A family in Winnetka is seeking a dependable, proactive, and discreet Family Assistant. This flexible, hands-on role supports the family with schedules, errands, household logistics, and travel planning. The family has five children of elementary through high school age. The ideal candidate is personable, organized, resourceful, and comfortable working independently.

Flexibility is especially important in this role.

While the anticipated schedule is approximately 40 hours per week, generally Monday through Friday from 9:00 AM–5:00 PM, the nature of the position requires someone who can pivot comfortably as household needs evolve and designated tasks and responsibilities vary. The family anticipates that the schedule will consist of 25% of time in the family home, 25% out running errands, 50% work-at-home admin.

• Help manage school, activity, and family calendars.
• Plan menus for the week, shop for groceries, and prep food.
• Keep house supplied and organized
• Errands including dry cleaning, returns, alterations, mail, car wash and service.
• Assist with reservations, shopping, appointments, and other family logistics.
• Plan and coordinate family travel, including transportation, lodging, and itineraries.
• Complete approved administrative tasks remotely when an on-site presence is not needed.
• Maintain discretion and respect for the family’s privacy and home.

• Experience as an assistant, or in similar role.
• Strong organization, communication, judgment, discretion and respect for privacy.
• Valid driver’s license, clean driving record, and reliable transportation.
• Professional references and successful background check.

· Legally authorized to work in the United States.

· Valid driver's license, clean driving record, and reliable transportation.

· Experience managing household administrative tasks remotely

· Available to work 40 hours per week, with flexibility based on household needs.

· Comfortable dividing time between the family residence, off-site errands, and administrative work as appropriate.

· Able to provide excellent professional references and successfully complete a comprehensive background check.

· Committed to maintaining the highest standards of confidentiality, professionalism, and discretion.

· Compensation: $40–$50 per hour, depending on experience and qualifications.

· Potential for a hybrid arrangement for administrative responsibilities, balanced with in-home support and off-site errands.

· Additional benefits to be discussed during the interview process.