Executive Personal Assistant to Entreprenuer / in Manhattan , Illinois
JOB REFERENCE NUMBER: 2474
POSTED ON May 1, 2026 — Executive Personal Assistant BY POCKETBOOK AGENCY
We are seeking a highly capable Executive Assistant / Personal Assistant to support a high-net-worth CEO primarily in personal, lifestyle, and day-to-day matters, with limited but critical business coordination. This role requires exceptional discretion, reliability, judgment, and the ability to operate independently with minimal oversight.
The ideal candidate anticipates needs, manages details quietly, and takes pride in protecting time, privacy, and personal well-being. This is a long-term role for someone comfortable working closely with a private individual and handling matters that require maturity and trust.
Primary Responsibilities
Secondary Responsibilities (Limited Business Support)
Required Traits
Experience & Qualifications
Confidentiality and Trust
This role requires a high level of trust and discretion. The Executive Assistant / Personal Assistant will have access to sensitive personal and private information and is expected to handle all matters with professionalism and confidentiality at all times.
A non-disclosure agreement will be required. Maintaining privacy, exercising sound judgment, and acting with integrity are core expectations of this role, both during and after employment.
What This Role Is (and Is Not)
This is not a traditional corporate administrative role. It is a personal support and trust-based position intended for someone who values reliability, discretion, and long-term commitment. The right candidate operates quietly, efficiently, and without ego.
Compensation
Highly competitive and commensurate with experience. Structured as a long-term role for the right individual, with stability and trust at its core.
Pocketbook Agency is acting solely as a recruiting and placement firm for this position and is not the employer of record for this role unless otherwise explicitly stated. All hiring decisions, compensation, benefits, and employment terms are determined by the client employer. By applying, you acknowledge that submission of an application does not guarantee placement or employment.
Pocketbook Agency is an equal opportunity recruiting firm and does not discriminate in its recruiting, screening, or placement practices based on race, color, religion, sex, gender identity, sexual orientation, national origin, age, disability, veteran status, or any other protected characteristic under applicable law.
The ideal candidate anticipates needs, manages details quietly, and takes pride in protecting time, privacy, and personal well-being. This is a long-term role for someone comfortable working closely with a private individual and handling matters that require maturity and trust.
Primary Responsibilities
- Manage personal calendars, travel, appointments, and daily logistics
- Coordinate residences, household staff, vendors, vehicles, and related needs
- Serve as a gatekeeper for personal communications, requests, and access
- Handle sensitive personal, legal, financial, and medical information with discretion
- Oversee personal projects, commitments, and obligations through completion
- Anticipate needs, solve problems proactively, and remove friction quietly
- Maintain organization across personal affairs, records, and digital systems
- Support personal travel planning and on-the-ground logistics
- Act as a trusted point of contact for close advisors, family, and select associates
- Protect privacy, boundaries, and personal time at all times
Secondary Responsibilities (Limited Business Support)
- Coordinate select business-related scheduling or travel as needed
- Prepare brief summaries, reminders, and notes where personal and professional priorities intersect
- Liaise with business staff when personal logistics require coordination
Required Traits
- High integrity and strong sense of responsibility
- Naturally discreet, composed, and trustworthy
- Highly organized with strong follow-through
- Calm and capable under pressure or in sensitive situations
- Emotionally intelligent and socially aware
- Proactive, observant, and self-directed
- Comfortable handling personal matters with professionalism
Experience & Qualifications
- Prior experience as a personal assistant, executive assistant, house manager, or similar role
- Demonstrated ability to manage confidential personal affairs responsibly
- Strong communication skills and attention to detail
- Technologically competent and security-conscious
- Flexible availability aligned with the CEO’s schedule and lifestyle
Confidentiality and Trust
This role requires a high level of trust and discretion. The Executive Assistant / Personal Assistant will have access to sensitive personal and private information and is expected to handle all matters with professionalism and confidentiality at all times.
A non-disclosure agreement will be required. Maintaining privacy, exercising sound judgment, and acting with integrity are core expectations of this role, both during and after employment.
What This Role Is (and Is Not)
This is not a traditional corporate administrative role. It is a personal support and trust-based position intended for someone who values reliability, discretion, and long-term commitment. The right candidate operates quietly, efficiently, and without ego.
Compensation
Highly competitive and commensurate with experience. Structured as a long-term role for the right individual, with stability and trust at its core.
Pocketbook Agency is acting solely as a recruiting and placement firm for this position and is not the employer of record for this role unless otherwise explicitly stated. All hiring decisions, compensation, benefits, and employment terms are determined by the client employer. By applying, you acknowledge that submission of an application does not guarantee placement or employment.
Pocketbook Agency is an equal opportunity recruiting firm and does not discriminate in its recruiting, screening, or placement practices based on race, color, religion, sex, gender identity, sexual orientation, national origin, age, disability, veteran status, or any other protected characteristic under applicable law.