Click to toggle mobile navigation menu.

Full-Time Family Assistant: $90K+ and Benefits

Gold Coast • Chicago, IL Full Time

Family living in Gold Coast of Chicago with three high school aged children is seeking an educated, experienced, professional, organized, meticulous and detail oriented full-time family assistant to manage a busy family and household. The schedule is on Monday – Thursday at 11:00am – 8:30pm and Friday at 9:00am – 6:00pm. Nanny is responsible for assisting with children between 3/4:00pm-8:30pm. Between those times, personal assistant and house management tasks should be completed: Running errands, managing family’s calendars, scheduling activities and camps for children, shopping for children and family, planning events, scheduling contractors and work to be completed at residence, organizational projects, etc. Flexibility is required to work occasional later evenings and weekends when family has events, residences need to be prepared for family’s arrival, meetings are scheduled with principal(s), travel is required, etc. Approximately 1-3+ weeks of international and domestic travel per year is required and approximately 1-3+ weeks of overnights at residence annually are required when parents are traveling without children. Children attend private schools, which are a short drive from the family’s home. Family has staff vehicle for transporting children and running errands. Candidates must be comfortable with dogs. Family Assistant is responsible for overseeing the general operation of main residence (potential for assisting with other domestic residences in the future), minimal amount of managing domestic staff in an environment where everyone is given clear expectations and loves coming to work daily (housekeeper, private chef, driver, tutors, etc.), collaborative to work directly with principals on a daily basis, assertive, proactive, resourceful, self starter, organized, detail oriented, hard working, service focused, kind, professional, ability to multi-task and wear many hats and capable of maintaining discretion (confidentiality agreement is required). Candidates must have previous experience in similar position(s) that includes working with high school aged children along with personal/family assistant and/or highly detailed and demanding house management responsibilities. Family is open to local candidates and domestic relocations (as long as candidate has connection to Chicago and will stay in location long term). Start date is ASAP, but flexible for the right candidate. 

RESPONSIBILITIES: 

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

• Ensure children’s healthy lunches and bags are packed for the following day (e.g., school work is completed, bags packed for sports and/or activities, etc.) 

• Daily walk through of residence to ensure that all systems are functioning properly

• Potential for management of other domestic residences in the future

• 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.

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

• Running errands (e.g., shopping for home supplies, returns and other requested items)

• Handling things around the home (e.g., receiving deliveries, service providers, contractors, sending emails, etc.)

• House projects (e.g., ensuring all lights are working, changing light bulbs, light bulb inventory, etc.)

• Organizational projects (e.g., storage units, children’s bedrooms, etc.)

• Managing domestic staff and supervising the quality of their performance (minimal amount required due to staff being self sufficient and employed by family for many years) 

• Coordinate staff schedules to ensure adequate coverage at all times based on family’s needs

• 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 security systems at residence and check/test on a regular basis

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

• Provide hospitality and attend to guests and family’s needs when visiting 

• Managing household schedules and calendars

• Event planning, organizing, coordination and flawless execution day of event

• Scheduling appointments for personal and occasionally professional needs of principals

• Scheduling and maintaining calendars for children and registering for activities/sports/camps/etc. 

• Vetting contractors/service providers, scheduling home maintenance and repair work and supervising projects

• Keep mail organized, handle household and family bills and administrative duties (accountant and/or executive assistant handles majority of bills)

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

• Assistance with travel arrangements and ensuring all logistics are planned in advance (executive assistant plans majority of travel for family) 

• Ensuring children are packed and unpacked for trips/travel (occasional assistance with principals) 

• Assistance with dogs (e.g., boarding prior to family travel, walking and letting out, feeding, routine grooming and veterinary appointments, etc.)

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

QUALIFICATIONS: 

• Capable of building good rapport with similar aged children (high school and older) 

• Ability to travel internationally and domestically whenever necessary (minimal amount required) 

• 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., scheduling landscaper if seasonal displays need to be changed, 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 develop and maintain solid working relationships with service providers, contractors and vendors

• Ability to work collaboratively with and oversee projects 

• Ability to easily take direction 

• Resourceful and ability to find the best tickets for sporting events, concerts, etc. (understanding that “no” isn’t an answer)

• Strong ability to communicate and collaborate efficiently and effectively with principals and domestic employees

• Strong technology skills and experienced working with Macintosh and PC 

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

• Active and fit

• Non-Smoker 

REQUIREMENTS:

• Bachelor’s degree 

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

• 3-4+ 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 Gold Coast of Chicago 

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

• Driver’s license and clean driving record 

• Comfortable with dogs 

COMPENSATION:

• $90K+ gross salary (based on experience and qualifications) 

• $150 per overnight gross (traveling with family and working overnights at residences) 

• Health insurance stipend 

• Two weeks (10 days) paid vacation

• Seven government holidays paid: New Year’s Day, Memorial Day, Independence Day, Labor Day, Thanksgiving, day after Thanksgiving, Christmas

• Three 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. Submit through our website at www.strollersandstilettos.com/job-opportunities. We look forward to hearing from you!

Fill Out an Application

Position: Full-Time Family Assistant: $90K+ and Benefits

Location: Gold Coast • Chicago, IL

  • Attachments

    We require cover letter, resume, references (email addresses, phone numbers required) and letter(s) of recommendation attachments in order to be considered for a position.
  • Accepted file types: jpg, gif, png, pdf, doc, docx.
  • Accepted file types: jpg, gif, png, pdf, doc, docx.
  • Accepted file types: jpg, gif, png, pdf, doc, docx.
  • Drop files here or
    Accepted file types: jpg, gif, png, pdf, doc, docx.
  • Accepted file types: jpg, png, pdf.