Pennwood Cyber Charter School – Engagement Specialist

Connections Education LLC; Pennsylvania; Hybrid; USD 42,000 - 56,000; Full time

Benefits offered by this job

Health coverage

403(b) retirement plan

Job summary

Pennwood Cyber Charter School is seeking an Engagement Specialist to support student engagement, attendance, intervention systems, and family partnerships for the 2026–2027 school year. Working remotely, you will serve as a key member of the student support team, helping students stay connected and supported academically, behaviorally, and socially in a virtual setting.

You will monitor engagement, conduct proactive outreach, assist with MTSS processes, attendance recovery, and re-engagement

Qualifications

• Experience working with students and families in educational settings.
• Experience supporting engagement, MTSS, and attendance initiatives.

Responsibilities

• Build and maintain positive relationships with students and families.
• Monitor attendance, participation, lesson completion, engagement trends, and intervention indicators.
• 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 culture initiatives.
• Participate in MTSS meetings, intervention discussions, and planning.
• Lead or support intervention follow-through and 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.
• Maintain accurate documentation related to student engagement, outreach efforts, and follow-up actions.
• Support PBIS implementation and belonging-focused activities.
• Participate in schoolwide engagement events and student support activities.
• Maintain confidentiality and professionalism with students and families.

Skills

Communication skills

Relationship-building

Facilitation

Virtual environment

Caseload management

Documentation

Organizational skills

Travel willingness

Tools

Microsoft Office

Student information systems

Job description

Job Category: Educational Services

Requisition Number: PENNW018405

• Posted : October 22, 2026
• Full-Time

Locations

Showing 1 location

Home-based, PA
2951 Whiteford Road Suite 204
York, PA 17402, USA

About Pennwood Cyber Charter School

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.

Position Summary and Responsibilities

Pennwood Cyber Charter School is seeking relationship-centered and student-focused Engagement Specialists to support student engagement, attendance, intervention systems, and family partnership initiatives for the 2026–2027 school year.

Working remotely, the Engagement Specialist serves 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. This role provides 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. These staff members support ongoing student engagement monitoring, attendance awareness, MTSS participation, intervention follow-through, and individualized student support planning.

Engagement Specialists assigned to grades K–5 support elementary homeroom teachers and serve as lead intervention support staff for attendance recovery efforts, family outreach, engagement monitoring, and student support initiatives. Because elementary Engagement Specialists do not maintain homeroom responsibilities, they may support larger intervention caseloads.

Each Engagement Specialist collaborates closely with teachers, counselors, coordinators, administrators, and student support teams to help identify barriers, strengthen family engagement, and support positive student outcomes.

Essential Duties and Responsibilities

Other essential functions include, but are not limited to, the following:

• 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; and
• Perform all other duties as assigned.

Education and Experience

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

Knowledge, Skills, and Abilities

• 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; and
• Ability to travel as needed for school events, training, or student support activities.

Equal Opportunity Employer
This employer is required to notify all applicants of their rights pursuant to federal employment laws.For further information, please review the Know Your Rights notice from the Department of Labor.