Q&A with an educator: It’s all business, and beyond, in the classroom Jen Massey teaches business at Pittsfield Middle High School. Courtesy Published: 12/28/2020 5:41:53 PM For Jen Massey, one of the best parts of teaching is seeing students expand their learning beyond the classroom, to projects that turn them into young entrepreneurs. Massey has been teaching business at Pittsfield Middle High School for the last 10 years, after a 20-year career in accounting. She teaches classes that include personal finance, accounting, careers and marketing, and is an advisor to the student council, the Yearbook Club and the Future Business Leaders of America Club.