Executive Bookish Jobs (NOW HIRING)

Job Title: House Manager / Family Assistant

Location: Chicago, IL 60657

Employment Type: Full-time, 30-35 hours per week

Compensation: $30-$35/hour

Start Date: Mid-August 2026

Schedule: Monday-Friday, with core childcare hours from 2:30-6:00/6:30 PM. Most days begin 1-2 hours earlier for household management before after school care begins. Mondays may include extended morning hours for meal prep, plus one standing date night (Thursday or Friday, ~4 hours/week). Summer schedule may vary.

Requirements

• Maintain a smoke-free environment.
• Reliable transportation (public transit, walking, or rideshare acceptable; personal vehicle not required.)
• Up-to-date vaccinations per CDC guidelines.
• CPR and First Aid certifications are plus, but not required.
• Must be comfortable around (and not allergic to) cats.
• Demonstrated experience working with neurodivergent individuals, particularly those with ADHD and/or high-functioning autism. Formal certification is not required, but candidates should be able to speak to their experience either professionally or personally.
• Must be authorized to work in the United States.

About Our Family

We are an active Chicago family of four living in a lively Roscoe Village/West Lakeview neighborhood home. Our household runs with a lot of heart, a healthy dose of structure, and a genuine desire to be collaborative rather than directive. We value systems, proactivity, and a culture where everyone including the kids has a voice in how things are organized and run.

Our two school-age children are at exciting and demanding stages. One is an energetic, social, big-hearted middle schooler who loves reading, musical theater, and staying busy. The other is a thoughtful, introspective high schooler who is creative, bookish, and navigating the world with a neurodivergent brain. Both are smart, capable kids who thrive with the right kind of structure and engagement, not hand-holding. One of our primary household goals right now is supporting them in building their own executive functioning skills.

Both parents work full-time, with one parent frequently traveling for business. We are a collaborative family who does not want to micromanage our household support person. We want someone who comes in, reads the room, and gets things done with initiative and warmth.

Who You Are / What We're Looking For

You are a mature, emotionally intelligent professional who brings calm, steady energy into a home. You do not need to be told what needs doing; you notice it, you plan ahead, and you take care of it. You understand the difference between doing things for kids and helping them build the skills to do things themselves, and you genuinely enjoy the latter. You are organized and proactive, but you are not a taskmaster. You build trust through consistency, warmth, and follow-through.

Experience or meaningful exposure working with neurodivergent children is important to us, particularly around ADHD, high-functioning autism, executive functioning challenges, and the emotional complexity of masking and decompression. You do not need a formal credential, but you should be able to speak to how you have approached this work thoughtfully and compassionately. You are the kind of person who co-creates systems rather than imposing them, who engages a distracted kid with curiosity rather than pressure, and who knows when to give someone space and when to gently redirect. You are comfortable in a household where one adult works from home but is not available as a resource during the day. You bring your own initiative and do not require constant direction to get through your day.

Key Responsibilities

Family Support and Child Assistance

• Provide after-school structure and check-ins for both children from the time they arrive home
• Support the older child with calm, compassionate redirection, medication reminders, homework completion, and gentle accountability around routines and chores; build trust and a genuine relationship over time
• Engage the younger child with high energy, creativity, and proactive prompting; redirect from unproductive habits and help channel energy into reading, projects, or productive activity
• Reinforce daily routines such as emptying lunchboxes, processing backpack contents, organizing cubbies, and the household reading-before-screen-time rule
• Oversee and teach lunch packing, snack prep, and backpack readiness with the children doing the work and the house manager providing oversight and guidance
• Coordinate occasional activity pickups or drop-offs for the younger child (rideshare, public transit, or family vehicle may be used)

