Personal Assistant

A private and discerning individual in downtown Chicago seeks a highly organized, discreet, and emotionally intelligent Personal Assistant to provide day-to-day administrative and personal support. The ideal candidate will be patient, polished, and trustworthy, with prior experience supporting high-net-worth or senior principals in private household settings. This full-time, in-person role requires exceptional attention to detail, adaptability, and the ability to work independently while maintaining absolute discretion. The Principal is an accomplished woman who remains actively engaged in her personal business and daily affairs. The role involves assisting with scheduling, communication, household organization, and light administrative support. The ideal candidate will be trustworth and provide reliable, long-term support in a calm, respectful, and professional manner.

Job responsibilities include, but are not limited to:
• Provide day-to-day personal and administrative support to the Principal
• Manage emails, calendar, and appointments with precision and discretion
• Coordinate errands, vendor communications, and general household organization
• Assist with bill payments, light bookkeeping, and invoice processing
• Support administrative and business-related tasks connected to the Principal’s ongoing ventures
• Maintain and update existing digital organization systems
• Assist with personal correspondence and document management
• Oversee deliveries, household scheduling, and vendor coordination
• Provide companionship and thoughtful assistance as needed in a respectful, non-intrusive manner • Potential future driving responsibilities once trust and familiarity are established
• Maintain a calm, professional presence and uphold confidentiality at all times
• Additional personal and administrative support tasks as requested

Requirements:
• Fluent in English with exceptional written, verbal, phone, and email communication skills
• Minimum of 3–5+ years of experience as a Personal Assistant or in a similar private household role • Excellent references required from both current and previous employers
• Experience supporting senior or high-profile principals preferred
• Highly organized, analytical, and detail-oriented with the ability to manage multiple priorities
• Proficiency in Google Workspace and Microsoft Office a plus
• Comfortable working in both structured and evolving environments; flexible with changing needs • Professional, discreet, and trustworthy with the ability to manage sensitive personal and financial information
• Resourceful and proactive with a “no task too small” mindset
• High emotional intelligence and ability to build rapport while maintaining professional boundaries • Composed and steady under pressure; able to adapt to strong personalities with grace
• Valid driver’s license
• Authorized to work within the United States without sponsorship or restrictions

Compensation: $75,000–$95,000 annually, depending on experience and background. (3–5 years of experience: $75,000–$85,000; 6+ years / highly experienced: up to $95,000)

Benefits: Base salary only to start, with openness to adding benefits or a stipend as needed to attract the right candidate.