Careers

Waynflete seeks teachers and staff who are inspired by our mission, want to work in a school environment, and are dedicated to serving the needs of children. We seek qualified individuals with the knowledge, skills, and ability to enhance the student experience and strengthen our community.

Waynflete prides itself on being a place where children are known, where relationships are at the core of the experience, and where students of all walks of life can excel. When hiring faculty and staff, we seek individuals who will embrace our values and want to continue to grow as professionals.

Waynflete has an institutional commitment to the principles of diversity, equity, and inclusion. Waynflete seeks candidates who are practicing, and want to continue to develop, inclusive methods in their teaching, team work, and leadership. We believe that all students benefit from more inclusive environments.

Current Opportunities

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Associate Dean of Admission and Affordability (3/25/25)

Waynflete seeks a highly motivated and compassionate Associate Dean of Admission and Affordability to join our team. This pivotal 12-month position combines strategic enrollment management, comprehensive student support, and proactive family engagement. The Associate Dean will provide vision and leadership in attracting and supporting a diverse student body, managing tuition assistance, and fostering a welcoming and inclusive school community. This role requires a blend of strategic thinking, exceptional interpersonal skills, and a deep commitment to student success.

Responsibilities:

Enrollment and Tuition Assistance:

Provide strategic vision and direction for student enrollment, with a focus on attracting and recruiting diverse candidates.
Oversee all aspects of the tuition assistance program, including file reviews, parent communications, and fund allocation.
Serve as the primary contact for families with tuition assistance needs.
Stay informed on tuition assistance trends.
Support the admission process, including application review, interviews, and decision-making.
Serve as the primary Designated School Official (DSO) for the Student and Exchange Visitor Program (SEVP).
Engage with CRM databases (e.g., Veracross, Ravenna) and tuition assistance platforms (e.g., Clarity, SSS).
Support the Student Ambassador program.
Help plan and execute admission events and programs.

Student Support:

Provide dedicated support to Waynflete’s Students Qualifying for Extra Support program (SQES students), including regular check-ins and resource management.
Maintain office hours for student support.
Collaborate with advisors to assess student needs and coordinate support services (tutoring, translation, etc.).
Collaborate with the Director of Support Services to address non-tuition-related needs

Family Engagement:

Serve as a liaison between families and the school, facilitating communication and support.
Support new family transitions.
Coordinate interpreter services.
Foster family participation in school events.
Collaborate with the Parents Association.
Develop and implement multicultural outreach strategies.
Foster an inclusive community that supports diverse students.
Participate in DEI initiatives, including co-organizing community events.

Preferred qualifications:

Bachelor’s degree required; master’s degree preferred.
Minimum of 3-5 years of experience in independent school admission or enrollment management.
Experience with tuition assistance management.
Experience working with diverse student populations and families.
Strong communication, interpersonal, and organizational skills.
Proficiency in CRM databases and tuition assistance platforms.
Experience with case management.
Demonstrated commitment to creating a welcoming and inclusive community.
Experience with SEVP and DSO responsibilities.

Desired Attributes:

Empathetic and patient.
Proactive and resourceful.
Culturally sensitive and inclusive.
Ability to build strong relationships.
Strong problem-solving skills.
Ability to maintain confidentiality.

To apply, please click here and upload a resume, cover letter, and contact info for three professional references. Applications will be reviewed immediately and the position will remain open until filled. No phone calls, please.

Middle School Director (3/25/25)

Waynflete School in Portland, ME, has engaged DovetailED to lead a search for a Middle School Director beginning July 2025. Interested candidates should review the opportunity statement and submit a cover letter, resume, and list of references as a consolidated PDF to Lynda Hamilton-Kirk, Managing Partner at .

