Family & Household Manager / Family Assistant (Live-In)

Family & Household Manager | Family Assistant (Live-In)

Location: Chicagoland, Illinois (Live-In)

Compensation: $40–47/hour DOE + overtime, benefits, private living accommodations, and strong long-term growth opportunity

About Our Family

We are a private family seeking an exceptional Family & Household Manager / Family Assistant to become a trusted, long-term part of our household.

Our family currently includes two parents, our young daughter, and a small dog, and we hope to grow our family in the future. Mom is a hands-on parent and actively involved in daily family life, so this position is built around partnership and support rather than replacement.

At its heart, this is a family operations role.

We are looking for someone who can see the household as a whole—understanding what needs attention today, anticipating what may be needed tomorrow, recognizing what can be handled independently, knowing what should be communicated, and exercising good judgment about what needs to be brought to the principals for a decision.

This role sits at the center of daily family life and blends household management, childcare, personal and executive assistance, hospitality, travel, and special projects. The balance naturally shifts depending on the day and season of life.

We also have a part-time housekeeper who works three days per week, making this a collaborative household where responsibilities are shared and coordinated.

We value a home that feels calm, joyful, warm, organized, and genuinely lived in. We are looking for someone who takes pride not simply in completing tasks, but in helping create an environment where a family can thrive.

Most importantly, we are looking for the right person, not simply the right résumé.

About the Role

No two days in this position will look exactly the same.

One morning might involve coordinating vendors, reviewing household priorities, scheduling appointments, or preparing for upcoming travel. Later that day, you may spend meaningful time with our daughter, run errands, research a purchase, organize a space, troubleshoot an unexpected household problem, help reset the kitchen, or help move one of Mom’s personal or family projects from idea to completion.

We are looking for someone who can move comfortably between the big picture and the small details.

This is a “notice it, own it, complete it” environment.

You should be able to recognize what needs to happen without waiting for a detailed list, take appropriate ownership, communicate clearly, and follow things through to completion. At the same time, excellent judgment means understanding when to act independently, when to communicate, and when a decision appropriately belongs with the principals.

A meaningful part of this position is supporting Mom directly—helping translate ideas, priorities, and intentions into action; keeping projects moving; researching and organizing possibilities; anticipating needs; creating systems where useful; and making sure important details do not disappear into the day-to-day.

This is a management-level position, but it is also intentionally hands-on.

We are not looking for someone who believes management means standing apart from the work. On any given day, helping the household run well might mean coordinating a contractor and managing a project—and it might also mean unloading the dishwasher, folding laundry, packing for a child, making a return, receiving a delivery, or stepping into childcare.

There is no “that’s not my job” mentality in our home. We all contribute to creating a beautiful, functional, welcoming household.

Who You Are

You bring maturity, curiosity, competence, warmth, and steadiness into a home. You are proactive and comfortable taking ownership, while having the judgment to know when to act independently, when to communicate, and when to ask. When the day doesn't go as planned, you are the calm in the storm — grounded, steady, and unshaken.

You are also warm, playful, and genuinely comfortable with young children—confident with toddlers and infants, willing to get down on the floor and be silly, and able to bring patience and creativity to their days.

You are someone who:

• Sees what needs to be done and takes initiative without waiting to be asked
• Takes full ownership of responsibilities and projects and follows through to completion
• Has excellent judgment about when to act, communicate, or ask
• Stays steady and solution-oriented when plans change, meeting busy seasons and unexpected problems with grace and follow-through
• Is highly organized without being rigid and can calmly prioritize competing needs
• Genuinely enjoys solving unfamiliar problems and researching a path forward
• Has substantial hands-on experience with toddlers and infants and brings warmth, patience, playfulness, and a sense of humor to their care
• Values discretion, integrity, professionalism, and privacy
• Is self-aware—knows both their strengths and where they are still growing
• Is looking to build something long-term with one family, not simply find their next position

Fluency in Italian is a bonus, but not required.

Prior longevity with a private family, UHNW household, or similarly high-accountability environment is strongly preferred.

We also welcome exceptional candidates whose backgrounds may not follow a traditional private-service path. Relevant experience may come from executive or personal assistance, household or estate management, operations, logistics, luxury hospitality, military service, childcare, education, doula work, project management, or another path that develops exceptional judgment, discretion, responsibility, and follow-through.

Schedule & Travel

This is generally a five-day live-in role, typically Monday–Friday, approximately 8:00/8:30 a.m.–7:30/8:00 p.m., averaging approximately 50–60 hours per week, with flexibility based on family needs.

Some weeks may shift to Tuesday–Saturday.

The schedule may occasionally extend to 5.5–6 days or beyond 60 hours during travel, events, particularly busy periods, or other family needs. Early mornings, evenings, weekends, or overnights may occasionally be required, with advance notice whenever possible.

