A family of five, in Chicago, needs to hire an experienced, highly organized, and proactive House Manager to oversee the day-to-day operations of their homes. Responsibilities include: overseeing a small, dedicated team of household staff and ensuring quality control, managing vendors, coordinating maintenance and repairs, conducting regular property walkthroughs, developing organizational systems, and rolling up their sleeves to assist with tidying and hands-on household needs when necessary. Additional responsibilities include: ensuring the homes remain fully stocked and well maintained, managing household inventories, coordinating projects, and serving as the primary point person for the overall operations of both Illinois residences. It is essential that the House Manager work collaboratively with other staff to ensure household logistics are coordinated well in advance while providing structure, accountability, and consistent communication across the household team. The family spends the majority of the year at their primary Chicago residence, with additional time spent at another Illinois home, as well as residences out of state. The House Manager will be required to help oversee the additional Illinois home, located approximately one hour outside of the city, though travel there will typically be limited to one or two times per month. This is an ideal opportunity for an experienced House Manager who excels at creating systems, improving organization, and ensuring a large household runs seamlessly. The typical schedule is Monday through Friday, generally from 8:00 or 9:00 a.m. to 5:00 or 6:00 p.m., with some flexibility required. Salary range: 100-150K range, depending on experience, along with medical benefits. While local applicants are preferred, the family is flexible to relocate the right fit. The start date is flexible, though someone must be in place by the fall.