Head of the Class: Dolly Sullivan Retires

April 08, 2025 · Champion of Educators and Learners On to the Next Chapter

After a career leading, promoting and supporting Maine educators, most notably in the Teacher of the Year program, Dolly Sullivan has retired to focus on her next chapter. Her statewide influence and the projects and programs she built during several decades as Maine’s top teacher advocate will persist indefinitely, according to her colleagues at Educate Maine, where her last day on the job was March 31.

Sullivan, of Orono, served as director of Maine Teacher of the Year for 27 years, and led the incorporation of the state’s County Teachers of the Year into the statewide program. Her enthusiasm and passion for teaching (the University of Maine alumna was trained as a classroom teacher) helped her connect with thousands of educators over the decades, beyond the 176 she got to know closely through CTOY.

She was instrumental in elevating the teacher recognition program and transforming it into a coveted year of professional development, networking and learning for the state’s top educators.

“It’s a chance to learn and grow in the profession,” Sullivan said frequently. “Teacher of the Year is about leadership and about advocacy.”

Sullivan also led the Education Leaders Experience program developed by Unum, and most recently launched the brand-new Teach Maine Center.

“Dolly's greatest strength has been supporting teachers in the field to develop their own leadership and advocacy skills,” said Jason Judd, Ed.D., executive director of Educate Maine.

Sullivan was a longtime supporter of increased educator wages to improve retention and recruitment of teachers in Maine. A signature “win” was the passing just last year of the Social Security Fairness Act, which restored earned federal benefits to teachers and other public servants. Sullivan had advocated tirelessly for years to advance that issue.

“The effect Dolly Sullivan had on the teaching profession is one thing, but we can’t ignore the thousands of Maine students her work touched and the ways she increased their educational opportunities,” Judd said. “Her influence has been tremendous.”

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