Michael Flynn
Michael Flynn Credit: —Courtesy

Following a leader like Steve Chamberlin as the superintendent of schools is no easy job. Michael Flynn says he’s up to the task. 

After a lengthy interview process, Flynn was hired to replace Chamberlin, who has superintendent of Hopkinton schools since 2009.  Flynn said he is ready to move the district in a new direction while keeping the values alive from its former superintendent.

“First of all, you don’t replace someone like Steve, you don’t replace anyone that’s been in a district for that long with that type of leadership,” Flynn said. “So certainly, it’s going to be my goal to follow him and continue to lead the work that he started,” Flynn said. 

The Hopkinton School Board announced Flynn’s hiring during a public meeting Thursday. 

Chamberlin will step down from his role on July 1, when Flynn will take over. Chamberlin has helped Flynn understand the responsibilities of the job and will continue to help him in the upcoming months to ensure a smooth transition. 

Flynn said he’s looking forward to to getting acquainted with everybody and becoming a part of the Hopkinton community, but he said he wished he could meet everyone in person instead of over Zoom. The board plans to hold an event introducing Flynn in July, but are unsure of what form it will be held. 

Jim O’Brien, the chair of the Hopkinton Select Board, praised Flynn’s financial acumen and stressed the importance of having a superintendent with fiscal knowledge and understanding fiscal responsibility. He also discussed a difficult part of the final interview process which involved a presentation of Hopkinton’s budget where Flynn had to make a presentation of the budget in less than three days. O’Brien said that Flynn’s presentation of the budget showed “systems thinking.” He additionally said that his ability to build personal relationships set him apart from the other applicants.

Flynn said that as he went through multiple interviews, he knew Hopkinton was going to be a great fit for him. He said the budget exercise was difficult without a thorough understanding of past budgets before creating his online presentation. But while he said that it was challenging, the whole process confirmed he wanted to work in Hopkinton. 

The board also mentioned Flynn’s impressive resume and experience for the job. 

Flynn is currently the Director of 21st Century Learning, Assessment, and Technology of the Hampstead School District. He has previously worked as the principal of Timberlane Regional Middle School, and the academic dean of Business and Information Communication Technologies Department at Timberlane Regional High School in Plaistow.

Flynn is a 2004 graduate of Southern New Hampshire University in Manchester and holds a master’s in business administration and a master’s in business education.

Flynn remains an adjunct faculty of the Graduate School of Education at SNHU and is also a teaching fellow of Marketing Management at Harvard University Extension School in Cambridge.

Hopkinton School Board member Norm Goupil said Flynn’s energy and genuine happiness when they officially offered him the job showed that he was the right fit.

“He’s just going to bring a new pair of eyes to this district. And I’m very happy that we came to him as a board. And also just to all the all the effort of this community into this process. I’m very happy with this selection,” Goupil said.

The district has about 30 applicants for the job, then they brought that number down to 10. It was down to Flynn and another candidate in the final round, but the board was positive that Flynn was the right choice. 

“I can’t wait to get started with local leaders, the school board,” Flynn said. “I’ve now gotten to meet the district leadership, school leadership. And I can’t wait to start meeting the staff and the students. We’re in this game for a reason. The bottom line is the students and everything that we do is with them in mind, and, and  I can’t wait to work and to begin building a plan to move this this district forward.”

Flynn currently lives in Windham with his wife and three children.