Pennwood Cyber Charter School – Engagement Specialist (26/27 SY)

Connections Academy•York Township, PA

1d•Remote

About The Position

Pennwood Cyber Charter School is a Pennsylvania public cyber charter school serving students in grades K–12 through a flexible, student-centered online learning model. As a cyber charter school, Pennwood provides students and families across Pennsylvania with access to high-quality virtual instruction, individualized support, and innovative educational opportunities designed to promote academic success, engagement, and career readiness. Pennwood operates on a unique school calendar that includes a Connections Term (CTerm), which provides additional instructional opportunities, enrichment experiences, intervention support, and credit recovery programming for students. The school is committed to fostering strong relationships, meaningful student engagement, and a collaborative virtual school culture that supports the whole child. Pennwood staff members participate in a competitive benefits package, including health coverage and retirement contributions through a 403(b) plan.

Requirements

Bachelor’s degree required
Strong communication, relationship-building, and facilitation skills
Ability to build trust and rapport with students and families in a virtual environment
Ability to manage student caseloads, outreach responsibilities, and documentation systems effectively
Ability to analyze engagement indicators and support intervention planning
Strong organizational skills and attention to detail
Technological proficiency with Microsoft Office products and student information systems
Ability to work independently while collaborating effectively within a team environment
Ability to adapt to changing priorities and student needs in a fast-paced virtual setting
Ability to travel as needed for school events, training, or student support activities

Nice To Haves

Experience working with students and families in educational settings
Experience supporting student engagement, intervention systems, attendance initiatives, or MTSS processes

Responsibilities

Serve as a key member of the school’s student support and MTSS framework by helping students remain connected, engaged, and supported academically, behaviorally, and socially in a virtual learning environment.
Provide proactive outreach, engagement monitoring, intervention support, attendance recovery assistance, and re-engagement planning across grades K–12.
Maintain homeroom responsibilities and serve as relationship anchors for assigned student caseloads (grades 6-12).
Support ongoing student engagement monitoring, attendance awareness, MTSS participation, intervention follow-through, and individualized student support planning (grades 6-12).
Support elementary homeroom teachers and serve as lead intervention support staff for attendance recovery efforts, family outreach, engagement monitoring, and student support initiatives (grades K-5).
Collaborate closely with teachers, counselors, coordinators, administrators, and student support teams to help identify barriers, strengthen family engagement, and support positive student outcomes.
Build and maintain positive, supportive relationships with students and families.
Monitor attendance, participation, lesson completion, engagement trends, and intervention indicators for assigned caseloads.
Conduct proactive outreach and ongoing family communication to support student success.
Support onboarding and transition processes for students and families entering the school community.
Promote student engagement opportunities including clubs, events, school activities, and school culture initiatives.
Participate in MTSS meetings, intervention discussions, and student support planning.
Lead or support intervention follow-through and student re-engagement planning efforts.
Assist with attendance recovery efforts and identification of engagement barriers.
Collaborate with teachers, counselors, coordinators, administrators, and support teams regarding student needs and interventions.
Maintain accurate documentation related to student engagement, outreach efforts, interventions, and follow-up actions.
Support PBIS implementation efforts, school culture initiatives, and belonging-focused activities.
Participate in schoolwide engagement events, intervention initiatives, and student support activities.
Maintain confidentiality and professionalism while working with students and families.
Perform all other duties as assigned.