Property Operations Manager Jobs in Connecticut (NOW HIRING)

Estate Operations Manager

Redding, CT 06896

Full-Time (40 hours/week)

Monday through Friday, generally 9:00 AM - 5:00 PM, with flexibility as needed for emergencies and occasional overnight pet care responsibilities.

$160,000-$220,000 annually, commensurate with experience.

ASAP

• 7-10+ years of experience in estate management, property operations, household management, or a related field required.
• Comfortable managing vendors, contractors, household staff, and estate operations independently.
• Financial literacy and comfort reviewing invoices, receipts, budgets, and operational expenses required.
• Experience supporting multi-property estates or coordinating renovation projects, contractors, architects, or capital improvements preferred.
• Comfortable using modern technology, online systems, and AI tools for research, organization, and problem-solving.
• Strong written and verbal communication skills required.
• Professional presentation and strong interpersonal communication skills required.
• Comfortable in a highly confidential, trust-based household environment.
• Reliable transportation and valid driver's license required.
• Comfortable working around dogs, chickens, pigs, goats, and other farm animals.
• Maintain a smoke-free environment.
• Must be legally authorized to work in the United States.

We are a warm, close-knit, and evolving family seeking an exceptional Estate Operations Manager to oversee our household estate and 50-acre property. Our environment is dynamic and multifaceted, with ongoing projects, vendors, staff, hobby farm operations, maintenance needs, and long-term property initiatives all happening simultaneously.

We deeply value a property that feels calm, exceptionally well-run, organized, and thoughtfully maintained, and we are looking for someone who takes pride in creating that kind of environment through strong operational leadership.

We are looking for someone with strong judgment and curiosity, who is comfortable operating across both structured systems and evolving, unstructured situations, and who enjoys bringing clarity to complexity.

This role blends estate management, property operations, and organizational leadership with significant variety and autonomy. Some days will focus on coordinating contractors, reviewing bids, and managing systems, while others will involve overseeing farm operations and seasonal land management, including planting, pasture rotation, animal care, and barn and infrastructure maintenance. The role also includes property improvements, renovations, vendor coordination, and broader operational initiatives across multiple properties, including a significant renovation and insurance-related project at a secondary residence, ensuring continuity and organization across both homes.

A key part of this role involves turning both structured needs and emerging opportunities into well-executed outcomes across the estate, spanning renovations, capital projects, and ongoing improvements to how the property functions, evolves, and is experienced over time. This may include reimagining or improving functional spaces, enhancing barn and animal environments, refining infrastructure, or developing new uses for existing areas of the property.

In addition, the role includes high-level executive and household coordination support, such as scheduling, communication, and logistics with vendors, contractors, and household professionals. Adaptability and the ability to move fluidly between structured planning and evolving, real-time needs are essential.

At its core, this is a long-term trusted partnership role focused on creating order, anticipating needs, and ensuring the smooth and thoughtful operation of a complex estate system. Over time, this person will serve as a central operational partner across the property and broader family ecosystem, helping bring consistency to systems, strengthening coordination across vendors and projects, supporting ongoing improvements, and contributing to both the structure and evolution of the estate in a deeply trusted capacity.

The ideal candidate enjoys taking loosely defined goals and transforming them into well-executed projects, whether that involves a major renovation, a property improvement, a new structure, an agricultural initiative, or an entirely new idea.

Important characteristics:

• Notice & Anticipate: You naturally see what needs to be done before being asked and thrive in environments with many moving parts.
• Order & Organization: You enjoy creating order out of complexity, balancing larger projects with the small details that keep a household running smoothly day to day.
• Operational & Detail-Oriented: Highly organized and operationally minded, capable of coordinating vendors, organizing systems, tracking expenses, and managing logistics with ownership and follow-through.
• Proactive: You anticipate needs before they become problems and approach tasks with foresight.
• Communication & Warmth: You communicate clearly and professionally while bringing warmth, emotional intelligence, and a sense of humor to your work.
• Leadership & Respect: Comfortable interacting with different personalities, able to lead with confidence while maintaining kindness and respect.
• Accountability & Follow-Through: Able to hold people accountable, manage timelines, oversee moving pieces, and keep projects progressing without constant direction.
• Calm & Engaged: Maintain a calm and respectful presence within the home while remaining highly engaged and effective.
• Adaptable & Trustworthy: Discreet, solutions-oriented, and able to exercise excellent judgment in evolving situations.
• Support & Satisfaction: Genuinely enjoy helping others and take satisfaction in creating environments that feel organized, supported, and calm.
• Strategic & Administrative Mindset: Naturally manages high-level administrative and executive assistant-style responsibilities, including scheduling, communication, vendor coordination, and travel logistics.
• Construction & Renovation Awareness: Experience or familiarity with managing renovation projects, contractor coordination, and serving as an owner's representative for capital or insurance-related work, particularly on a second property, with the ability to translate broader estate needs and ideas into structured execution.
• Excited & Growth-Oriented: Motivated by a role that will evolve over time and become an important source of support for a busy, dynamic household.