Travel is a meaningful part of this role and may include domestic and occasional international trips, ranging from long weekends to extended stays of two months or more.

Thanksgiving is a working/travel holiday.

Candidates should genuinely enjoy travel and be comfortable adapting to different homes, hotels, schedules, environments, and routines while maintaining consistency for the family.

Responsibilities

This position is intentionally broad and will continue to evolve with our household. The right person will eventually develop a deep understanding of our family’s preferences, systems, rhythms, priorities, and standards and become an important source of continuity within the home.

Household Operations & Management

• Oversee and help coordinate the day-to-day operations of the home
• Coordinate vendors, contractors, appointments, repairs, deliveries, and services
• Maintain household calendars, systems, inventories, supplies, and recurring needs
• Track household projects and ensure they are carried from initial idea through completion
• Research and source vendors, products, services, and solutions
• Collaborate closely with our part-time housekeeper and help coordinate household priorities
• Assist with onboarding and coordinating additional household staff as our team grows
• Identify inefficiencies or recurring issues and thoughtfully suggest and create better systems
• Anticipate seasonal and upcoming household needs
• Maintain an exceptionally organized and beautifully functioning home
• Assist with daily household resets
• Laundry and wardrobe care
• Changing bed linens as needed
• Closet, pantry, refrigerator, storage, and seasonal organization
• Mail and package management
• Donation coordination
• Plant care
• Guest preparation
• Maintain household supplies and ensure the home remains stocked, welcoming, and running smoothly

Childcare & Family Support

• Provide warm, attentive, engaged childcare for toddlers, infants, and future children
• Support daily routines, meals and snacks, naps, diapering, potty training, bathing, and dressing
• Provide age-appropriate care for infants, including feeding, soothing, sleep routines, developmental play, and maintaining a safe environment
• Transportation to activities, appointments, classes, and outings
• Reading, creative play, imaginative play, arts and crafts, outdoor adventures, and age-appropriate educational activities
• Encourage curiosity, independence, confidence, emotional regulation, and age-appropriate responsibility
• Support early learning naturally through conversation, exploration, books, nature, art, music, and everyday life
• Help create interesting activities and experiences rather than relying on screens for entertainment
• Prioritize safety while still allowing children to explore and develop confidence
• Pack and prepare for children during outings and travel
• Maintain children’s belongings, supplies, clothing, activity materials, and travel needs
• Assist extensively with childcare during family travel
• Be comfortable with future infant care and additional children as our family grows
• Confidently manage the needs of multiple young children
• Partner closely with parents to maintain consistency, routines, expectations, and boundaries
• Help create a childhood that feels safe, loving, playful, curious, creative, and full of meaningful experiences
• Bring warmth, patience, humor, imagination, and a willingness to be silly and playful with our child

Personal & Executive Assistance

• Calendar management and scheduling
• Appointment coordination
• Travel logistics and reservations
• Research and information gathering
• Correspondence and household administration
• Document and digital organization
• Personal and family project management
• Gift research, purchasing, wrapping, and coordination
• Returns and exchanges
• Errands and personal shopping
• Expense tracking and receipt organization
• Vendor and service research
• Technology troubleshooting and support
• Vehicle-related coordination
• Photo and family archive organization
• Researching purchases, experiences, classes, services, travel, and other family needs
• Helping Mom organize ideas and translate them into actionable next steps
• Maintaining project lists and proactively following up on open items
• Helping move personal, creative, philanthropic, household, and family projects forward
• Anticipating needs and taking initiative before tasks become urgent
• Owning projects from initial idea through completion and communicating progress along the way

Kitchen & Hospitality

• Grocery shopping and household food stocking
• Meal-planning support
• Assist with simple meal and snack preparation as needed
• Kitchen organization
• Weekly refrigerator organization and maintenance, ensuring the refrigerator contains only fresh, safe, and currently usable food
• Monthly minimum pantry organization and maintenance, including checking dates, consolidating items, identifying low supplies, and removing expired or unusable products
• Monitor food freshness and household food inventory, proactively identifying items that need to be used, replaced, or discarded
• Post-meal cleanup
• Washing dishes and loading/unloading the dishwasher
• Maintain clean counters and appliances
• Help prepare the home for family gatherings and guests
• Hospitality support
• Fresh flowers and thoughtful home touches
• Help maintain a warm, comfortable, welcoming atmosphere throughout the home

A love of cooking or baking is wonderful and welcomed, but professional cooking experience is not required.

