Full-Time Live In/Live Out Nanny in Hartland and Milwaukee

Strollers and Stilettos - Milwaukee, WI


Family living between Hartland and Milwaukee, Wisconsin with 1 year old boy and 13 year old girl is seeking an educated, experienced, professional, active, and engaging Full-Time Live In/Live Out Nanny. Schedule will be spilt between two full-time live out nannies to ensure the family has seven day per week coverage (nanny lives in and stays overnight with monitor on days scheduled). When working at residences in Wisconsin, Nanny should expect to work on three or four days per week. This schedule will ensure that each Nanny works half the time, receives approximately two+ weekends off per month and travel is split equally. Nanny should be comfortable working many days consecutively (e.g., if traveling for one or two weeks at a time, only one nanny will travel with family and the other nanny is off work). The position requires extreme flexibility as family's schedule changes at various times in the year (e.g., school holidays, summer, travel, etc.). Approximately 6-8+ weeks of domestic and international travel per year is required. Applicants need to be honest, trustworthy, understand the importance of maintaining discretion, collaborative and experienced working with other family office and domestic staff (full-time private chef/house manager, full-time housekeeper, full-time nannies, etc.), experienced working with Principals that are at residence often (discreet and staying out of the way is important) and comfortable with dog (family has small dog). Family provides vehicle for transporting kids. Older child is enrolled in full day school, which is driving distance from the family's residences. This is a newly created position. Local candidates in Milwaukee or individuals moving back to Wisconsin after a few years away is required. Start date is ASAP, but highly flexible for the right candidate.


  • Experienced working with similar aged children (toddlers, preschool, school aged, etc.)
  • Experienced working with at least two children in a nanny position
  • Toddler experience and knowledgeable about routines, sleep training, reading and communicating to child as often as possible, etc.
  • Willing to transport children to and from school, scheduled activities, sports, play dates, outings, etc.
  • Experienced with meal planning and preparing fresh and healthy meals for children that introduce them to new foods
  • Willing to pack healthy lunches and prepare school bags for the next day
  • Experienced with play-based learning and creating educational activities (e.g., planned engaging activities at home, developmentally appropriate games and activities, engaging projects and crafts, themed weeks, scheduled outings, etc.)
  • Willing to assist children with homework and school projects
  • Support teaching and reinforcement of manners and other social skills
  • Provide developmentally appropriate games and activities, engaging projects and crafts at home and schedule/plan fun outings and events
  • Responsible for domestic duties relating to children (e.g., washing dishes after meals, tidying playroom and bedroom, assistance with children's laundry, packing and unpacking children for trips/travel, etc.)
  • Responsible for organizational projects relating to children (e.g., taking toys and clothing to donation, rotating children's clothes seasonally, rotating books and toys quarterly or bi-annually, etc.)
  • Responsible for packing children for trips, researching/planning activities at destination and ensuring appropriate gear is available other residence, hotel or resort
  • Diligent team player and willing to work collaboratively with other domestic staff, family office and Principals
  • Experienced and willing to be an extension of the parents collaborating and communicating frequently (previous experience working with Principals that are around residence is ideal)
  • Experienced assisting with dogs (e.g., letting out, taking on walk, feeding, dropping at vet or groomer, etc.)
  • Excellent communication skills
  • Flexible schedule
  • Professional
  • Active
  • Engaging
  • Creative
  • Energetic
  • Positive
  • Nurturing
  • Calm demeanor
  • Organized and detail-oriented
  • Proactive, resourceful and take initiative to get things done
  • Ability to multi-task
  • Willing to assist with day-to-day functioning of a busy family and household


  • Capable of building good rapport with children
  • Ability to travel internationally and domestically whenever necessary
  • Highly organized, detail oriented, proactive, excellent time management, efficient and service focused
  • Attentive to Principals' preferences and style (intuitive to their needs)
  • Observant to the needs of family and home to anticipate their needs (e.g., finding and registering children for activities that are age appropriate, planning engaging activities at home, etc.).
  • Ability to maintain discretion (confidentiality agreement is required)
  • Ability to be discreet with respect for employer’s privacy
  • Professional presentation of self and great personality
  • Ability to easily take direction
  • Strong ability to communicate and collaborate effectively with domestic staff and Principals
  • Positive attitude and ability to handle position with ease and calm demeanor
  • Active and fit


  • Bachelor’s degree and/or Master's Degree in Early Childhood Education, Elementary Education or Early Childhood Development is most ideal, but bachelor's degree is required
  • Passionate about education, child development, etc.
  • 2-5+ years of full-time consistent and recent nanny experience
  • 3-4 references from professional positions
  • Seeking longevity (e.g., 2-5+ year commitment)
  • Live a close proximity to the family's residences in Hartland and Milwaukee, Wisconsin
  • Ability to swim and snow ski
  • Ability to complete extensive background checks, motor vehicle checks, drug tests and psychological evaluation
  • Proof of good credit history will be required (A poor report may result in elimination from consideration for this position)
  • Driver's license and clean driving record
  • CPR Certification
  • Vaccinations (e.g., TDap, MMR, Flu shot)
  • Comfortable with small dog


  • $65K+ gross annual salary (based on experience and qualifications)
  • $300-500 per month gross health insurance stipend
  • Three weeks (15 days) paid vacation
  • Discretionary annual bonus and raise (performance evaluation required)

Please read the job description carefully and kindly apply with your cover letter, resume, references (email address and phone number), letter(s) of recommendation and professional photo if you meet all of the requirements. Submit through our website at www.strollersandstilettos.com/job-opportunities. We look forward to hearing from you!

Job Type: Full-time

Salary: $65,000.00 to $75,000.00 /year


  • Full-Time Nanny: 2 years (Required)


  • Bachelor's (Required)


  • Milwaukee, WI (Preferred)


  • Driver's license and clean driving record (Required)


  • English (Required)

Work authorization:

  • United States (Required)

Required travel:

  • 25% (Required)