Position: Estate Manager / Personal Assistant (Full-Time)
Location: Litchfield County, CT (Must live within a 20-30 minute commute or be open to relocation
Travel: Occasional travel to NYC and Miami required
Compensation: $90,000- $130,000 annual + bonus and eligible for salary increase in 2026, both based on performance
Benefits: Medical, dental, vision, PTO, holidays aligned with firm’s calendar
Schedule : Monday - Friday 9:00 am - 5:00pm/6:00pm (must be flexible and available to work over the weekend, if needed)
Position Overview: Our client is seeking a highly driven, detail-oriented, and dynamic Estate Manager / Personal Assistant to join a hands-on, fast-paced household and assist in the daily operations of an active principal’s lifestyle and home. This is a unique opportunity to work closely with a collaborative team, including an Executive Assistant, and take ownership of multiple projects ranging from estate management to event coordination.
This role is ideal for someone who is tech-savvy, self-motivated, and passionate about providing top-tier support. The right candidate will bring a “no job is too big or too small” mindset, a sharp eye for detail, and a strong work ethic with 24/7 availability as needed. They should also embody a proactive and professional demeanor, and thrive in a role that blends personal and executive assistant responsibilities with estate management oversight.
Must be proficient with Google Docs, Dropbox, and Microsoft 365 (Word, PowerPoint, Excel, and Outlook)
Property Management & Maintenance
Help manage CT homes (Farm and Lake); work closely with caretaker, various housekeepers, gardeners, and all service providers Help maintain & organize NYC and Miami apartments, including keeping refrigerators stocked before arrivals & communicating with local staff, etc. Understand and assist with maintaining all house systems, manuals & utility rooms – requires the ability to learn all mechanical systems Lightbulb Management and ensuring the house is stocked with all necessary items to run the home Help keep all homes organized and well-maintained, including updating all household manuals in Google Docs Help manage any construction work being done at any of the 4 properties Will oversee care of garden, orchard & greenhouse so some experience required Run errands for homes as needed, including grocery shopping, taking dogs to vet or grooming
Staff & Vendor Coordination
Work closely with caretaker, various housekeepers, gardeners, and all service providers Assist with finding new support staff as needed Coordinate deliveries of furniture and other items (with design assistant) Work with housekeeper &/or chef to plan healthy meals
Personal & Executive Assistance
Help manage wife’s calendar, making appointments, etc. – will need to work with husband’s assistant to coordinate schedules Make phone calls, respond to invitations, organize bills, help maintain effective filing systems for all family paperwork (including wife’s office) Provide sourcing, personal shopping, gift purchasing Help maintain wife’s wardrobe, organize all closets, purchase fashion items as needed and help pack for travel
Event & Social Planning
Help execute dinner parties and other social events (find party staff for NYC & Miami), coordinate social calendar, make dinner reservations, and find fun, new activities, shows, etc. Coordinate travel – airlines, car services, restaurant reservations, etc. Proactive in communicating with the husband’s assistant to ensure all events, dinners, trips, etc are accounted for on both calendars
Mail, Packages & Admin
Help managing mail and packages; opening, sending and returning Help maintain effective filing systems for all family paperwork (including wife’s office)
Technology & Correspondence
Computer Skills & Tech Support: Must be computer savvy and proficient in: Outlook, Word, Excel, PowerPoint, Google Docs and Dropbox. Must know how to use both PC and Mac. Must know how to get outside support when necessary. Must know how to write proper correspondence. Must have a solution oriented mindset
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