Travel Support

• Research and help coordinate family travel
• Create and assist with itineraries, reservations, logistics, and travel preparation
• Create and maintain packing lists
• Pack and unpack for family members
• Prepare the home before departure
• Help reset and reorganize the household after returning
• Maintain organization while traveling
• Support children’s routines and family logistics while away
• Coordinate luggage, supplies, purchases, activities, and other travel needs
• Help ensure trips feel as organized and seamless as possible

Pet Care

• Assist with the daily care of our small family dog
• Feeding and fresh water
• Letting the dog in and out
• Walks as needed
• Grooming and veterinary appointment coordination
• Purchasing and maintaining pet supplies
• Help coordinate pet needs during family travel

Special Projects

Every week is different.

Special projects might include organizing a newly completed space, preparing for holidays or a family gathering, researching an unusual purchase, helping coordinate a home improvement project, creating a better household system, sourcing children’s activities, preparing for extended travel, organizing family photos, researching something Mom is interested in pursuing, onboarding another staff member, or solving an unexpected problem.

We want someone who finds this variety interesting rather than frustrating and who is energized by taking an idea, creating a plan, and seeing it through.

Long-Term Growth

We are intentionally looking for someone who wants to grow with one family.

Our household and family will evolve over the coming years. We hope to have additional children, our travel may expand, household projects will change, and additional staff may eventually join the team.

As that happens, this role has the potential to evolve as well.

The person who succeeds here will develop an increasingly deep understanding of our family, household, preferences, systems, standards, and rhythms and may take on greater responsibility for family and household operations over time.

We are looking for someone who finds that kind of continuity and long-term partnership meaningful.

Minimum Requirements

To be considered for this position, candidates must:

• Be legally authorized to work in the United States
• Be fluent in spoken and written English
• Possess a valid driver’s license with a clean driving record
• Hold a valid passport or be able to obtain one promptly
• Be willing and able to travel domestically and internationally, including extended trips and holidays
• Be comfortable living in the family residence
• Be comfortable working collaboratively with other household staff
• Be a proficient swimmer and confident supervising children in and around pools and water
• Have substantial experience caring for toddlers and infants
• Hold current CPR and First Aid certification or be willing to obtain both
• Be willing to undergo comprehensive background checks, reference checks, and employment verification
• Be willing to sign a confidentiality agreement/NDA as a condition of employment
• Be available for occasional evenings, weekends, holidays, overnight support, and schedule flexibility when family or travel needs require
• Be comfortable with dogs
• Refrain from wearing strong perfumes, colognes, scented lotions, fragranced detergents, or other strongly fragranced products while working in the home or around the family

Privacy, Discretion & Confidentiality

This is a highly private household, and discretion is essential to the success of this role.

The nature of the position requires regular exposure to personal, family, household, scheduling, financial, travel, and operational information that is private and must remain strictly confidential.

We expect the highest level of professionalism in how information is handled both during and after employment.

A formal NDA will be required prior to in-person interviews, and strict confidentiality is a core condition of employment.

HOW TO APPLY

To Be Considered, Please Answer ALL of the Following

Please submit a written introduction answering each question individually.

Specific examples are much more helpful to us than general statements.

1. Your Background & Why This Role

Please briefly tell us about your relevant professional experience and why this particular long-term family role appeals to you.

Of the different parts of this position—household management, childcare, personal/executive assistance, travel, organization, hospitality, projects, etc.—which genuinely interest you most and why?

2. Ownership & Initiative

Tell us about a responsibility, project, or problem that you personally owned from beginning to completion.

What was the situation?

What did you personally take responsibility for?

What did you notice or do without being prompted?

What decisions did you make?

When did you communicate or ask for input?

What was the final outcome?

We are particularly interested in examples demonstrating initiative, judgment, problem-solving, organization, and follow-through.

3. Prioritization & Judgment Scenario

Imagine you begin the morning with several planned household and family priorities.

A vendor arrives and discovers an unexpected problem that requires attention. Something needed for the child later that day has been forgotten. Mom asks for help moving an unrelated project forward. At the same time, you notice another household issue that should be addressed.

Walk us through how you would approach the situation.

How would you determine what comes first? What would you handle independently? What would you communicate? What, if anything, would you bring to Mom for a decision?

There is no single correct answer—we are interested in understanding how you think.

4. Experience Across the Role

Please describe your experience in each of the following areas:

• Personal or executive assistance
• Household operations or management
• Childcare, particularly with toddlers and infants

Which is your strongest area?

Which is your least experienced area?

If there is an area where you have less experience, how comfortable are you learning it?

5. Childcare Experience

Please describe your experience caring for young children, particularly toddlers and infants.

Have you independently cared for multiple young children at the same time?

If so, please describe their ages, your responsibilities, and the circumstances.

What do you enjoy most about caring for toddlers and infants?

How do you balance safety, routines, developmental needs, independence, and fun?

