Executive Family Assistant | Family Operations (Live-In)
Location: Chicagoland (Northwest Suburbs), Illinois (Live-In)
Compensation: $40–47/hour DOE + overtime, benefits, private living accommodations, and strong long-term opportunity.
About Our Family
We’re a private family looking for a steady, trusted Executive Family Assistant to become a long-term part of our home. Our family includes two parents, our toddler daughter, and a small dog, and we hope to grow our family in the near future. Mom is very hands-on and actively involved in parenting, so this role is built on partnership and support rather than replacement.
This role sits at the center of daily family life, blending executive support, household operations and management, childcare, hospitality, and early childhood learning. We value a calm, organized home and are looking for someone who naturally notices what’s needed, takes initiative, and helps bring consistency, structure, and thoughtful follow-through to each day.
We also have a part-time housekeeper who works three days a week, making this a collaborative environment where responsibilities are shared and coordinated. We’re looking for someone who enjoys working as part of a team, communicates openly, and takes genuine pride in helping create a joyful, organized home where our family can thrive.
About the Role
No two days in this role look exactly the same. One morning might be spent coordinating vendors and preparing for travel; the afternoon could involve time with our daughter, running errands, organizing the home, or helping move personal and family projects forward. This is a true hybrid role that blends household operations and management, executive and personal assistance, childcare, pet care, travel support, and special projects. The balance naturally shifts with our family’s needs, so we’re looking for someone who enjoys variety, embraces flexibility, and is excited to step in wherever they’re needed most. Responsibilities naturally evolve as our family’s needs change, so flexibility and adaptability are essential.
We’re looking for someone who takes initiative without prompting, communicates clearly, and genuinely enjoys making life easier for others. This is a “notice it, own it, complete it” environment—someone who naturally anticipates needs, follows through without being asked, remains calm under pressure, and adapts easily as priorities shift. A meaningful part of this role is supporting the mother directly by helping her stay ahead of responsibilities, keeping projects moving, anticipating needs, and ensuring important details don’t get lost in the day-to-day.
We welcome candidates with backgrounds in executive or personal assistance, household or estate management, operations, logistics, luxury hospitality, military, doulas or similar roles requiring exceptional organization, discretion, ownership, and follow-through where long-term responsibility and consistency are key. Above all, we’re looking for someone who takes genuine pride in supporting others and helping create a calm, organized, joyful home where our family can thrive.
Who You Are
You are someone who brings both steadiness and heart into a home. You move through the day with quiet confidence, grace under pressure, and the ability to keep things flowing even when life gets full or unpredictable. You don’t just manage tasks—you create ease around you. You are the kind of person who can weather life’s inevitable ups and downs with resilience, good judgment, and a calm, solutions-focused mindset, helping create stability for everyone around you.
You are someone who:
- Notices what needs to be done and takes ownership of it
- Is steady, organized, proactive, and highly dependable
- Communicates clearly and follows through fully
- Enjoys both structure and people
- Is warm, patient, and confident with young children
- Is unafraid to be delightfully goofy, energetic, playful, and creative with children
- Supports early learning through everyday interaction and play
- Adapts gracefully to changing priorities and busy days without losing sight of what matters most
- Brings a lightness and good sense of humor to the work, knowing that a well-run home also benefits from warmth and the ability to laugh when things don’t go perfectly
- Naturally anticipates needs several steps ahead
- Values discretion, professionalism, integrity, and long-term commitment
- Takes pride in creating order, calm, beauty, and hospitality in a home
- Has experience in operations, hospitality, executive support, logistics, or similar high-accountability roles
- Has worked in environments where ownership, initiative, and consistency are essential
- Being fluent in Italian is a bonus
Prior longevity with a private family, UHNW household, or similar environment is strongly preferred.
Schedule & Travel
This is generally a five-day live-in role, typically Monday–Friday, around 8/8:30am–7:30/8pm, averaging 50–55 hours per week with flexibility based on family needs. Some weeks may shift to Tuesday–Saturday.
The schedule may extend to 5.5–6 days or over 55+ hours depending on travel, events, or household needs. Early mornings, evenings, weekends or overnights may be required with advance notice when possible.
Travel is a meaningful part of this role and may include domestic and occasional international trips, from long weekends to extended stays of two months or more. Thanksgiving is a working travel holiday.
Responsibilities
This role is fluid and will evolve with the household. Additional responsibilities may naturally arise, including supporting other staff, new projects, and shifting family needs.
Household Operations & Management
- Overseeing the day-to-day operations of the home by coordinating vendors and contractors, scheduling appointments and deliveries, maintaining household systems, managing inventories and supplies, collaborating with and helping oversee our part-time housekeeper, coordinating future household staff as needed, and ensuring projects are thoughtfully carried from start to finish.
