Two Full-Time Nanny / Family Assistants: $100K+ and Benefits

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Family living in Lincoln Park of Chicago, Illinois with 3 and 4 year old boys is seeking two educated, experienced, professional, organized, and detail oriented full-time nanny / family assistants to manage a busy family and household. Schedule will be spilt between two full-time nanny / family assistants to ensure the family has seven day per week coverage. Schedule on days working will be a combination of 6:00 – 9:00am to 6:00 – 9:00pm or later. When working at main residence in Chicago, nanny / family assistants should expect to work on three to five days per week. This schedule will ensure that each nanny / family assistant works half the time (26.5 weeks per year), receives approximately two weekends off per month, and travel is split annually. Nanny / Family Assistants will proactively make monthly schedules at least two to three months in advance. Nanny / Family Assistants should be comfortable working many days consecutively (e.g., if traveling for two or four weeks at a time, only one nanny / family assistant will travel with family and the other nanny / family assistant is off work). Family spends at least 10-12+ weeks of summer months in Nantucket, Massachusetts. The position requires extreme flexibility as family’s schedule changes at various times in the year (e.g., school holidays, summer, travel, etc.). Approximately 10-15+ weeks of international and domestic travel per year is required (in addition to summer months in Nantucket) and approximately 4-6+ weeks of overnights at residences when principals are traveling without children. Applicants need to be honest, trustworthy, understand the importance of maintaining discretion, collaborative and experienced working with domestic staff (full-time housekeeper and full-time nanny / family assistant), comfortable with dogs (family has Golden Retriever), experienced working with stay-at-home mom and principals that are at residence often (discreet and staying out of the way is important). Children are enrolled in private schools, which are short driving distance from the family’s main residence. Staff vehicle is provided for transporting children and running errands. These are newly created positions. Family is open to local candidates in Chicago and domestic relocations. Start date is flexible for the right candidates. 


• Play-based learning and creating educational activities (e.g., planned engaging activities at home, developmentally appropriate games and activities, engaging projects and crafts, scheduled outings, etc.)

• Provide developmentally appropriate games and activities, engaging projects and crafts at home, and schedule/plan fun outings and events 

• Knowledgeable about child development (e.g., firm when necessary and capable of teaching children manners and etiquette, but also capable of being laid back and fun) 

• Support teaching and reinforcement of manners and other social skills

• Assist children with homework, school projects, studying for tests, etc. and keep parents informed of progress and needs 

• Transport children to and from school, activities, play dates, camps, etc.

• Fresh and healthy meal planning and preparation for family 

• Pack children’s healthy lunches and bags for the following day (e.g., ensure all school work is completed, pack gear for sports and activities, etc.) 

• Pack and unpack children for trips/travel (create pack lists in advance to ensure children have everything needed prior to travel) 

• Inventory checklists for household items, food, children’s essentials, principals’ essentials, etc. and order through Amazon, Instacart, etc.

• Event planning for children’s themed birthday parties and other events (e.g., plan, organize, and oversee flawless execution day of event) 

• Maintain comprehensive household manuals setting priorities for tasks on daily, weekly, monthly, quarterly, and annual basis

• Maintain file systems including those for household operations, warranty manuals, household equipment, invitations, entertainment logs, etc. 

• Maintain contacts lists that include family members, vendors, contacts, businesses, etc.

• Management responsibilities of 7,500 square foot single family homes in Chicago and Nantucket 

• Schedule and oversee vendors and contractors (e.g., winterizing irrigation system for winter months, seasonal landscaping displays, interior design projects, etc.)

• Run errands (e.g., shopping for home supplies, returns, purchasing school supplies for beginning of school year and needed throughout the year, purchasing gifts for birthday parties children are attending, and other requested items)

• Handle things around the home (e.g., receiving deliveries, service providers, contractors, sending emails, going through mail and sorting bills and junk, etc.)

• Organizational projects (e.g., children’s bedrooms, playrooms (toys, crafts, etc.), closets, rotating clothes seasonally, getting rid of outgrown toys and clothing, taking things for donation, etc.)

• Assist domestic staff with projects when necessary (e.g., creating a collaborative/team environment)

• Ensure pantry, refrigerator and wine cellar are properly stocked in accordance with the principals’ and children’s travel and entertaining schedules

• Maintain vehicles, fill gas tank, take for service appointments and keep accurate records of services completed

• Manage family and household schedules and calendars

• Schedule and maintain calendars for children, registering for activities/camps/etc., planning play dates/outings with friends, etc. 

• Manage household petty cash (including proper documentation) and submission of house credit card purchases/receipts

• Assistance with travel arrangements and ensuring all logistics are planned in advance (e.g., equipment for sports and activities, etc.) 

• Schedule meetings with principal(s) as needed to discuss their schedule, children’s schedules, travel plans, upcoming events, special projects, etc. 


• Capable of building rapport with similar aged children (toddlers, school aged, etc.) 

• 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 

• 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 develop and maintain solid working relationships with service providers, contractors, and vendors

• Ability to work collaboratively with vendors and oversee projects 

• Ability to easily take direction 

• Strong ability to communicate and collaborate effectively with principals (extension of parents and consistent childcare philosophies)

• Strong technology skills and experienced working with Macintosh 

• Positive attitude and ability to handle residences and staff with ease and calm demeanor

• Active and fit (e.g., swimming, snow ski, etc.)

• Non-Smoker 


• 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 

• Experienced working with at least two children in nanny position 

• 2-5+ years of full-time consistent and recent domestic experience working as a nanny / house manager / family assistant 

• 2-3+ references from domestic positions

• Seeking longevity / long term commitment (e.g., at least 2-5+ years)

• Live a close proximity to family’s residence in Lincoln Park or willingness to relocate within a commutable distance

• Ability to complete extensive background checks, motor vehicle checks, drug tests, and psychological evaluation 

• Vaccinations (e.g., COVID-19, MMR, TDap, Flu Shot) 

• COVID-19 testing

• Driver’s license and clean driving record 

• Pediatric CPR Certification


• $100K+ gross annual salary (based on experience and qualifications) 

• $500+ gross per month health insurance stipend 

• Two weeks (10 days) paid vacation 

• Five sick days paid 

• 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. We look forward to hearing from you!

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