Department: Transportation 

Reports to: Transportation Coordinator 

Position Type: Part-time, Non-exempt

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.

We empower students to be themselves, make their own choices, and experience a true sense of belonging—resulting in young adults who lead lives of purpose and meaning and understand the power of relationships.

Job Summary

Westover School is seeking detail-oriented and dependable drivers to support student transportation needs. Drivers are responsible for safely transporting students to and from appointments, athletic events, and school-related activities within Middlebury and surrounding areas.

This is a flexible, part-time position with hours scheduled on an as-needed basis. The ideal candidate demonstrates a strong commitment to student safety, professionalism, and reliability.

Responsibilities and Duties

• Coordinate daily driving assignments with the Transportation Coordinator and adapt to schedule or route changes as needed
• Conduct pre-trip safety inspections, including brakes, lights, horn, windshield wipers, emergency equipment, and overall vehicle condition
• Safely operate school vehicles to ensure timely and secure transport of students
• Refuel, clean, and return vehicles to designated parking areas; record mileage and complete post-trip inspections
• Report maintenance issues, safety concerns, or vehicle damage promptly
• Follow established procedures in the event of an accident, including contacting emergency services and completing required reports
• Maintain all required licenses and endorsements for assigned vehicles
• Demonstrate professionalism, courtesy, and strong customer service when interacting with students, families, and colleagues

Required Qualifications & Skills

• Valid Connecticut driver’s license required
• Public Passenger Endorsement (A or V) or willingness to obtain one
• CDL with Passenger (P) Endorsement preferred for operation of larger vehicles, but not required
• Clean driving record and ability to pass background checks and drug screenings
• Familiarity with vehicle safety checks and routine maintenance
• Strong communication skills and ability to remain calm under varying conditions
• Ability to work a flexible schedule, including evenings and weekends as needed
• Knowledge of local and state traffic laws and safety regulations
• Commitment to confidentiality and student privacy
• Ability to drive for extended periods (up to five hours or more)

Working Conditions

• Work is performed in school vehicles and throughout the local and regional area
• Schedule is flexible and based on transportation needs, including evenings and weekends
• Regular interaction with students, faculty, and families
• Driving may occur in varying weather and traffic conditions

Physical Requirements

• Ability to sit and drive for extended periods of time
• Ability to assist with minor vehicle-related tasks as needed
• Ability to lift up to 25 pounds

Compensation & Benefits

This is a part-time, non-exempt position. Compensation is based on an hourly rate commensurate with experience.

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.

Associate Director of Admission 

Department: Office of Admission 

Reports to: Director of Enrollment Management 

Status: Full-time, 12-month position

About Us

Westover School is a vibrant independent boarding and day school dedicated to empowering young women through rigorous academics, leadership opportunities, and a supportive community. Our mission-centered admission process is essential to sustaining a diverse, engaged, and thriving student body.

The Office of Admission plays a critical role in shaping the future of Westover by identifying, recruiting, and enrolling students who will contribute meaningfully to the academic and community life of the school.

Westover School in Middlebury, CT has engaged DovetailED to lead a search for an Associate Director of Admission to start July 1, 2026. Interested candidates should review the Opportunity Statement and submit a cover letter, resume, and list of references as a consolidated PDF to Madison Sunley, Senior Recruiter at DovetailED Talent Sourcing, at madison@dovetailedsourcing.com.        

Westover School Associate Director of Admissions Opportunity Statement Link: https://bit.ly/westover-admission.

Job Summary

The Associate Director of Admission plays a key role in recruiting and enrolling mission-appropriate students who can thrive at Westover School. Reporting to the Director of Enrollment Management, this position is responsible for managing an assigned recruitment territory, cultivating relationships with prospective families and educational partners, and contributing to all aspects of the admission process.

This role requires a high level of initiative, strong interpersonal skills, comfort with extensive travel, and the ability to balance strategic planning with day-to-day execution in a fast-paced, student- and family-centered environment.