Director of Performing Arts (1/13/25)

Waynflete School seeks to hire an experienced and dynamic Director of the Performing Arts to begin in the 2025-26 school year. This is an exciting time at Waynflete as the School has spent the last seven years responding to a Curricular Review that inspired major changes in performing arts programming and pedagogy, and strengthened the experience in all performing arts areas and at all school levels. We are looking for a visionary individual to lead the team as it continues to strengthen and expand the program and innovate for the future. The ideal candidate will bring experience in leading curricular development efforts in instrumental and choral music, theater arts and dance. The responsibilities of the Director will include, but are not limited to, the following:

Provide a vision and advocacy for the performing arts at Waynflete.
Design and support performing arts programming across the three divisions of the school working closely with Division Directors and the Performing Arts faculty.
Manage, lead and supervise the part-time and full-time performing arts faculty.
Facilitate long-range planning and goal setting for the group.
Manage the Performing Arts Budget.
Collaborate with the other 6-12 Department Chairs and Lower School Team Leaders on curricular leadership and strategic initiatives.
Teach in one of the performing arts areas (required); preference will be given to choral directors.

With an institutional commitment to the principles of diversity, equity, and inclusion, Waynflete seeks candidates who are committed to developing inclusive methods in their teaching, teamwork, and leadership. We believe that all students benefit from more inclusive environments. Taking inspiration from our mission, we seek qualified faculty and staff with the knowledge, skills, and abilities to enhance the student experience and strengthen our community.

To apply, please click here and upload a resume, cover letter, and contact info for three professional references. If available, letters of recommendation and unofficial transcripts are appreciated. No phone calls, please. Applications will be reviewed immediately and the position will remain open until filled.

Summer Camp Positions (1/13/25)

Looking for a fun and rewarding way to spend your summer? Join our team at camp! We’re hiring for a variety of positions, from leading outdoor activities to arts and crafts, sports, and more. It’s a great chance to work with a fantastic team, enjoy the outdoors, and make a positive impact on campers’ summer experiences. If you’re ready to combine work and fun, we’d love to hear from you!

Bus Driver - Trips & Weekends (11/1/24)

Waynflete is seeking a licensed school bus driver beginning with the 2024-2025 school year for approximately 20 to 30 hours per week during the school year — hours fluctuate between busy sports seasons and quieter weeks. Duties include providing transportation for field trips, athletics, and other school-related events; training to be a substitute route driver is possible if desired. Weekend and evening availability is key. The successful candidate must have a flexible schedule, positive attitude, enjoy children, work well in a team setting, and pass a school-required physical. Strong driving experience and a commitment to safety are essential. Commercial driver’s license with P and S endorsements and DOT physical clearance is required.

With an institutional commitment to the principles of diversity, equity, and inclusion, Waynflete seeks candidates who are committed to developing inclusive methods in their teaching, teamwork, and leadership. We believe that all students benefit from more inclusive environments. Taking inspiration from our mission, we seek qualified faculty and staff with the knowledge, skills, and abilities to enhance the student experience and strengthen our community.

To apply, please click here and upload a resume and contact info for three professional references. Applications will be reviewed immediately and the position will remain open until filled. No phone calls, please.

Transportation Director (10/11/24)

Waynflete School, serving 565 students in grades Early Childhood through 12th grade, seeks a Transportation Director. The Director will develop, organize and manage all transportation needs for the Waynflete community. Waynflete seeks employees who are inspired by our mission, want to work in a school environment, and are dedicated to serving the needs of children.

The Director is responsible for maintaining a safe fleet; ensuring compliance with state, federal and local laws; supervising our Transportation Team; providing efficient transportation to students on daily routes from Auburn, Bath, Kennebunk, Westbrook and Cape Elizabeth as well as for all athletic and field trips. The successful Director will collaborate with people throughout the school to ensure transportation needs are met in a safe, professional, and timely manner. The Director will promote teamwork and effective communication, and will embody the mission and values of Waynflete School.

Essential Duties and Responsibilities include the following:

To supervise the daily work of the Transportation team, evaluate their efforts, and support their work as a team;
To manage the hiring process as needed to maintain a full Transportation Team;
To ensure compliance with all transportation reporting, safety, training, licensing, and maintenance standards as required by local, state, and federal law;
To plan, prioritize, implement, manage, and oversee the maintenance and repairs of the fleet;
To oversee and manage expenditures within the transportation operating and capital budgets;
To work cooperatively with all members of the school community, and in particular to develop collaborative relationships with the Division Directors and Assistants, the Athletics Director and Assistant Director, and the Auxiliary Programs Director.
To drive for activities and fill in for Route drivers as needed.
To perform other duties as assigned by the Associate Head of School and/or Head of School.

