Greenwich Director of Residences

Private Family Office seeks an exceptional, highly organized, and action-oriented Director of Residences to oversee all aspects of their residential portfolio, including operations, daily upkeep, logistics, and ongoing development. This individual will assume full responsibility for property operations, staffing, project oversight, budgeting, and infrastructure development across approximately 12–14 properties, including owned residences, rentals, pre-construction projects, and active builds. The portfolio represents a highly complex operational environment, requiring oversight of multiple entities, payroll structures, and a large network of staff and independent contractors.

This role calls for a seasoned leader who can effectively parachute into a large-scale, dynamic operation currently experiencing operational gaps and recent staff turnover, and quickly establish structure, accountability, and control. The Director of Residences will be responsible for building and implementing a comprehensive estate management infrastructure, including filling key staff roles, documenting institutional knowledge and processes, upgrading technology and security systems, and leveraging digital tools to improve project tracking, financial oversight, and vendor management. A critical component of success in this role will be the ability to centralize fragmented information, improve communication and accountability across teams, and create scalable systems that support long-term efficiency and continuity.

The Director will serve as a trusted partner and extension of the principals, overseeing all day-to-day operations and long-term strategic planning across the portfolio while ensuring each property is maintained to the highest standards. This includes direct oversight of active construction and renovation projects, management of multiple operating entities, and supervision of both full-time staff and a broad network of part-time employees and contractors. The role requires a hands-on, solutions-oriented professional with exceptional project management and leadership skills, capable of navigating complex, multi-jurisdictional environments, including regions such as Puerto Rico, where local expertise is essential.

This is a highly collaborative, service-driven role requiring discretion, adaptability, and a proactive mindset. The ideal candidate is a strategic thinker and strong operator who is equally comfortable building systems from the ground up as they are managing ongoing operations, and who approaches the role as a true team player—willing to step in wherever needed while maintaining the highest level of professionalism, discretion, and respect for privacy at all times. This role is deeply focused on preserving and enhancing the long-term value of the family’s real estate assets through strategic construction oversight, renovations, and both seasonal and day-to-day maintenance.

Key Responsibilities include but are not limited to:

• Serve as the primary liaison between the principals, family office, contractors, vendors, and staff across all residences, ensuring clear communication and seamless alignment with expectations
• Relieve the principals of operational oversight by proactively managing all property-related matters, anticipating needs, and providing regular updates without prompting
• Oversee all aspects of multi-property operations, including daily upkeep, logistics, maintenance, and long-term planning across a geographically diverse portfolio
• Establish and implement operational infrastructure, including systems, workflows, SOPs, and reporting structures
• Centralize and organize fragmented information and improve communication across teams
• Assess staffing gaps and recruit, hire, and onboard key personnel
• Document and maintain institutional knowledge, including property manuals, systems, and procedures to support long-term continuity and scalability
• Evaluate, implement, and manage technology solutions to enhance property management, project tracking, financial reporting, and vendor coordination
• Oversee and continuously improve property technology and security systems to ensure best-in-class functionality across all residences
• Manage large-scale financial operations, including budgeting, expense tracking, and coordination with the family office across multiple entities and high-volume payment activity
• Ensure financial efficiency and accountability by monitoring expenditures, negotiating contracts, and maintaining appropriate controls and approval processes
• Oversee all phases of construction, renovation, and capital improvement projects, from planning and budgeting through execution and completion
• Coordinate architects, designers, contractors, and specialty trades, ensuring projects are delivered on time, within budget, and to the highest standards
• Manage vendor relationships across all properties, including sourcing, contract negotiation, performance oversight, and ongoing relationship management
• Navigate multi-jurisdictional operations, ensuring compliance with local regulations, employment practices, tax requirements, and insurance obligations across all regions
• Leverage local expertise in specialized markets such as Puerto Rico to effectively manage hiring, logistics, and vendor coordination
• Conduct regular site visits and inspections, proactively identifying issues and implementing solutions to maintain property standards
• Ensure all residences are consistently maintained in a guest-ready, fully operational state, aligned with the principals’ standards and preferences
• Build and maintain strong, long-term relationships with contractors, vendors, and service providers to support seamless property operations
• Act as a hands-on leader and collaborative team player, willing to step in wherever needed while maintaining the highest level of discretion, professionalism, and respect for privacy

   

Requirements:

• Strong command of the English language; superb written, verbal, and interpersonal communication skills
• Excellent references required from both current (if possible) and previous employers
• Minimum of 10–15+ years of experience in estate management, construction oversight, or related fields, with prior experience supporting UHNW families and overseeing multiple residences
• Exceptional organizational and project management skills, with the ability to manage complex, multi-property operations while balancing both big-picture strategy and meticulous attention to detail
• Proven ability to build structure, systems, and accountability within complex environments, including experience stabilizing teams and rebuilding operations following periods of transition
• Demonstrated experience supporting UHNW principals in high-touch environments, with the ability to operate as both a strategic leader and hands-on executor
• Strong background in high-end residential construction and renovation, with expertise in designing and implementing operational infrastructure, systems, and workflows
• Experience evaluating and implementing technology platforms for property management, project tracking, and operational efficiency, with strong overall technical proficiency across modern systems and tools
• Strong financial acumen, including experience managing large budgets, multi-entity structures, and high-volume financial activity
• Ability to centralize fragmented information, establish clear reporting structures, and create accountability across staff and vendors
• Experience stabilizing teams and rebuilding operations
• Experience hiring, developing, and managing high-performing teams, along with a strong network of vendors, contractors, and service providers and the ability to negotiate effectively on behalf of the principals
• Ability to navigate multi-jurisdictional environments, with familiarity with Puerto Rico operations strongly preferred, including local hiring practices and logistical considerations
• Analytical, solutions-oriented mindset with a demonstrated ability to identify inefficiencies andimplement scalable improvements
• Strong financial acumen managing large budgets and multi-entity structures
• Ability to centralize information and create accountability systems
• High level of discretion, professionalism, emotional intelligence, and commitment to confidentiality and safety
• Service-oriented mindset with a proactive, above-and-beyond approach and willingness to assist wherever needed
• Ability to operate as both a strategic leader and hands-on executor
• Technologically savvy, with the ability to implement and manage digital systems; complete comfort with computers, internet-based tools, email, apps, calendaring programs, Microsoft Office (Outlook, Word, Excel), Google Suite, and home automation/operations software
• Experience implementing technology platforms for property and project management
• Self-starter with the ability to work independently and maintain consistent productivity with minimal oversight
• Proficiency in both property management systems (HVAC, landscaping, building systems) and hospitality-level service standards
• Physically capable of lifting up to 50 lbs
• Valid driver’s license and passport; willing and able to travel domestically and internationally as needed
• Legally authorized to work in the United States for any employer

Compensation: $400K - $425K per year; potential discretionary, performance based annual bonus

Benefits: Full, noncontributory medical benefits

All salary offers are depending on experience, references, and the results of Federal Background Report