Estate Manager​/PA

After a long, accomplished career in corporate leadership, a recently retired executive is ready for her next chapter, one with more freedom and far less to manage on her own. She and her husband split their time across several properties in the Midwest, a home on the East Coast, and a property in the Caribbean, and she needs a steady, sharp, trustworthy partner who can run the details of it all so she never has to think twice about leaving town.

It's a chance to build this role directly alongside a warm, informal family who value honesty and hard work over titles.

• Manage a busy personal calendar and handle day‑to‑day administration (the primary focus of this role, roughly 30 hours per week)
• Oversee maintenance schedules, spreadsheets, and vendors across all five properties, eventually becoming the main point of contact for vendors
• Serve as lead point of contact for the Dominican Republic property, monitoring accounts closely to prevent overcharging, with occasional on‑site visits as needed
• Oversee construction and renovation projects, and manage seasonal boat and dock needs at the lake house
• Support entertaining: planning casual dinners, prepping for events, and sourcing vendors
• Coordinate travel logistics alongside the family's existing travel agent
• Take on ad hoc projects such as organizing spaces, working with designers, and light physical tasks
• Conduct a basic technology audit across properties

• Hard‑working, honest, and an excellent communicator
• Physically fit and comfortable with light physical tasks
• A natural problem‑solver who is systems‑ and process‑oriented
• Comfortable working within a casual, informal household
• Dog‑friendly (two resident dogs: a goldendoodle and an Australian labradoodle)
• Willing to relocate within driving distance of Kohler, WI (Milwaukee acceptable with 2‑3 days per week on‑site)

Monday – Friday, 9:00 am – 5:00 pm with flexibility

$130,000–$165,000, commensurate with experience. Benefits, PTO and sick leave included.