Remote Student Engagement & Support 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

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