5th Quarter Summer Learning - Regional Site Director (Summer 2026)

Boston Public Schools•Boston, MA

22h•Onsite

About The Position

The 5th Quarter program provides equitable access to high-quality academic and enrichment opportunities for Boston students, using the city’s resources as an extended classroom. It is designed to increase school engagement, support academic and social-emotional growth, strengthen relationships, and enhance college and career readiness. The 5th Quarter Summer Learning Academy Regional Site Director oversees a cluster of BPS summer sites, serving as the primary liaison between Central Office and assigned schools in collaboration with Operational Leaders. This role requires a commitment to equity, teamwork, and safety, along with the ability to adapt to changing priorities, make timely decisions, and provide strong on-site support.

Requirements

Bachelor’s degree.
Massachusetts teaching license or school administrator license.
At least 2 years of professional teaching or administrative experience
Willing to support student academic growth through engaging, project-based curriculum
Willing to work in close collaboration with community-based organizations as needed to meet shared goals in a student-centered, school-aligned, results-focused initiative.
Competency with relevant technology platforms, including but not limited to Google Suite, Microsoft Office Suite, Aspen, SchoolMint, etc.
Demonstrated ability to serve as a visionary instructional or operational leader with the capacity to coach and supervise educators, provide constructive feedback, and foster collaboration.
Experience working with diverse student populations, including historically marginalized groups such as economically disadvantaged students, students with disabilities, and English Language Learners.
Demonstrated strong commitment to equity.
An understanding and commitment to the implementation of the district’s Culturally and Linguistically Sustaining Practices (CLSP) framework.
Current authorization to work in the United States.
Candidates must have such authorization by their first day of employment.

Nice To Haves

Current teacher or administrator in the Boston Public Schools.
Prior experience working in a BPS summer learning program and/or in close collaboration with a community-based organization
BPS values linguistic diversity and believes that candidates who speak another language bring added value to the classroom, school, and district culture and diversity.
BPS is particularly interested in candidates who are fluent in one of BPS' official languages: Spanish, Creole (Cape Verdean), Creole (Haitian), Chinese, Vietnamese, Portuguese, & Somali.
Specialization and/or licensure in Special Education and/or English as a Second Language

Responsibilities

Provide on-site oversight on July 6 to ensure all logistics are in place for the first day of summer programming.
Regional Site Directors (RSDs) are responsible for supporting their assigned Site Coordinators with key setup tasks, including (but not limited to): site scheduling, coordination between programs sharing a school, classroom assignments, building walkthroughs, supply storage, and nurse access to medical supplies and office space.
Organize and facilitate regular team meetings with all Site Coordinators assigned to the school buildings in your region after programming has begun to provide open lines of communication and quick responses to on site issues.
Provide oversight of Site Coordinators to ensure they follow all BPS and ELO expectations, including accurate attendance tracking, parent and visitor communication, staff payroll and timekeeping, field trip approvals, emergency cards, communication requirements, and compliance with BPS policies and circulars.
Provide consistent feedback and oversight in collaboration with the ELO team using the Assessment of Program Practices Observation Tool (APTO).
Collaborate with Operational Leaders to ensure smooth summer programming by aligning district operations with on-site execution.
Operational Leaders manage logistics, safety, emergency response, staff concerns and troubleshooting, while Regional Site Directors oversee staff and ensure program compliance.
Conduct regular site visits to ensure sites are operating in accordance with established expectations and metrics; providing regular oversight of daily attendance, student academic progress, student support and other tasks as needed to support coordinators with execution of high quality programming
Support site coordinators with creating a Master Daily Schedule for all programs assigned to the building and sharing this with the Chief and district ELO team.
Engage and collaborate with families as partners in planning and problem-solving by fostering a culturally competent, trauma-sensitive learning environment that implements culturally and linguistically sustaining practices.
Engage in regular, proactive communication with Office of Expanded Learning regarding program challenges and concerns as needed
Complete end-of-summer closeout tasks, including required paperwork, feedback activities, and any additional duties assigned by the Chief of Family Advancement or Designee.