability to interact graciously with people at every level.

Experienced in complex travel, personal logistics, appointments, and lifestyle management.

Comfortable working independently and collaboratively with an established team.

Demonstrated loyalty, longevity, and a genuine desire for a long-term professional relationship.

Flexible and willing to travel as needed.

Excellent driving record and willingness to undergo an extensive background check.