Every season, Optimist Theatre employs approximately 35 artists and staff each season to bring Shakespeare in the Park to life.

All positions for the 2026 Shakespeare in the Park summer season have been filled. Thank you for your interest. We encourage you to check back for future opportunities.

We encourage you to reach out regarding future possibilities. A few things to know ahead of time about working with Optimist Theatre:

• All positions we post here are paid.
• Although we rarely actively seek them out, we are extremely grateful for volunteers. Volunteers are engaged on a case-by-case basis based on interest and organizational need. If you’d like to get involved, please reach out via the contact form below.
• Optimist Theatre is an Actors' Equity Association company and all actors are employed within those parameters. Crew members, designers, etc are hired as Independent Contractors.
• Rehearsals typically begin the first or second Monday in June. Performances run Saturdays and Sundays from the weekend after July 4 through mid-August.
• If you work in the cast or crew, lunch is provided on show days.

Optimist Theatre is deeply committed to equity and inclusion.

• We gratefully and strongly encourage BIPOC and LGBTQ+ artists and professionals to apply. If you have questions about the type of work and qualifications, please reach out.
• Optimist Theatre has a fledgling BIPOC apprenticeship program. If you're interested in knowing more, please reach out.

Optimist Theatre also maintains a small number of year-round positions. We are currently seeking:

Grants Manager

The Grants Manager oversees the calendar of foundation grants that support Shakespeare in the Park. This role works closely with the Executive Director to ensure all applications and reports are completed accurately and submitted on time.

The workload varies throughout the year, depending on grant cycles and reporting deadlines, with some months requiring more time than others.

Qualifications:

• Familiarity with nonprofit operations (arts/theatre experience preferred)
• Exceptionally organized and detail-oriented
• Strong sense of responsibility and follow-through
• Comfortable working in Google Docs and Sheets
• Experience with databases; familiarity with Little Green Light is a plus

Position Details:

• Start date: August 2026
• Includes a two-month overlap with the current Grants Manager for training and transition
• Compensation is currently a flat monthly rate, designed to balance lighter and busier periods across the year
• This position can be done remotely; however, familiarity with the greater Milwaukee area and the ability to meet in person are preferred

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