Personal Assistant to UHNW Entrepreneur + Luxury Real Estate Founder

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

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

Compensation: $150,000 annually + Bonuses, Wellness Benefits, PTO + year-end holiday leave (Dec 23–Jan 2)

Start Date: ASAP

🦋 About the Role

We are seeking a highly organized, loyal, 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 California, 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: 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.
• Animal 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.

Caretaker Couple for Historic Private Estate (Live-In Optional)

Estate Caretaker Couple – Historic Home, Household Support & Property Management

Location: Mayfield, Kentucky
Schedule: Full-Time | Live-In or Live-Out
Start Date: ASAP
Compensation: DOE – Salary commensurate with experience and housing arrangement

🌿 Overview

We are seeking an experienced, trustworthy domestic couple to help care for a cherished 150-year-old family estate known as The Grand Home in Mayfield, KY. This is a rare, long-term opportunity to become part of a family legacy — maintaining a historic property, supporting an active elderly couple, and growing into expanded responsibilities as the estate undergoes thoughtful improvements.

The ideal couple is hands-on, proactive, and deeply dependable — with one partner focused on housekeeping, meals, and light caregiving and the other on property care, maintenance, and construction oversight. Over time, this role will evolve as the estate expands and new projects come to life.

👩‍🍳 Household Manager / Cook Responsibilities (Partner 1)

• Daily housekeeping of a historic home following established weekly/monthly checklists
• Laundry, organization, and household inventory management
• Healthy, home-style meal preparation (breakfast, lunch, and dinner prep)
• Grocery shopping and errand running as needed
• Light caregiving support, including companionship and occasional transportation
• Ability to adapt and assist as needs increase with a family member experiencing Alzheimer’s

👨‍🔧 Property Caretaker / Maintenance Responsibilities (Partner 2)

• Routine property and exterior maintenance (e.g., fence and gutter repair, painting, seasonal tasks)
• Lawn care, garden maintenance, and riding mower operation
• Vendor scheduling and supervision for larger projects or repairs
• Vehicle care and maintenance (washing, scheduling service, etc.)
• Tool and equipment upkeep
• Construction project liaison: Assist in planning and overseeing major renovations and additions, including a new garage, a one-story home, and surrounding property expansions.

🏡 About the Estate

• A beautifully preserved 150-year-old home with unique maintenance needs — ideal candidates will have prior experience with historic properties or be highly coachable and detail-oriented.
• The property is currently just under 2 acres and will expand to 4+ acres with future land acquisitions and construction projects.
• Long-term plans include creating an accessible, single-story home on the property for the elderly residents while preserving the historic home’s integrity.

📆 Schedule & Employment Details

• Full-time, 5 days per week (some flexibility required for projects or occasional weekends)
• Live-in optional — if chosen, on-site housing, utilities, and use of a household vehicle are provided.
• Meals: Breakfast and lunch provided while on duty; dinner preparation for residents, then off-duty.
• Employment type: W-2 or independent contractor (based on candidate preference)

💼 Qualifications

• Prior experience in private household, estate, or property management roles preferred
• Must be a non-smoker and maintain a smoke-free environment while on the property
• Strong work ethic, discretion, and a team-oriented approach
• Comfort working independently and anticipating needs
• General handyman skills and ability to supervise contractors
• Compassionate demeanor, especially when supporting seniors or individuals with cognitive changes
• Valid driver’s licenses and legal authorization to work in the U.S.

💰 Compensation

• DOE and housing arrangement:
• Live-in: Typically ranges $60,000–$80,000/year combined depending on experience. (Live-In will be a separate house on property.)
• Live-out: Typically ranges $75,000–$95,000/year combined due to added housing costs. (Live-out must be within 10-minutes of the Grand Home)
• Wellness Program
• Bonuses for assistance with on-time, on-budget projects
• Benefits and perks negotiable based on experience and arrangement.

📩 How to Apply

• A resume (individual or combined, if applying as a couple)
• A brief cover letter describing your relevant experience and why you’re interested in this role
• “Just a friendly Hello” - Provide a video introduction - up to 1-minute (phone video is fine!), where you introduce yourselves, share a bit about your background, and tell us why you’d love to be part of The Grand Home team.

✨ Ideal Candidates Will…

• Treat this home as if it were their own — with care, respect, and pride.
• Be comfortable growing into larger roles as the property and family’s needs evolve.
• Be grounded, kind-hearted, and dependable — becoming an integral part of the family’s support system for years to come.

Please submit a resume, cover letter and video (or household portfolio if applying as a couple) to:

[email protected]

PLEASE NOTE:  the above email applies ONLY to this position.  Click the "Apply Now" button to complete the information in the form below and then use the above email to submit your experience details.

