Personal Assistant to UHNW Entrepreneur + Luxury Real Estate Founder

Location: Upper West Side, New York City (Primary with travel to Hamptons and occasionally Kentucky and South Carolina)

Schedule: 4 days per week, flexible schedule (core availability after 11:00 AM)

Compensation: $150,000 annually + Bonuses + PTO + Benefits Stipend

Start Date: ASAP

🏙️ About the Role

We are seeking a highly organized, discreet, and proactive Personal Assistant to support an ultra-high-net-worth entrepreneur, real estate founder, and philanthropist in her next chapter. This role is ideal for someone who thrives in a dynamic, fast-paced environment, has experience supporting high-profile individuals, and understands the demands of a luxury lifestyle.

The ideal candidate will bring a mature, disciplined approach to their work — someone who can self-manage their time, anticipate needs, and execute tasks with precision, while knowing when to ask for guidance.

This is not a traditional 9–5 role. Flexibility, proactivity, and emotional intelligence are essential.

🧭 Key Responsibilities

• Coordinate and manage complex personal and professional calendars, including appointments, events, and travel.
• Arrange domestic and occasional international travel (commercial and private), including flights, ground transport, hotels, and itineraries.
• Oversee scheduling and logistics for dinners, Broadway shows, social events, and philanthropic engagements.
• Communicate with vendors, contractors, and service providers to manage property-related projects (Homes in Kentucky, South Carolina, Manhattan’s Upper West Side, and the Hamptons).
• Coordinate pet care and support animal-related needs — must be an animal lover. Candidates with a socialized dog are welcome to bring them to work during on-site days.
• Ensure homes are properly stocked and maintained (inventory, groceries, household essentials).
• Assist with onboarding other team members (e.g., estate manager, chef, personal trainer) and collaborate with them once hired.
• Handle emails, calls, and messages with discretion and professionalism.
• Provide administrative support: document prep, filing, meeting follow-ups, and basic content coordination.
• Support occasional event planning and execution (charity events, dinners, etc.) in collaboration with the principal.
• Coordinate and track lifestyle and household projects to ensure timely completion.

📍 Location & Travel

• This role is based in New York City and requires in-person work.
• Occasional travel to Kentucky and South Carolina may be required (rarely over weekends).
• Occasional international travel may occur, but only if desired by the candidate.

✅ Ideal Candidate Profile

• Experience: 2–3+ years supporting high-profile individuals, executives, or celebrities in real estate, entertainment, or luxury lifestyle settings.
• Skills: Tech-savvy with Google Workspace, Trello, Kajabi, and Canva. PC-proficient. Strong written and verbal communication skills.
• Personality: Professional, discreet, fun, and collaborative. Anticipatory, proactive, and solution-oriented. Not a “yes” person — a strategic thinker who takes initiative after learning the principal’s style.
• Work Style: Accountable, organized, calm under pressure, and self-directed. Capable of creating their own workflow and managing multiple priorities.
• Soft Skills: Emotional intelligence, humility, strong boundaries, and a natural ability to read the room.
• Bonus: Pet lover (non-negotiable). Must demonstrate comfort and joy around animals.
• Preferred: Experience working with ultra-high-net-worth clients or celebrity clientele.

💼 Compensation & Benefits

• $150,000 annual salary + bonuses
• Flexible 4-day workweek
• 2 weeks PTO
• Health benefits stipend 
• Wellness Program
• Potential for future growth into a Chief of Staff or Director of Lifestyle role as the team and portfolio expand

🪩 Additional Details

• NDA and confidentiality agreement required.
• Driver’s license required (for emergency or rare driving needs).
• Must be eligible to work in the United States.

📬 How to Apply

To be considered, please submit:

• A resume highlighting relevant experience.
• A brief cover letter explaining why you’re a perfect fit for this role and describing your relationship with animals.
• Up to 1 minute video introduction introducing yourself and sharing whatever you want.