6. A Hands-On Private Household

This is a highly varied and hands-on role.

There will be responsibilities outside anyone’s primary professional specialty—for example, unloading the dishwasher, helping with laundry, making a return, troubleshooting a household issue, preparing something for a child, receiving a delivery, cleaning up after a meal, or unexpectedly stepping into childcare.

How do you approach responsibilities that may fall outside your primary area of expertise or usual job description?

7. Schedule, Live-In & Travel

This is a live-in position averaging approximately 50–60 hours per week.

It requires meaningful schedule flexibility and may occasionally include early mornings, evenings, weekends, overnights, 5.5–6 day weeks, or hours beyond 60 during travel, events, or particularly busy periods.

The position includes domestic and occasional international travel, including extended trips.

Thanksgiving is a working/travel holiday.

Please confirm that you are comfortable with each of these requirements and share anything we should know regarding your availability, scheduling needs, ability to live in, or ability to travel.

8. Self-Awareness

What are two or three professional strengths that you believe genuinely distinguish you?

Please give us an example of how at least one of those strengths has shown up in your work.

What is one professional skill or area that is not one of your natural strengths or that you are actively working to improve?

9. Curiosity & Learning

Tell us about something you have become genuinely interested in, researched, learned, or taught yourself about within the last year.

It can be completely unrelated to work.

What drew you to it?

We would also love to hear about the books, podcasts, hobbies, subjects, activities, creative pursuits, or interests that tend to capture your attention.

10. Who You Are Outside of Work

We would love to learn more about you as a person beyond your professional experience.

What do you enjoy doing when you are not working? Please tell us about your hobbies, interests, creative pursuits, favorite activities, communities, or subjects you naturally gravitate toward.

There is no particular type of answer we are looking for. We are simply interested in understanding what brings you joy, what makes you curious, and what you enjoy sharing with others.

11. Your Ideal Working Environment

Please describe the working environment and relationship with principals in which you do your best work.

How do you prefer to receive feedback?

What does good communication between you and an employer look like?

We believe the best long-term placements happen when expectations are aligned from the beginning, so please also share any preferences, boundaries, or non-negotiables that are important to you when working in a private home.

There are no “right” answers. We simply want to understand what allows you to thrive so we can determine whether we are the right long-term fit for one another.

PLEASE ALSO INCLUDE

• Your compensation expectations, including hourly or annual range and benefit expectations
• Your earliest available start date
• Professional references; private family/household references are strongly preferred
• A recent photo; this does not need to be a formal headshot

OPTIONAL SHORT VIDEO INTRODUCTION

If you are comfortable doing so, we would also love to receive a short video introduction.

Please introduce yourself, tell us why you believe you would thrive in this particular role, and share a little about who you are beyond your résumé.

Speak naturally. This is simply an opportunity for us to get a sense of your communication style, personality, and presence.

All applications will be handled with strict discretion and privacy. We expect the same confidentiality from candidates regarding our family, home, and any information shared throughout the process.

A formal NDA will be required prior to in-person interviews.

Interview Process

• Initial review of written application and optional video submission
• Introductory video interview with Mom
• Secondary video interview with both parents/principals
• Reference checks
• In-person interview
• 1–3 day paid in-home trial for final candidate(s)

The paid trial is designed to ensure mutual fit, working-style alignment, and comfort within the household before either party makes a long-term commitment.

Compensation & Benefits

• $40–47/hour, depending on experience and expertise
• Overtime paid in accordance with applicable law
• Employer-sponsored health insurance
• 401(k) with 4% employer match
• Paid vacation, sick time, and holidays
• Private bedroom with en-suite bathroom
• Company phone and laptop
• Relocation assistance may be available for an exceptional candidate

Our Goal

We are looking for more than someone who can complete a list of tasks.

We are looking for a highly proactive, capable, curious, thoughtful person who wants to see what needs to be seen, take ownership of what they are doing, understand how our household works, anticipate what will make life run better, and take genuine pride in helping build it.

Someone who can be a responsible adult beside us, weather busy seasons and unexpected challenges with grace, and stick with a problem until it is truly resolved.

Someone who can manage a complicated household problem calmly and then sit on the floor and be wonderfully silly with a young child.

Someone who is genuinely confident and experienced with toddlers and infants, while also being capable of managing the broader operations of a busy household.

Someone who understands that excellent support is a combination of initiative and communication, independence and partnership, systems and humanity.

Someone who wants their work to matter.

In return, you will be welcomed into a respectful, appreciative household where your judgment, ideas, contribution, and care genuinely matter.

If you find satisfaction in creating order from complexity, enjoy solving problems and learning new things, love being around children and family life, and are looking for a place where you can build something meaningful over the long term, we would genuinely love to hear from you.