Executive Director - Lookingglass Theatre Company, Chicago, IL

"Cascabel" "Cascabel" Photo by Liz Lauren

Applications for this position are now closed - Thursday Oct. 25th, 2017

Nearly three decades ago, eight graduates of Northwestern University formed an artist-centered institution in the theater-rich city of Chicago. The ensemble named it Lookingglass Theatre Company (LTC) after Lewis Carroll’s famed story Alice’s journey of imagination, transformation, and beauty. This gutsy and forward-thinking group of artists – the Ensemble – has tenaciously shepherded the artistic work of Lookingglass for more than a generation. In 2011, Lookingglass Theatre Company received the Special Tony Award for Outstanding Regional Theatre, a remarkable achievement in just over two decades of producing. Additionally, in 2016, LTC received the MacArthur Award for Creative and Effective Institutions.

LTC’ s Ensemble remains an important part of the organization’s collective leadership model regarding major artistic decisions. The Ensemble elects the Artistic Director (AD) – with Board confirmation – and the AD serves a term of up to three years (although historically, the AD’s tenure is longer). In addition to Artistic Director Heidi Stillman, two other Ensemble members currently hold fulltime staff posts with LTC: Producing Director Philip Smith and Connectivity and Engagement Director Andrew White.

Most of the work produced by LTC is new work, many of which are adaptations of literature, created from within the company. Imagination and theatricality are fundamental to their approach. Although many of its pieces are conceived, written, and directed by Ensemble members, LTC also engages outside actors and sometimes outside writers and directors. There are often significant movement and physical theater skills incorporated into LTC’s productions. To teach and hone these acrobatic abilities, LTC has established a long-term partnership with The Actors Gymnasium. 

Seasons are determined in a rigorous process which includes Ensemble members pitching projects to the entire Ensemble and deciding together what might make the best season. The AD and the Executive Director(ED) take that feedback, and in consultation with the staff, put forward a season slate that the Ensemble votes up or down.

Guided by its three core values – collaboration, transformation, and invention – LTC lives its mission to offer theater that invites – even demands – interaction with its audience. More information about LTC can be found on its website: www.lookingglasstheatre.org.


LTC is located on the north end of Chicago’s Magnificent Mile (www.themagnificentmile.com) and its theater is quintessentially Chicago. Since 2003, the historic Water Tower Water Works building has been LTC’s theatrical home. With a 240-seat maximum (generally about 200-seats), completely configurable space, the audience finds a newly conceived interior with each production, including black box, proscenium, thrust, and end stage. This stunningly beautiful building continues to be an active water pumping station for the city; its enormous pumps can be viewed on ingress/egress. LTC leases the theater space on a long-term arrangement with the city. Office space is a short one-block walk away in the famed John Hancock Tower, where LTC leases approximately 7000 square feet for artistic, administrative, and production staff. The scenic shop is approximately two miles away in West Town; the costume shop is currently in the John Hancock Tower.


LTC operates on an annual operating budget of approximately $5 million, with slightly more contributed income (53%) than earned (47%). There are three (and sometimes four) productions each season, with runs varying from five/six weeks to several months. Full-time employee count is 28, with dozens of part-time and seasonal employees as well. Most actors and all stage managers are engaged on an Actors’ Equity Association CAT contract (tier 4 or 5). This year LTC has approximately 2500 subscribers (1200 households). Ticketing is handled in-house; box office, education, and development transactions are conducted through Total Info software, a patron-centric system (www.easy-ware.com). There is no formal endowment. Two recent one-time gifts of $1 million each have provided LTC with funds for capacity building research, planning, and execution.


• Heidi Stillman has been the Artistic Director of LTC since 2016 and has been an ensemble member since 1989. Immediately before becoming AD, Heidi was on staff for 10 years as the Artistic Development Director. She was previously AD  from 1997-2000. Her bio may be found here: https://lookingglasstheatre.org/people/heidi-stillman/

• Rachel Kraft has been Executive Director since 2005 and will be stepping down from this post in December 2017. Her bio may be found here: https://lookingglasstheatre.org/people/rachel-e-kraft/ 

• The Ensemble consists of 24 actors, writers, designers, directors, and choreographers. A full listing may be found here: https://lookingglasstheatre.org/ensemble/ 

• The Board of Directors is populated by 45 members who are business leaders, community volunteers, artists, and philanthropists. The AD and ED hold ex officio positions on the Board. A full listing of trustees is here: https://lookingglasstheatre.org/about/board/ 

Commitment to the Community:

LTC commits significant resources to education and engagement activities. Primary programs include multiple kids’ summer camps, student matinees, artists-in-residence (approximate 20 area schools), Young Ensemble (an audition-based program, grades 3-12), classes, and workshops.


