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

Connections AcademyYork Township, PA
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.

Benefits

  • health coverage
  • retirement contributions through a 403(b) plan
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