Chicago, IL | Confident Lead Nanny Wanted For Busy And Private Family

This warm and busy family in Chicago, IL is seeking an organized, professional, and proactive Lead Nanny to care for their five young children while providing thoughtful leadership and support to their household team.

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• Location: Chicago, IL
• Ages of children: Young children
• Start date: As soon as they find the right fit!
• Schedule: Full-time, guaranteeing 40–45 hours per week once the household routine is established; core hours begin at 7:00 a.m. through the evening, with all-hands-on-deck availability expected for the first several months as the Lead Nanny assesses the team and builds the schedule.
• Compensation: The family is offering an estimated base annual compensation in the $150,000–$180,000/year range, and may be open to candidates seeking a higher compensation commensurate with experience.
• Benefits: The family is open to providing health insurance reimbursement/stipend, matching 401(k), a vehicle for professional use, relocation assistance, and an extended Airbnb-based trial period prior to full relocation to ensure mutual fit.
• Live-in/Live-out: Live-out. Candidates must be local or willing to relocate within commuting distance of Chicago.

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Household dynamic: 

• This warm, busy, and private Chicago, IL family is seeking a Lead Nanny to support their children and team! They have five little ones who keep the household lively and full of energy. This is a high-capacity, multi-age household where the days are hands-on and full, and the family favors meaningful engagement and enrichment over screens. 

• The family has an established household team and is looking for a Lead Nanny who can bring consistency and thoughtful leadership to the childcare side of the home. This person will serve as the primary point of communication between the parents and care team, helping translate the parents’ priorities into day-to-day practice while also addressing questions or challenges within the team before bringing matters to the parents when appropriate. The parents value structure, proactive communication, discretion, and good judgment, and they hope to give the right person significant autonomy once trust has been established. The family travels approximately two to four weeks per year with caregiving support as needed. They hope to find a professional candidate who can build trust, grow into full autonomy over time, and become a long-term partner to the household.

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Ideal candidate: 

• This position is ideal for a confident, proactive, and intuitive lead nanny who genuinely loves hands-on childcare and brings warmth, enthusiasm, and real stamina to full, busy days with multiple young children. The family is looking for a nanny first, someone who thrives in the day-to-day of caring for multiple little ones, understands age-appropriate development across infants through grade-school ages, and shows up ready to be the person who fills the gap and keeps things running smoothly. Genuine enjoyment of children and the energy to keep pace with five young kids is essential. The perfect candidate is warm and engaged, while maintaining clear, consistent boundaries, and equally comfortable leading the childcare team and stepping directly into care wherever needed.
• As the Lead Nanny, this person should also be a collaborative leader who knows how to join an established team thoughtfully. The family is also seeking a discreet, low-drama, and diplomatic leader who leads through competence. The right candidate listens to the team, observes the household, understands what’s working, and builds trust before introducing change. A central part of this role, the Lead Nanny will understand the parents’ priorities and communicate them clearly and appropriately to the team, while also determining what can be resolved independently. Excellent judgment around what to handle, what to communicate, and what truly needs to be escalated to the parents will be essential. The family will appreciate someone direct and confident offering thoughtful input or professional pushback when needed, while remaining discreet, flexible, diplomatic, and adaptable. 
• 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, before and after school routines, coordinating activities, and traveling with the family throughout the year. Family assisting duties include running errands, coordinating vendors and household staff, and managing the family calendar. This role is roughly 40% management and 60% hands-on care, so the Lead Nanny will also pinch in when staff is out, build SOPs, checklists, and a nanny handbook, help onboard new childcare hires, and serve as the point of contact between the parents and the care team.
• While not a requirement for the role, the family would love to work with a candidate who is Mandarin-speaking, has Lead Nanny or management experience, has knowledge of an authoritative parenting approach, has experience or familiarity with Montessori, and has prior team leadership, onboarding, or SOP-building experience and career experience outside of nannying with a more formal business structure. 

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Qualifications: 

• 3 years of professional childcare experience
• Knowledge and experience with age-appropriate developmental milestones for infants, toddlers, and preschool through grade school children
• Experience working in a team or a fully staffed environment
• Family assisting experience
• Travel experience
• Valid driver's license 
• Valid passport
• Able to swim and care for children in the water
• Dog-friendly 
• Ability to prioritize tasks, communicate proactively, and work both independently and as part of a team
• High energy and stamina for long, hands-on days with five young children
• Local or willing to relocate within a commutable distance of Chicago, IL
• 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!