Head of High School

12M Recruiting; Prides Crossing (MA); On-site; USD 120,000 - 180,000; Full time

Job summary

Landmark School in Prides Crossing, MA, seeks a visionary Head of High School (HHS) to oversee the day and residential program for grades 2–12 with dyslexia and related language-based learning differences.

The HHS will lead faculty, shape key initiatives, and drive academic leadership for the high school." This executive role reports to the Head of School and offers the opportunity to build on Landmark's proven Language-Based Learning Model while guiding growth and excellence for the next

Responsibilities

• Oversee the high school day and residential program.
• Develop faculty and instructional leaders.
• Lead the implementation and evolution of key high school initiatives.
• Support all high school faculty and lead the High School Leadership team.

Job description

SUMMARY

Landmark School is a coeducational day and boarding school serving students in grades 2–12 with dyslexia and other language-based learning differences (LBLD). Landmark believes that dyslexic minds deserve an education as remarkable as their thinking. For more than 50 years, the school has developed a distinctive approach that combines individualized instruction, small classes, one-to-one tutorials, highly trained faculty, and evidence-based practices designed around how students with language-based learning differences learn best. At the heart of the Landmark experience is its Language-Based Learning Model, which integrates structured literacy instruction, critical thinking and exploration, executive function skill building, and empowerment and advocacy. The model is intended to shape the entire student experience, helping students not only address areas of difficulty but also understand themselves as learners, develop confidence and independence, and apply their strengths in increasingly complex academic and real-world contexts. Landmark seeks its next head of high school (HHS), a thoughtful, experienced, and deeply relational academic leader who can build on this strong foundation and help the high school realize its full potential. The HHS will oversee the high school day and residential program, develop faculty and instructional leaders and lead the implementation and evolution of key high school initiatives. In addition to supporting all high school faculty, the HHS oversees the High School Leadership team including, the dean of students, the dean of engagement and culture, the dean of learning, and the dean of leadership development and recruiting. The opportunity comes at an important moment as Landmark has undertaken significant organizational and programmatic work in recent years. The HHS will enter a school with substantial expertise and commitment, alongside a clear appetite for continued growth. Landmark’s vision for its next 50 years is ambitious: to establish the educational gold standard for students with dyslexia and language-based learning differences, invest deeply in its people, continue to innovate, and steward the resources necessary to sustain its mission. The HHS will help translate that ambition into an increasingly coherent, rigorous, and empowering high school experience. This is not a role that calls for preserving the status quo or imposing sweeping transformation. Rather, it calls for a leader who can understand what makes Landmark distinctive, identify where greater coherence and excellence are possible, and work collaboratively to turn priorities into sustainable practice. For a leader energized by specialized education, academic excellence, faculty development, and organizational leadership, Landmark offers a rare opportunity: to help define what educational excellence for dyslexic learners should look like for the next generation.The HHS reports directly to the Head of School and will begin July 1, 2027.

IMPORTANT INFORMATION

Priority Deadline: October 25, 2026

Quarterfinal Round: Early November

Semifinal Round: Mid-November

Final Round: Early December

Decision Announced: December 31, 2026

Start Date: July 1, 2027 (or earlier by mutual agreement)

Reports To: Head of School

Classification: Full-time, Exempt