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Theater ,
submitted by
Douglas Clayton

Managing Director - Lookingglass Theatre - FINALISTS COMPENSATED

Through theatre, which invites, even demands, interaction with its audience, our goal is to fire the imagination with love, to celebrate the human capacity to taste and smell, weep and laugh, create and destroy, and wake up where we first fell —
changed, charged, and empowered.

Who We Are
Founded in 1988 by graduates of Northwestern University, Lookingglass Theatre Company is a nationwide leader in the creation and presentation of new, cutting-edge theatrical works and in sharing its ensemble-based theatrical techniques with Chicago-area students and teachers through Education and Community Programs. Guided by an artistic vision centered on the core values of collaboration, transformation, and invention, Lookingglass seeks to capture audiences’ imaginations leaving them changed, charged, and empowered.
Recipient of the 2011 Tony Award for Outstanding Regional Theatre, Lookingglass has built a national reputation for artistic excellence and ensemble-based theatrical innovation. Notable world premieres include Mary Zimmerman’s Tony Award-winning Metamorphoses, The Arabian Nights, and The Odyssey, David Schwimmer’s adaptation of Upton Sinclair’s The Jungle and Studs Terkel’s Race: How Blacks and Whites Think and Feel about the American Obsession, and David Catlin’s circus tribute to Lewis Carroll, Lookingglass Alice. Lookingglass’ work has been produced in more than a dozen US cities.

Lookingglass consists of a 33 member artistic ensemble, currently led by Artistic Director Kasey Foster. The ensemble partners in a distinctive collaborative leadership model with a 27 member Board of Directors, to be led beginning on September 1 by Board Chair Richard Chapman. Together an anticipated staff of 17 and a variety of contracted artists, technicians, and educators, the ‘three legs of the Lookingglass stool’ connect together to center a unique style of artistic work that flourishes through the appreciation and humility of each individual and each part of the company appreciating the others. Currently, the staff is co-led by General Manager Sarah Burnham, Director of Development Aurélia Fisher Cohen, and People and Culture Director Jazmin Jones-Oliver. In the period prior to the election of Kasey Foster, Lookingglass was led artistically by an artistic team that included Kasey, Kareem Bandealy, J. Nicole Brooks, and Phil Smith.
Lookingglass’ distinctive by-laws that illuminate the relationship between the Ensemble and the Board are available here. Next season’s anticipated operating budget is 4.36 million dollars.

Our Core Values
From the seminal, self-produced collegiate production of Alice in Wonderland, Lookingglass has always believed that the power of the whole is greater than the sum of its parts. Lookingglass sees immense value in group history and experience, a collective vision, the dynamics of teamwork and the importance of leadership within that collaborative construct. Each performance is a collaboration between artists, story, and audience. Collaboration informs every aspect of how we produce theatre.
Transformation is certainly at the core of all theatre and particularly vital to Lookingglass. Lookingglass uses visual metaphor, gesture, and daring theatricality to create transcendent staging. Fiction and non-fiction are converted into stage pieces. Actors are often required to play multiple characters outside their traditional range. Even the physical theatre itself reflects the core value of transformation – the infinitely flexible facility changes in configuration to best suit each new production. Transformation is reflected in the Lookingglass Mission Statement…to change, charge and empower.
Lookingglass seeks to redefine the limits of theatrical experience. The ensemble uses multi-disciplined arts training and an ambition for innovation to invent new ways to develop and tell stories.

Anti-Racism, Equity, and Inclusion Commitments
Lookingglass is committed to a set of Anti-Racism, Equity, and Inclusion guidelines, which have been developed by a task force of representatives from our Board, Associates Board, Staff and Ensemble. These specific commitments and goals are available on our website, and we encourage active discussion of these guidelines with current and future members of the Lookingglass team.

Our Theater
Opened in June 2003, Lookingglass Theatre Company is located inside the Water Tower Water Works building on the Magnificent Mile in Chicago. The company shares this facility with the still-functioning water utility, which pumps 250,000 gallons of water to the north side of Chicago every day.
The main stage allows Lookingglass to reconfigure the stage and audience seating as dictated by the needs of each production, allowing for a maximum capacity of 240 persons, 60 of whom may be seated at the balcony level. There is a multi-purpose studio space, used for special events, classes, rehearsals, and other activities.
In 2024, Lookingglass began an extensive lobby renovation, adding a bar and space for community engagement. This renovation aims to make the theater a center for arts, history, and social events in Chicago, with programming reflecting ongoing initiatives set to begin in November. We expect construction to complete in mid-December, with programming beginning in January 2025.

