Executive/Personal Assistant

Overview

We are seeking a proactive, organized, and tech-savvy Executive/Personal Assistant to support a busy professional with a blend of business and personal responsibilities. This dynamic role requires flexibility and will include a mix of onsite work, client visits, event site coordination, and minimal remote responsibilities. The ideal candidate thrives in a fast-paced environment, enjoys bringing structure to chaos, and can handle sensitive information with the utmost discretion. Occasional domestic or international travel may be required.

Executive Assistance Responsibilities

- Coordinate all aspects of travel and accommodations, including transportation, dining arrangements, and activity planning.

- Conduct in-person and online procurement of supplies, equipment, and business-related items.

- Manage organization and transportation to storage facilities; must be capable of lifting up to 50 lbs and standing for extended periods.

- Facilitate donation drop-offs and maintain accurate records of charitable contributions.

- Assist in the planning, setup, and coordination of events, including vendor communication and on-site logistics.

- Evaluate and assess potential venues for meetings, events, and special gatherings.

- Oversee and maintain multiple email accounts, ensuring timely responses and professional communication with both internal teams and external clients.

- Manage complex calendar systems for multiple stakeholders, including scheduling and coordinating appointments, meetings, and events.

- Prepare and manage client invoicing, billing processes, and related communications.

- Support organizational volunteer initiatives, subject to availability.

- Execute various administrative and ad hoc tasks as needed to support daily operations.

- Create and edit reports, presentations, and other business documentation with a high degree of accuracy.

- Conduct thorough online research and compile findings into clear, actionable summaries.

- Manage expense reports, invoices, and perform light bookkeeping duties.

- Liaise with vendors, service providers, and professional contacts to coordinate business services and maintain strong working relationships.

Personal Assistance Responsibilities

- Coordinate and manage household-related appointments, maintenance schedules, and service provider communications.

- Handle online shopping tasks, including order placement, tracking, returns, and gift procurement for various occasions.

- Plan and manage personal travel arrangements, including flights, accommodations, transportation, and detailed itineraries.

- Organize and coordinate personal events and social engagements, such as dinners, celebrations, and gatherings, including venue reservations and logistics.

- Maintain and manage reminders for important dates and tasks, including birthdays, anniversaries, renewals, and appointments.

- Oversee the pickup and drop-off of packages at USPS, FedEx, UPS, and DHL, ensuring timely and secure delivery.

- Manage the pickup and return of garments from dry cleaners and tailors, ensuring items are handled and delivered on schedule.

Job Requirements & Ideal Background

Required Qualifications:

- Minimum of 3–5 years of experience in a combined Executive Assistant and/or Personal Assistant role, preferably supporting a senior executive, entrepreneur, or high-demand household.

- Exceptional organizational skills and attention to detail, with the ability to manage multiple priorities and deadlines simultaneously.

- Strong verbal and written communication skills, including professional email correspondence and document preparation.

- High proficiency with productivity and collaboration tools (e.g., Google Workspace, Microsoft Office Suite, Zoom, Dropbox, project/task management platforms such as Asana, Notion, or Trello).

- Proven ability to exercise sound judgment, discretion, and confidentiality when handling sensitive information and high-profile relationships.

- Comfortable lifting up to 50 lbs and performing physical tasks such as storage runs and event setup as needed.

- Tech-savvy with the ability to conduct efficient online research and troubleshoot basic technical issues.

- This is expected to be 8-10 hrs perweek. The ideal candidate can be onsite in either Old Town Chicago or Lombard, IL four days a week 10am-12pm (hours may fluctuate).

Preferred Qualifications:

- Experience in event planning, travel coordination, household management, or vendor relations.

- Familiarity with light bookkeeping, invoicing software, or expense tracking tools.

- Background supporting a private household or small business with both professional and personal tasks.

Additional Requirements:

- Must possess a valid driver’s license and have consistent access to a reliable personal vehicle.

- Comfortable driving for errands, meetings, appointments, donation drop-offs, or transporting materials as needed.

- Availability for occasional evening or weekend work in support of events or time-sensitive tasks.

Ideal Candidate Attributes:

- Self-starter with a proactive, can-do attitude and the ability to anticipate needs before they arise.

- Adaptable and resourceful under pressure, with a solutions-oriented mindset.

- Trustworthy, dependable, and professional in appearance and demeanor.

- Enthusiastic about contributing to both the personal and professional success of the individual or executive they support.

Job Types: Part-time, Contract

Pay: From $20.00 per hour

Ability to Commute:

• Chicago, IL 60610 (Required)

Work Location: In person