Basic Skills, knowledge & abilities:

Exceptional personal, organizational and communication skills;
Implement strong supervisory skills and able to work collaboratively with a team;
Understand and implement state and federal laws, codes, rules and regulations related to Transportation;
Detail oriented with strong technological skills (Google suite, Veracross);
Proven success developing and meeting an annual budget;
Flexibility, time management and prioritization skills;
Able to work independently; anticipate, plan and organize work;
Ability to relate effectively with a diverse community.

Qualifications:

Bachelor’s degree
CDLB license with P and S endorsement
DOT Card
Prior experience in transportation in an educational or similar institution
Prior management experience

Position details:

This is a year-round, full time position; salary will be commensurate with experience.

Benefits include:

Medical Insurance
Dental insurance
Life, AD&D, and long-term disability insurance
403(b) retirement plan with generous school matching contribution
Medical and dependent care flexible spending accounts
Tuition benefit and financial aid
Discounted summer camp and after-care programs
Employee education/professional development grants
Use of school library and fitness room
Paid leave

With an institutional commitment to the principles of diversity, equity, and inclusion, Waynflete seeks candidates who are committed to developing inclusive methods in their teaching, teamwork, and leadership. We believe that all students benefit from more inclusive environments. Taking inspiration from our mission, we seek qualified faculty and staff with the knowledge, skills, and abilities to enhance the student experience and strengthen our community.

To apply, please click here and upload a resume, cover letter, and contact info for three professional references. Applications will be reviewed immediately and the position will remain open until filled. No phone calls, please.

General interest in working at Waynflete

If you would like to submit an application for general consideration for future openings, please click here: Submit a General Application

Waynflete seeks teachers and staff who are inspired by our mission, want to work in a school environment, and are dedicated to serving the needs of children. We seek qualified individuals with the knowledge, skills, and ability to enhance the student experience and strengthen our community. Waynflete has an institutional commitment to the principles of diversity, equity, and inclusion. Waynflete seeks candidates who are practicing, and want to continue to develop, inclusive methods in their teaching, team work, and leadership. We believe that all students benefit from more inclusive environments.

Apply

Click here to apply for one of Waynflete’s open positions.

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Application Procedure

For teaching positions, a bachelor’s degree in relevant field is required; a master’s degree and teaching experience preferred. For administrative staff positions, we look for relevant experience and education for the posted job. We are particularly interested in candidates with a proven commitment to teaching and working in a diverse and multicultural setting.

Full background checks are required for all positions including fingerprinting as required by Maine State Law.

Procedures:

Click here to apply to all positions.
In accordance with Maine law, all persons hired to work at Waynflete must hold a current Criminal History Records Check (CHRC) certification from the Maine Department of Education. Click here for more information on obtaining a CHRC.

Benefits

Medical Insurance
Dental insurance
Life, AD&D, and long-term disability insurance
403(b) retirement plan with generous school matching contribution
Medical and dependent care flexible spending accounts
Tuition benefit and financial aid
Discounted summer camp and after-care programs
Employee education/professional development grants
Use of school library and fitness room
Paid leave

Living in Maine

Portland is a diverse, creative, and beautiful city that offers virtually everything a person could want. It is a walking city with accessible arts, cultural, and outdoor activities. The food scene is renowned as one of the best in the country. Portland has frequently been listed as one of America’s top cities to live, work, play, and visit.

Greater Portland boasts residents from all over the world, making it a vibrant and diverse global city. The local public elementary school, Reiche, has students from twenty-two nations represented, with twenty-nine languages spoken.

Visit Portland Maine

Portland Downtown: Moving to and living in Portland

7 Reasons “Not” to Move to Maine

US News and World Report: Living in Portland, Maine

Portland, Maine, Is the 2018 Restaurant City of the Year

Equal Opportunity Statement

Waynflete School provides equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sexual orientation, gender identity or expression, ancestry, national origin, age, disability, sex, genetic information, protected veteran status or any other category protected by federal, state, and local laws.

This policy applies to all terms and conditions of employment, including hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.

Waynflete School expressly prohibits any unlawful form of employee harassment based on race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, disability, sex, genetic information, protected veteran status, or no other category protected under federal, state, and local laws. Improper interference with the ability of Waynflete School employees to perform their expected job duties is absolutely not tolerated.