Posted: Mar 31, 2026
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Summer Programs Counselor

Westover School - Middlebury, CT
Temporary
Application Deadline: N/A

Department: Auxiliary Programs 

Reports to: Auxiliary Programs Manager 

Position Type: Seasonal (July), Live-in

 

About Westover School

Westover School is a gender-inclusive girls boarding and day school serving grades 9–12, where smart, motivated students become confident, connected adults. We are committed to providing a college preparatory education in a small community atmosphere that emphasizes student-adult interaction. Through our programs and faculty, Westover fosters the confidence and strength each student needs to shape their own life.

Westover’s summer programs extend this mission by offering themed, week-long experiences to middle school students, grounded in community, empowerment, and joyful learning.

Job Summary

Westover School seeks enthusiastic, responsible Summer Program Counselors to support daily programming and serve as essential members of the residential life team. Counselors work closely with faculty and the Auxiliary Programs Manager to supervise students, facilitate activities, and help create a warm, inclusive, and community-centered environment.

This is a live-in, seasonal role ideal for college students, college-aged adults, and Westover graduates. Counselors serve as role models, mentors, activity leaders, and residential life supervisors throughout the month of July.

Program Timeline:

  • Training & Orientation: Begins July 1
  • Boarders Arrive: July 5
  • Program Duration: Full month of July

Responsibilities and Duties

Program Support

  • Assist faculty and program leadership with daily activities, workshops, and themed sessions
  • Support setup, cleanup, transitions, and materials preparation
  • Engage actively with students during instructional time, recreation, and group activities

Student Supervision & Community Culture

  • Provide attentive supervision during meals, transitions, free time, and evening programming
  • Serve as a positive role model, helping to foster a respectful, inclusive, and supportive community
  • Support students’ social-emotional needs, including peer dynamics and homesickness, with guidance from program leadership

Residential Life

  • Live on campus and participate fully in duty rotations, including evenings and weekends
  • Supervise dormitory spaces, curfews, and community expectations
  • Support and model Westover’s standards for safety, respect, and community conduct

Safety, Risk Management & Logistics

  • Maintain active supervision of students at all times
  • Follow emergency procedures, incident reporting protocols, and health and safety guidelines
  • Assist with field trips, off-campus activities, and transportation as needed
  • Ensure program spaces remain safe, clean, and organized

Required Qualifications and Skills

  • Must be at least 18 years of age
  • CPR/First Aid certification, or willingness to obtain during onboarding
  • Experience working with youth (e.g., camps, coaching, tutoring, mentoring, babysitting)
  • Strong communication, collaboration, and interpersonal skills
  • Ability to live on campus for the duration of the program and participate in duty rotations
  • Commitment to fostering an inclusive, supportive, and developmentally appropriate environment

Preferred Qualifications

  • Experience in a residential life, camp, or youth development setting
  • Familiarity with independent school environments or prior connection to Westover
  • Valid driver’s license preferred, but not required

Working Conditions

  • Residential, live-on-campus role for the duration of the July program
  • Schedule includes evenings, weekends, and on-call responsibilities as part of duty rotations
  • Fast-paced, active environment with both indoor and outdoor responsibilities
  • Regular supervision of minors in both group and residential settings

Physical Requirements

  • Ability to lift up to 25 pounds
  • Ability to walk across campus, navigate stairs, and supervise physically active programming
  • Ability to work outdoors in summer weather conditions for extended periods

Compensation and Benefits

This is a seasonal, live-in position. Compensation is provided as a stipend commensurate with experience. On-campus housing and meals are included for the duration of the program.

Equal Employment Opportunity Statement

Westover School is an Equal Opportunity Employer and does not discriminate on the basis of race, color, religion, national or ethnic origin, sex, sexual orientation, gender identity or expression, age, disability, veteran status, or any other characteristic protected by applicable law. We are committed to building a diverse and inclusive community and strongly encourage candidates from historically underrepresented backgrounds to apply.