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

Connections Academy•York, PA

3d•Remote

About The Position

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.

Requirements

Active Pennsylvania School Counselor Certification or eligibility to obtain certification
Advanced degree in counseling, education, educational leadership, or a related field
Minimum of 5 years of leadership experience overseeing counseling or student support programs in a K–12 setting
Minimum of 10 years of counseling, student support, teaching, or related educational experience preferred
Experience in a virtual or blended learning environment strongly preferred
Pennsylvania supervisory certification/license preferred; willingness to obtain certification required
Demonstrated ability to effectively lead, communicate, and manage within a remote and technology-driven environment
Strong knowledge of Pennsylvania graduation requirements, Act 158 pathways, Section 504 compliance, and student support best practices
Ability to develop and sustain collaborative relationships with students, families, staff, community organizations, and external stakeholders
Strong organizational, communication, problem-solving, and leadership skills
Ability to travel within and out of state as needed for school business
Technologically proficient, including experience with Microsoft Office Suite and Google Workspace
Two-step authentication setup is required for access to school systems upon hire.

Nice To Haves

Minimum of 10 years of counseling, student support, teaching, or related educational experience
Experience in a virtual or blended learning environment
Pennsylvania supervisory certification/license

Responsibilities

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.
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.
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.
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.
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.
Ability to travel and represent the school for legislative, compliance, and school-related purposes.
Perform other duties as assigned.