Estate Operations & Multi-Property Management

• Oversee the full operational functioning of a large, multi-property estate system, ensuring both the primary estate and secondary property are consistently maintained, supported, and operating at a high standard across daily, seasonal, and long-term needs.
• Conduct regular walkthroughs and operational reviews across both properties to proactively identify maintenance needs, infrastructure issues, safety concerns, vendor performance issues, and opportunities for improvement or optimization.
• Serve as the primary operational lead for a secondary property undergoing a significant insurance-driven renovation and restoration, acting as the owner's representative across contractors, architects, engineers, consultants, inspectors, and insurance professionals throughout the full project lifecycle.
• Manage project planning, budgeting, timelines, scope alignment, contractor sequencing, and execution oversight across concurrent estate and construction initiatives, ensuring clarity and momentum across multiple workstreams.
• Ensure alignment between long-term estate planning, active capital projects, seasonal operations, and day-to-day property execution across both properties.
• Develop and continuously refine operational systems, workflows, preventative maintenance schedules, documentation, and reporting structures to support long-term estate clarity, efficiency, and reliability.

Staff Leadership & Vendor Management

• Directly oversee the on-site caretaker, providing clear priorities, structured direction, and accountability for all day-to-day and seasonal estate operations.
• Take ownership of translating the caretaker's institutional knowledge into documented systems, ensuring that all key processes, maintenance routines, vendor relationships, schedules, and operational workflows are formally captured, organized, and maintained for long-term continuity.
• Lead, manage, and hold accountable a broad ecosystem of vendors, contractors, service providers, and specialty trades across both properties.
• Establish operational cadence, communication rhythms, and expectations for staff and external partners to ensure consistency, responsiveness, and high-quality execution.
• Source, evaluate, and maintain relationships with architects, engineers, designers, consultants, inspectors, and specialty contractors across ongoing and future projects.
• Lead structured bid processes, compare proposals, evaluate scope alignment, and ensure transparency across cost, timeline, and quality expectations.
• Maintain active oversight of vendor performance, ensuring follow-through, accountability, and alignment with estate priorities.

Construction, Renovation & Owner's Representative Oversight

• Lead oversight of a secondary property undergoing a major insurance-driven renovation and restoration process, which may include multi-phase construction, remediation, and rebuild efforts over an extended timeline.
• Coordinate across architects, general contractors, subcontractors, engineers, inspectors, consultants, and insurance adjusters throughout all phases of planning and execution.
• Manage scope definition, budgeting, contract review, scheduling, sequencing of work, and ongoing project tracking to ensure alignment with ownership goals.
• Review progress, quality of work, change orders, and contractor performance to ensure projects remain on track and within agreed parameters.
• Oversee infrastructure improvements, repairs, and long-term capital planning initiatives across both properties as needed.

Estate Operations, Grounds & Agricultural Systems

• Oversee daily and long-term functioning of estate infrastructure, including residential buildings, outbuildings, grounds, utilities, and operational systems across both properties.
• Oversee agricultural operations and seasonal farm cycles, including planting, pruning, harvesting, pasture rotation, soil management, barn maintenance, fencing upkeep, and weather-related preparation and recovery.
• Direct care and coordination of farm animals (including chickens, pigs, goats), ensuring feeding schedules, habitat maintenance, health monitoring, veterinary coordination, and vendor support are properly executed.
• Manage seasonal transitions across grounds and agricultural areas, including spring/summer preparation, fall cleanup, winterization, and storm readiness.
• Maintain high standards of organization, safety, cleanliness, functionality, and aesthetic consistency across all estate and farm environments.

Financial & Administrative Oversight

• Oversee operational budgets, vendor billing, invoices, and ongoing expense tracking across both properties and active projects.
• Review financial documentation to identify inefficiencies, discrepancies, and opportunities for improved cost management and operational alignment.
• Maintain structured records of contracts, vendor relationships, active projects, maintenance schedules, and operational systems.
• Coordinate with accountants, bookkeepers, insurance professionals, and external advisors as needed to support financial clarity and reporting.

Systems, Strategy & Operational Leadership

• Build, refine, and continuously improve systems that support long-term estate efficiency, operational clarity, and consistency across both properties.
• Lead organizational and infrastructure improvement initiatives across buildings, grounds, systems, and operational workflows.
• Conduct research, evaluate options, and present structured recommendations for vendors, systems, improvements, and long-term estate strategy.
• Ensure alignment between day-to-day execution, seasonal operations, and long-term estate planning and capital priorities.

Executive Coordination & EA Support

• Coordinate communication and alignment across vendors, contractors, consultants, inspectors, and internal stakeholders across both properties.
• Manage cross-property scheduling, calendars, and operational coordination across multiple residences, projects, and workstreams.
• Support travel coordination for family members, guests, and household logistics, including planning, scheduling, and execution support.
• Provide executive-level administrative support including communications, follow-ups, documentation, and coordination across estate and project stakeholders.
• Maintain continuity of information flow across vendors, staff, and leadership to ensure smooth execution and avoid gaps in communication or follow-through.
• Support coordination of meetings, site visits, project updates, and operational priorities across active initiatives.

Home & Operational Logistics Support

• Support day-to-day operational flow across both properties to ensure seamless functioning of estate systems, vendors, and household operations.
• Coordinate materials, supplies, deliveries, and service needs across estate and property operations as part of ongoing execution.
• Maintain organization and continuity across household, estate, and operational systems to support smooth functioning across all areas of responsibility.
• Provide flexible, hands-on operational support across properties and initiatives as needed to ensure contin...