Springfield Community Leader Kylie Stack Jackson Helps SLT Play ‘The Great Game of Business’

Kylie Stack Jackson has always appreciated the hard work, dedication, and attention to detail that goes into doing a job right. Jackson is now a learning and development manager at the Great Game of Business, but she is also a talented performer with an enduring passion for the Springfield arts community.

“Anything for the Landers,” she says.

She began acting at Springfield Little Theatre in Kindergarten. Year after year, she put in the time and training to land a mainstage leading role by middle school, secure a spot in Y.E.S Troupe through high school, and was accepted to study theatre at Stephens College before working as a talent agent in Chicago. Jackson was drawn in by the fun and energy of the stage, but she distinctly remembers the work that went into making a show a success.

“I just wanted so badly to be a part of Y.E.S. Troupe. Chomping at the bit to be part of this group. We had insane discipline with that and part of that was the prestige. It was an honor to be a part of it,” Jackson recalled. “What we had to do at that time [as a member of Y.E.S. Troupe] was very similar to what Stephens College does. We had to work the box office. We had to work tech. We had to do lighting.”

As a young girl, Jackson’s mother took her to see a production of ANNIE WARBUCKS, the musical sequel to ANNIE. The show immediately captured Jackson’s imagination. “I remember looking at my mom and saying, ‘I want to do that,’ and that is when she signed me up for Summer Stages.”

As fate would have it, Jackson would be the next to play the famous red-headed orphan on the Landers stage in the 2000 production of ANNIE, sharing the title role with Lawren Askinosie. A new generation will bring the Broadway classic to life when SLT kicks off the 91^st season with ANNIE.

Cast lists are posted digitally now, but when Jackson was a child, it was a time-honored ritual to check for your name on the Landers door. “I remember so many times looking at the cast list on the door. My mom would just have her car right out on the curb, and you would run in and look at the cast list and go, ‘Yes!’”

Jackson continued her training at SLT performing through high school in favorites like HOW TO EAT LIKE A CHILD and SEUSSICAL. She eventually took Executive Director Beth Domann’s advice to apply to Stephens College and was accepted to the prestigious performing arts school. In the summers, she worked and performed at the summer stock theatre company Okoboji. She credits Y.E.S Troupe with preparing her for the demanding schedule that called for her to work in every facet of production.

 “What was really cool was it was a mirror of what Beth had done at Stephens in college,” she remembered. “At Okoboji summer theatre, when you weren’t in rehearsal, you were building sets, you were in the costume shop, you were working the box office.”

After graduating, fellow SLT alum Brianna Firestone helped Jackson apply for an internship at Goodman Theatre in Chicago where she worked in marketing. She later interned in bookkeeping at the Shirley Hamilton agency where she became a talent agent. She ascended to work as a commercial agent and voiceover agent and, ultimately, the theatre department talent agent.

“I got to book a handful of people in HARRY POTTER on Broadway,” Jackson revealed. “I got to see a lot of people on Steppenwolf [Theatre Company]. It was a very rewarding career, but I was pretty exhausted. It’s not for the faint of heart. Especially somebody who wants to start a family. I was seeing five shows a week.”

Jackson developed her skills for curating talent and believes companies are strengthened when people have the confidence and resources they need to thrive. She took away very important advice for actors nervous stepping into auditions.

“I loved talking people into why they deserved to audition for certain things. I loved helping people realize that the person on the other side of the table wasn’t hoping that you fail even though we talk ourselves into thinking that, ‘This casting director is so mean,’” Jackson acknowledged. “Actually, they’re wanting you to help them do their jobs. I love filming auditions and seeing the rawness of actors. Again, cut to my job today, it’s really about believing people can and unlocking their potential by just giving them the tools.”

Jackson recognizes similarities between her theatre training and her job at the Great Game of Business. Both require a comprehensive understanding of operations and being able to guide everyone to a unified end goal.

“What’s really funny is you think, I’m a theatre kid now teaching business, but it’s amazing what kind of an ensemble member you are when you understand how the entire theatre works. That’s basically the parallel I draw with the Great Game of Business,” she explained. “It’s amazing what a great team member you are when you understand how the business is run. When you are appreciative of all aspects of the production people who build the sets. You didn’t have to be great at all of those things, but you did have to understand the hard work that goes into it. Sometimes when we have people join SRC, we say, ‘Go work the factory line.’ You need to understand what it’s like to be there. To be them and you’ll appreciate everything that they do a little more.”

Thanks to the Great Game of Business founder and Jackson’s father, Jack Stack, SLT began playing the Great Game of Business in the 2000s. When a few thousand dollars was holding the doors open, Stack stepped in to help the organization recover and secure their financial footing. Jackson is thrilled to see SLT grow with more programs and new facilities like The Judy, Springfield Little Theatre’s education facility.

“You realize that education is the great thing that happens even when the economy turns down a little bit, education thrives,” Jackson noted. “The Judy is such a great investment for [SLT] because they’re always going to have kids who want to learn and parents who want them to be involved in the arts. That’s part of their diversification is the school and making sure that they can withstand markets. The fact that they can get the shows that the regional theatres in Chicago were getting at the same time as SLT. That was really cool to see.”

Jackson’s focus has turned to business, building the community, and raising her family, but she continues to be an SLT patron. Her last on-stage role at the Landers was The Witch in the 2012 production of INTO THE WOODS alongside Broadway veteran Kim Crosby. The role was a standout for Jackson, but she has considered that she may revisit it in the future now that she’s had a daughter of her own.

“Now as a mom, man, I didn’t even know the heartbreak. I could play that character with so much more gravitas being a mom now,” she reflected. “It was unreal being able to be around Kim Crosby. What’s really cool is when she went back to PETER PAN on tour, I got to go see her when I was living in Chicago, so that was really special to reconnect with her in a different professional setting was kind of fun.”

Jackson’s daughter is even younger than she was when she was introduced to SLT, but she hopes that she may be curious to try the summer programs one day. She even joked with her husband, furniture designer and carpenter Austin Jackson, that they foresee many trips downtown in their future.

“We went to SCHOOL OF ROCK and as we were in the car, Austin goes, ‘This is gonna be our life, isn’t it? I’m going to be building sets and taking her to rehearsal.’ I was like, ‘If we’re lucky!’”

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