Hire Society
Overview
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 trustworthy and provide reliable, long-term support in a calm, respectful, and professional manner.
Responsibilities
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
Qualifications
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 & Benefits 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.
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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 trustworthy and provide reliable, long-term support in a calm, respectful, and professional manner.
Responsibilities
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
Qualifications
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 & Benefits 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.
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