Maine School Administrative District 75 has chosen its director of special education, Heidi O’Leary, to serve as interim superintendent of schools for the coming academic year. O’Leary grew up in Harpswell and said her years as a student there taught her the value of caring educators. J. Craig Anderson / Harpswell Anchor

The district’s board of directors approved O’Leary’s appointment in a 12-2 vote on Thursday, with board members Eric Lusk, of Harpswell, and Brandy Robertson, of Bowdoin, voting against. The two dissenting board members expressed reservations about O’Leary’s relative lack of executive leadership experience.

O’Leary, who has led the district’s special education programs for the past six years, grew up in Harpswell and said her years as a student there gave her “a deep appreciation for the value of caring, good people and the impact (they) can have on a person’s life.”

“I am committed to leading with compassion and empathy, to ensure that every student in the district feels seen, heard and supported,” O’Leary told the board just after the vote. “I am committed to providing every student with access to a high-quality education regardless of their background and circumstances.”

The outgoing superintendent, Steven Connolly, chose to resign effective June 30 after just one year in the role. His announced departure set up what will be the district’s sixth executive leadership transition in five years.

In a resignation letter dated Feb. 9, Connolly cited his own difficulty managing “the implicit divisions that exist (within the district) based on political, personal, and ideological beliefs” as the primary reason. He was absent from Thursday’s board meeting.

“Upon joining the District on July 1, 2022, I believed I would be the person to bring continuity to a staff and community seeking to move forward,” Connolly said in his resignation letter. “Unfortunately, that will not be the case.”

The board immediately selected a superintendent search committee made up of school board Chair Frank Wright, of Harpswell, and one board member from each of the district’s four towns: Doug Dumont, of Topsham; Hutson Hayward, of Bowdoinham; Ryan Larsen, of Harpswell; and Kim Totten, of Bowdoin.

In May, the committee’s top choice to become the next permanent superintendent decided to withdraw, forcing the district to again turn to an interim leader for the coming academic year.

Wright addressed the withdrawal and the status of the search in a May 1 letter to the community.

“A leading, strongly qualified, and enthusiastic candidate was identified with unanimous support from the Board,” Wright said in the letter. “However, for unforeseen personal reasons, the candidate found it necessary to withdraw their application during final negotiations.”

The appointment of an interim superintendent will give the board “sufficient time to conduct a thorough hiring process for a permanent superintendent to steward the District for years to come,” he wrote.

At Thursday’s meeting, several board members voiced their enthusiastic support for O’Leary in the interim role, including Wright.

“I think Heidi is an excellent candidate,” Wright said just before the vote. “When the going gets tough, the tough get going, and that’s Heidi.”

Board member Michael Timberlake, of Topsham, was among those who expressed strong support for O’Leary’s candidacy.

“She’s a very caring person, and she is very committed to this district,” Timberlake said.

Since the retirement of Brad Smith, superintendent from 2011-2018, the district has often relied on interim leadership.

Interim superintendents Dan Chuhta and Bob Lucy split the 2018-19 school year. Shawn Chabot was superintendent in 2019-20 and much of 2020-21 before reporting for active duty as a National Guardsman. Lucy filled in for the rest of 2020-21 and all of 2021-22, then Connolly took over.

At Thursday’s meeting, Lusk and Robertson both expressed reservations about O’Leary’s relative lack of executive leadership experience.

“The superintendent job is a very big one, as we’ve had a chance to see,” Lusk said before the vote. “There are about 2,400 students and about 500 employees (in the district). Being the superintendent means swimming in a very big body of water, and jumping over the assistant superintendent job and going straight to being a superintendent I think is asking more than we should be asking.”

Totten said she had initially shared the two dissenting board members’ concerns, but that hearing O’Leary’s answers to the board’s questions during the selection process caused her to have a change of heart.

“I really felt like we needed somebody experienced,” Totten said. “The last interview we did with Heidi changed my mind.”

Robertson said that although she chose to vote against O’Leary’s appointment to the interim position, she would support the district’s new leader however she could.

“I look forward to saying that I was wrong,” Robertson said.