Pennwood Cyber Charter School – Engagement Specialist

Connections Academy•York, PA

6d•Remote

About The Position

Pennwood Cyber Charter School is seeking relationship-centered, student-focused Engagement Specialists for the 2026–2027 school year. Working remotely, the Engagement Specialist supports student engagement, attendance, intervention systems, and family partnerships as part of the school’s student support and MTSS framework. The role helps students stay connected and supported academically, behaviorally, and socially in a virtual learning environment through proactive outreach, engagement monitoring, intervention support, attendance recovery assistance, and re-engagement planning across grades K–12. Engagement Specialists assigned to grades 6–12 maintain homeroom responsibilities and serve as relationship anchors for assigned student caseloads, supporting engagement monitoring, attendance awareness, MTSS participation, intervention follow-through, and individualized student support planning. Specialists assigned to grades K–5 support elementary homeroom teachers and lead intervention support for attendance recovery, family outreach, engagement monitoring, and student support initiatives. They do not maintain homeroom responsibilities and may support larger intervention caseloads. Each Engagement Specialist works closely with teachers, counselors, coordinators, administrators, and student support teams to identify barriers, strengthen family engagement, and support positive student outcomes. The position requires a bachelor’s degree. The school operates a flexible, student-centered online learning model and offers a competitive benefits package that includes 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 preferred.
Experience supporting student engagement, intervention systems, attendance initiatives, or MTSS processes preferred.

Responsibilities

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.
For grades 6–12 assignments, maintain homeroom responsibilities and support assigned student caseloads.
For grades K–5 assignments, support elementary homeroom teachers and lead intervention support for attendance recovery, family outreach, engagement monitoring, and student support initiatives.