Chicago, IL | Proactive ROTA Nanny/Family Assistant Wanted For Team-Oriented Family

This structured and intellectually curious family in Chicago, IL is seeking a proactive and highly organized rotational nanny/family assistant to join their fully-staffed home. 

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• Location: Lincoln Park, Chicago, IL
• Ages of children: 4.5 years, 3 years, 1.5-year-old twins, and 6 months
• Start date: As soon as they find the right fit
• Schedule: Full-time, rotational schedule of 1 week on/1 week off. Candidates can expect to work between the hours of 7:00am to 8:00pm during every other rotation, and be on duty 24/7 and covering overnights for every other rotation. The family will communicate specific weekly hours in advance. Flexibility for evenings, travel, and occasional overnight shifts during the rotation will be key for the right candidate!
• Compensation: The family is offering an hourly and overtime rate equivalent to an annualized base compensation of $140-150k/year dependent on candidate experience. The family may be open to candidates who are seeking a higher compensation package commensurate with experience.
• Benefits: The family is open to providing benefits including a health insurance reimbursement/stipend, matching 401k contributions, a vehicle for professional use, and relocation assistance for the right candidate.
• Live-in/Live-out: Live-in or live-out while on duty, live-out while off duty. 
• Other notes: This role is not open to fly-in/fly-out candidates.

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Household dynamic: 

• This busy, structured, and inquisitive Chicago-based family is seeking a rotational nanny/family assistant to join their fully-staffed household. They described their five children as curious, active learners who thrive on reading and hands-on enrichment. They prioritize engaging activities and conversations over screen time and appreciate caregivers who warmly encourage questions and foster independence. This fall, their oldest, at 4.5 years old, will begin junior kindergarten, while their 3-year-old will start preschool. Currently, their 1.5-year-old twins attend Montessori school once a week, and will transition to five times a week next year. Their youngest, at 6 months old, is cared for at home. The family also shares their home with four adorable small dogs, so candidates should be comfortable around them and willing to provide occasional light pet-related care as needed.
• This is a collaborative, fully-staffed household designed to provide seamless coverage for the children. The nanny team includes four rotational nannies, with two nannies working together during each rotation and one providing overnight coverage. A dedicated weekend nanny provides support Friday through Sunday, along with additional flexible hours on Mondays. The family also employs a private chef, a team of three housekeepers who provide support throughout the week, and a property manager who oversees the home remotely. Both parents are frequently in and out of the home throughout the day and value caregivers who are proactive, collaborative, and confident taking ownership of their responsibilities. The family enjoys traveling for approximately 2-4 weeks each year for vacations and holidays, and the rotational nanny/family assistant will accompany them as needed.

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Ideal candidate: 

• This position is ideal for an experienced, proactive, team-oriented, and professional nanny/family assistant who thrives in a collaborative, fully staffed household. The ideal candidate is calm, driven, adaptable, and highly organized. Strong prioritization skills, tech-savvy, open communication, and sound judgment are essential, as the family values professionals who can confidently manage the day, help create consistency across rotations, support coordinating children’s activities with Mom, and work independently without constant direction. The family would love to work with someone who genuinely enjoys engaging children's curiosity. They value a nanny who embraces meaningful engagement that encourages learning through reading and hands-on experiences, answers children's questions with warmth, and creates an environment where each child can grow and thrive.
• Responsibilities include creating an environment for the children to grow and thrive, child-related household tasks including but not limited to meal prep, tidying, organizing children’s areas, occasional errands, before- and after-school routines, coordinating activities, and traveling with the family throughout the year. Family assisting duties include light pet care, managing packages, and the family calendar. 
• While not a requirement for the role, the family would love to work with a candidate who speaks Mandarin and is knowledgeable about the authoritative parenting approach. 

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Qualifications: 

• 3 years of professional childcare experience
• Experience working in a team or fully-staffed environment
• Able to swim and care for children in water
• Travel experience
• Family assisting experience
• Valid passport
• Valid driver's license
• Dog-friendly and willing to provide light pet care
• Ability to live-out while off duty and live-in during monthly 24/7 ROTA shift
• Willingness to relocate within a commutable distance of Chicago
• Partners, family members, and/or pets cannot be housed in any temporary or long-term accommodations provided by the family

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This position is open to all Adventure Nannies candidates who are legally able to work in the US. Out of respect for the privacy of the families we work with, we cannot provide any additional information about this position other than what has already been provided in the job description. If you are interested in learning more about the position, please apply!