Personal Executive Assistant & House Manager

Personal Executive Assistant & House Manager (Part-Time to Full-Time)

Location: Chicago, IL (North Side) with flexible home-office work Schedule: 25 to 30 hours per week, with potential for full-time Type: Independent contractor

About the Role

We are looking for a resourceful, self-directed Executive Assistant and House Manager to support the professional activities of a commercial real estate executive and a busy family. This is a hybrid role. Roughly half the work is household management, family logistics, and personal administration. The remaining half supports various real estate related activities.

The person who thrives here is entrepreneurial. You see what needs doing before being asked. You are comfortable calling a vendor, a title company, a contractor, or a customer service line and staying on the phone until you have a real answer. You do not wait for a perfect set of instructions. You take a partial brief, figure out the rest, and come back with the problem solved and a short summary of how you solved it.

If you like variety and take satisfaction in being the person who keeps everything moving, this role will fit.

Household Operations

· Oversee day-to-day household running and keep common areas organized

· Potentially plan simple, healthy meals around family preferences and schedules

· Manage grocery lists, shopping, and pantry and fridge inventory

· Occasionally family laundry and general household upkeep

· Manage household purchases and online orders

Family Coordination

· Coordinate cleaners, babysitters, and other household help, including scheduling and follow-up

· Manage kids’ activity schedules, appointments, and related logistics

· Occasionally serve as the point of contact for service providers, activity organizers

· Run local errands (post office, returns, dry cleaning, pharmacy, and similar)

Personal Administration and Bookkeeping

· Pay household and property bills and track due dates

· Maintain basic bookkeeping records, categorize expenses, and reconcile statements

· Organize receipts and documentation for accountant handoff

· Manage shared calendars across family and professional commitments

Travel

· Plan and book flights, hotels, and ground transportation

· Build itineraries and packing lists, handle pre-trip preparation

· Resolve changes and disruptions in real time

Real Estate and Property Support

· Coordinate maintenance, repairs, and vendor scheduling for personal properties

· Track leases, renewals, insurance, and property-related paperwork (leveraging existing software)

· Communicate with tenants, property managers, and service providers as needed

· Property management experience is a strong plus, not a requirement

Business Development Support

· Research and organize data sources to identify prospective clients

· Build and maintain accurate contact records in the CRM (working with an in-place team)

· Execute outreach and follow-up campaigns as directed

· Track responses, report results, and flag what is working

· Proofread and edit correspondence and marketing materials

What Makes Someone Successful Here

· Initiative. You act on incomplete information and ask sharp questions rather than waiting for direction.

· Phone confidence. You would rather call than email when calling gets the answer faster, and you follow up until the loop is closed.

· Judgment. You know which decisions are yours to make and which need to be escalated.

· Multi-tasking. You can hold several projects and deadlines at once without dropping threads.

· Discretion. You will have access to family, financial, and confidential business information. Impeccable integrity is non-negotiable.

· Follow-through. Tasks get finished, and the person who assigned them knows they were finished.

Qualifications

· 2+ years in a house manager, executive assistant, personal assistant, nanny, or similar support role

· Strong organizational and time-management skills

· Strong written and verbal communication, including proofreading and editing

· Comfort with technology: shared calendars, Microsoft Office or Google Workspace, online ordering, and CRM or database tools

· Basic bookkeeping or bill-pay experience (not required but helpful)

· Real estate license, property management, or commercial real estate exposure is a plus but not required (desire to attain a real estate license is a plus)

· Valid driver’s licen…