Olly secured a place to study English Literature at Trinity College, Oxford, and soon became an integral part of the university's dramatic society. Upon graduating, he was awarded a prestigious scholarship to train at the renowned London Academy of Music and Dramatic Art (LAMDA),where he spent two years honing his craft.
Upon completing his studies at LAMDA, Olly had the opportunity to work with Gregory Doran, the Artistic Director of the Royal Shakespeare Company (RSC). Doran was so impressed with Olly's talent that he offered him the title role in Shakespeare's "lost play" Cardenio. Under Doran's direction, Olly's performance received widespread critical acclaim, with Mark Shenton of The Stage describing it as a "dashing professional debut" for Olly.
Olly's success in Cardenio caught the attention of many, with Mark Taylor of The Independent praising his "beguiling" performance, and Simon Tavener of WhatsOnStage predicting that he was a "talented young man on the path to future stardom." While at the RSC, Olly also had the opportunity to work with acclaimed British playwright Antony Neilson.
In addition to his work with the RSC, Olly has appeared in a number of other theatre productions, including The City Madam and I Am A Camera. Most recently, he reunited with Neilson for his original play Narrative, which was specifically written for Olly and performed at the Royal Court.