(2627 SY) Pennwood Cyber Charter School- Director of Student Services

More Results Previous jobDirector of Admissions and Tuition... Assistant Director of Student ServicesNext job (2627 SY) Pennwood Cyber Charter School- Director of Student Services Employer Connections Academy Location Longstown, PA Closing date May 28, 2026 View more categoriesView less categories Specialty Student & Scholar Services Position Type Director Hours Full-time Employment Type Permanent Organization Type Other Apply on website You need to sign in or create an account to save a job. Send job Job Details About Pennwood Cyber Charter School Pennwood Cyber Charter School is a tuition-free, K-12 public cyber charter school serving students across Pennsylvania. Pennwood provides flexible virtual learning supported by a proven curriculum, individualized student support, and innovative educational opportunities designed to promote academic achievement, engagement, and long-term student success. Pennwood operates on a unique school calendar that includes a three-week Connections Term (CTerm), extending the school year to 195 instructional days. The Connections Term provides additional opportunities for intervention support, enrichment experiences, relationship-building, career readiness exploration, and personalized student learning. Pennwood is committed to fostering a collaborative, relationship-centered virtual school culture where students, families, and staff feel connected, supported, and empowered to succeed. Pennwood staff members participate in a competitive benefits package, including health coverage and retirement contributions through a 403(b) plan with a 5% employer match in place of PSERS. Position Summary And Responsibilities Pennwood Cyber Charter School is seeking a strategic, student-centered, and collaborative Director of Student Services to lead and oversee the school’s comprehensive counseling and student support programs for grades K-12. This senior leadership role provides vision, oversight, and strategic direction for student support services designed to promote academic success, student wellness, engagement, retention, and postsecondary readiness within a virtual learning environment. The Director of Student Services oversees counseling programs and student support systems related to academic planning, graduation pathways, Section 504 compliance, college and career readiness, crisis response, student wellness, and family support services. This role is responsible for ensuring students and families receive high-quality, proactive, and student-centered support while maintaining compliance with state and federal requirements. As a member of the Senior Leadership Team, the Director collaborates closely with school leadership, families, community organizations, Pearson Virtual Schools, and external partners to support whole-child success through a proactive, data-informed, and relationship-centered approach. The Director supervises counseling staff, supports retention and engagement initiatives, coordinates student intervention efforts, and leads programs focused on postsecondary preparation and student well-being. This position is primarily remote, with required travel to the York office and other locations for meetings, events, training, state testing support, and legislative or compliance-related responsibilities. Key Responsibilities Leadership and Team Management Supervise, coach, support, and evaluate counseling and student services staff to ensure high-quality performance, professional growth, and compliance with school expectations and applicable regulations; Lead counseling staff meetings, communication, collaboration, and professional development initiatives to support team effectiveness and engagement; Serve as a member of the K12 Leadership Team and collaborate with school leadership to support strategic initiatives, student success, and school culture; Communicate regularly with the CEO and leadership team regarding counseling operations, student support initiatives, trends, and team performance; Contribute to a positive school culture through participation in engagement initiatives, recognition programs, staff events, and collaborative leadership efforts; Counseling and Student Support Programs Develop, implement, and monitor a comprehensive K-12 counseling program focused on academic planning, student wellness, graduation readiness, and postsecondary success; Ensure students and families receive timely, proactive, and student-centered support related to academic progress, graduation requirements, scheduling, transition planning, and social-emotional needs; Support and oversee student intervention and retention efforts in collaboration with academic, engagement, and leadership teams; Design and implement innovative virtual engagement opportunities that foster student connection, belonging, wellness, and community within a cyber school environment; Lead the resolution of complex student and family concerns by collaborating with counseling staff, school leadership, and cross-functional teams to ensure timely and supportive outcomes; Graduation, Postsecondary Readiness, and Academic Planning Demonstrate expertise in Pennsylvania graduation requirements, including Act 158 pathways, state assessment requirements, community service expectations, and alternative graduation pathways; Collaborate with school leadership to oversee the course selection process according to graduation requirements, student needs, and postsecondary goals; Research, develop, implement, and monitor programs related to Advanced Placement (AP), Dual Enrollment, college entrance preparation, FAFSA support, scholarships, and career readiness initiatives; Manage and maintain dual enrollment articulation agreements with postsecondary institution partners; Coordinate and support high school graduation planning and ceremonies; Generate and authorize official transcripts for families and postsecondary institutions upon request; Oversee transcript review, entry, maintenance, and delivery within the Education Management System to ensure accuracy, compliance, and timely updates; Compliance, Crisis Response, and Student Wellness Provide oversight and support for the development, implementation, and compliance of Section 504 plans, ensuring accommodations are appropriate, consistently implemented, and aligned with federal and state guidelines; Monitor counseling and student services practices to ensure compliance with PDE requirements, FERPA, Section 504, and applicable state and federal regulations; Support and oversee the school’s Student Assistance Program (SAP) process by collaborating with multidisciplinary teams to identify, monitor, and assist students experiencing academic, behavioral, attendance, or crisis-related concerns; Report and refer critical incidents impacting student well-being in accordance with legal, ethical, and administrative requirements; Coordinate crisis response efforts, student wellness supports, and intervention planning in collaboration with school leadership and support teams; Lead school teams in identifying and maintaining school and community resources for students and families; Serve as the primary liaison for the Cook Center for Human Connection and other mental health or wellness partnerships, coordinating family resources, staff professional development, and student support initiatives; Data, Reporting, and Strategic Planning Collect, analyze, monitor, and present counseling and student support data to identify trends, support continuous improvement efforts, and guide strategic decision-making; Utilize data to monitor graduation progress, retention trends, student engagement, intervention effectiveness, and postsecondary readiness outcomes; Support school improvement efforts through collaboration, reporting, and strategic planning related to counseling and student services initiatives; Additional Responsibilities Ability to travel and represent the school for legislative, compliance, and