As it approaches its 30th season, LTC will cross that important threshold with pride and celebration, honoring its past accomplishments while focusing on what is yet to come. This is an institution that has built its reputation through assiduously hard work; that reputation places it in the top-tier of recognition – and quality – in Chicago’s venerable theater community and beyond. With an iconic performance space, a remarkable coterie of artistic talent, innovative productions, and a committed Board, LTC has significant and enviable assets. With its many successes come inevitable challenges tied to its maturation institutionally. These include:

• Building a major gifts program in its development efforts – a primary area identified in the capacity building research report.

• Making the best use of the Ensemble’s talents and continuing to hone its role in the organization’s governance.

• Balancing artistic ambition with available resources.

• Stabilizing some staff positions (especially more junior roles) that have seen significant turnover.

• Becoming increasingly strategic in moving projects from page to stage.

• Adjusting to a smaller office footprint, including the recent loss of a rehearsal studio. 

• Creating annual strategic and development plans and holding stakeholders accountable for achieving stated goals.


The next ED of LTC will be chosen through a search process conducted by an eight-member committee with representation from the Board, Ensemble, and staff. The ED and AD operate in a co-leadership model; the ED reports directly to the Board through the Chair. The central roles of the ED are:

• Forge an effective and positive working relationship with the AD and, by extension, the Ensemble.

• In concert with the AD, align human and financial resources in a way that most effectively realizes LTC’s mission.

• Build key relationships internally and externally that are essential to LTC’s vitality. 

• Serve as a key participant in LTC’s fund-raising activities with a strategic focus on major gift development, working closely with the development team.

• Act as a principal voice for LTC externally both locally (with the City of Chicago and fellow nonprofits) and nationally (with fellow regional theatres).

• Manage and motivate the staff team and, in partnership with the AD, set the tone for a positive working environment for all working at LTC. 

• Forge an effective and productive working relationship with the Board Chair and, by extension, the Board Leadership and Board Members.


The chosen candidate will be someone able to establish a strong and productive working partnership with the AD; prior experience with such partnerships will be deemed useful. S/he will also have the following skill sets and experience:

• A management career within the professional arts community; although a background in regional theater will be seen as highly beneficial, the search committee is open to reviewing candidates from other disciplines.

• A highly collaborative approach, with the ability to balance the many voices at LTC with the need to move the organization forward in a strategic manner.

• Prior success in fund-raising.

• Prior success in working actively with a Board of Directors.

• A clear knowledge of the ramifications of artistic and budgetary decisions and the need to align them strategically, drawn from experience in budget forecasting, and controls sufficient to offer analysis to the Board and staff.

• Experience in developing near and longer-term strategic plans and seeing them through to fulfillment.

• Experience in moving productions to other theaters and cities. 

Additionally, the search committee will look for candidates who have the following personal qualities:

• An appetite for innovative theatrical production and, therefore, able to be a true advocate of LTC.

• A visionary leader with the tenacity, drive, and grit to make dreams happen. 

• Very strong social and interpersonal skills, including taking delight in representing the organization in multiple social and business contexts.

• Ability to derive deep satisfaction from facilitating the best work of others.

• Believer in the benefits of best practices and process in running an efficient organization.


The salary will be highly competitive with other companies of comparable stature and size. Benefits will include: 

• Medical/vision insurance plans (largely employer funded).

• Paid vacation/holidays. 

A review of prospective candidates will commence immediately, continuing until the position is filled. Interested and qualified individuals are encouraged to submit their credentials as soon as possible for full consideration to the consulting firm retained for the search as listed below.  Recommendations of qualified candidates are also welcome.  Complete credentials should be submitted electronically and should include cover letter; résumé or CV; a minimum of three professional references, including name, email, phone, and relationship. Application materials should be sent electronically – Word or PDF only, please – with the applicant’s name included as part of each file name.

Management Consultants for the Arts, Inc.
Attn: David Mallette / Louise Kane 

Email only:  This email address is being protected from spambots. You need JavaScript enabled to view it.
Subject Line: Lookingglass ED Search

Last modified on Wednesday, 08 November 2017 08:09