Household Organization & Maintenance

• Maintain and improve household organization systems throughout the home, with openness to suggesting improvements
• Perform daily resets and light tidying, including dishes, surfaces, and high-traffic areas
• Help manage litter box cleaning or ensure the older child follows through on that responsibility
• Help manage cat food and water refill and cleaning or ensure younger child follows through on that responsibility
• Complete Monday evening prep to clear surfaces and floors ahead of Tuesday cleaning service
• Maintain mudroom organization at both front and back entry (cubbies, backpacks, coats, seasonal gear)
• Oversee indoor plant care (approximately 20 self-watering plants; refill monthly)
• Change batteries, light bulbs (including knowledge of fixture-specific types such as dimmable vs. non-dimmable and candelabra bulbs), and smoke detectors as needed
• Manage occasional guest room prep ahead of visits as needed
• Support travel packing quality checks for children
• Assist with post-trip equipment check-in (e.g., ski gear storage and condition after trips)

Deep Cleaning & Special Projects

• Maintain a monthly rotation of targeted deep clean tasks (refrigerator, pantry, windows, baseboards, cabinet faces, etc.); note items for the cleaning service where appropriate and handle independently if needed when time allows
• Manage organizational projects for storage areas including the garage, mudroom, and gear storage
• Support garage system resets and bike storage organization
• Proactively prepare bikes seasonally: check tire pressure, coordinate with the bike repair shop before the season begins rather than reactively
• Proactively prepare skis seasonally: coordinate kid ski and boot rental, prep adult boots and skis, ensure ski equipment and accessories are in good working order and fit check ski gear for kids (ski jackets, snowpants, helmets, goggles, etc.)

Inventory & Errands

• Maintain running household supply lists and restock as needed
• Manage household inventory for supplies such as paper goods, toiletries, sunscreen, medications, pet supplies, laundry items, and linen closet contents
• Manage monthly donation drop-offs from the designated hall closet donation area
• Handle midweek grocery runs for urgent staples or perishables (Target and Whole Foods are within walking distance); add items to the family's Sunday shopping list throughout the week
• Process returns at FedEx, UPS, and USPS (all within walking distance)

Meal Support

• Complete Monday meal prep (2-3 meals worth of prep work: chopping vegetables, cooking rice, pressing tofu, advanced prep of longer lead-time ingredients)
• Midweek fresh produce prep as needed
• Daily after-school snack prep: slicing fruit, setting out vegetables/hummus, monitoring healthy snacking
• Keep the snack station and refrigerator organized with healthy options at eye level
• Check expiration dates and flag low or missing items for the weekly grocery list
• Flag pantry and refrigerator gaps proactively throughout the week
• Support kitchen clean-up and general kitchen maintenance
• Be comfortable with a household that cooks primarily vegetarian meals; familiarity with tofu, beans, roasted vegetables, and mild flavor profiles is helpful. Note that one child has texture sensitivities and safe foods, and some family members prefer dairy-light and non-spicy cooking.

Laundry & Linens

• Full laundry service for adults: wash, fold, organize, and put away
• Hand wash delicate and special-care garments
• Coordinate dry cleaning drop-off and pickup
• Maintain organized linen cabinet
• Work collaboratively with the older child on her personal laundry system (she has a specific three-bin setup and strong preferences); support accountability and step in when necessary to take more direct action
• Support younger child in taking over responsibility for personal laundry and bed linen rotation (already in process, but still needs oversight)

Vehicle Upkeep

• Weekly interior clean of the family vehicle: remove garbage, address spills, vacuum
• Coordinate quarterly professional detailing or car wash when the vehicle is available

Vendor & Property Oversight

• Act as on-site point of contact for vendors and contractors as trust develops
• Coordinate with the household's primary contractor on handyman punch lists, furniture deliveries, and project tracking
• Oversee scheduled services such as quarterly HVAC maintenance, monthly filter changes, and monthly pest control; proactively schedule seasonal service (heating, cooling, gutter cleaning, exterior window washing) rather than managing reactively
• Monitor and flag household maintenance needs as they arise

Administrative & Personal Assistant Support

• Manage incoming mail and packages: open, sort, put items away, break down boxes, set bills aside, and maintain children's individual school work/mailbox areas
• Monitor the family digital calendar and proactively flag scheduling conflicts, appointment reminders, and coverage needs, especially during periods of parental travel

How to Apply

If interested, please submit the following:

• A brief letter explaining why you would be a great fit for this position
• Your updated resume
• At least 3 professional references with contact information

Note that this role requires a background check.

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