The Pike School, a diverse PreK-9 community of 404 students on 35 acres in Andover (about 20 miles north of Boston), seeks a dedicated and energetic Upper School Dean of Student Life (grades 5-9) to begin mid July 2026 or sooner. This individual collaborates with and reports to the Head of Upper School and primarily oversees student life and programming, ensuring a vibrant, inclusive, and supportive environment that fosters student growth and community engagement. The Upper School Dean of Student Life plays a pivotal role in shaping the student experience, promoting a culture of respect, responsibility, and resilience. This position offers an exciting opportunity to make a meaningful impact within a dynamic educational community.

This search process is open to candidates interested in starting in the role in either mid July 2026 or sooner. Candidates should indicate their preference and availability to start in their letter of interest as part of their application materials. All candidates, regardless of start-date preference, will be considered equally in this process.

Contracts for subsequent years of employment will be on an August 1 start-date. In the traditional cycle of this role, it is an 11-month, non-administrative team position with an annual salary range of $100,000–$120,000 and a benefits package that includes health insurance, life insurance, and access to a retirement 403(b) plan. 

This is a retained search with Educational Directions. Please learn more at https://edudx.com/wp-content/uploads/2025/11/Pike-School-Position-Profile-US-Dean-of-Students.pdf and direct all inquiries, applications, and nominations in confidence to Nicole McDermott (she/her) at nicole.mcdermott@edudx.com. 

About The Pike School, Inc.

The Pike School in Andover, Massachusetts, is an independent day school of 440 students in grades Pre-kindergarten through Grade Nine. The Pike School community represents culturally and socio-economically diverse families from 38 communities. Pike seeks candidates who possess skills in multicultural teaching and leadership practices and a dedication to working in a diverse community. Candidates must also have demonstrated a commitment to collaboration and lifelong learning, as well as an expertise in best practices in elementary education.

Connections working at The Pike School, Inc.