Hannah Shatinsky Roskin

Hannah, the Director of Middle and Upper School at Bennett, brings nearly a decade of experience in Chicago’s independent school community as an educator and leader committed to progressive, student-centered learning. Prior to this, she served as the Upper School Division Chair at Bennett, where she led the faculty team, facilitated programming and logistics, and supported the development of a strong, inclusive learning culture for students in grades 9–12. Hannah is excited to expand her role to work with middle school students.

Before joining Bennett, Hannah primarily worked with students in grades 5–8, teaching a wide range of subjects with a focus on the humanities. She has also previously served as a MAP NWEA Coordinator, where she led data analysis and implementation efforts to inform instruction and track student growth with intention and care.

Hannah’s deep belief in progressive education is rooted in firsthand experience: she has seen how powerful learning becomes when adolescents are trusted, challenged, and supported with the right tools. Hannah is committed to cultivating a learning environment where students are not only academically successful but also seen, valued, and empowered to make meaningful contributions to their communities.