Responsibilities and Duties

Student Recruitment and Enrollment

• Serve as a primary recruiter for assigned geographic territories, including setting recruitment goals, monitoring metrics, and executing strategies to increase yield from target markets.
• Travel extensively (approximately 50% or more of the time) to represent Westover at conferences, school fairs, and recruitment events, coordinating with other Westover offices and partner boarding schools as appropriate.
• Cultivate and maintain relationships with educational consultants, placement directors, and school partners.
• Interview prospective students and families and serve as a key ambassador for Westover’s mission and values.

Admission Operations and Data Management

• Enter interview notes, contact records, communications with prospective families, and travel details into the admission database in a timely and accurate manner.
• Utilize and maintain database systems (including Blackbaud K–12) to track recruitment activity, manage communication, and support enrollment goals.
• Apply market research, demographic data, and enrollment trends to inform recruitment strategies.

Campus Programs and Events

• Collaborate with the Admission team on all aspects of Westover’s campus visit program.
• Strategize, plan, and execute admission events and initiatives in collaboration with the Office of Admission.
• Support broader enrollment management initiatives as needed.

Collaboration and Communication

• Partner with colleagues across campus to support recruitment efforts and ensure a cohesive admission experience for prospective families.
• Educate families on the financial aid process in collaboration with the enrollment and business offices.
• Contribute positively to a collaborative, professional, and mission-aligned admission team culture.

Required Qualifications and Skills

• Mid-level recruitment experience at an independent boarding school required.
• Exceptional written, verbal, and interpersonal communication skills.
• Strong analytical, organizational, and technological skills.
• Understanding of market research, demographics, and student recruitment strategies.
• Basic financial acumen to effectively communicate about the financial aid process.
• Experience with database management systems; familiarity with Blackbaud K–12 strongly preferred.
• Ability to multitask, remain flexible, and work effectively in a fast-paced, customer-centric environment.

Working Conditions

This role involves extensive travel, including evenings and weekends, particularly during peak recruitment seasons. Work includes extended periods of sitting, computer use, data entry, and standing or walking during tours, fairs, and events. Frequent stair use and occasional lifting are required.

Physical Requirements

• Ability to travel frequently and work flexible hours.
• Ability to stand and walk for extended periods during tours, visits, and recruitment events.
• Ability to lift and carry materials related to travel and events.
• Ability to work at a computer and communicate effectively in person, by phone, and electronically.

Compensation and Benefits

This is a full-time, 12-month position. Compensation is commensurate with experience. Westover School offers a comprehensive benefits package for eligible employees, including health and vision insurance, dental reimbursement, health reimbursement arrangement (HRA), life insurance, retirement plan with employer contributions, and professional development support.

Equal Employment Opportunity (EEO) Statement

Westover School is an Equal Opportunity Employer and does not discriminate based on race, color, religion, national origin, ancestry, citizenship status, age, disability, sex, marital status, veteran status, sexual orientation, gender identity or expression, genetic information, or any other characteristic protected by applicable law. We are committed to building a diverse and inclusive community and strongly encourage applications from candidates from historically marginalized or underrepresented backgrounds, as well as those with non-traditional career paths.

Westover School in Middlebury, CT has engaged DovetailED to lead a search for an Associate Director of Admission to start July 1, 2026. Interested candidates should review the Opportunity Statement and submit a cover letter, resume, and list of references as a consolidated PDF to Madison Sunley, Senior Recruiter at DovetailED Talent Sourcing, at madison@dovetailedsourcing.com.        

Westover School Associate Director of Admissions Opportunity Statement Link: https://bit.ly/westover-admission.

Department: Student Life 

Reports to: Director of Community Life & Culture and Assistant Director of Community Life 

Status: Full-time, 10-month, residential position

About Us

Westover School is a gender-inclusive girls boarding and day school for grades 9–12. Our community is built on close student–adult relationships, shared responsibility, and a deep belief that young people thrive when expectations are clear, care is consistent, and belonging is intentional.

The Office of Community Life plays a central role in shaping the lived experience of students at Westover. This work requires presence, sound judgment, compassion, and the ability to translate values into daily practice within a residential school environment.

Job Summary

The Traditions & Activities Coordinator is a central operational member of the Student Life team and is responsible for the design, coordination, and execution of student activities and school traditions. This role ensures that community programming is vibrant, inclusive, and well-organized, and that students experience a strong sense of connection, celebration, and belonging through shared experiences.

