Two Nannies

Strollers and Stilettos - Chicago, IL


Family with main residence in Bucktown of Chicago with two year old girl, one year old boy and infant boy is seeking two experienced, professional, active, and engaging full-time nannies. Schedule will be spilt between two full-time nannies to ensure the family has seven day per week coverage. Schedule on days working could be a combination of 6:00/7:00/8:00am - 6:00/7:00/8:00pm or later. When working at main residence in Chicago, Nanny should expect to work on three to five 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 annually. Nannies will receive monthly schedules at least one to two months in advance. 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). Family has another residence in Michigan, where family spends at least 2-3 weekends per month and majority of the summer months. The position requires extreme flexibility as family's schedule changes at various times in the year (e.g., school holidays, summer, travel, etc.). Approximately 15-20+ weeks of international and domestic travel per year is required (in addition to summer months in Michigan) and approximately 8-10+ weeks of overnights at residence when parents are traveling without children. Applicants need to be honest, trustworthy, understand the importance of maintaining discretion, collaborative and experienced working with domestic staff (estate manager, personal assistant, housekeepers, nannies, baby nurse), experienced working with principals that are at residence often (discreet and staying out of the way is important) and comfortable with dog. Staff vehicle is provided for transporting children. These are newly created positions. Family is open to local candidates in Chicago and domestic relocations. Start date is ASAP, but highly flexible for the right candidate.


  • Experienced working with similar aged children (newborns, toddlers, preschool, school aged, etc.)
  • Nanny experience working with at least three to four children close in age (family hopes to have at least four children)
  • Newborn experience and knowledgeable about routines, sleep training, reading and communicating to baby as often as possible
  • Willing to transport children to and from school, scheduled activities, sports, play dates, outings, etc.
  • Experienced with preparing fresh and healthy meals for children that introduce them to new foods and pureeing baby food for infant
  • 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 (when age appropriate)
  • 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
  • Domestic duties relating to children (e.g., washing dishes after meals, tidying playroom and bedrooms, packing and unpacking children for trips/travel, etc.)
  • 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.)
  • 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)
  • 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


  • 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 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
  • 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 residence in Bucktown of Chicago
  • Ability to swim and snow ski (rooftop pool at main residence and Lake Michigan at Michigan residence)
  • United States passport
  • Ability to complete extensive background checks, motor vehicle checks, drug tests and psychological evaluation
  • Driver's license and clean driving record
  • CPR Certification
  • Vaccinations (e.g., TDap, MMR, Flu shot)
  • Comfortable with dog


  • $70-90K+ gross annual salary (based on experience and qualifications)
  • $300-500 per month gross health insurance stipend
  • Two weeks (10 days) paid vacation
  • Discretionary annual bonus and raise (performance evaluation required)

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

Job Type: Full-time

Salary: $70,000.00 to $90,000.00 /year


  • full-time nanny: 2 years (Required)


  • Bachelor's (Required)


  • Driver's license and clean driving record: I am currently acquiring this license/certification and it will be complete in the next 30 days (Required)


  • English (Required)

Work authorization:

  • United States (Required)

Required travel:

  • 25% (Required)