Prison Educator Jobs in Springfield, MA (NOW HIRING)

Managing Director of Correctional Education & Organization Growth

Position summary

The Managing Director of Strategic Growth will launch, lead, evaluate, and scale Phoenix’s prison education initiative as a statewide network priority. The role begins by building a high-quality pilot connected to Phoenix Springfield that serves 25 currently justice involved young adults, ages 18–25, and supports each student on a path to graduation, whether graduation occurs while the student is incarcerated or after release or transfer.

This is a senior leadership role for someone who can move fluently between daily implementation and long-range strategy. The Managing Director will work at the correctional facility each day during the launch phase, participate in Phoenix Springfield all-staff activities, coordinate academic design and quality across network and school leaders, build a rigorous data and learning partnership with the MA Department of Education, and turn pilot evidence into an actionable statewide growth strategy.

Reporting and key relationships

• Chief Operating Officer, who oversees operations & atrategic planning, will serve as the supervisor of record and own performance management, strategic alignment, and execution.
• The Phoenix Springfield Head of School will have a formal “dotted-line” coaching relationship, focusing on campus integration, school operations, and culture.
• As the academic leader of the organization, the Chief School Officer, will have a formal “dotted-line”, focusing on the implementation of instructional model, curriculum, assessment, and student supports,
• This role will also be in close partnership with correctional-facility leadership and staff; Department of Education partners; Phoenix network teams; educators; students and their support networks; and community reentry programs.

Core responsibilities

Pilot launch and operational leadership

• Own the full planning, launch, and implementation of the 25 student pilot at the Hampden County House of Corrections, including program design, budgeting, staffing, timelines, partner coordination, operational readiness, risk management, and ongoing performance.
• Build trusted working relationships inside the correctional facility and translate facility requirements into reliable daily operations.
• Establish student recruitment, eligibility, enrollment, records, scheduling, safety, communication, and continuity procedures.
• Lead rapid problem-solving while maintaining clarity, documentation, and accountability across partners.

Strategy, data, and organizational learning

• Develop the pilot’s academic program, learning agenda, performance measures, and data-review processes to assess implementation quality, student outcomes, and the conditions required for success.
• Partner with the Massachusetts Department of Elementary and Secondary Education and other state agencies to evaluate the Hampden County pilot and determine how Phoenix can be positioned to expand the model to additional correctional facilities.
• Use quantitative data, qualitative evidence, student experience, and partner feedback to strengthen the pilot, identify limitations, and establish clear criteria for future expansion.
• Assess Phoenix’s organizational readiness to expand beyond Hampden County, including academic capacity, staffing, operating infrastructure, technology, partnerships, funding, and leadership requirements.
• Develop the strategy, budget, staffing model, implementation plan, and multiyear financial projections required for responsible statewide expansion.
• Identify and evaluate potential expansion sites using clear readiness criteria, including student need, facility commitment, operating feasibility, academic quality, technology access, cost, and sustainability.
• Build the state, correctional, education, workforce, postsecondary, philanthropic, and community partnerships required to launch and sustain additional sites.
• Lead the planning and implementation of approved expansion efforts, establishing timelines, ownership, quality controls, performance measures, and continuous-learning processes for each new site.
• Codify the pilot’s academic model, operating practices, costs, decisions, and lessons in a replicable playbook that can guide future implementation without compromising quality or student outcomes.

Academic program leadership

• Along with the Chief of Schools Officer and Managing Director of Curriculum and Teaching Development, co-design and implement a rigorous, responsive academic model for students entering with varied educational histories and needs; this includes providing oversight, supervision and support of the special education program and teacher.
• Ensure each student has a complete academic profile, credit audit, individualized graduation plan, and progress-monitoring cycle.
• Coordinate curriculum, instruction, assessment, special populations support, professional learning, and academic quality with dotted-line academic leadership.
• Protect continuity of learning and graduation support when students are released, transferred, or remain incarcerated as well as support career and post secondary opportunities.
• Develop and continually adapt the academic calendar, daily schedule, course sequence, and instructional model to meet student needs within the operational and security constraints of the Hampden County House of Corrections.

Student-centered culture and support

• Collaborate with the Phoenix Springfield Head of School and the Managing Director of Equity to set and steward a student-centered culture grounded in dignity, belonging, clear expectations, and restorative justice practices - establishing the conditions for students to thrive academically and personally within a correctional environment.
• Create structures and supports that center student voice, agency, and leadership in program design and improvement, creating meaningful opportunities for students to shape their learning experience and own their academic goals.
• Coordinate student supports and partnerships that remove barriers to graduation, strengthen connections to community, and ensure continuity of support during, and after incarceration.

Team and cross-functional leadership

• Create effective cross-functional operating tools that align across the network, schools, and state partners.
• Hire, manage, coach, or influence staff and partners as the initiative’s structure evolves.
• In conjunction with the Phoenix Springfield Head of School, coordinate schedules of Phoenix Springfield staff members to provide in person and remote academic and student support to students at Hampden County House of Corrections.
• Contribute as a member of Phoenix’s statewide leadership group and participate in Phoenix Springfield all-staff activities.

Qualifications

Required

• Commitment to educational equity, the dignity and potential of incarcerated young people, and Phoenix’s mission.
• Strong understanding of secondary education, alternative education, postsecondary pathways, youth development, or a closely related field.
• Exceptional project management, communication, relationship building, and cross functional leadership skills.
• Experience launching or transforming complex programs across multiple organizations or systems.
• Experience using data for improvement and decision making; ability to partner effectively with evaluators, researchers, or public agencies.
• Demonstrated ability to lead both strategy and hands on implementation in a high accountability environment.
• Strong understanding of secondary education, alternative education, postsecondary pathways, youth development, or a closely related field, with the judgment to lead an academically rigorous program.
• Ability to work daily inside a correctional facility and comply with all access, safety, screening, and training requirements.

Preferred

• Experience in prison education, juvenile or adult corrections, reentry, education policy, or public-sector partnership.
• Teaching and school leadership experience
• Experience scaling a pilot into a multi-site or statewide model.
• Experience with managing data systems, longitudinal data, program evaluation, and privacy-sensitive data-sharing.
• Graduate degree or equivalent advanced experience in education, public policy, organizational leadership, business, or a related field.