Working in close partnership with the Assistant Director of Community Life, the Traditions & Activities Coordinator collaborates extensively with community life colleagues, student leaders, faculty, and staff. This role includes residential responsibilities as a dorm parent, coaching one season, and maintaining a visible and relational presence with students in daily life.

Responsibilities and Duties

Student Activities and Community Programming

• Design and implement a diverse range of on- and off-campus weekend activities, including programs with area consortium schools, in collaboration with the Student Activities Committee and student leadership.
• Coordinate the monthly Community Dinner program for boarding students.
• Collaborate with the Community Life team and Rasin Center staff to implement cohesive and intentional community programming, including grade-level initiatives, leadership development, student organizations, and affinity group opportunities.
• Partner with faculty and staff colleagues to expand co-curricular offerings beyond the traditional social activities calendar.
• Participate in and support programming connected to the Westover Institute.
• Collaborate closely with the Assistant Director of Community Life, the Community Life Coordinator, and the Rasin Center team to ensure alignment between student activities and broader institutional goals.

Traditions Coordination and Stewardship

• Oversee and manage Westover’s traditions, ensuring continuity while fostering student engagement and evolving practices to reflect the needs and values of current students.
• Coordinate logistics, student involvement, and faculty/staff support for major school-wide tradition-based events.
• Serve as a primary liaison for students, faculty, and alumni in upholding and celebrating community traditions.
• Support the development, training, and mentorship of student leaders related to traditions and school culture.
• Serve as advisor to key student leadership groups connected to traditions, including Spirit Heads, Dorcas Heads, and Student Heads of School.
• Provide stewardship for long-standing traditions that foster community connection and school spirit

Additional Responsibilities

• Coach one season in an interscholastic or co-curricular program, as assigned.
• Participate actively in evening and weekend residential duties as part of the dorm parent role.
• Support community life initiatives and special projects as needed to ensure smooth program operation.

Required Qualifications and Skills

• Bachelor’s degree preferred.
• Experience working with adolescents in a residential, school, or youth development setting.
• Strong organizational skills and attention to detail.
• Ability to manage multiple priorities and respond flexibly to changing needs.
• Strong interpersonal skills and ability to build positive relationships with students and colleagues.
• Commitment to student well-being, inclusion, and community values.

Working Conditions

This is a residential position requiring regular evening, weekend, and overnight duty as part of the dorm parent rotation. The role involves frequent interaction with students, faculty, and staff and requires flexibility to support a dynamic activities and traditions calendar. Work is performed primarily on campus in school and residential settings, with some off-campus travel for activities and consortium events.

Physical Requirements

The physical demands described here are representative of those that must be met to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform essential functions.

• Ability to move throughout campus, including residence halls and academic buildings.
• Ability to stand for extended periods during events and activities.
• Ability to lift or move up to approximately 25 pounds (event supplies, materials).
• Ability to work at a computer and communicate in person, by phone, and electronically.

Compensation and Benefits

This is a full-time, 10-month, residential position with a salary range of $45,000–$55,000, commensurate with experience. Westover School offers a comprehensive benefits package, including:

• Health and vision insurance
• Dental reimbursement
• Health Reimbursement Arrangement (HRA)
• Life insurance
• Retirement plan with employer contributions
• Professional development support
• On-campus housing is provided in accordance with school residential policies.

Equal Employment Opportunity (EEO) Statement

Westover School is an Equal Opportunity Employer and does not discriminate based on race, color, religion, national origin, ancestry, citizenship status, age, disability, sex, marital status, veteran status, sexual orientation, gender identity or expression, genetic information, or any other characteristic protected by applicable law. We are committed to building a diverse and inclusive community and strongly encourage applications from candidates from historically marginalized or underrepresented backgrounds, as well as those with non-traditional career paths.

Reports to: Department Head and Associate Head of School 

Status: Full-time, 10-month faculty position

About Us

Westover School is a gender-inclusive girls boarding and day school for grades 9–12. Our community is built on close student–adult relationships, shared responsibility, and a deep belief that young people thrive when expectations are clear, care is consistent, and belonging is intentional.

