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Faculty and Staff Directory

Cynthia Quiñones

Librarian and Upper School Study Support

B.A. George Washington University

M.F.A. Warren Wilson College

Meghan Randall

Pre-K Assistant

Meghan Randall has been a pre-K assistant teacher at Pine Cobble since 2021. She has been working in early childhood with various age groups consistently over the past two decades. While she relishes every aspect of this experience, she will tell you that snuggling babies is her favorite. Meghan has enjoyed continuing her education to successfully finish her bachelor’s degree. In her personal time, she enjoys running, hiking, and baking with her two children and husband. Molly, their sweet dog, is ever eager to hike with them.

Pine Cobble School Michael Richardson Director of IT

Michael Richardson

Director of IT

Michael Richardson was born and raised in Berkshire County. He brings to Pine Cobble School more than forty years of experience in computer software and hardware use, support, and training. For twenty-five years, he worked in various IT support roles at the Williams College Office for Information Technology.

Michael is not only technologically proficient, but he also brings the people skills to this position that are so important when issues arise with technology. He is a patient and empathetic listener, and he is able to assist and work well with people of all ages and with a broad range of technological experience. 

In his free time, Michael works with local charities such as PopCare and also provides free “Selfies with Santa” pop-up sessions for families in the local community leading up to the holiday season.

Mary Ann Sacco


Mary Ann Sacco joins Pine Cobble with almost forty years of experience in elementary education. In her previous position, at Mackintosh Academy, an International Baccalaureate World School in Boulder, Colorado, she taught first grade outdoors for her first year, due to pandemic restrictions, and found great value in outdoor learning, leading her to structure the two years that followed to include plenty of classroom time outside. Mary Ann was attracted to the outdoor teaching possibilities at Pine Cobble School and intends to continue inspiring young minds with the beautiful natural setting around them while providing them with a strong academic curriculum and a warm, loving classroom culture. As a veteran elementary educator, she is aware of the strong foundation that must be built in these early years and understands how this foundation is critical to students’ success as they advance in school.

Mary Ann grew up in central Massachusetts, where she developed a lifelong love of nature, and she has family connections in metro Boston, Vermont, and New Hampshire. After a career spent in North Carolina, overseas, and in Colorado, she is excited to return to her roots. She is also excited about all the outdoor activities the Berkshires have to offer—paddleboarding, kayaking, skiing, running, biking, and more—and about sharing her passion for enjoying the great outdoors with our students in the classroom, in Winter Sports, and beyond.

BS, Carnegie Mellon University

Christy St. John

Business Manager

B.S. Massachusetts College of Liberal Arts

Kristy Samson

ASK Coordinator

Ellery Schiller

Grade 4

Ellery Schiller is a fourth-grade teacher here at Pine Cobble. They came to Pine Cobble as a teaching fellow after graduating from Bennington College in ’21 and are originally from Philadelphia. As a teacher they enjoy engaging students through discussion and exploration, allowing student interests, as well as current world events, to take the lead when it comes to creating lessons and projects. They have experience as a playwriting educator, Hebrew school teacher, and tutor. Ellery puzzles obsessively, currently enjoying many 1,000-piece puzzles. When not puzzling, they are a devoted playwright whose work centers on the ideas of becomingness, the limitations of communication, Wittgenstein, and Judaism. 

BA, Bennington College

Enrique Segura

Early Childhood and Lower School Spanish Teacher

Originally from Southern California, Enrique Segura has spoken Spanish his entire life and considers it his mother tongue. After attending Fullerton College he went on to have a successful career as an actor for over forty years, performing throughout the United States, Canada, and Europe. He is very proud to be teaching Lower School Spanish at Pine Cobble and considers passing on his native language as a great privilege and joy.

Vanessa Simo

Dean of Academics and Reading Specialist

Vanessa Simo stepped into the role of dean of academics at Pine Cobble School in September 2023 after a year as a reading specialist there. She earned her MEd from the Massachusetts College of Liberal Arts, with a focus on meeting the needs of diverse learners. She is trained in Orton-Gillingham, a structured, multisensory approach to phonics instruction, and she has a strong educational background in psychology and human development. Prior to joining Pine Cobble School, Vanessa taught history and worked as a reading intervention professional.

Vanessa brings to this position her educational philosophy that every classroom should be representative of its students, because students need to see themselves in what they are learning. She believes that when lessons are built around student interests and strengths, learners are better able to explore, create, and succeed. She also believes that every student must learn self-advocacy skills and be given opportunities to give and receive constructive feedback. Vanessa strives to support the creation of spaces in which students feel represented, heard, seen, and empowered.

MEd, Massachusetts College of Liberal Arts