Executive Assistant

Play On Shakespeare; 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 in Chicago, IL is seeking a part-time Executive Assistant to support the Executive Director with calendars, correspondence, and day-to-day operations. This role requires strong organization, discretion, and proactive communication within a small team.

The Executive Assistant will report in person several days a week at 4809 Ravenswood and will work regular hours 10 AM–6 PM CST, Monday through Friday, with scheduling to be set by the Supervisor.

Qualifications

• Highly organized and proactive in a fast-paced environment.
• Excellent written and verbal communication skills.
• Strong tech-savviness with scheduling software and Google Suite.

Responsibilities

• Manage 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.
• Maintain organized digital records and documents.
• Manage email inbox and prioritize communications.
• Draft and proofread correspondence as needed.
• Handle general office tasks at the organization’s HQ.

Skills

Highly Organized

Proactive & Resourceful

Strong Communicator

Tech-Savvy

Trustworthy & Confidential

Detail-Oriented

Adaptable

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

Applications open: November 12, 2026 at 9AM CST
Applications due: November 20, 2026 at 5PM CST

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.