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Full-Time House Manager/Family Assistant: $65K+ and Benefits

Chicago and Winnetka, IL Full Time

Family with residences in Chicago and Winnetka, Illinois is seeking an experienced, professional, organized and detail oriented house manager/family assistant to manage a busy family, 6,000 square foot residence in Chicago and 8,000 square foot residence in Winnetka. Schedule is on Monday – Friday at 9:00am – 5:00pm, but flexible with hours based on candidate’s preference (e.g., 10:00am-6:00pm, 11:00am-7:00pm, etc.). Family assistant will report to residence in Winnetka approximately three days per week and residence in Chicago approximately two days per week. Flexibility is required to work occasional evenings and weekends when family has events, residences need to be prepared for family’s arrival, meetings are scheduled with principal(s), etc. Safe vehicle for transportation is required (parking is provided at both residences). House Manager/Family Assistant is responsible for overseeing the general operation of two residences; minimal amount of managing domestic staff in an environment where everyone is given clear expectations and loves coming to work daily; collaborative to work directly with principals and their personal assistants, family office, domestic staff at all residences, security, etc. on a daily basis; comfortable with dog; assertive; proactive; resourceful; self starter; organized; detail oriented; service focused; kind; professional; ability to multi-task and wear many hats; respectful and capable of maintaining discretion (confidentiality agreement is required). Family has many residences across the country, which each have a house manager. Start date is highly flexible for the right candidate.


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

• Managing two residences that are domestically in Chicago and Winnetka, Illinois

• 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, contractors, businesses, etc.

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

• Responsible for handling things around the home (e.g., receiving deliveries, service providers, contractors, answering phone calls, sending emails, etc.)

• Responsible for house projects (e.g., ensuring all lights are working, changing light bulbs, annual assistance with projects such as vacuuming draperies/wiping window sills/etc.)

• Responsible for organizational projects when requested by principals

• Managing domestic staff for residences 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 principals’ 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 all residences and check/test on a regular basis

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

• Responsible for dog (e.g., scheduling vet appointments, grooming, etc.)

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

• Managing household schedules and calendars (majority would be handled by principals’ executive/personal assistants)

• 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 (e.g., dentist appointments when home from college, arranging logistics with travel to residences, 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 (family office and/or accountant handle bills)

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

• Occasional assistance with packing principals and children for trips

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


• 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, dog is due for check up, 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 interior design projects

• Ability to easily take direction

• Strong ability to communicate and collaborate efficiently with principals, children, family office, domestic staff, security, etc.

• Strong technology skills and experienced working with Macintosh

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

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

• Active and fit

• Non-Smoker


• Bachelor’s degree

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

• 3-4 references from professional positions

• Ability to complete extensive background checks and drug tests

• Safe vehicle for transportation

• Driver’s license and clean driving record


• $65K+ gross salary (based on experience and qualifications)

• Health insurance stipend = $7,000 gross annually

• Two weeks (10 days) paid vacation

• Five paid sick days

• Eight government holidays paid: New Year’s Day, MLK Day, Presidents Day, Memorial Day, Independence Day, Labor Day, Thanksgiving, Christmas

• 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 feel that you meet ALL of the requirements. Submit through our website at We look forward to hearing from you!

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Position: Full-Time House Manager/Family Assistant: $65K+ and Benefits

Location: Chicago and Winnetka, IL


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.