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Theater ,
submitted by
Dan Grycza

Associate Director of Development

About Chicago Shakespeare Theater

A leading international theater company and recipient of the Tony Award for Outstanding Regional Theatre, Chicago Shakespeare Theater’s year-round season offers a vibrant array of classics, musicals, new works, and family programs for 225,000 audience members annually. The Theater is Chicago’s leading international presenter and, through its education efforts, has impacted the learning of over 2 million students. The opening of The Yard at Chicago Shakespeare, with its innovative design that changed the shape of theater architecture, together with the Jentes Family Courtyard Theater and the Thoma Theater Upstairs, positions Chicago Shakespeare as the city’s most versatile performing arts center.

Associate Director of Development

Position Overview

The Associate Director of Development is a senior staff member of the Theater and leads the Advancement Department in partnership with the Director of Development. This person is responsible for directing the Theater’s individual giving program, which includes serving as the lead writer and communications strategist for donor-facing communications, supporting overall department operations to ensure effective use of data in driving strategy, cross-team accountability, and efficient use of systems and practices. This position reports to the Director of Development and also works closely with the Artistic Director, Executive Director, Board of Directors and other Theater staff. This is a full-time, salaried position.

Reports To:

Director of Development


Individual Giving Manager

Advancement Coordinator

Patron Relationship and Data Coordinator

Work Hours:


Some evenings and weekends



• Develop and manage execution of a growth plan for individual donors.

• Create, in partnership with the Director of Development, and manage systems and practices that promote a culture of collaboration and information exchange inside the department and across the organization.

• Oversee a moves management system to support donor pipeline development and high performance among team members.

• Manage system for gift processing and acknowledgments and analytic reporting.

• Partner with the Director of Development to monitor and update development policies and procedures.

• Motivate staff toward daily, weekly and programmatic objectives.

• Support the Director of Development in staffing the Development and Membership Committees of the Board of Trustees and help drive follow-up activities with individual Board members.


• Develop annual plan for direct donor communications, including timing, channel, segmentation, and messaging strategy.

• Manage a personal portfolio of 50-75 donors and prospects qualified to make mid-level and major gifts to support the Theater’s annual and long-term needs.

• Support solicitation efforts for direct reports and other relationship managers across the organization (theater leadership, program managers, and Trustees) by prospecting, coaching, and co-creating custom proposals.

• Oversee and drive execution of a comprehensive stewardship program, from standard acknowledgement letters to high-touch activities that acknowledge extraordinary giving.


• Manage the external communications and lead matrix calendars in collaboration with the Director of Marketing.

• Help interpret giving motivations and guidelines for individual and institutional donors (stated and otherwise) and proactively engage colleagues across the organization for information collecting.

• Cultivate an in-depth knowledge of all streams of Chicago Shakespeare programming and curate and document the most compelling stories to reach donors.

• Develop and maintain a case messaging repository that will serve as foundational language for external facing donor communications, including letters, emails, proposals, and impact reports.

• Serve as lead writer for special donor communications.


• Proficiency writing compelling, donor-facing communications.

• Background in the cultivation and solicitation of individual donors, including major gift fundraising.

• Experience working with a wide range of people and personality types to help build a culture of philanthropy.

• Knowledge of recent funding trends and motivations in the individual giving arena.

• A working knowledge of Chicago philanthropists is a plus.

• 5-7 years progressive experience as a fundraising professional.

• Experience and proficiency in MS Office suite.

• Comfort using a donor database experience (Tessitura is preferred).


• Highly organized and driven, with the ability to plan and manage strategically.

• Excellent verbal and written communication skills.

• Ability to analyze and interpret reports to direct or redirect fundraising efforts.

• Capable of setting priorities, while having the ability to shift work seamlessly when priorities change.

• Ability to work collaboratively and independently in a fast-paced theater environment.

• Personable, positive, and diplomatic.

• Possess exceptional work ethic and a sense of humor in order to work effectively with trustees, donors, volunteers, and inside staff.

• Enjoy taking an active, public role in the cultivation and solicitation of donors, as well as a representative of the Theater.

• Ability to work nights and weekends.


Salary is competitive within the non-profit performing arts industry and commensurate with qualifications and experience. Benefits package includes health, dental, vision, 403b, paid time off, life insurance, and commuter spending plan.

To apply

To be considered for this position, please submit your resume and a brief cover letter describing your interest, experience, and how you heard about this position at Candidates of interest will be contacted by a representative of the Theater, no phone calls, please.

Chicago Shakespeare is dedicating itself to creating paths that lead to a more inclusive and diverse institution. We encourage inquiries from applicants who will reflect the plurality of our culture and our global audience. Chicago Shakespeare does not discriminate on the basis of age, race, creed, color, religion, marital status, gender identity and/or expression, sexual orientation, veteran status, national origin or disability status.

Job Type: Permanent
Location: Chicago