Kristen Jackson
Kristen Jackson in her new dual role as Woolly Mammoth’s associate artistic director and connectivity director; Credit: Darrow Montgomery

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“I’m a native Washingtonian, born and raised. I lived outside of the city, but was compelled to come back home to D.C. in a very specific way,” shares Woolly Mammoth Theatre’s Kristen Jackson. In November, Jackson began a newly created dual role of associate artistic director and connectivity director. She currently lives in Anacostia with her mother, her pit bull, Skye, and their many houseplants. 

Jackson has been Woolly’s connectivity director since 2014, but with the new dual appointment, she works closely with Artistic Director Maria Manuela Goyanes to further develop the theater’s connectivity program, which links the theater’s artistic mission and its social and political missions. It’s the first time that audience and community engagement has been the focus for the role, as opposed to play production. 

“The thinking behind this dual position is to bring connectivity to the forefront of our organizational activities,” Jackson says. “Part of what I’m tasked with doing is really thinking about how connectivity can function not just as a department, but as an organizational strategy for relationship building throughout Woolly, and how those kinds of deep transformative relationships can activate different departments within the organization. How can we make Woolly more relevant? More relevant, not just as a theater in D.C. but as a theater that is for D.C.?”

Jackson is an architect, building bridges with different community partners. Asking questions about the role of the theater within the community, she finds the central civic crux of each play to create innovative engagement opportunities, open up new avenues for audience and community discussions, and activates the actual theater to create brave spaces of exploration and discovery. For her, all of Woolly’s programming and connections must be two-way streets, transformational rather than just transactional. 

Established community partners and programming include Howard University’s Department of Fine Arts, THEARC, N Street Village, a D.C. organization that empowers low-income and housing insecure women, Theatre Lab, and Spit Dat, D.C.’s longest running open mic night, which recently expanded arts and cultural programming to incarcerated people in the DC Jail.  

In January, Woolly launched the second round of an arts and social justice fellowship for high school students, a demographic that has been historically underserved by Woolly due to the content of the plays produced. “This work allows us to expose young people to a variety of artistic experiences at Woolly, Strathmore, and other cultural institutions, to provide them with the tools to discuss systemic change and how to integrate these bigger social ideas into their artmaking,” Jackson says. 

The connectivity initiatives also include a fully funded fellowship for adults: the Miranda Family Fellowship for early career theater administrators of color. At a time when many theaters have abandoned their unpaid or underpaid internship programs for tomorrow’s theatermakers, Woolly has forged ahead with a new, more equitable model for fostering new creative talent. Fellows also learn about theater workers across different departments throughout local theaters, and have opportunities to attend professional conferences, as well as plays in the District, at various fringe festivals, and in New York, too, such as the Tony Award-winning A Strange Loop, which played at Woolly before opening on Broadway. 

Within Woolly’s walls, connectivity programming also includes curated gallery exhibits and audience engagement initiatives that link each play’s themes to an online “liberation library” on topics such as feminism, capitalism, and queer pride.

Under Jackson’s leadership, Woolly hosted its first “Black Out Night” during the run of Ain’t No Mo’, at which all ticketed seats were reserved for Black patrons. Jackson wrangled the preplanning, working with leaders and organizations in the local Black community to reach new audiences. The process also involved ensuring staff and volunteers were trained against microaggressions and biases, as well as at making small but meaningful changes to “create a space that was welcoming and activating the theater in a specific, beautiful way,” she says.

“Audiences were excited for this event, and asked for more opportunities for other Black Out Nights,” Jackson says. Another Black Out Night will take place at the March 3 performance of seven methods of killing kylie jenner. “There was appreciation for creating the space and the talkback that was hosted afterwards,” Jackson says. 

For Jackson, the new position builds upon the work she has been doing, but in a more cohesive and holistic fashion. “It’s all integrated because the large-scale connectivity projects are artistic projects. During season planning, we can think about these projects alongside the plays we’re considering producing, making sure that we are investigating the connectivity possibilities that exist within or around any of the things that we’re considering for the season.”