Jessi started her Theatre training at a young age in the School of Musical Theatre at Repertory Company Theatre. At age 16, she officially joined the Company, where she performed regularly for three years as an actress and dancer. She is a proud alum of Booker T. Washington High School for the Performing and Visual Arts (BTWHSPVA) where she studied Theatre & Dramatic Arts. From 2016 - 2017, she studied Theatre & Performance at Emerson College. She has performed works by artists including Stephen Sondheim, Aristophanes, Thornton Wilder; and has studied under various teachers, including Karon Cogdill, Christie Vela, Charlton Gavitt, Ruth Zapporah, Cassie Tunick, and Erin Schwall.​ She continues to use her theatre training to facilitate community engagement in site-specific performance and activation with the Reciprocity Collaborative.

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Along with her stage work, Jessi has acted in student films and wrote/directed her own short, Queen Kevin, which was included in the La Vie Theaters Rising Star Film Festival in 2016. For this film, she worked under the mentorship of Italian Cinematographer Raoul Torresi. ​