MONROE, CT — Candidates showing interest in an advertisement for Masuk High School’s open principal position can also rely on added assurance from the last administrator to fill the role. Jacob Greenwood, who recently accepted the same position at Ridgefield High School, says he will always look upon his years at Masuk fondly.
“The administrators in that school and the district are so good,” Greenwood said. “The district is going to land on its feet. I know that. It’s a good situation. The community is in good hands.”
Greenwood said Monroe public schools enjoy strong support from parents and the entire community, adding Acting Superintendent of Schools Joseph Kobza, who has been guiding the district, and his team are “exceptional.”
Greenwood’s first job in education was as a biology teacher for Ridgefield public schools in 1999 and he went on to work there for 12 years, being named a dean of students and chairman of the science department in the district.
“It definitely didn’t come easy,” he said of his decision to leave Masuk. “It’s never easy to leave any district. It was truly about going home to the place I was for 12 years. I do love Monroe.”
Greenwood grew up in Greene, Maine. He now lives in Middlebury with Janessa, his wife of 20 years, and their three children. One is in elementary school, another in middle and the oldest is in high school.
While in Ridgefield, Greenwood got into running and biking, going on to complete three Ironman Triathlons. Since leaving his job as assistant principal of Darien High School to accept Masuk’s top job in 2018, Greenwood has participated in the last three Ultra Marathons, in which participants run over 26 miles.
Among his fondest memories at Masuk were the bonfires and pep rallies. “We have the best pep rallies I’ve ever been in,” Greenwood said. “Those things stick out to me.”
He is most proud of the way teachers, administrators and students adjusted to distance learning amid the coronavirus pandemic this year, and of how the community came together to plan seniors’ graduation ceremony.
“It’s unbelievable to ever predict that you’d have to close a school year like that,” Greenwood said, adding the district’s administrators are among the best he’s worked with and can handle any challenge.
His favorite memory was “the graduation by far,” Greenwood said, “because, soup to nuts, we created it and the community rallied around it. We celebrated the seniors properly.”
He said he was pleased at how the graduation, while not traditional, allowed seniors to experience different scenarios, from an informal atmosphere at Fireman’s Field, “sort of walk down memory lane,” then seeing the teachers on the way out of the school parking lot.
“Graduation really put on display truly how great a community this really is,” Greenwood said. “The parents have welcomed me with open arms from the moment I walked into that school and I definitely have always felt like part of the community. That will always stick in my mind as the high point of my career — the relationships. Some of the parents will probably be my friends forever.”