Westover teachers are not only educators but mentors, advisors, and community members who contribute meaningfully to the academic, social, and residential life of the school.

Job Summary

Westover School seeks a Mathematics Teacher who is passionate about mathematical reasoning, problem-solving, and collaborative teaching practice. This teacher will be responsible for delivering rigorous, engaging, student-centered instruction while fostering a classroom environment grounded in clarity, inclusion, and high expectations. 

This educator fosters analytical thinking, problem-solving skills, and a deep understanding of mathematical concepts while supporting students’ intellectual growth, confidence, and readiness for college-level work. The teacher participates fully in the life of the school community through teaching, advising, residential life participation, and collaboration with colleagues.

Responsibilities and Duties

Teaching and Learning

• Teach a full course load or equivalent thereof, which may include Algebra II, Precalculus, Calculus, Statistics, or other advanced offerings, depending on program needs 
• Encourage mathematical reasoning, problem-solving, and analytical thinking.
• Plan and deliver engaging, developmentally appropriate instruction aligned with departmental curriculum.
• Create a classroom environment that supports belonging, respect, student engagement, and academic risk-taking.
• Assess student learning regularly and provide timely, meaningful feedback.
• Maintain accurate and up-to-date grading and course materials.
• Differentiate instruction to meet the needs of diverse learners and learning styles.

Student Support and Community Engagement

• Serve as an Advisor to a small group of students, providing academic and personal support.
• Communicate regularly and professionally with students, families, and colleagues regarding student progress and expectations.
• Support students beyond the classroom through meetings, extra help sessions, and informal connection.
• Support the residential life program including evening and weekend responsibilities during the academic year.
• Participate in school events, traditions, and community activities.

Professional Responsibilities

• Collaborate with colleagues within the department and across disciplines on curriculum development, alignment, and instructional improvement.
• Attend faculty meetings, professional development, and required school functions.
• Uphold school policies, community standards, and professional expectations.
• Contribute positively to a respectful, inclusive, and collegial faculty culture.

Required Qualifications and Skills

• Bachelor’s degree in Mathematics or a related field required; advanced degree preferred.
• Experience working with adolescents in an educational setting.
• Strong classroom management and organizational skills.
• Commitment to diversity, equity, inclusion, and culturally responsive practices.
• Excellent communication and collaboration skills.
• Passion for teaching mathematics, commitment to student development, and enthusiasm for ongoing collaboration with colleagues.

Working Conditions

• Work is performed in classrooms and across the school campus in a dynamic, student-centered environment
• Maintain an active and visible presence in the community, including participation in meetings, student support, and co-curricular activities
• Engage in the broader life of the school, contributing to a collaborative boarding school environment
• Participate in occasional evening and weekend responsibilities, including student events, family programming, and community gatherings
• Demonstrate flexibility and responsiveness to the evolving needs of students and the school community

Physical Requirements

• Ability to move throughout campus and stand for extended periods.
• Ability to work at a computer and communicate in person and electronically.
• Ability to lift or move up to approximately 25 pounds.

Compensation and Benefits

This is a full-time, 10-month faculty position with a salary range of $45,000–$55,000, commensurate with experience and aligned with Westover’s faculty salary scale. Westover School offers a comprehensive benefits package for eligible employees, including:

• Health and vision insurance
• Dental reimbursement
• Health Reimbursement Arrangement (HRA)
• Life insurance
• Retirement plan with employer contributions
• Professional development support

Equal Employment Opportunity (EEO) Statement

Westover School is an Equal Opportunity Employer and does not discriminate based on race, color, religion, national origin, ancestry, citizenship status, age, disability, sex, marital status, veteran status, sexual orientation, gender identity or expression, genetic information, or any other characteristic protected by applicable law. We are committed to building a diverse and inclusive community and strongly encourage applications from candidates from historically marginalized or underrepresented backgrounds, as well as those with non-traditional career paths.

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.

Department: Summer Programs 

Reports to: Summer Programs Director

Type: Temporary, Summer Position (2 Weeks)

About Us

Westover School is a gender-inclusive girls boarding and day school, 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 emphasizing student-adult interaction. Westover, through program and faculty, endeavors to develop in each student the confidence and strength to shape their own life.