What We Do
Lookingglass’s staff, board, and ensemble has just completed an intensive business plan/sustainability process, guided by David Schmitz and Doreen Sayegh of Amplify Leadership Advisors. The new plan focuses on the aspects of our work that are uniquely Lookingglass, while laying out a path to financial sustainability. We are eager for our new Managing Director to carry forward and build on this plan in the years ahead. Some aspects of this business plan include:

  • Initially presenting two productions per year each winter and summer, as well as the annual unGALA, with the 2024-2025 season announced in June 2024
  • Building co-production relationships with complementary theatre companies
  • Supporting new works with artistic development intensives and an artist in residence program
  • Increasing baseline audiences to extend beyond traditional theatre audiences
  • Incorporating more education offerings to reflect programming and implementing additional youth and adult classes through the Department of Education
  • Expanding touring companies and productions of Lookingglass works

How this Search will Operate – Values, Communication, and Compensation
Overall Estimated Timeline:

  • Preferred Application Period: May 28 to July 8, 2024
    After the end of the application period, please reach out if you
    are still interested and we will let you know if there is still an
    opportunity for consideration.
  • Initial Candidate Meetings & Semi-Finalist Presentations: June 22 to July 30, 2024
  • Finalist Deep Dive Calls and Explorations: August 1 to August 20, 2024
  • Interviews On-Site in Chicago, IL: August 23 to 26, 2024
  • Employment Begins: Fall 2024

After an initial submission of interest, selected candidates will be invited for a virtual Candidate Meeting with Rebecca Novick, Dr. Kim Davis, and/or Doug Clayton from Creative Evolutions. Following the initial meetings, a group of candidates will be advanced to virtual Semi-Finalist presentations that allow for engagement with the board, staff, and ensemble. Candidates who advance as Finalists will be invited to participate in a series of virtual Deep Dive calls in particular areas and to come to Chicago in late August to tour the theater and meet the team in person.
Semi-finalist candidates will all be compensated $500 for their participation.

Finalists will be compensated an additional $1,200 plus reimbursement of their reasonable travel, lodging, and food expenses for their trip.
This search process is rooted in values shared by Lookingglass Theatre Company and Creative Evolutions, and will include the following elements:

  • It is important to us that you are treated with respect and are appreciated for the value you create for Lookingglass Theatre Company through your participation in this process. Candidates who do not advance will be notified promptly.
  • Throughout the process we commit to active communication with you, so you are never wondering what is happening or where things stand with your application or the hiring process.
  • It is important that the full company, including the staff, board, and ensemble, participate in the selection process. Final candidates will have the opportunity to come on site and meet the team before a hiring decision is made.

In addition, Creative Evolutions is engaging paid Industry advisors who will be collaborating with Creative Evolutions to design and conduct the Deep Dive finalist topic sessions as part of the process. These advisors will provide their perceptions and evaluations on finalists to the board and will also commit to be available for quarterly calls each for the selected Managing Director during their first year of employment at Lookingglass Theatre Company. This ongoing support is intended to strengthen Lookingglass as an organization and to provide strong collegial or mentorship support to the new Managing Director during the transition period.

What We Are Looking for in Our New Managing Director
Our next Managing Director will be a collaborative partner who appreciates that they are joining a complex team in the "middle of the story." The Managing Director should appreciate where Lookingglass has been and be ready to support the next chapter. Similarly, we expect our Managing Director to also be in the middle of their theatrical journey – informed by a rich history of working in the American theater, and excited about how that experience will be different or could grow and change in new ways at Lookingglass.
They may not currently live in Chicago, but if they are not from here they will have a clear ability to learn about new people and a new city and gain an appreciation of what makes Chicago distinct. On the other hand, our Managing Director will also have a clear national perspective that will be invaluable to us as we expand our touring work and national presence. Most of all, they will love the specific artistic aesthetic that makes Lookingglass special, and will have vision for how that art adds to the broader theater landscape of Chicago and the world.

Human Expectations and Personal Values
Please be joyful! Collaboration is essential to Lookingglass, and successfully fostering collaboration across the team needs a person who is not only thoughtful, but who builds their own excitement and positive vibes from finding the path that pulls together the threads of all the people of Lookingglass into a single tapestry.
To find our ways forward together will also require personal commitments to Transformation and Invention – Lookingglass is not like all other theaters and may not be in the future what it has been in the past! Our Managing Director will not be a ‘No’ person, or a ‘Yes’ person – instead they will be a ‘I hear all of you – what if we did it THIS different way’ person who can surprise, inspire, and energize us with new approaches and solutions.

