HNW Estate Property and Operations Director

POSITION OVERVIEW

We seek an experienced, highly professional Property & Operations Director to oversee the operation, maintenance, and ongoing enhancement of multiple luxury private residences in FL, MA, and NY. Supporting a high-profile family in a private residential environment, this role ensures each property operates seamlessly and is maintained to the highest standards.

The Property & Operations Director will provide hands-on leadership across all household and property operations, including staff management, vendor relationships, capital projects, construction oversight, budgeting, and hospitality services. This individual will serve as a trusted partner to the family, proactively anticipating needs, managing priorities, and delivering exceptional service and discretion.

The ideal candidate is a proven leader who can balance hands-on involvement with high-level oversight, foster a collaborative team culture, and uphold a commitment to excellence across every aspect of the properties.

The Director will oversee several construction projects in multiple states, as well as maintenance and upkeep of the interior and exterior of all properties. As the leader, you will meet regularly with the owners to provide updates, anticipate needs, and align priorities.

The goal is to form a long-term, familiar working relationship based on trust and communication while maintaining a safe, healthy, productive, and engaging work environment.

KEY RESPONSIBILITIES

Property & Estate Operations

• Oversee the maintenance, repair, improvement, and overall presentation of multiple private residences.
• Conduct regular property inspections to ensure all homes, grounds, equipment, and systems are maintained in impeccable condition.
• Coordinate seasonal opening and closing procedures and ensure each residence is fully prepared for family and guest arrivals.
• Manage household inventories, supplies, furnishings, equipment, and personal property.
• Develop, maintain, and continuously improve household procedures, manuals, emergency plans, and property records.

Construction & Capital Projects

• Oversee renovation, remodeling, and construction projects across multiple states.
• Manage architects, contractors, consultants, and vendors throughout all project phases.
• Review bids, negotiate contracts, monitor budgets, and ensure projects are completed on schedule and to expected standards.
• Provide regular project updates and recommendations to ownership.

Staff Leadership & Vendor Management

• Recruit, onboard, train, develop, and lead household staff and third-party caretakers.
• Foster a positive, collaborative, and service-oriented culture across all properties.
• Establish clear expectations, operating procedures, and accountability measures.
• Manage vendor relationships and ensure quality performance from all contractors and service providers.
• Identify the developmental needs of others and coach, mentor, or otherwise help employees improve their knowledge and skills.

Financial Management & Administration

• Develop and manage annual operating and capital budgets for each property.
• Monitor expenditures and identify opportunities for efficiency while maintaining exceptional standards.
• Review, approve, and track property-related expenses.
• Implement and maintain digital systems for records management, maintenance tracking, and information organization.

Family Service & Hospitality

• Serve as a primary liaison with the family regarding property operations, priorities, and upcoming needs.
• Meet regularly with ownership to provide updates and recommendations.
• Anticipate family and guest requirements and ensure exceptional hospitality and service.
• Maintain the highest level of discretion, privacy, professionalism, and trust.

Technology & Security Oversight

Support and oversee household technology systems, including:

• Smart home systems
• Security and surveillance systems
• Computers and mobile devices
• Digital records and media archives
• Ensure systems remain functional, secure, and appropriately maintained.

QUALIFICATIONS

Required Experience

• Minimum of 5 years of experience managing luxury estates, private residences, or high-end hospitality operations.
• Demonstrated success overseeing multiple residential properties across different geographic locations.
• Extensive experience managing domestic staff, contractors, vendors, and service providers.
• Strong knowledge of residential property maintenance, construction, and project management.
• Comprehensive knowledge of property management principles, maintenance practices, and relevant local regulations.
• Willingness to engage directly in operational and day-to-day activities.

Leadership Competencies

• Proven ability to build, lead, mentor, and develop high-performing teams.
• Strong interpersonal skills with the ability to build trusted relationships at all levels.
• Excellent problem-solving, decision-making, and organizational abilities.
• Ability to balance competing priorities while maintaining exceptional attention to detail.
• Demonstrated ability to anticipate needs and proactively drive solutions.
• Maintains a hands-on leadership style, providing direct support when needed to drive results.
• Establishes and maintains interpersonal relationships: Develop constructive and cooperative working relationships with others and maintain them over time.

Professional Attributes

• Service-oriented mindset with a commitment to hospitality excellence.
• Exceptional discretion, professionalism, and integrity.
• Highly organized with strong documentation and follow-through skills.
• Flexible, adaptable, and comfortable working in a dynamic family environment.
• Technology-savvy and comfortable working with property management and productivity software.
• Exceptional interpersonal and communication skills to interact effectively with owners, family members, guests, staff, and external stakeholders.
• Develop, design, and create new applications, processes, and systems to support the growth of the facilities.
• Decision-Making and Problem-Solving: Analyze information and evaluate results to choose the best solution.

Pay: $150,000.00 - $200,000.00 per year

Benefits:

• 401(k)
• 401(k) matching
• Dental insurance
• Flexible schedule
• Health insurance
• Paid time off
• Retirement plan
• Vision insurance

Education:

• Bachelor's (Required)

Experience:

• Property management: 5 years (Required)
• Facilities management: 5 years (Required)

Location:

• Martha's Vineyard, MA 02539 (Preferred)

Ability to Relocate:

• Martha's Vineyard, MA 02539: Relocate before starting work (Preferred)

Willingness to travel:

• 50% (Preferred)

Work Location: In person

Salary : $150,000 - $200,000