Proactive Household Manager / Executive Assistant Needed in West Town, Chicago, IL

Start: ASAP (for the right fit)

Compensation: $90,000–$130,000+/year (flexible for the right candidate)

Schedule: Monday–Friday, 10:00am–6:00pm (40 hours/week guaranteed; high degree of flexibility required)

Description: 

Proactive Household Manager / Executive Assistant Needed in West Town, Chicago, IL

Start: ASAP (for the right fit)

Compensation: $90,000–$130,000+/year (flexible for the right candidate)

Schedule: Monday–Friday, 10:00am–6:00pm (40 hours/week guaranteed; high degree of flexibility required)

Description:

Proactive Household Manager / Executive Assistant Needed in West Town, Chicago, IL
Start: ASAP
Household: Two busy professionals with multiple residences (within walking distance of each other)
Benefits: 2 weeks paid vacation, 5 paid sick days, paid major federal holidays, healthcare stipend

A dynamic and entrepreneurial household in West Town, Chicago is seeking a full-time Household Manager / Executive Assistant to provide high-level personal, household, and administrative support. This role is ideal for a proactive, detail-oriented professional who thrives in fast-paced environments, thinks several steps ahead, and enjoys managing both life and work logistics seamlessly.

The position is hybrid, with approximately 60% of time spent between the household’s nearby residences and offsite support, and some remote flexibility. The household values initiative, follow-through, discretion, a good sense of humor, and long-term commitment. This individual will serve as a true partner in keeping daily life, properties, and professional obligations running smoothly—acting as a stabilizing force and trusted right hand.

The principals lead busy professional lives, including entrepreneurship and frequent travel. They are seeking someone who can grow with them long-term, anticipate needs, and manage complex schedules and responsibilities without constant direction. Thorough onboarding will be provided, with dedicated time at the start to ensure deep understanding of household systems and workflows.

Domestic travel readiness is required (passport-ready preferred but not required), though travel will be infrequent.

Primary Responsibilities:

• Manage professional and personal calendars, appointments, and scheduling

• Inbox and correspondence management, including follow-up and contract coordination

• Arrange domestic travel, transportation, and accommodations as needed

• Coordinate vendors, contractors, permits, inspections, and property maintenance

• Oversee household organization, inventory management, and stocking of supplies

• Process shipments, break down boxes, track deliveries, and maintain inventories

• Create and maintain a comprehensive household manual

• Make reservations, manage gifting, and handle personal errands

• Serve as liaison between residences, staff, and service providers

• Ensure nothing “falls through the cracks” by proactively tracking deadlines and needs

• Support efficiency across both personal and professional spheres

• Provide attentive pet care for two dogs, including support for an aging dog with medical needs

• Act with discretion, initiative, and ownership across all responsibilities

Qualifications:

• Prior experience as a household manager, executive assistant, or similar high-level support role

• Exceptionally proactive, self-starting, and solution-oriented

• Strong organizational skills with the ability to manage multiple busy lifestyles

• Comfortable supporting entrepreneurs and understanding the rhythm of their professional lives

• Adequate computer and technology skills (email, calendars, documents, basic systems)

• Reliable personal vehicle required (vehicle available for on-the-job driving if needed)

• Comfortable with dogs and hands-on pet care

• Open-minded, flexible, and easygoing with a good sense of humor

• Mature and experienced enough to manage property-related matters, yet physically capable of handling stairs and lifting boxes

• Willingness to make a long-term commitment and grow with the household

• Authorized to work in the U.S.

If you are a highly capable, proactive Household Manager / Executive Assistant who enjoys taking ownership, thinking ahead, and supporting both life and work at a high level, this is a unique opportunity to become a deeply trusted, long-term partner within a dynamic household. We would love to hear from you.