Position Overview
A private multigenerational family based in the Greater Boston area is seeking an experienced Director of Residences to provide strategic leadership and operational oversight across a portfolio of high-end residences. Reporting to the Head of the Family Office, the Director of Residences will be responsible for ensuring each property is exceptionally maintained, operationally sound, appropriately staffed, and consistently prepared for family use.
This role will serve as the central point of integration across the family's residential portfolio, overseeing property operations, facilities and building systems, household staff, vendors, preventative maintenance, security coordination, technology, and ongoing capital and construction projects. The Director will balance the day-to-day requirements of individual properties with a broader portfolio-wide approach, establishing consistent standards, systems, and processes while accounting for the unique needs of each residence.
The Director of Residences will act as a trusted representative of the Principals, translating their priorities into clear direction for staff, vendors, contractors, and external partners while minimizing the need for their involvement in day-to-day property matters. This individual will bring structure and foresight to a complex residential environment, anticipating needs, identifying risks, resolving issues, and ensuring decisions and projects move forward efficiently.
The ideal candidate is an experienced residential or estate operations leader who combines strong facilities and property management expertise with exceptional leadership, judgment, and organizational skills. This individual will be equally comfortable establishing long-term property strategies, managing complex projects, developing staff, and stepping into operational details when needed.
Key Responsibilities
Residential Operations & Property Management
- Lead operations across the family's residential portfolio, ensuring each property is maintained to exceptional standards of safety, functionality, presentation, and readiness
- Establish consistent operating standards, processes, and service expectations across residences while recognizing the unique requirements of each property
- Develop annual and seasonal operating plans, preventative maintenance schedules, property readiness protocols, and long-term maintenance priorities
- Oversee seasonal openings, closings, and transitions, ensuring properties are fully prepared for family occupancy
- Maintain comprehensive property manuals, maintenance records, warranties, vendor information, equipment documentation, and other critical records
- Establish systems to proactively identify property needs, risks, and deferred maintenance before they become operational issues
- Coordinate residential service delivery across facilities, housekeeping, culinary, and personal support functions to ensure each residence operates cohesively and is appropriately prepared for family occupancy
- Coordinate modest facilities support for additional family residences, as appropriate, while maintaining clear priorities and service expectations
- Partner closely with those responsible for construction and capital projects to ensure project activity is aligned with residential operations, property readiness, and family occupancy
Facilities, Building Systems & Technology
- Oversee the performance and maintenance of all major residential systems, including HVAC, electrical, plumbing, generators, water systems, roofing, elevators, pools, landscaping, and other property infrastructure
- Direct preventative and corrective maintenance programs across the residential portfolio
- Manage inspections, testing, servicing, and regulatory requirements to ensure properties and systems remain safe and compliant
- Oversee residential technology infrastructure, including AV, networking, smart home and automation systems, ensuring reliability and ease of use
- Partner with the Family Office and external specialists on residential security systems, access controls, emergency protocols, and privacy safeguards
- Develop and maintain emergency preparedness and property response plans, including severe weather, power outages, water intrusion, and other potential property events
- Evaluate the condition and lifecycle of major building systems and develop recommendations for repair, replacement, and capital investment
Staff Leadership & Organizational Development
- Lead, develop, and coordinate the residential team, including facilities, maintenance, housekeeping, culinary, and Personal Assistant staff
- Provide direct oversight and leadership to residential team members, establishing clear roles, responsibilities, reporting structures, and performance expectations
- Ensure effective coordination across property operations, household services, culinary, and personal support functions, particularly around family occupancy, seasonal transitions, and changing priorities
- Partner with the Family Office on workforce planning, recruiting, hiring, onboarding, and retention of residential staff
- Develop and maintain SOPs, training programs, property protocols, and service standards
- Conduct performance reviews, provide ongoing coaching, and create opportunities for staff development
- Foster a professional, collaborative, accountable, and low-ego working environment