Appreciation, empowerment, and development of others will be the basis of the Managing Director’s work. The last year has demonstrated that the ensemble, staff, and board can work effectively with one another, and the Managing Director will see this as a great opportunity and asset and will foster further connections, explicitly rejecting ‘gatekeeper’ tendencies. Cultivating leadership and capability in others from a servant leadership lens will be a fundamental instinct for our Managing Director.

Where Our Managing Director will be Exceptional
Our new Managing Director at Lookingglass Theatre Company will be a truly exceptional champion for the art and a brilliant strategist for moving the company forward. They will be someone who understands the nuts and bolts of nonprofit theatres and who can bring people together to try new options with the people and resources available. Our Managing Director will move smoothly from questioning to listening to ideating to unifying to energizing people to action, both with the internal team and with outside partners and communities important to Lookingglass. When our Managing Director leaves any room, people will feel excited about Lookingglass and ready and able to move forward and take action.

What Our Managing Director Will Handle Directly
The Lookingglass Theatre Company team brings many capabilities to the table, but there are specific tasks and responsibilities that our Managing Director must be able to handle personally, bringing particular strengths and skills to these areas.
These include:

  • Communications and Marketing. Clear, comprehensive, and intentional sharing of information throughout the organization and with external stakeholders is a crucial skill for the Managing Director. Given the structures of Lookingglass, communicating thoroughly and effectively is a lynchpin that can strengthen the team or that can be the downfall of the theatre. Prioritizing being as transparent as possible with all parts of the organization, or being assertively clear and communicative when transparency is not possible, needs to be a fundamental practice of the Managing Director.

    Lookingglass has just engaged a Marketing Consultant/Strategist who will be laying out marketing plans for the coming season. Collaborating jointly with the Strategist, the Managing Director will need a strong basis in external communications and marketing to bring focus to growing the relationships with Lookingglass’ current and future audiences and patrons.
  • Fundraising. Working closely with the Director of Development, Board, and Artistic Director, the Managing Director will use their capabilities as a champion of Lookingglass to personally and directly engage new individual and institutional supporters, and grow their excitement about Lookingglass. Being a vibrant presence in the lobby with patrons and around town with historic, current, and new donors will be an exciting aspect of the role for the Managing Director.
  • Activating Anti-Racism, Equity, and Inclusion. Lookingglass has made specific and public commitments as an organization, and continues to grapple with shifting perspectives and behaviors in the day to day. Our Managing Director will provide pro-active leadership and empowerment support for others in ways large and small to continue moving Lookingglass forward in these areas. We expect that the Managing Director will already have a track record for creating inclusive and respectful environments with diverse groups of people as a way of daily operating.
  • Board engagement. The board brings many assets and insights to the table at Lookingglass, and has been instrumental in carrying it through the last few years and bringing it to this new era. Moving forward, they look to the Managing Director to approach the board through the lens of talent management – being effective in activating the unique talents and bringing in the unique perspectives of each person to support progress of the organization.
  • Financial management. The Managing Director is the primary individual responsible for the financial health and decision-making in the organization. This includes handling both long-term and short-term budget strategies, and a tool kit of creative approaches to both revenue and expense. The Managing Director will also engage individuals throughout the board, staff, and ensemble about the financial narrative, priorities, and key places to focus attention in financial management or decision making as a team.
  • Staff management. The Managing Director and Artistic Director are together responsible for HR policies and responsibilities, capacity management, defining roles and responsibilities, bringing people into or out of the organization, and maintaining open and honest dialogue with all team members for continual refinements of focus and operational improvements.

What Our Managing Director Needs to Understand
Working with and alongside the rest of the team, there are important areas where we do not expect our Managing Director to be more knowledgeable and capable than other people in Lookingglass Theatre Company, but where we do need them to have enough expertise to collaborate with us effectively.
These include:

  • Ensemble-Based and Physical-Based Artistic Creation. The Managing Director does not need to be a generative theater artist themselves, but they do need to have an understanding and appreciation for how ensemble-based and physically-based artistic work is different than theaters with playwright/artistic director centered processes.
  • Touring and Co-Production Structures. They will have (or will rapidly gain) a clear understanding of where Lookingglass’ particular artistic work fits into the national theatre field, and can collaborate around what opportunities are best for potential work with other companies as co-producers or presenters. The Artistic Director and ensemble will lead many of these conversations, but understanding from a structural, business, and brand positioning point of view will be a valuable contribution to this area of the business plan for the future.
  • Intergenerational Dynamics. Expectations continue to evolve around art, culture, process, and workplace dynamics between generations, and that is a present reality at Lookingglass across the ensemble, board, and staff as well. Having experience navigating these realities as they evolve and insights into how to support various activities and teams will be valuable on a daily basis.
  • The Role and Value of Educational Programming. Lookingglass has a distinctive approach to educational and community activities through the Department of Education. The Managing Director isn’t expected to be an expert in these areas, but will have future-oriented ideas of how these goals and efforts can be woven together deeply with other artistic work of the ensemble to provide cohesive impact.
  • Legal and contractual oversight. The Managing Director will be comfortable negotiating contracts as necessary and adjusting standard agreements for implementation by other members of the staff. While they do not need direct legal expertise provided by counsel, they will be confident in understanding potential legal issues or pitfalls for a non-profit theatre.

