Kerry Jupina: Leading with Compassion to Help Every Student Write Their Story
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Every student’s educational journey begins with a different story. Some enter the classroom with confidence and clear aspirations. Others arrive carrying responsibilities, setbacks, interrupted learning, or circumstances that have caused them to question whether graduation is still possible. For those students, education must offer more than a path to a diploma. It must provide an environment where they can rebuild confidence, recognize their potential, and begin imagining a future beyond the obstacles they have faced.
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Kerry Jupina has built her career around helping create those environments. As Director of Operations for Buckeye Community Schools under the New Leaf Organization, she brings decades of experience spanning counseling, social services, school leadership, administrator development, and executive oversight. Her leadership is grounded in compassion and service, but strengthened by the depth of experience that has allowed her to understand students, families, educators, schools, and educational systems from multiple perspectives.
At Buckeye Community Schools, that experience supports a deeply personal mission: helping students understand that where they have been does not have to determine where they are going. From the moment they enter the school, students are encouraged to “Write Their Story”—and Kerry is helping ensure they have the support, opportunities, and belief in themselves to do exactly that.
The Experiences That Shaped a Leader
Born in Buffalo, New York, and raised in nearby North Boston, Kerry grew up in a close-knit, faith-centered family where service to others was a way of life. Responsibility, integrity, compassion, and humility became foundational values long before they became principles that would guide her leadership.
Athletics also helped shape her approach to life and work. A dedicated athlete throughout high school and college, Kerry learned the value of discipline, teamwork, perseverance, accountability, and resilience—lessons that would prove equally important in a career devoted to helping young people and leading others through complex challenges.
Kerry initially entered college intending to pursue athletic training, but a formative internship redirected her path. Working with young people facing difficult circumstances revealed a deeper calling: helping others navigate challenges and recognize possibilities they might not yet see for themselves.
She earned a bachelor’s degree in Health Science with a concentration in Substance Abuse Counseling from SUNY Brockport and later earned her social work license through Youngstown State University. What followed was not a straight path into school administration, but a career built through firsthand experience with young people and families in some of life’s most challenging circumstances.
Rediscovering Purpose Through New Leaf
Years before joining the New Leaf Organization, Kerry encountered a dropout prevention and credit recovery program led by the same executive leadership team that would later guide New Leaf.
What stayed with her was not simply the educational model. It was the culture.
Students who had struggled in conventional educational environments were welcomed rather than defined by their past experiences. The program was intentionally designed around their individual needs, and the atmosphere reflected dignity, flexibility, accountability, and genuine care.
“It felt different because it was different,” Kerry recalls. “It was personal, compassionate, and focused on understanding each student’s circumstances instead of treating everyone the same.”
The experience remained with her as evidence of what could happen when educational systems were designed around the students they served.
Years later, when the opportunity arose to join New Leaf and support Buckeye Community Schools, Kerry recognized an alignment between the work she had spent her career doing and the purpose that had always driven her.
Today, as Director of Operations, she brings that extensive experience to an educational model built specifically to serve students through dropout prevention, credit recovery, individualized learning, and pathways toward graduation and life beyond high school.
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