In 2019 Jessamy took on a different role for YYT’s production of Chicago; the Musical Director and she loved every minute of it! Jessamy led an orchestra (all under 18) through a week long run of performances at the Octagon Theatre in Yeovil, while also teaching the cast through the rehearsal process. Jessamy now teaches regular workshops every other Sunday for Yeovil Youth Theatre. Alongside this, Jessamy also teaches some, one to one performance/vocal lessons. Below are some of the projects Jessamy directed and produced during the lockdown. She arranged the music, wrote multiple string parts, created and taught all the harmonies online.