[Hiring] Dean of Student Retention and Engagement @Connections Academy

Role Description

The Dean of Student Retention and Engagement is a senior school leader responsible for developing, implementing, and monitoring strategies that improve student attendance, persistence, engagement, and overall school connectedness in a K–12 environment. This role focuses on proactively identifying students at risk of disengagement or withdrawal and coordinating timely, student-centered interventions that promote continuous enrollment and academic success.

The Dean partners closely with school leadership, teachers, counselors, support staff, and families to strengthen student engagement, reduce chronic absenteeism, and foster a positive school culture aligned to Missouri Connections Academy’s mission and accountability requirements. This is a 10-month role reporting to the School Leader.

Key Responsibilities

• Uphold and model the mission, vision, and values of Missouri Connections Academy.
• Support student persistence, engagement, and overall success by meeting annual school goals and accountability requirements.
• Develop and implement strategies to improve student attendance, engagement, and retention across grade levels.
• Proactively identify students at risk of disengagement or withdrawal and coordinate timely, student-centered interventions.
• Collaborate with school leadership, instructional staff, counselors, and support teams to align retention and engagement efforts.
• Build and maintain strong relationships with students and families to promote consistent participation and enrollment continuity.
• Provide high-quality communication and customer support to families and colleagues.
• Use data to monitor attendance, engagement, and retention trends and inform decision-making and continuous improvement.
• Support schoolwide initiatives, professional development, and collaborative practices.
• Contribute to a positive, inclusive, student-centered school culture in a virtual environment.
• Ensure compliance with applicable state and federal requirements related to attendance, enrollment, and student engagement.
• Participate in state testing administration and ensure adherence to applicable guidelines.
• Develop and monitor systems to track data related to late-enrolled students, including enrollment timing, engagement patterns, attendance trends, course pacing, and persistence outcomes.
• Analyze late-enrollment data to identify barriers to success and drive strategies.
• Design and implement differentiated onboarding processes for late-enrolled students that support both the student and family, ensuring clarity, connection, and early academic momentum.
• Create structured transition plans for students enrolling mid-semester to reduce instructional gaps and accelerate engagement.
• Partner with teachers, counselors, and support staff to provide coordinated wraparound support for newly enrolled students.
• Use innovative and creative engagement strategies to build meaningful connections with families and increase sustained participation in a virtual environment.
• Perform other duties as assigned.

Capabilities

• Customer Centric: Demonstrates a strong student and family support mindset and uses feedback to improve experiences and outcomes.
• Effective Communication: Communicates clearly and professionally with students, families, and colleagues; produces high-quality written and verbal communication.
• Team Collaboration: Builds trust, collaborates effectively in a matrixed organization, and contributes positively to team culture.
• Accountability & Follow Through: Takes ownership of responsibilities, meets deadlines, and adapts to changing priorities.
• Growth Mindset: Engages in professional learning, uses data effectively, and seeks continuous improvement.
• Technology Proficiency: Comfortable navigating virtual learning platforms, student information systems, and Microsoft and Google productivity tools.
• Data-Driven Decision Making: Uses quantitative and qualitative data to identify trends, address root causes, and implement targeted interventions, particularly for late-enrolled and at-risk students.
• Strategic Innovation: Applies creative, forward-thinking approaches to family engagement and student onboarding to improve connection, participation, and long-term retention.

Requirements

• Valid Missouri administrative, educational leadership, or applicable professional license (as appropriate to the role).
• Residency in Missouri.
• Minimum of 5+ years of experience in K–12 education, student services, school leadership, or a related field.
• Bachelor’s or Master’s degree in Education, Educational Leadership, Counseling, or a related field from an accredited institution.
• Experience with virtual or blended learning environments preferred.
• Ability to work effectively and manage responsibilities in a remote/virtual environment.
• Ability to travel in-state as needed.
• Must be able to use personal electronic devices for two-step authentication and school communications.
• Technological proficiency with Microsoft Office and Google Suite.

Benefits

Benefits available to eligible employees can be seen at Connections Academy Benefits .