Academy Dean of Students SY

Opportunity Academy Dean of Students SY26-27

Holyoke Public Schools OPPORTUNITY ACADEMY - HOLYOKE, Massachusetts Open in Google Maps

This job is also posted in Holyoke Public Schools

Job : 5758165
Final date to receive applications: Jul 01, 2026 11:59 PM (Eastern Standard Time)
Posted: Jun 03, 2026 4:00 AM (UTC)
Starting Date: Aug 17, 2026

DISTRICT OVERVIEW Holyoke Public Schools is a PreK-12 public school district serving nearly 5,100 students, of whom 80 percent are Latino/Latina, in 11 schools. We employ nearly 1,300 people who together educate and support a richly diverse community of learners. We are committed to recruiting and retaining top-quality educators who believe all children can and will learn and who strive daily to make school a joyful place of discovery, support, and belonging.

Holyoke Public Schools’ strategic plan, "Moving Forward Together," builds on the strengths of our past while serving as a call to action to accelerate student learning by thinking differently about how we teach, how we work together, and how we support students’ well being. Our Equity Commitments are pledges we are making to address systemic equity challenges. We intentionally build a community that is anti‑racist, inclusive, and culturally responsive.

We ensure that students, families, and staff get the support they need to be successful. We seek out and incorporate the voices of those impacted, with a commitment to include those who have been excluded in the past. We promote access and inclusion for all students, staff, and families. We respect, embrace, and honor the diversity of our students, families, staff, and community.

We reflect on our own behavior to minimize harm to others. We create a culture of acceptance and empathy so that everyone feels valued and is able to contribute to our community’s success. Please visit the Holyoke Public Schools website to learn more about us as well as some of our recent accomplishments.

HPS has engaged in a high school redesign process starting in 2018, with the founding of HHSOA as one of the three main high school campuses as a critical piece of that redesign. Built upon choice, flexibility and access to diverse and challenging educational opportunities, HHSOA’s unique approach to the alternative model deepens student engagement and provides families and business and civic leaders explicit opportunities to partner with educators to help guide students’ career and college plans, as well as strengthen our local economy;

while simultaneously addressing each student’s path to graduation and post‑secondary readiness through an individualized approach.

The Dean of Students supports the Principal in building and maintaining a strong, consistent, and positive school culture. This role is responsible for leading systems that ensure students are engaged, meeting expectations, and able to access learning every day.

• Establish and maintain clear, consistent expectations for student behavior
• Serve as the primary point person for discipline and culture
• Serve as the primary authority for student behavior and discipline, including supporting teachers with in-class disruptions, removing students when necessary, and ensuring responses are consistent, restorative, and aligned to school expectations
• Build a school environment that is structured, predictable, and focused on learning
• Maintain a visible presence throughout the school day

• Lead and supervise the engagement team to ensure consistent outreach and student support
• Monitor student attendance and engagement
• Implement strategies and systems to improve attendance and participation
• Work with staff to ensure students are in class and engaged in learning
• Address barriers that impact student attendance and engagement

• Coach staff on effective implementation of the primary person model
• Support systems for student check‑ins, goal setting, and ongoing communication
• Ensure consistency in outreach, relationship‑building, and student support practices
• Monito…