Amy Woogmaster ’07 Alumni Profile

Amy knew she wanted to be a teacher long before it became her profession. In fact, as early as elementary school, she believed she had found her calling and her passion kept growing through childhood. During her Gann years, she worked with non-profits and helped at her temple, always seeking out chances to mentor and teach.  

Her experiences as a student at Gann were a huge influence as well. She still points to Gann teachers like Mr. Kadden and Dr. Proll as formative mentors on her teaching journey. These educators brought material to life, pushed her writing further than she thought possible, and modeled what it means to hold students to high standards with deep care.  

After a gap year in Israel teaching English and volunteering as a medic with MDA (Magen David Adom), she returned to Boston University’s School of Education for her bachelor’s and gained invaluable experience as a student teacher. She would spend over a decade in Brookline teaching in fifth and sixth grades and later, after completing her master’s degree, she worked as a K–8 literacy specialist. While she was focused on teaching, she was inspired by a colleague to explore school administration. The seeds were planted for her second masters’ degree and the next stage of her career.  

Today, Amy is in her third year as an assistant principal at a middle school in Waltham – a leap she made on a week’s notice and has never looked back. In the school community she now helps lead, Amy carries that legacy forward. A few years ago, Amy reached out to Mr. Kadden, who helped her reconnect to Gann to start a volunteer mentorship program at the middle school. Since last year, a total of eleven Gann students have been paired one-on-one with a middle school student for weekly academic support and role modeling. Amy has been impressed with how the Gann tutors are responsible, eager for feedback, and well-loved by the middle schoolers. Both she and her students see the program as highly successful and she is grateful for their support and this opportunity to reconnect meaningfully with Gann, her alma mater just down the road.