Charlestown High School teacher wins $100,000 award for work with Diploma Plus Program

He received 39 percent of over 8,000 votes cast.

Sunny Pai speaks with two students in the Diploma Plus program at Charlestown High School. Nellie Mae Foundation

Last month Sunny Pai teared up when he thought about what winning $100,000 would do for the Diploma Plus Program he leads at Charlestown High School.

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“With $100,000 it opens up the door to so many types of things we can do,” he said in an interview with last month. “Before we’ve had dreams and and say, ‘Oh, it might be nice,’ and move on, but with this kind of money we could actually have a conversation about how to make them happen.”

Now, the dreams Pai had for the program can become a reality. He was named the winner of the Nellie Mae Foundation’s Lawrence W. O’Toole Award, which grants $100,000 to a school, community organization, or district to continue the advancement of student-centered learning approaches.


Pai was one of six nominees selected through an internal nomination process at the foundation, with one teacher representing each New England state. He received 39 percent of over 8,000 votes cast during a public voting period that lasted from May 23 to June 3.

“The magnitude of support voiced for Sunny shows us the amazing strides he and his team have made in rethinking teaching and learning to meet students where they are in their education, helping them thrive during and beyond high school,” Nick Donohue, President & CEO of the foundation, said in a statement. “Sunny has been the leading force behind Diploma Plus’s performance-based model, where students move ahead based on mastery of content, not seat-time.”

The program is designed to help students who haven’t been successful in traditional school environments or who have dropped out of the system altogether. Many of the students lead complex lives, Pai said, and have families that are going through difficult times. To gain entry into the program, students must have at least one year of failing grades.

“The truth is, that students who come to us are brilliant, but they have not been successful in school so they don’t have confidence in themselves,” he said. “It’s a pretty amazing group of adults we have that take on that challenge every day.”


The grant will allow educators to further experiment with methods to teach students, though they haven’t yet decided how the money will be used. Possible uses include a student exchange trip in Africa, providing student internships, and upgrading technology in the program.

“I am incredibly grateful and humbled to accept such an honor on behalf of our Diploma Plus community – students, families, staff, partners, and friends,” Pai said in a statement. “I am so thankful to everyone in our extended community who voted in the past two weeks. We believe strongly that our graduates are the kind of leaders who will change the world, and the overwhelming support we received validates the importance of our mission.”


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