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Educator Experience: Jennifer Stillman, Director of Evaluation

April 27, 2021 New Classrooms

This teacher appreciation month, we are honoring teacher voices and experiences through our Educator Experiences series. Our New Classrooms and Teach to One team possesses a collective 300+ years of teaching experience, and we’d like to tell those stories. Read Rosa Pynes’ story of success through relationship building and skill centers here. Watch James Jackson’s interview about working in Houston, at Teach for America and more here. Read Matt Driscoll’s experiences as a math teacher and coach in New Orleans here.

Tell us about your teaching experience.

I started my career teaching AP Government and Politics in a suburban high school outside of D.C. I then moved to New York City, where I taught a variety of social studies courses at a law-themed high school in Brooklyn. These highly contrasting experiences made it clear that what it takes to be a good teacher is very much context-dependent. I experienced both my greatest adulation and humiliation in the classroom. Teaching is the hardest job I have ever done, as it requires a reservoir of creativity, stamina, and resilience difficult to maintain.

Tell us what you’re doing now and how you transitioned into this career path.

I am now the Director of Evaluation at New Classrooms, where I analyze student performance data and offer ideas for improving Teach to One. I took a break from teaching to earn a Ph.D. in Politics and Education, and used this policy study and research training as a springboard to a new career.

What is one piece of advice or encouragement you would give to teachers today?

If you’re new, give yourself a couple of years before deciding whether or not this is the career for you. It’s really hard, and it takes time to find your footing.

How would Teach to One have changed your teaching experience?

It would have made my teaching experience more collaborative. I shared ideas with other teachers, but there was very little co-planning and discussion around student learning and how we, as a team, could improve our instruction.

How does Teach to One improve the craft of teaching?

Teach to One gives teachers more time to focus on instruction. The auto-grading of exit slips and the scheduling algorithm free up more brain space for teachers to focus on improving their pedagogy.

How has your experience as an educator helped you in your current position?

My experience as an educator is the greatest strength I bring to my current position. To understand and act on student outcome data, it is imperative to understand the context in which that data was generated and the complexity of everything both inside and outside the classroom that is feeding each data point.

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