- Maintaining an exceptionally organized, beautifully functioning home through daily household resets, laundry and wardrobe care, changing bed linens, closet, pantry, and refrigerator organization, seasonal organization, mail and package management, donation coordination, plant care, preparing for guests, and ensuring the home is always clean, stocked, welcoming, and running smoothly.
Executive & Personal Assistance
- Managing calendars, scheduling, appointments, travel logistics, reservations, research, correspondence, household administration, document organization, project management, gift purchasing, returns, errands, personal shopping, expense tracking, sourcing vendors, coordinating services, technology support, vehicle support, photo organization, and helping move both personal and family projects forward.
Childcare & Family Support
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Providing warm, engaged childcare while supporting daily routines, meals and snacks, naps, diapering and potty training, baths, transportation, outings, creative play, reading, educational activities, outdoor adventures, emotional regulation, age-appropriate learning, encouraging independence and confidence, fostering curiosity through everyday experiences and play, prioritizing safety, packing for children, assisting during travel, future infant care and additional children as our family grows, confidently managing the needs of multiple children at once, and partnering closely with parents to create a calm, loving, fun, respectful, and secure environment where children feel deeply supported and encouraged to thrive.
Kitchen & Hospitality
- Grocery shopping, meal planning support, assisting with meal and snack preparation as needed, kitchen organization, post-meal cleanup, washing dishes, loading and unloading the dishwasher, maintaining clean countertops and appliances, hospitality support, fresh flowers and thoughtful home touches, and creating a warm, welcoming atmosphere throughout the home.
Travel Support
- Planning and coordinating family travel, packing and unpacking, preparing the home before departures and after returns, maintaining organization while away, supporting family routines during travel, assisting with childcare, and ensuring trips run as seamlessly as life at home.
Pet Care
- Assisting with the daily care of our family dog, including feeding, filling water bowl, letting them in and out, walks as needed, grooming and veterinary appointments, purchasing supplies, and supporting pet care during travel.
Special Projects
Every week is different. We value someone who enjoys variety and is excited to jump in wherever needed—whether that’s organizing a new space, preparing for holidays or family gatherings, researching purchases, supporting home projects, creating new systems, onboarding future household staff, or taking ownership of the countless details that help our family thrive.
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 working collaboratively with other household staff.
- Proficient swimmer and confident supervising children in and around pools or water.
- 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.
- Refrain from wearing strong perfumes, colognes, scented lotions, detergents, or other fragranced products while working in the home or around family.
Privacy, Discretion & Confidentiality
This is a highly private household, and discretion is essential to the success of this role. The nature of the work requires regular exposure to personal, family, and operational details that are not public and must remain strictly confidential at all times.
We expect the highest level of professionalism in how information is handled, both during and after employment. This includes, but is not limited to, refraining from discussing the family, household operations, schedules, personal matters, or any internal details with anyone outside the home.
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 you MUST answer/do ALL of the following questions.
Submit the following:
A written introduction including:
- Your relevant experience
- Why this type of long-term family role appeals to you
- Any experience with children, household management, or executive support
- What are you naturally curious about outside of work? We’d love to hear about the books, podcasts, hobbies, philosophies, or subjects that capture your attention.
- Your general availability and willingness to live-in and travel
- Your compensation expectations (hourly or annual range, benefits etc), and what type of long-term arrangement you are ideally looking for
- Specific examples of times you have supported areas like household organization, childcare, executive assistance, travel coordination, or operations (please be concrete and describe what you personally handled and the outcome)
- Please tell us about your ideal working environment.
- We believe the best long-term placements happen when expectations are aligned from the beginning. Please share any preferences or non-negotiables that are important to you when working in a private home.
- There are no “right” or “wrong” answers. We’d simply like to understand what helps you do your best work so we can determine whether we’re the right long-term fit for one another.
2. A recent photo (does not need to be a formal headshot). If open please submit a short video: introduce yourself, share what makes this the right role for you, share a little about yourself. Speak naturally—this is simply to get a sense of your communication style and presence
3. References (professional and/or family household references preferred)
All applications will be handled with strict discretion and privacy. We expect the same level of confidentiality from candidates regarding our family, home, and any details shared during the process. A formal NDA will be required prior to in person interviews.
Interview Process
- Initial review of written + video submission
- Introductory interview (video call)
- Secondary interview with both parents/principles (video call)
- In-person interview (if local or during travel window)
- 1–3 day paid trial period in the home for final candidates
The paid trial is designed to ensure mutual fit, working style alignment, and comfort within the household before any long-term commitment is made.
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 the right candidate
Our Goal
We’re looking for someone who wants to build something long-term with one family. In return, you’ll be welcomed into a respectful, appreciative home where your presence, judgment, and care genuinely matter.
If you find satisfaction in creating calm from chaos, enjoy building thoughtful systems, and want to play a meaningful role in young children’s early years and development, we would love to hear from you.