The Maine School Administrative District 75 School Board is taking the “interim” out of Superintendent Heidi O’Leary’s title.

The board voted Thursday to appoint O’Leary to lead the district effective Jan. 1. She will oversee the district’s schools in Bowdoin, Bowdoinham, Harpswell and Topsham, earning an annual salary of $160,000.

In his letter to members of the district community Friday morning, School Board Chairperson Hutson Hayward wrote that as interim superintendent, “Ms. O’Leary has looked only to set the district up for success, regardless of who might be leading it.” He described O’Leary as “a candidate with extensive classroom and administrative experience, a hard worker dedicated to providing for the needs of students, and someone who prioritize[s] clear communication, even in difficult situations.”

Originally from Harpswell’s Bailey Island, O’Leary has held several positions in the district, including special education teacher, special services director, substitute teacher, adult education instructor and field hockey coach.

“I’m really committed because I am leading folks and families and teachers that I had in school, and now I see their children, or their children’s children,” O’Leary said in an interview Friday. “It’s a deep connection, I’m deeply rooted in it … and I’m here to make sure that we move forward and get back to a good balance.”

The district’s previous superintendent, Steve Connolly, resigned in June. It was the district’s sixth leadership transition in the past five years.


Since stepping up as interim superintendent this summer, O’Leary has weathered divisions in the district over a policy granting greater privacy and autonomy to transgender students. Unlike Connolly, however, who cited his unwillingness to manage “the implicit divisions [in the district] that exist based on political, personal and ideological beliefs,” O’Leary has taken them in stride.

“I’m here to listen and hear both sides,” said O’Leary, “and use that to help us move forward in any conflict that we have.”

The first step, she said, is to “train our staff and understand what the policy means and how we’re going to implement it. After the holidays, I’m working on getting a training set up districtwide so that we can talk about that.” O’Leary said she anticipates working alongside OUT Maine, an organization that supports LGBTQ+ youth, to deliver that training.

O’Leary says her primary goal as superintendent will be to “increase public trust and confidence” among the community, school board, and district staff.

“I’m learning a lot,” says O’Leary. “Do I still have things to learn? Of course I do. I mean, it’s a new position. But I think we’ve set some good strategies in place and have really worked to come together as much as we can in the last six months, and that’s helping us to move forward.”

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