Lead Nanny in Chicago, IL (Lincoln Park)
City: Chicago (Lincoln Park)
State: Illinois
Compensation: $150,000–$180,000 per year | 45 guaranteed hours per week
Start Date: ASAP, with flexibility for the right fit
Children: 4-year-old boy, 3-year-old girl, 15-month-old twin boys, and 4-month-old baby girl
Benefits: 5 Paid sick days, 10 Paid vacation days (5 days aligned with family’s prearranged vacation time; 5 at the nanny’s discretion), Paid major federal holidays, and monthly Health-care stipend if needed
Schedule: Monday–Friday, 7:00 a.m.–4:00 p.m. | 45 guaranteed hours per week. Significant flexibility for mornings, evenings, and weekends will be expected during the first three months while learning the household and childcare team. Occasional weekend or date-night support is preferred.
Description:
About the Family
A busy, highly organized family in Lincoln Park is seeking an experienced Lead Nanny to provide hands-on care while managing a team of four ROTA nannies. The family has five children: a 4-year-old boy, 3-year-old girl, 15-month-old identical twin boys, and 4-month-old baby girl. The children follow a very active and structured routine supported by a fully staffed household and established ROTA nanny team.
Dad works full-time outside the home, while Mom is a stay-at-home parent with an extremely active schedule and is frequently in and out of the home. The family travels periodically and maintains a busy lifestyle. They have four Pomeranians, and while pet care is not a primary responsibility, comfort around dogs is important. There are no household dietary restrictions or allergies, although one child has occasional food sensitivities.
About the Role
This is a 50% childcare and 50% team-management position. The Lead Nanny will serve as the direct manager of the ROTA nanny team, communicate directly with the parents, and ensure seamless coordination of childcare schedules, school logistics, activities, transitions, and coverage. The role also includes driving the children to activities, birthday parties, errands, and appointments using the family-provided nanny car.
The children are sweet, active, and developmentally engaged. The 4-year-old is silly, observant, affectionate, and has an incredible memory; the 3-year-old is bright, spirited, determined, and strong-willed; the 15-month-old twins are affectionate, active, and increasingly mobile; and the baby is very alert and developmentally advanced for her age. The ideal candidate will provide nurturing, developmentally appropriate care while confidently leading a sophisticated childcare team.
Management responsibilities include creating and maintaining childcare SOPs, policies, onboarding materials, schedules, and household-specific procedures; training and onboarding caregivers; serving as the primary communication bridge between the parents and childcare team; and helping the Family Assistant understand priorities and where support is most needed.
The first three months will require significant schedule flexibility, including occasional mornings, evenings, and weekends, as the Lead Nanny learns the household, family preferences, and existing team dynamics. Domestic and international travel is required.
The ideal candidate is an exceptionally organized, proactive, and independent professional with strong executive functioning, judgment, discretion, time management, and communication skills. They should be comfortable both giving and receiving feedback and have demonstrated experience leading or managing a team of nannies and caregivers. Experience creating systems, procedures, schedules, and documentation is essential.
Requirements:
Significant professional nanny experience (10+ years)
Previous experience leading or managing other household staff
Previous experience working in an office or as an Executive Assistant
Proven experience in a Lead Nanny, Nanny Manager, or similar leadership role
Strong understanding of child development
Excellent executive functioning, organization, and time-management skills
Exceptional judgment and discretion
Highly proactive and independent
Excellent written and oral communication skills
Comfortable giving and receiving feedback
Experience creating systems, procedures, schedules, SOPs, and documentation
Strong team leadership and interpersonal skills
Comfortable managing a busy, fully staffed household
Experience caring for infants, toddlers, twins, and preschool-aged children
Willingness to provide both hands-on childcare and team management
Valid driver’s license and strong driving experience
Comfortable driving children regularly using a family-provided vehicle
Flexibility to work occasional mornings, evenings, weekends, and travel
Comfortable around dogs
Excellent references from previous families and employers
Legally authorized to work in the U.S.
Pets: Four Pomeranians. Comfort with dogs required; pet care is not a primary responsibility.
Transportation: Family provides a nanny car for all on-the-job driving. Driving is an important part of the role and includes transportation to activities, birthday parties, errands, and appointments.
Travel: Domestic and international travel required