How We Will Support Our New Managing Director
We know that the arrival of a new collaborator at Lookingglass Theatre Company means everyone will need to adapt to new ways of working and a different collaborative partnership. As we discover that together, it is important that our new Managing Director feels supported and engaged from all sides of the company.

To that end, Lookingglass Theatre Company commits to providing:

  • Starting annual salary of $120,000.
  • Benefits include:
    • Insurance - Choice of PPO or HMO; Organization covers the cost of 95% of the HMO plan. If PPO plan is elected, staff member pays the difference between the PPO plan and 95% of the HMO plan.
    • Paid Time Off including 12 paid holidays, 10 Vacation days, 5 Personal days, and 5 Sick days.
  • A shared office space within the theater building, with available areas within the building that staff can move to for more private conversations. Current office hours are hybrid with most individuals working from home Mondays, Wednesdays, and Fridays, and In-Person on Tuesdays and Thursdays, though anyone is welcome to the office space Monday-Friday, however they prefer. New office space is on the list to explore over the next two years. The work schedule for the Managing Director is expected to be flexible as it would be for many theaters and will vary based on artistic events, fundraising meetings, and community responsibilities at times and locations in Chicago. Some travel outside of Chicago will be necessary as well and will be paid for by Lookingglass Theatre Company.
  • An onboarding and transition plan, developed by the team and ready to adapt to the realities of the Managing Director.
  • Commitment to regular meetings with the Board Chair and Artistic Director.
  • Mentorship or Advisory support during the first year with Creative Evolutions and up to four industry peers (see the Search Process above).

How to Express Your Interest
Apply through the Creative Evolutions online portal. Throughout the process, you will be in communication with Rebecca Novick, Douglas Clayton, and Dr. Kim Davis. You will not at any time go more than two weeks without an update on where you are in the search process.
With your submission, please include:

  • Your resume. The resume can be of any length and style, though we encourage you to adjust it as appropriate to help us see how your history and experience connect to the current circumstances, intentions, and hopes for Lookingglass Theatre Company.
  • Instead of providing a standard cover letter, please provide written responses (through the portal) to answers to the following questions:
    • Who are you and what is most exciting for us to know about you?
    • What inspires you about ensemble-created theatre, physical-based theatre, or Lookingglass Theatre Company in particular?
    • How have you activated a leadership approach centered on empowering and bringing together many different kinds of people?
    • What are some inventive or distinctive ways you have approached challenges in other situations that aren’t the ‘best practice’ ways of doing things?
    • What are ways you have navigated team dynamics, that embrace the individuality of the needs and expectations of each team member while also using limited time and resources to accomplish collective goals?
  • If you wish, feel free to share how you self-identify so we can honor your preferences and perspectives in our communications with you!

If possible, please have any attachments be included in pdf format.
If you have any questions about the position or your submission, please feel free to e-mail and we will be happy to discuss with you at any time!
Rebecca Novick –
Douglas Clayton –
Dr. Kim Davis -

About Creative Evolutions
As the Executive Search support team for Lookingglass Theatre Company, we believe that we can do better. We believe that it is our moral excitement to be responsive to one another as human beings, and to continually adapt to the humanity around us. We believe that the world is constantly changing around us, and we are most fulfilled and healthy when we are growing together to meet the moment.
Our purpose is more than to provide Executive Search or Management Consulting services. We are centered in building a stronger and more interconnected ecosystem, where individuals and organizations are linked together in mutually supportive ways and where the advances of one become the advances of all. All of our processes and recommendations come back to these concepts of ecosystem building, new adaptations that respond to the moment, and putting human beings first.
In Executive Search support, Creative Evolutions has pioneered new processes that include commitments to active communication, paying semi-finalist and finalist candidates for their time, engaging paid industry advisors as part of the evaluation process, building onboarding and mentorship into hiring, and structuring executive positions around healthy organizational team dynamics.

Job Type: Permanent
Compensation: $120,000
Location: Chicago