In April 2013, Roland participated in the first reading of Be More Chill, wherein he read the role of Michael. He then departed the production and re-auditioned for the lead in 2015 when it was casting for its world premiere, whereupon he did not get cast. Around this time, he also became involved in the as then Untitled PPL Project. Starting in July 2014, Roland participated in readings and workshops of the show that would become Dear Evan Hansen, playing the role of Jared Kleinman. The show made its premiere in Washington, D.C. at the Arena Stage and ran from July 10, 2015, to August 23, 2015.
