Director of Special and Planned Gifts

Chicago Shakespeare Theater is seeking a Director of Special and Planned Gifts.


Recipient of the 2008 Regional Theatre Tony Award, Chicago Shakespeare Theater (CST) offers a broad spectrum of theatrical experiences year-round, engaging and entertaining audiences from all walks of life and from around the world. CST believes that Shakespeare speaks to everyone. A global theatrical force, CST is known for vibrant productions that reflect Shakespeare’s genius for storytelling, musicality of language and empathy for the human condition. CST is dedicated to producing extraordinary productions, unlocking Shakespeare’s work for the next generation, and serving as Chicago’s ambassador through its World Stage Series.

CST has a worldwide reputation as an American Shakespeare company whose mastery of textual analysis brings remarkable clarity to the canon and other complex works. This legacy is directly linked to the Theater’s founding days, when Barbara Gaines brought to Chicago a series of First Folio acting workshops that turned into public performances and ultimately led to the founding of CST in 1986, with the city galvanizing around an audacious vision for Shakespeare’s Chicago home.
In 1999, the company moved to its permanent facility that serves as the cultural heart of historic Navy Pier on downtown Chicago’s lakefront. Guided by the leadership of founder and Artistic Director, Barbara Gaines, and Executive Director Criss Henderson, CST’s work has expanded to include family productions, musicals, world premieres, and visiting international tours that sit alongside plays from the canon to inspire an inclusive dialogue with its audiences.

Today, Chicago Shakespeare’s year-round producing and presenting season features as many as 18 plays and 650 performances with work that engages 225,000 audience members in the theater’s two intimate theater spaces at their Navy Pier home, in culturally underserved neighborhoods throughout Chicago, in Illinois schools and communities, and across the globe. The Theater’s subscriber base of nearly 16,000 routinely outperforms the industry standard for renewal rates, averaging more than 80% for over ten seasons. In total, CST productions exceeded 87% capacity in 2013. The majority of CST’s subscription and single-ticket audiences represent populations within metropolitan Chicago who demonstrate high cultural participation. CST also advances model initiatives to overcome real and perceived barriers to participation among those who are traditionally disengaged from large cultural institutions, including audiences who are young, low to middle income, living in underserved inner-city neighborhoods and in rural areas, and those with hearing or visual impairments. Through these efforts, Chicago Shakespeare brings extraordinary live theater to approximately 100,000 students and audiences of all ages who otherwise would not have the opportunity to participate. These audiences include 40,000 middle and high school students, 25,000 culturally disengaged residents in the inner city, and 35,000 families. CST’s free and reduced price initiatives represent the region’s most extensive commitment to providing multigenerational access to professional theater, and today one in four CST visitors is under the age of 18.

The Theater’s tradition of excellence and civic leadership has been honored with numerous national and international awards. In addition to the Regional Theater Tony Award, CST has received three Laurence Olivier Awards and 77 Joseph Jefferson Awards. CST was the 2012 recipient of the Folger Shakespeare Library’s national Shakespeare Steward award for its innovative teaching of Shakespeare in American classrooms. Among its many international engagements, CST participated in the Royal Shakespeare Company’s 2006 Complete Works Festival and was selected to represent North America at the Globe to Globe festival for the London 2012 Cultural Olympiad.

CST has a full time staff of 70 and is governed by a 62 member Board of Trustees. The annual operating budget for 2015 is approximately $15.6 million, with $6.8 million coming from contributed income. The Theater is preparing to construct a third theatre space adjacent to its current building and is presently in the middle of a $35 million capital and endowment campaign to support that effort. To date, $21.5 million has been raised towards that goal. The Director of Campaign and Major Gifts will play a key role in this campaign. 

Position and Responsibilities

The Director of Special and Planned Gifts will play an active role in donor cultivation and solicitation, with a particular focus on gifts above $10,000. The position is a senior member of the Advancement Team, reporting to the Director of Institutional Advancement. S/he will also work closely with the Artistic Director, Executive Director, Board and other theater staff.

The Director of Special and Planned Gifts will:

  • Work with the Director of Institutional Advancement to create a growth strategy for annual and specialized partnership opportunities with lead individual donors ($10,000+).
  • Manage a portfolio of 125-150 individual donors and prospects, forging meaningful relationships that deepen their connections to CST.
  • Create a donor-centered moves management system to direct the identification, cultivation, solicitation and stewardship of individual contributors.
  • Drive the cultivation and stewardship plan for individual major contributors and planned giving prospects, including the management of private donor entertaining hosted by theater leadership and VIP donor services and programs.
  • Conduct research on donors and overall funding trends with a goal of identifying strategies for increasing support and uncovering viable prospects.
  • Work with Trustees and theater leadership to broaden CST’s network of individual donors.
  • Brief CST staff and board leadership for meetings and events.
  • Serve as a visible, articulate spokesperson for the theater and member of the solicitation team.
  • Maintain detailed, accurate systems and files.
  • Possess an in-depth knowledge of all streams of CST programming and serve as an articulate, passionate representative for the theater and its artists.


The successful candidate will:

  • Have a background in the cultivation and solicitation of individual donors, including major gift fundraising, and a proven track record in the management of successful development programs.
  • Have direct experience managing relationships with lead donors, successfully securing major sources of funding for a non-profit organization, and working effectively with civic and business leaders on a campaign or fund raising committee.
  • Possess expertise in and knowledge of recent funding trends and motivations in the individual giving arena. A working knowledge of Chicago philanthropists is a plus.
  • Be very well-organized, able to plan and manage strategically, set priorities and focus on details while not losing sight of the big picture, with the flexibility to welcome and embrace change, and the ability to work collaboratively in a fast-paced theater environment.
  • Possess excellent verbal and written communication skills, good business sense, and computer literacy. Proficiency in MS Office and a working knowledge of Tessitura preferred.
  • Be a personable, positive, and diplomatic individual with integrity, an exceptional work ethic, and a sense of humor, who works effectively with trustees, donors, volunteers, and inside staff, and who enjoys taking an active, public role in the cultivation and solicitation of donors, and as a representative of CST.
  • Be someone with initiative, creativity, energy, and an entrepreneurial spirit, who enjoys working as a team player but also has the capability to work independently and as a self-starter.
  • Possess a passion for the performing arts, understand and support CST’s mission and have the ability to articulate this mission and role to others. Special consideration given to those with a knowledge of American theater and the Chicago theater community.
  • Have, at minimum, a Baccalaureate degree, and 7 years progressive experience as a fund raising professional.


Salary will be competitive with the level of experience required for this position.

Start Date

The position will be filled as soon as possible.

To Apply

Interested candidates should send a cover letter, resume, and references to Candidates of interest will be contacted by a representative of the Theater. No calls, please.

Chicago Shakespeare Theater is an equal opportunity employer and encourages all to apply.

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