Jason Cuyler is a lifelong resident of Berkshire County and was raised on the westside of Pittsfield. He attended both public and private schools before graduating from St. Joseph Central
High School and going on to attend the University of Massachusetts where he earned his bachelor's degree in Sociology, along with a certificate in Criminology.
High School and going on to attend the University of Massachusetts where he earned his bachelor's degree in Sociology, along with a certificate in Criminology.
Following graduation, Jason began his professional career at Hillcrest Educational Center, later working for the Department of Social Services, before joining the Berkshire County Sheriff's
Office in 2000 as an entry-level Case Manager. Over the past 25 years, he has worked his way through the organization and currently serves as the Assistant Deputy Superintendent of
Community Engagement.
Jason strongly believes in the importance of community and collaboration. He previously served on the Berkshire United Way Board and currently serves on the Christian Center Board of
Directors, Hillcrest Educational Centers Board of Directors, Berkshire Community College Board of Trustees, Mill Town Capital Advisory Board, Berkshire Health Systems Community
Benefits Advisory Committee, the Berkshire County Sheriff's Charitable Foundation, and the Second Street Second Chances Board of Directors.
Jason is married to Brianna Cuyler and has three daughters, Nyla, Brooklynn, and Emerson.