Estate Director | Owner’s Representative
Location: Stamford, CT with extensive travel
Compensation: 400k to 450k base, depending on experience
Schedule: 50 to 60 hours with a 24 7 mindset
The Role
This is a senior leadership role overseeing a complex multi property residential portfolio, with equal responsibility across domestic operations, staffing, and construction. The portfolio currently includes 12 to 14 properties. Two are in pre-construction, and others are in active renovation.
This is not a maintenance role. This is a build role. This role sits at the intersection of how the homes are built and how they are lived in day to day. The portfolio is active, evolving, and not yet fully structured. There are multiple moving parts across properties, staff, vendors, and systems that require alignment. You are being brought in to take control of that.
Scope and Complexity
This role carries real operational weight.
• A high level of fluency across software platforms supporting construction, residential operations, and financial reporting is required
• A planned annual operating budget across the residential portfolio, with payment systems in place through the family office
• Two properties are in pre-construction, and others are in active renovation
• Oversee two separate management entities including financial operations and compliance
• 6 full time staff positions, with several currently vacant and being rebuilt
• 60 plus part time staff and independent contractors across properties
Centralize communication and create clear accountability across all properties and staff
How This Role Operates
This is a field driven role. You are not sitting in an office. You are moving between properties, walking job sites, working directly with contractors, and managing staff in real time. Some weeks will be heavier travel than others. Priorities will shift. You need to be comfortable stepping into different environments and taking control quickly. You are the extension of the principals across all properties.
Core Responsibilities
• Full oversight of all residential properties across the portfolio
• Lead all construction and renovation projects from active development through completion
• Full ownership of domestic operations across all homes, including staffing, service standards, and day to day functionality
• Manage contractors, architects, and vendors with full accountability to timelines, budgets, and deliverables
• Build and implement systems that create consistency across both household operations and property management
• Establish and document operating procedures for each residence
• Oversee budgets, expenses, and financial reporting across all properties
• Make day to day decisions independently while keeping principals informed
• Ensure each property is fully operational, maintained, and running to a consistent standard at all times
• Maintain a regular physical presence across properties, prioritizing active sites and operationally complex homes
Domestic Operations and Staffing
• Lead all hiring across the residential portfolio, from Estate Managers and House Managers through to Executive Housekeepers, Housekeepers, and support staff
• Build, structure, and lead domestic teams across all properties
• Set the standard for how each home operates day to day, including service levels, readiness, and overall presentation
• Rebuild current gaps in staffing and stabilize existing teams
• Manage and align a large network of part time staff and independent contractors
• Establish clear accountability, reporting lines, and performance expectations across all staff
• Ensure consistency in how each home is run regardless of location
Home and Estate Operations
This role requires a high level of fluency across software platforms that support residential operations across multiple properties.
Software is not a support tool in this role. It is a core part of how the estate is managed.
The Estate Director must be comfortable operating across systems that coordinate staff, vendors, schedules, and day to day household activity across all homes.
This includes:
• Residential and home management systems used to coordinate staff, vendors, and property operations (like 9’s)
• Tools that support financial tracking, reporting, accountability, and visibility across multiple properties
You are expected to use these systems to create structure, maintain accountability, and provide clear, real time visibility across the estate.
Construction and Project Management
This role requires real experience in construction project management.
You need to understand how projects actually move. Timelines, budgets, change orders, punch lists, and how to hold vendors accountable.
You must be able to read and interpret architectural, mechanical, electrical, plumbing, sprinkler, and technology drawings, plans, and specifications with confidence. You should be comfortable walking a job site, identifying gaps, and aligning the work to the plans.
This includes:
• Construction and project management platforms such as Procore, Buildertrend, CoConstruct, or similar
You should be just as comfortable on a job site reviewing drawings as you are reviewing a project from your laptop.
Regional Complexity
Puerto Rico requires specific attention.
Hiring, payroll, logistics, and vendor relationships operate differently and require local knowledge. This role must be able to navigate those nuances and leverage the right local resources to ensure things run properly.
What Matters
• A high level of fluency across software platforms supporting construction, residential operations, and financial reporting
• Experience across multiple high level residences
• Strong construction and renovation oversight
• Strong command of domestic operations with a clear understanding of how a private home should be run day to day
• Proven experience hiring across the full structure of a home, from Estate Managers to Housekeepers
• Ability to read and understand architectural drawings and plans
• Comfort using project management software as a core tool
• Ability to operate independently without constant direction
• Strong judgment and discretion
• Clear communicator who can represent the principals directly
• Calm, steady presence in complex environments
• Highly organized with the ability to manage scale
What This Role Is Not
This is not a desk role
This is not a coordinator position
This is not for someone who manages from a distance
You are expected to be present, engaged, and in control
Bottom Line
This role requires someone who understands both the operational side of a home and the technical side of how it is built.
This role is expected to remove operational noise from the principals and replace it with structure, visibility, and control.
This is a field driven role. The expectation is to be where the work is, not where the desk is.