References will be required for finalists.

Director of Residences / Estate Manager

Location: Based in New York City, NY (with frequent travel to other residences in Hamptons, Kentucky, South Carolina, and California)
Schedule: Full-time, Exempt
Compensation: $200,000–$275,000 DOE + annual performance bonus, wellness benefits, 2 weeks PTO + paid year-end holiday leave (Dec 23–Jan 2)
Travel: Up to 40%

🦋 About the Role

The Director of Residences will serve as the central operational leader for a portfolio of private estates located in New York City, the Hamptons, Hilton Head, and Malibu, with additional oversight of The Grand Home — a historic 150-year-old residence in Kentucky. This individual will uphold and continuously refine The Monarch Standard — a set of elevated service protocols designed by the principal — ensuring each property operates seamlessly and reflects the same level of comfort, security, and grace regardless of location.

This is a highly autonomous, hands-on position that requires discretion, organization, and an intuitive understanding of luxury residential operations.

Key Responsibilities

• Implement, maintain, and refine The Monarch Standard across all residences, ensuring consistency in service, design, presentation, and guest experience.

• Oversee and mentor all household staff, including local property teams and the traveling housekeeper/personal attendant.

• Manage budgets, vendor contracts, maintenance schedules, and construction or renovation projects.

• Coordinate all travel logistics and property readiness prior to principal’s arrival.

• Conduct regular property inspections, ensuring mechanical systems, grounds, and technology are fully functional and visually impeccable.

• Oversee household inventories, purchasing, and detailed expense reporting.

• Ensure the highest levels of security, privacy, and confidentiality.

• Stay current with innovations in smart home technology, energy efficiency, and estate management best practices.

• Act as liaison with architects, builders, and designers for new projects, particularly on The Grand Home expansion.

• Provide anticipatory service and proactive solutions to maintain a peaceful, efficient household environment.

Qualifications

• Minimum 7+ years of experience managing multiple high-end private residences or luxury hospitality operations.

• Strong project management and construction oversight experience.

• Advanced knowledge of home automation, AV systems, and security technology.

• Proven ability to lead, train, and manage domestic teams with professionalism and empathy.

• Exceptional organizational, communication, and problem-solving skills.

• Financial acumen with ability to manage budgets and vendor payments.

• High integrity, loyalty, and emotional intelligence.

• Animal-friendly: Must be comfortable and affectionate around pets, including dogs, cats, and small animals.

• Willingness and ability to travel regularly to other properties.

• Valid driver’s license and passport required.

 

Traveling Housekeeper / Personal Attendant

Location: Based in New York City, NY (varied travel to Hamptons, Kentucky, South Carolina, and California)
Schedule: Full-time, including travel flexibility
Compensation: $90,000–$120,000 DOE + travel per diem, housing accommodations as needed, wellness benefits, 2 weeks PTO + paid year-end holiday leave (Dec 23–Jan 2)
Travel: Up to 30%

🦋About the Role

The Traveling Housekeeper/Personal Attendant ensures a consistent sense of comfort, beauty, and calm for the principal and her beloved English bulldog, Daisy Grace, across all residences. This position requires exceptional attention to detail, warm professionalism, and the ability to anticipate needs with grace.

The ideal candidate has luxury household or yacht experience, impeccable standards, and a natural love for animals. They thrive in motion — traveling ahead of the principal to prepare each home, ensuring that every arrival feels seamless and familiar.

Key Responsibilities

• Maintain household order, cleanliness, and presentation across all properties in alignment with The Monarch Standard.

• Travel in advance of the principal to set up each residence — preparing closets, stocking essentials, arranging flowers, and coordinating with local staff.

• Manage wardrobe, laundry, and closet organization for the principal.

• Oversee packing, unpacking, and travel logistics for both principal and pet.

• Care for the principal’s pets with love, attention, and reliability during travel.

• Assist with errands, personal shopping, and maintaining inventory lists.

• Ensure consistency of personal preferences and inventory (candles, linens, toiletries, pantry items) across all homes.

• Support event preparation and hospitality for guests as needed.

• Communicate daily updates and travel details with the Director of Residences.

Qualifications

• Minimum 5+ years’ experience in high-end private service, hospitality, or yachting.

• Impeccable housekeeping skills and knowledge of fine garments, materials, and surfaces.

• Excellent organizational and multitasking abilities.

• Warm, professional, and respectful demeanor with a high level of discretion.

• Loves animals and comfortable traveling with them (including dog care).

• Flexibility to travel frequently, sometimes on short notice.

• Valid passport and driver’s license required.