Personal Assistant - Chicago, IL

Work Setting: Principal’s Private Residence & Family Office Headquarters
Hours/Schedule: 8am-6pm; Monday-Friday (with flexibility)
Employment Type: Full-Time
Compensation: $150,000, DOE
Benefits: All benefits are included, including savings/retirement plans, if desired
Parking: Street parking is available in the neighborhood and requires a parking sticker. The cost of the required sticker is covered by the company.
Travel: Extensive domestic and international travel required with limited notice

About the Role

A private family office in Chicago is seeking an exceptionally organized, proactive, and highly resourceful Personal Assistant / Executive Assistant to provide comprehensive support to a very busy CEO/Founder. This is a unique hybrid role that crosses between personal and executive support. The Principal’s professional and personal responsibilities are highly intertwined, so no two days will look exactly the same. The ideal candidate will be comfortable moving seamlessly from managing a busy executive calendar and coordinating meetings to handling personal errands, travel, gifting, wardrobe, household matters, and special projects. The right person will be highly anticipatory and naturally think several steps ahead. Rather than waiting to be told what needs to be done, they should be the type of person who hears the Principal mention something and can respond, “Already taken care of.” This position is based in Chicago and will work between the Principal’s private residence and the family office’s soon-to-be-established headquarters.

Key Responsibilities

Executive & Personal Assistance

• Manage a complex and constantly changing calendar, including professional and personal commitments.

• Coordinate meetings, appointments, agendas, scheduling, and follow-up.

• Serve as a trusted gatekeeper and help prioritize competing demands.

• Seamlessly transition between executive and personal responsibilities throughout the day.

• Handle personal errands, appointments, purchases, returns, deliveries, and other day-to-day needs.

• Coordinate medical and healthcare appointments and related logistics.

• Anticipate needs and proactively resolve tasks before being asked.

Travel & Logistics

• Coordinate extensive domestic and international travel from start to finish.

• Book flights, hotels, ground transportation, private aviation, security, and other travel logistics.

• Build detailed travel itineraries and ensure all arrangements are confirmed and organized.

• Pack and unpack for short- and long-haul travel, meetings, and events.

• Manage complex wardrobe and travel packing, including steamer trunks and specialized personal items.

• Maintain and restock travel supplies.

• Be available for travel-related needs and limited-notice changes.

Wardrobe, Shopping & Procurement

• Manage clothing, wardrobe organization, alterations, dry cleaning, and packing.

• Handle purchasing and procurement for personal and household needs.

• Coordinate returns, exchanges, shipping, reboxing, and deliveries.

• Assist with fashion-related purchases and ensure items are properly organized and prepared.

• Manage household and personal supplies, inventory, and reordering.

Household & Property Support

• Coordinate with household staff, vendors, contractors, and service providers.

• Assist with property maintenance, service schedules, and household projects.

• Support multiple properties and coordinate services across locations.

• Manage high-volume shipping, receiving, unpacking, and returns.

• Order, stock, and replenish household, cleaning, personal care, and other supplies.

• Help ensure vendors and service providers are properly scheduled and followed up with.

Events, Entertaining & Gifting

• Coordinate personal and professional events from planning through execution.

• Assist with in-home entertaining and event preparation.

• Manage gifting throughout the year, including purchasing, wrapping, shipping, and tracking.

• Assist with holiday preparation and special occasions.

• Take ownership of details to ensure events and experiences run seamlessly.

Administrative & Family Office Support

• Maintain organized digital and physical records.

• Assist with expense tracking, household budgets, invoices, and monthly expenses.

• Support CRM/database management and maintain accurate information.

• Utilize Microsoft Office and other technology to manage information, communications, and projects.

• Assist with family office administrative projects and special assignments.

• Maintain complete confidentiality when handling personal, financial, business, and family information.

The Ideal Candidate

The ideal candidate is a true Personal Assistant who is hands-on, energetic, resourceful, and highly proactive. They naturally anticipate needs, take ownership, and turn requests into action without waiting for direction. They can seamlessly balance executive responsibilities with personal tasks, including travel, wardrobe, errands, and household matters, while effectively prioritizing competing demands. The right person is organized, polished, discreet, detail-oriented, calm under pressure, and comfortable working in a large, multi-level private residence and handling the physical aspects of the role.

Qualifications

• 10+ years of professional Executive Assistant and Personal Assistant experience.

• Proven experience supporting CEOs, Founders, UHNW principals, entrepreneurs, or similarly demanding executives.

• Extensive domestic and international travel coordination experience.

• Experience managing complex calendars and meeting schedules.

• Advanced proficiency with Microsoft Office Suite, including Outlook, Word, Excel, and PowerPoint.

• Strong technology skills, including CRM/database management.

• Experience with complex packing, wardrobe management, shipping, returns, and personal procurement.

• Experience coordinating vendors, household services, and property-related matters.

• Strong organizational and project-management skills.

• Excellent written and verbal communication.

• Bachelor’s degree preferred.

• Must be based in Chicago; relocation assistance is not provided.

• Must be comfortable with extensive domestic and international travel.

• Must be able to provide a minimum of three professional, verifiable references that can be contacted and completed prior to an interview.

• Must successfully complete the family office’s required vetting and background process.

What Success Looks Like

Success in this role means staying one step ahead—anticipating needs, taking ownership, and handling details before the Principal has to ask. The ideal candidate is resourceful, proactive, and focused on making the Principal’s professional and personal life run as seamlessly as possible.