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Woodrow Proctor has a diverse work experience in various roles. In 2017, they worked as an actor at the Alabama Shakespeare Festival, where they not only performed in productions but also taught classes and understudied lead roles. Woodrow continued their acting career in 2018, working at the SARATOGA SHAKESPEARE COMPANY INC and the Arts Center of Coastal Carolina. In the same year, they also worked as Quality Assurance and Recruiting for Trusted Guardian. In 2019, they worked as an actor at the Franklin Stage Co and as a barista at Park Terrace Hotel. In 2020, they served as a C#/Unity developer at XR Terra, contributing to the creation of minimum viable product presentations for Roy Rodenhauser at Ryot Studios. Recently, in 2021, they have worked as a software developer at both The Glimpse Group and Foretell Reality.

Woodrow Proctor's education history begins in 2012 when they enrolled at Skidmore College. Woodrow pursued a Bachelor of Applied Science (BASc) degree with a focus on Computer Science and Theater. Woodrow successfully completed their studies in 2016.

In 2020, Woodrow Proctor attended XR Terra, where they participated in an educational program specializing in XR (Extended Reality) Development for the Unity Platform. While the program did not lead to a specific degree, it provided him with knowledge and skills in this field of study.