Bessie Oster's background is in public health, and she has worked with teens in a variety of community-based settings (teens experiencing homelessness in NYC, children's services, incarcerated youth and teens in substance abuse treatment). For the 12 years before joining Gilman's team, she worked in independent schools in NYC and DC, teaching and developing health education programs, pre-k-12. At Packer Collegiate Institute, she taught health education pre-k thru 12, and served as the middle school dean of student life, where among other responsibilities, she overhauled the advising program. In 2021, she served as a health education consultant at Georgetown Day School.

Ms. Oster grew up in Baltimore, and her father is a Gilman alum.

In her role as health educator, she teaches health education in the Upper School and is working to expand the health program at Gilman pre-k-12.  

When Ms. Oster attended St. Paul's School for Girls for high school, she was among the group of youth co-founders of the Donald Bentley Food Pantry, named for Gilman alum who was tragically killed shortly after graduation. Since moving back to Baltimore in 2022, she has been serving at the pantry on Saturday mornings. 

Q&A

What was your best teaching moment?
I am really enjoying my work with Peer Educators as we collaboratively work to deepen the efficacy of the freshmen seminar. They have proven to be highly committed and yet refreshingly flexible as we continuously refine the teaching model.

What is your favorite spot on Gilman's campus?
Recently I came to school early for a meeting in the Gilman Room, and I was awestruck by the gorgeous sunrise. 

Why do you enjoy teaching at Gilman?
My role at Gilman affords me the opportunity to work kindergarten through 12, which is exciting, both in thinking about the opportunity to positively impact boys across many phases of their young lives and their Gilman experience, AND I am excited for the opportunity to collaborate with colleagues across divisions.