Connetquot Central School District

Debra Winter brings over four decades of dedicated service to public and private education, with a distinguished career rooted in special education and student services. She began her journey as a special education teacher and quickly emerged as a visionary leader, shaping systemic improvements and student-centered policies across multiple districts.

Debra served for eight years as Director of Pupil Personnel and sixteen years as Assistant Superintendent for Student and Community Services in the Longwood Central School District. In this role, she oversaw a wide array of programs and initiatives, including special education, technology integration, career and technical education (CTE), fine arts, federal and competitive grant acquisition, student attendance, civil rights compliance, and support services for vulnerable student populations. Her leadership extended to Positive Behavioral Interventions and Supports (PBIS), Dignity for All Students Act (DASA) implementation, services for homeless students, alternative education programs, and specialized programs for students with autism.

She later served as Superintendent of the Springs School District for seven years, where she successfully completed a $23 million bond project during the unprecedented challenges of the COVID-19 pandemic. Most recently, she supported Just Kids in establishing a New York State-approved 853 school for autistic students on the North Fork of Long Island.

Debra’s career has been defined by her unwavering commitment to inclusive education, collaborative leadership, and advocacy for equity. Now in her twenty-first year as a facilitator for special education leaders, including CSE chairpersons, coordinators, assistant directors, and aspiring administrators, Debra continues to mentor and guide the next generation of educational leaders. Her collegial circle offers a trusted space where professionals can navigate challenges, exchange innovative ideas, and align their work with best practices.

In addition to her professional roles, Debra volunteers with FIRST Long Island, a branch of the global FIRST Robotics program, which fosters teamwork, innovation, and belonging for students through hands-on problem-solving and competition.

Debra remains a passionate advocate for empowering all educators to ensure every student receives the support and opportunities they deserve. She believes in clear communication, high expectations, and meaningful partnerships with families, staff, and the broader community. She looks forward to serving the Connetquot community!