We are empowering students to be themselves, make their own choices, and appreciate belonging and mattering—resulting in young adults who find lives of purpose and meaning, understand they can make a difference, and recognize the power of relationships.

Position Summary

Westover School seeks a dynamic, innovative, and relational STEM Teacher to design and teach GLOW: Girls Leading the World, a two-week immersive summer program for rising 5th–8th grade students. This experience centers on engineering, robotics, coding, innovation and invention, sustainability, and artificial intelligence.

The STEM Teacher will create an engaging, inclusive, and high-energy learning environment that integrates hands-on design, real-world problem solving, and makerspace fabrication tools. The program culminates in a Showcase of Learning, where students present prototypes, designs, and reflections.

Responsibilities and Duties

Curriculum Design & Instruction

• Design and implement a cohesive two-week curriculum aligned with engineering, robotics, coding, innovation/invention, sustainability, and AI in collaboration with Summer Programs Admin team. 
• Lead daily lessons with clear objectives, hands-on learning, collaboration, and reflection
• Integrate design thinking and the engineering design process
• Utilize makerspace equipment (e.g., Cricut, laser printer, 3D printer, robotics kits) safely and effectively
• Differentiate instruction to support varied readiness levels and learning styles

Classroom Environment & Management

• Establish clear routines, expectations, and norms appropriate for students ages 10–14
• Foster a safe, inclusive, and growth-oriented environment that promotes confidence in STEM
• Use proactive classroom management strategies that support engagement and collaboration
• Ensure safe and responsible use of tools, materials, and technology

Assessment & Feedback

• Monitor student understanding and skill development throughout the program
• Provide timely, actionable feedback that promotes reflection and iteration
• Track student progress through observation, check-ins, and student work
• Facilitate student self-assessment and peer feedback

Relationship Building & Student Engagement

• Build strong, supportive relationships with students
• Encourage leadership, collaboration, and student voice
• Create culturally responsive learning experiences that empower girls in STEM
• Communicate effectively with program leadership and families as needed

Showcase of Learning

• Design and coordinate a culminating showcase event
• Support students in preparing presentations that highlight their design process and learning
• Curate a professional, celebratory exhibition of student work

Required Qualifications and Skills

• Bachelor’s degree in a STEM field, Education, or related area (Master’s preferred)
• Experience teaching upper elementary or middle school students
• Demonstrated expertise in engineering design, robotics, coding, sustainability, and/or AI
• Experience with makerspace tools (e.g., 3D printers, laser cutters, Cricut machines)
• Strong classroom management skills for pre-teen learners
• Ability to design scaffolded, differentiated lessons for mixed-ability groups
• Experience with project-based learning and culminating student exhibitions
• Commitment to fostering confidence and leadership in girls in STEM

Working Conditions

• Work is performed in classrooms, makerspaces, and other campus learning environments
• Requires active facilitation of hands-on STEM activities and movement throughout the classroom
• Regular interaction with middle school-aged students in a fast-paced, high-energy summer program setting
• May include preparation time before and/or after program hours and participation in a culminating showcase event

Physical Requirements

• Ability to stand, walk, and move around the classroom for extended periods
• Ability to lift, move, and set up materials and equipment up to 25 pounds
• Ability to safely operate and supervise student use of makerspace tools and equipment

Compensation & Benefits

This is a temporary, two-week summer position. Compensation is competitive and commensurate with experience.

In addition to compensation, Westover School provides:

• Access to campus facilities and resources, including makerspaces and instructional materials
• Daily lunch provided during program days
• A collaborative, mission-driven work environment with a supportive Summer Programs team
• The opportunity to design and lead an innovative STEM curriculum in a hands-on, student-centered setting 

Equal Employment Opportunity (EEO) Statement

Westover School is an Equal Opportunity Employer and does not discriminate based on race, color, religion, national origin, ancestry, citizenship status, age, disability, sex, marital status, veteran status, sexual orientation, gender identity or expression, genetic information, or any other characteristic protected by applicable law. We are committed to building a diverse and inclusive community and strongly encourage applications from candidates from historically marginalized or underrepresented backgrounds, as well as those with non-traditional career paths.