- Evaluate staffing models and recommend changes as the family's properties and operational needs evolve
- Ensure appropriate staffing coverage across properties, including seasonal periods, family occupancy, projects, and other periods of increased activity
Vendor & External Partner Management
- Manage relationships with contractors, service providers, tradespeople, and other external partners supporting the residences
- Establish a consistent approach to vendor selection, onboarding, performance management, and contract oversight
- Review scopes of work, proposals, service agreements, and pricing to ensure quality, appropriate coverage, and value
- Hold vendors accountable for service standards, timelines, documentation, and contractual commitments
- Develop and maintain a network of reliable vendors and contingency resources across key property functions
- Coordinate vendor access and activity to ensure work is performed safely, efficiently, and with minimal disruption to the family
Principal & Family Office Coordination
- Serve as the primary point of contact for the Principals on residential operations, property priorities, projects, and significant decisions
- Translate Principal preferences and priorities into clear direction for staff, vendors, and project teams
- Establish structured communication and reporting protocols that provide appropriate visibility without requiring the Principals to manage operational details
- Consolidate decisions, recommendations, and open items for efficient review and resolution
- Maintain clear tracking of property requests, projects, maintenance items, and follow-up actions
- Partner closely with the Head of the Family Office and other Family Office team members to coordinate residential priorities with broader family needs
- Escalate material risks, issues, and decisions appropriately while independently resolving routine operational matters
Property Systems, Records & Asset Management
- Develop and maintain centralized systems for property information, maintenance schedules, inventories, warranties, service records, and vendor documentation
- Establish standards for tracking residential assets, furnishings, equipment, collectibles, vehicles, storage, and other property-related inventories, as appropriate
- Maintain accurate documentation of major building systems, equipment specifications, service histories, and replacement schedules
- Leverage technology and project management tools to improve operational visibility, accountability, and efficiency across properties
- Ensure critical residential records and documentation are organized, current, secure, and accessible to appropriate stakeholders
Financial & Administrative Oversight
- Develop and manage annual operating and capital budgets for the residential portfolio in partnership with the Family Office
- Monitor expenditures, forecasts, and budget-to-actual performance, identifying material variances and emerging needs
- Review and approve property-related invoices, purchases, proposals, and contracts within established authority levels
- Identify opportunities to improve cost effectiveness while maintaining the family's standards for quality and reliability
- Coordinate with accounting and financial teams on vendor payments, expense coding, capital projects, insurance documentation, and financial reporting
- Support insurance reviews, property valuations, claims, and risk-management initiatives as needed
Qualifications
- Bachelor's degree preferred, with 10+ years of progressive experience in private residential, estate, luxury property, facilities, hospitality, or similarly complex property operations
- Significant leadership experience overseeing multiple high-end residences or a complex residential portfolio strongly preferred
- Demonstrated expertise in residential property operations, preventative maintenance, building systems, vendor management, and facilities planning
- Experience leading and developing multidisciplinary residential teams and managing external contractors and service providers
- Strong understanding of high-end residential construction, renovation, and capital improvement projects, including the operational implications of design and construction decisions
- Experience developing operating procedures, preventative maintenance programs, property documentation, and scalable systems
- Strong financial acumen, including experience with operating and capital budgets, forecasting, contract review, purchasing, and vendor negotiations
- Ability to assess competing property priorities, identify risk, and make sound recommendations with limited oversight
- High level of technological fluency and comfort utilizing property management, project management, Microsoft Office, Google Workspace, and related systems
- Exceptional written and verbal communication skills with the ability to synthesize complex information and communicate recommendations clearly
- Demonstrated commitment to discretion, confidentiality, security, and the protection of family assets
Job Type: Full Time, primarily in-person and based in Greater Boston, MA, with regular presence across the family’s residences, including travel to Massachusetts properties and occasional travel to Florida
Compensation: Annual salary range of $250,000 - $350,000 based on experience and qualifications, with comprehensive benefits