Lawrence O’Toole Award Winner 2016: Sunny Pai of Diploma Plus – Charlestown HS

This post, originally published on June 3, 2016, provides an overview of the wonderful work Sunny Pai does everyday as the Director of Diploma Plus at Charlestown High School. Sunny is still the Director at Diploma Plus. He is currently part of the Nellie Mae Education Foundation Speaker’s Bureau and you can watch a fall 2017 presentation he led on the importance of mastery for historically underserved young people here.

The Nellie Mae Education Foundation has named Sunny Pai, Director of the Diploma Plus programs at Charlestown High School, as the winner of its 2016 Lawrence W. O’Toole Award. Named in honor of Nellie Mae’s founding President & CEO, the annual award grants $100,000 to a school, community organization, or district to continue the advancement of student-centered approaches to learning for all students. Pai was one of six nominees selected through an internal nomination process at Nellie Mae, with each nominee representing a New England state.

I am incredibly grateful and humbled to accept such an honor on behalf of our Diploma Plus community – students, families, staff, partners, and friends. 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,” said Pai. “I would also like to express my gratitude to the Nellie Mae Education Foundation for the opportunity to receive such an honor. With this generous grant, we will be able to bring ideas to reality – ideas that provide innovative, student-centered education – so our students can succeed in high school and for the rest of their lives. I look forward to collaborating with our students, families, and staff to continue building on our success.”

As Director of the Diploma Plus (DP) Programs at Charlestown High School (Boston Public Schools), Pai is dedicated to reimagining alternative education so that it is relevant, meaningful, and individualized for all students. He is the leading force behind DP’s performance-based model for students who have not yet been successful in high school. Pai is committed to establishing a culture of growth, where all students – especially students who have struggled in traditional academic models – can achieve at the highest levels. Under Pai’s leadership, DP ensures students graduate with the skills they need to be truly ready for college. Possible uses of the $100,000 grant include supporting DP’s aspirations to hold a student exchange trip, provide student internships, and upgrade technology in the program.

During a time in which too many students leave high school unprepared for college or a career, I’m thrilled with all of the work this year’s O’Toole nominees are doing to ensure bright, prosperous futures,” said Nick Donohue, President & CEO of the Nellie Mae Education Foundation. “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. 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. We are so pleased to present him with the 2016 O’Toole Award.”


Nellie Mae established the Lawrence W. O’Toole Leadership Award in 2011 and has awarded $500,000 in honor of O’Toole and his success in laying the groundwork to establish the Foundation.

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