Jenna served as clerk to the judges of the City of Alexandria Circuit Court from 2019 to 2021, where she reviewed hundreds of cases relating to family law and military divorces. She drafted numerous legal memoranda and orders for the judges for both criminal and civil matters. Following her clerkship, Jenna practiced as an Assistant Commonwealth's Attorney in Arlington County. During her time as an Assistant Commonwealth's Attorney, she worked closely with victims and witnesses to understand the facts unique to each case and to explain and demystify the legal process.