Second/Third Grade Teacher (Grades 2–3)
Hillside School – Marlborough, MA
Start Date: August 2026

Position Summary
Hillside School, a junior boarding school serving grades 4–9 and launching an inaugural Lower School (K–3), seeks a dynamic and student-centered Second/Third Grade Teacher. This is a unique opportunity to help build a Grades 2–3 program within a collaborative and mission-driven environment.

Hillside is an International Baccalaureate (IB) Primary Years Programme (PYP) candidate school, and the successful candidate will play an active role in developing an inquiry-based, concept-driven curriculum grounded in best practices in elementary education.

Key Responsibilities

• Design and deliver engaging, developmentally appropriate instruction for students in Grades 2–3
• Implement inquiry-based learning aligned with the IB PYP framework (training provided)
• Differentiate instruction to support a range of learners
• Foster a positive, inclusive classroom culture that supports the whole child
• Integrate experiential learning, including work with Hillside’s Farm-Based Learning Lab
• Collaborate closely with Lower School colleagues on curriculum development and interdisciplinary planning
• Communicate effectively with families regarding student progress and classroom life
• Maintain accurate records and provide timely, constructive feedback

Qualifications

• Bachelor’s degree required; Master’s degree preferred
• Minimum of 3 years of elementary teaching experience (Grades 2–3 preferred)
• Strong understanding of child development and elementary pedagogy
• Experience with inquiry-based learning; IB PYP experience a plus
• Familiarity with Singapore Math or willingness to train (supported by the school)
• Excellent communication, organization, and collaboration skills
• Commitment to inclusive practices and whole-child education

Compensation and Benefits

• Competitive salary, commensurate with experience
• Comprehensive benefits package (health, dental, vision, retirement)
• Professional development, including IB PYP training
• Supportive, collaborative faculty culture
• On-campus housing available for eligible candidates

About Hillside School
Hillside School is a small, mission-driven independent school in Marlborough, Massachusetts, serving boys in grades 4–9. With the launch of its Lower School, Hillside is expanding its commitment to character development, academic growth, and experiential learning for younger students.

To Apply
Please submit a cover letter, résumé, and three professional references to:
Thomas Pipoli, Dean of Faculty & Academics
tpipoli@hillsideschool.net

Subject line: Second/Third Grade Teacher – Lower School

• Bachelor’s degree required; Master’s degree preferred
• Minimum of 3 years of elementary teaching experience (Grades 2–3 preferred)
• Strong understanding of child development and elementary pedagogy
• Experience with inquiry-based learning; IB PYP experience a plus
• Familiarity with Singapore Math or willingness to train (supported by the school)
• Excellent communication, organization, and collaboration skills
• Commitment to inclusive practices and whole-child education

About Hillside School

For over 100 years, Hillside School has been teaching boys the core values of compassion, determination, honesty, respect, and brotherhood. Since its founding, Hillside School has committed to offering an all-boys educational experience in a structured, inclusive, supportive environment. Our boarding and day program for boys in grades four through nine is unique in its ability to meet each student at his learning threshold and then truly maximize his potential, creating a transformative experience for our students. In 2025, Hillside will be opening its new coed Lower School, serving grades K-3.

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