Alyssa Henn graduated from Principia Upper School (’97) and Principia College (’01) with a double major in education and English. Following graduation, Alyssa spent three years teaching English for grades 7–9 at Berkeley Hall School in California. She then came to Principia where she taught English for grades 10–12 for three years. She is now in her third year as Middle School director. Alyssa is currently working on a master's degree in educational leadership from Maryville University.

Alyssa’s other experiences working with children and youth include serving as assistant director and director of Principia’s Summertime Discovery Program, assistant director of Camp Newfound for girls for three years, and as a soccer coach for students of all ages.