Executive Assistant

Play On Shakespeare, Inc.; Chicago (IL); On-site; USD 38,000 - 53,000; Part time

Benefits offered by this job

CTA Transit Card

403b plan with employer contributions

generous leave policy

cell phone stipend

Job summary

Play On Shakespeare, Inc. seeks an Executive Assistant in Chicago for part-time, in-office support to the Executive Director. The role focuses on calendar management, communications, and day-to-day administrative tasks, with a schedule set between 10 AM and 6 PM CST, Monday–Friday.

The ideal candidate is highly organized, proactive, and capable of handling multiple priorities in a fast-paced environment. Local candidates in Chicago are required; start date is February 1, 2027.

Qualifications

• Experience organizing calendars and coordinating meetings.
• Excellent written and verbal communication.
• Ability to handle confidential information with discretion.
• Proficient with scheduling tools and office software.

Responsibilities

• Manage and coordinate the Executive Director's calendar, meetings, and travel.
• Prepare agendas and materials for meetings; track action items and deadlines.
• Maintain organized digital records and email inbox; draft correspondence.
• Assist with in-office tasks at the Chicago HQ and organize mail.
• Support travel logistics and general day-to-day tasks.
• Collaborate with supervisor to streamline workflows and calendars.

Skills

Highly Organized

Proactive

Clear Communicator

Tech-Savvy

Tools

Google Suite

Monday.com

Scheduling tools

Job description

Role: Executive Assistant
Employee Status: Part-Time (12 to 15 hours/week), Non-Exempt
Location: Chicago, IL (Not a remote position)
Compensation: $33.00 per hour.
Benefits Package: CTA Transit Card, 403b plan with employer contributions, generous leave policy, & cell phone stipend.
Work Schedule: Regular hours between 10AM - 6PM CST, Monday - Friday to be set.
Supervisor: Executive Director
Projected Start Date: February 1, 2027

Position Summary

The Executive Assistant provides essential administrative and personal support to the Executive Director of Play On Shakespeare. This part-time role focuses on organizing schedules, managing key communications, and assisting with general tasks that help streamline day-to-day operations. The ideal candidate is highly organized, proactive, and able to manage multiple priorities efficiently.

This position is for local hires in Chicago only and is not a remote position. The Executive Assistant will be required to report in person to Play On Shakespeare's office at 4809 Ravenswood in Chicago several days a week. Work time is flexible within the hours of 10 AM - 6 PM CST, Monday through Friday but a schedule will be set with the Supervisor.

Key Responsibilities

Administrative & Scheduling Support (75%)

• Manage and coordinate the Executive Director's calendar, scheduling meetings and appointments.
• Assist in preparing agendas and materials for meetings.
• Track action items, deadlines, and follow up on key tasks, including tasks that are waiting on the Executive Director from other departments.
• Maintain organized digital records and documents.
• Manage email inbox and assist with prioritizing communications.
• Draft and proofread correspondence as needed.
• Manage general office tasks at the organization's physical headquarters including sorting mail.

Personal Assistance & General Support (25%)

• Organize and manage schedules to ensure efficient workflow.
• Provide general assistance for day-to-day needs, including professional and personal reminders and task prioritization.
• Assist with occasional personal and professional errands.
• Help coordinate travel arrangements and logistics.
• Support in organizing and streamlining commitments, both professional and personal.

Core Competencies and Traits

• Highly Organized - Able to create and manage multiple tasks, calendars, and files efficiently within limited hours.
• Proactive & Resourceful - Anticipates needs and takes initiative.
• Strong Communicator - Excellent written and verbal, clear communication skills with a good sense of humor.
• Tech-Savvy - Proficient in Google Suite, Monday.com, and scheduling tools.
• Trustworthy & Confidential - Exercises discretion with sensitive information.
• Detail-Oriented - Ensures smooth scheduling and communication processes.
• Adaptable - Able to support someone whose attention is divided across priorities.

Don’t meet every qualification, but still believe you can make a difference?

Research shows that women and people from underrepresented groups often apply to jobs only if they meet 100% of the qualifications. We recognize that it is highly unlikely that someone meets 100% of the qualifications for this role. If much of this job posting describes you, we encourage you to apply.

More information including timeline available at the provided job posting link.