Leadership Team


Sasha Wilson

School Director

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It is such a privilege to be Director of Montclare Children’s School. I work with a wonderfully warm and knowledgeable staff supporting children and families through relationship building, intentional practice and humor.

I have been in early childhood education for 26 years.  First as a teacher for 9 years and school leadership for the past 17 years.  I began my career in Westchester NY and was lucky enough to come to Montclare in 2016 as the Associate Director. After 2 years at another independent preschool in New York it feels great to be back.  I studied sociology at the University of Wisconsin and went onto Teachers College at Columbia University where I earned my MA in education and obtained my teaching certification. I am also a member of the Hunter College faculty working as an adjunct professor and mentor for students pursuing their degree in education. 

Born and raised in New York City, I have a firsthand understanding of city life and all the unique opportunities it offers families. I am the proud mother of two children now in their mid-twenties and enjoy spending time with my family going to live music events, hiking, running and sailing, along with a variety of other outdoor pursuits.

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Brenna Riley

Education Director

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I am delighted to be the Education Director for Montclare Children’s School. Prior to becoming the Education Director, I had been a teacher and member of the Montclare community for fifteen years. In that time, I worked with multiple age groups ranging from the youngest two-year-olds all the way up to the oldest four-year-olds. I earned my Master’s Degree in Education from Hunter College and hold professional teaching certification in Early Childhood Education.

As an educator, I have always believed that children learn in many ways and it is essential to expand and adapt teaching philosophies in order to inspire many types of learners. As Education Director, it is my pleasure to work with students and families while supporting the ever-evolving best practices in classroom curriculum.

I am looking forward to meeting your family at the start of your Montclare journey and continuing to get to know you all the way through the end!

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Sharona Grossberg

Director of Admissions

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I am thrilled to be at Montclare Children’s School as Director of Admissions. Born and raised in upstate NY, I spent many years in Boston where I earned an M.Ed in Guidance and Counseling from Boston University and a BA from Brandeis University. Over the past 20 years, I have worked as a professional and volunteer in educational institutions and non-profit organizations.  I taught children with traumatic brain injuries and have directed student services, admissions and public relations, most recently at a NJ private school for toddlers through eighth graders. I am the proud mother of four daughters and I served on the board of trustees and as PTO president at the private school they attended. Please feel free to reach out any time – and share with me what you love about MCS!


Mimi Dupuis

Director of Exmissions

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When I came to Montclare in 2007, I knew I found a home. I was drawn to the spirit of community and impressed by the commitment to provide the best possible learning foundation for all students. After six years as a head teacher in the Panda Room, I took on my current role in Exmissions.

I began my teaching career in a parochial school on the Lower East Side, and then spent seven years teaching at a private school on the Upper East Side. With a focus on literacy, I became certified in Elementary Ed at St. Peter’s University. In Jersey City, I worked with learning-disabled children in under-served communities. My experience led me to children with communication disorders, especially those on the autistic spectrum, teaching at Learning Spring Elementary and The Rebecca School.

As a head teacher, I was privileged to team with a host of talented educators and related-service providers. At that time I also did private work and collaborated with psychologists to help children with attentional issues and anxiety disorders meet success in the classroom. After a decade of special needs work, I returned for my Masters in Early Childhood at Hunter College.

It is now my privilege to help Montclare families find the right fit for their children as they pursue their educational life in the ongoing schools.

Montclare School - New York City

Billie Castiglia

Director of Operations

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I joined Montclare in 2000, when its doors first opened.  Actually, before the doors opened! My most vivid memory of those early days is of sitting in the basement, putting address labels (old-school) on hundreds and hundreds of postcards announcing the opening of our school.  We held an open-house on the 2nd floor when it was just a big open space.  Before the construction of all the beautiful classrooms you see today, this 2nd floor could have been a roller-skating rink.

After raising my two sons and prior to joining the Montclare team I worked for many years in HR. Now, my day begins by greeting smiling faces at the door and hearing a chorus of “good mornings. Sometimes, on a really good day, I hear “good morning Billie!”  Then the real work begins. As the Director of Operations, it is my job to ensure that the school runs smoothly on a daily basis.  Feel free to call me a “smooth operator.”

I consider myself to be extremely fortunate to have a job that I love and I am deeply proud to be a part of the Upper West Side, Montclare Community we have built together over the years.