CHERRYFIELD — When Rob Riley saw an ad for a Cherryfield School Department superintendent, he was intrigued.
Not only was he interested enough to make the three-hour-and-20-minute trip from his home in Saco for an interview, but also enough to come out of retirement to accept the position. Since he started his duties Jan. 2, he makes the trip once a week.
His days as superintendent are filled with the usual duties such as meetings, budgets and overseeing personnel, but he tries to visit the department’s only school — Cherryfield Elementary — each day.
“I get a wonderful sense of community in that building,” he said. “And I think it’s pretty neat.”
Riley began his career in banking and business development. He and his wife, Judy, also owned a bed and breakfast in Portland for 10 years.
“Then I got into education,” he said.
He spent four years as assistant principal at Lawrence Junior High School in Fairfield before becoming principal, a post he held for two years. Then he served as principal at Gorham Middle School for 12 years before retiring.
Riley, who holds a bachelor’s degree in U.S. history and education, also served as a hockey coach in the 1970s at St. Francis College, which is now the University of New England.
In Cherryfield, he replaces former Superintendent Katherine Mayo-Reese, who is still the school principal. At the start of the school year, she filled an otherwise vacant full-time position as a math teacher.
“I was principal, superintendent and teacher,” Mayo-Reese said. “I was working long hours, and then making teaching plans as well, so I made the decision, after great thought and reflection, that I would give up the superintendency.”
Riley praised Mayo-Reese’s work.
“It’s amazing to me that she did the job as well as she did, and she did it very well,” he said. “I respect her for making the choice.”
Mayo-Reese said the decision to step down was the right one.
“I have found that it is more rewarding, and the students and parents were very appreciative that I stepped back to the classroom to teach their children,” she said.
At this time, Riley said, he is still getting to know the school, including the approximately 100 students and 28-member staff of teachers and support personnel. His next step will be to consider goals for the school.
Riley said although Saco is more densely populated, schools in both areas share many of the same challenges. Among them is the need to adapt teaching to changes in technology that allow students to connect with the outside world.
“The teacher is no longer the smartest person in the room,” he said.
Not all kids learn the same way, so teachers must adapt to the students rather than expecting the students to adapt to the teacher, he said. The trend of pushing kids toward college also is ending.
“We’ve got to figure out a way to provide our communities with all the people we’re going to need, not just doctors and lawyers,” he said. “One size does not fit all. Ever.”
He said he relies on Administrative Assistant Alice Tucker, who has worked for the School Department since 2017.
“There isn’t a superintendent in the state who won’t look to their secretary or administrative assistant,” he said, describing the people holding these positions as “the backbones of the organization.”
Despite the drive, Riley said he generally doesn’t stay overnight, except on the second Tuesday of the month, when the board meets. He may stay overnight during budget season, however.
Riley, who has two grown children and three grandchildren, said he doesn’t plan to move to Cherryfield. He likes to get up early and spends the time in the car listening to books on tape.
He has been to Cherryfield only in the winter and is looking forward to being there during the other seasons.
“I can’t wait to see it in the spring,” he said, “[and] in the summer and in the fall.”