A private family in Chicago is seeking an experienced, polished, and highly capable Lead Nanny/Childcare Team Lead to help oversee the care and day-to-day operation of a busy household with five children, all aged five and under.

This is a highly hands-on leadership position. The Lead Nanny will spend approximately 60% of her time providing direct childcare and 40% focused on leadership, communication, administration, and team development. This will be a Monday through Friday role about 45 hours per week. For the first 30-90 days, the Lead Nanny should expect much longer hours, shifts, and coverage while learning the home, roles, and family life. 

Hands-On Childcare

The Lead Nanny must first and foremost be an excellent childcare professional. Responsibilities will include:

• Providing warm, attentive, developmentally appropriate care for the children.
• Managing daily routines, transitions, activities, meals, naps, outings, and bedtime as needed.
• Supporting the children's emotional, social, and developmental needs.
• Maintaining consistency across caregivers and throughout the children's routines.
• Modeling the standards and behaviors expected of the broader childcare team.
• Stepping into hands-on coverage wherever the household requires it.
• Building genuine relationships with each child while maintaining appropriate boundaries and structure.

Team Leadership & Communication

The Lead will serve as the primary communication link between princpals and the childcare team.

Responsibilities include:

• Receiving and understanding direction from the parents.
• Translating parental expectations into clear, actionable guidance for the team.
• Communicating updates, concerns, and relevant observations to the parents.
• Helping filter emotion or noise from situations and keeping communication productive.
• Ensuring that agreed-upon expectations are consistently carried through.
• Facilitating effective communication between caregivers.
• Identifying gaps, inconsistencies, or recurring issues before they become larger problems.
• Helping onboard and train new caregivers.
• Providing appropriate day-to-day leadership without creating an unnecessarily hierarchical or authoritarian environment.
• Building credibility and trust with both the family and the team.

The Lead should be comfortable appropriately clarifying expectations with Nicole and David when something is unclear or additional context is needed. At the same time, she must understand that Princpalsare the employers and ultimate decision-makers.

Systems & Administration

A particularly important aspect of this role is the ability to create and improve systems, rather than simply follow systems developed by others.

The successful candidate may be responsible for developing and maintaining:

• SOPs and household procedures
• Checklists and daily/weekly workflows
• Childcare policies and protocols
• Nanny handbooks
• Onboarding programs
• Training materials
• Child-specific routines and reference materials
• Communication protocols
• Scheduling and coverage systems
• Household/team documentation
• Standards for consistency across caregivers

The Lead should be someone who naturally looks at an operation and asks, “How can we make this clearer, more consistent, and easier for the team to execute?”

However, improvements should be thoughtful and appropriately timed. The expectation is to observe first, understand the household, build relationships and trust, and then make informed recommendations—not arrive with an assumption that existing systems or team members need to be immediately overhauled.

Leadership Philosophy

The right candidate will demonstrate autonomous execution within clearly established boundaries.

We are looking for someone who:

• Thinks independently.
• Anticipates needs.
• Takes initiative.
• Makes sound day-to-day decisions.
• Does not require constant supervision.
• Is comfortable asking thoughtful questions when clarification is genuinely needed.
• Can implement direction consistently once expectations are established.
• Understands the difference between leadership and imposing personal preferences.
• Can respectfully challenge or clarify when appropriate without undermining the parents' authority.
• Not looking for someone whose definition of autonomy is, “I have extensive experience, therefore I will do things my way.”

The successful candidate will bring her expertise to the household while remaining aligned with the family's established philosophy and expectations.

• Significant professional nanny experience, ideally in complex private households.
• Demonstrated experience leading or coordinating a childcare team.
• Experience caring for multiple young children simultaneously.
• Strong organizational and administrative abilities.
• A proven history of creating or implementing systems, SOPs, handbooks, onboarding programs, or training processes.
• Excellent communication skills.
• Strong emotional intelligence and interpersonal judgment.
• The confidence to lead without being controlling.
• The humility to observe and learn before making changes.
• The ability to receive and implement feedback without defensiveness.
• Strong discretion and professionalism.
• Excellent judgment and initiative.
• A calm, solutions-oriented approach under pressure.
• The ability to work effectively within a clearly defined family hierarchy.
• Previous Lead Nanny, Nanny Manager, Household Manager, or similar leadership experience.
• Experience with five or more young children or similarly complex childcare environments.
• Experience managing or mentoring other caregivers.
• Experience working with high-profile, UHNW, or otherwise highly structured private households.
• Formal childcare, education, child development, or related training.

Most importantly, the candidate should understand that being a Lead Nanny is not simply being the most experienced or capable nanny on the team. It requires a distinct combination of excellent childcare, leadership, communication, operational thinking, and emotional intelligence.

• Extensive professional childcare experience.
• Proven experience working in a high-demand private household.
• Experience working as part of a multi-caregiver team.
• Demonstrated leadership or team-coordination experience.
• Excellent verbal and written communication skills.
• Strong organizational and administrative skills.
• Ability to develop and implement household systems and procedures.
• Professional references demonstrating reliability, judgment, discretion, and professionalism.
• Willingness to be highly hands-on during the initial 30–90-day period.
• Ability to work in Chicago or relocate to Chicago.

DOE $150,000–$180,000 annually, with flexibility above this range for an exceptional candidate whose experience and capabilities warrant it.

- Health insurance STIPEND and 401k matching 

The family is open to candidates who need to relocate to Chicago and may provide temporary housing/Airbnb accommodations during the initial transition period while both the family and candidate determine long-term fit.