At Hillside School, we educate the whole child by instilling the values of compassion, determination, honesty, respect, and responsibility in a structured, supportive, and nurturing environment. Our mission is to support each boy’s academic and personal growth, preparing him for success in secondary school and beyond.

Hillside School is excited to open a brand-new Lower School division in September 2025 and is seeking a resourceful and community-oriented Administrative Assistant & Substitute Teacher to support the launch and day-to-day operations. This hybrid role combines front office administrative support, classroom coverage, and student transportation responsibilities. As a residential staff member, the employee will live on campus and be a vital part of Hillside’s collaborative and mission-driven environment.

Key Responsibilities

Administrative & Front Desk Duties

• Serve as the welcoming presence at the Lower School front desk
  
• Manage attendance, student arrivals/departures, and general inquiries
  
• Communicate effectively with parents, staff, and school leadership
  
• Maintain records, calendars, and supplies to support school operations
  

Substitute Teaching

• Provide classroom coverage for grades 4–6 when faculty are absent
  
• Implement teacher-provided lesson plans and ensure classroom continuity
  
• Foster a supportive and respectful learning environment in line with Hillside’s values
  

Transportation & Logistics

• Safely transport students between the Lower and Upper School areas using a school vehicle
  
• Maintain punctual and consistent shuttle service
  
• Uphold student safety and positive behavior during transitions

Qualifications

• Experience in an administrative, educational, or youth-support role
  
• Strong organizational and communication skills
  
• Positive attitude and ability to work independently and as part of a team
  
• Valid driver’s license and clean driving record
• Proficiency in Google Workspace and standard office technology

Requirements

• Bachelor’s degree or related coursework
  
• CPR/First Aid certification 

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.

Connections working at Hillside School