stewart new pps director

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Jennifer Stewart Named Director of MPS Pupil Personnel Services



MILFORD – The Milford Public School district is pleased to announce the appointment of Jennifer Stewart as the new Director of Pupil Personnel Services.  Ms. Stewart will replace current PPS Director Christopher Brown, who will be retiring at the end of the school year.  She will start in Milford on June 15, 2023.


Ms. Stewart began her career in 2000, working first as a teacher primarily involved in special education and continued on to progressively more responsible roles throughout her entire career. During those early years, Stewart gained valuable experience as a key figure in developing and implementing individualized educational plans in the Stratford, Trumbull, and Westport Public School districts. She was a driving force in these districts, notably launching a well-defined 18-21 program for students with special needs.


Beginning in 2010, Stewart was deeply involved in coordinating and managing the extended school year programming for Westport and Trumbull, becoming a department chair in Trumbull in 2014, overseeing and implementing a consistent structure for special education for preschool through age 21.


In July 2016, Ms. Stewart was named assistant director of special education for Regional School District 16 in Prospect, CT.  While there, she performed a wide variety of administrative duties, including the development and implementation of a three-year strategic plan for the department.  


But it was in 2017 that Ms. Stewart began her vibrant administrative trek in the North Haven Public School system.  Beginning as a special education coordinator, Stewart supervised the middle school, high school, and transition programs there.  One year later, she was promoted to the position of interim director of student services and successfully converted the program to a remote environment during the COVID-19 pandemic. She was permanently assigned as the director of student services there in July 2020.  


Ms. Stewart was a dual degree recipient from Southern Connecticut State University in 1999 earning a Bachelor of Science degree in education and a Bachelor of Arts in psychology. She later earned a Master's degree, in the area of learning disabilities and certification for special education from Southern.  In 2008, she earned her advanced certification in Education Administration (092), also from SCSU.  


Stewart is eager to begin her post in Milford. “I look forward to collaborating and building relationships with families and staff to continue the development of student learning in the Milford Public Schools.”


Dr. Anna Cutaia, Superintendent of Schools, commented “I believe Ms. Stewart will continue to build on the excellent work that provides all our students with individualized services with a focus on our district’s Vision of the Learner.  Ms. Stewart has a track record of innovation and creativity and I look forward to what she will bring to our system’s future work.”


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