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Dean of Students

Gladwyne Montessori
Philadelphia, PA Full Time
POSTED ON 4/9/2026
AVAILABLE BEFORE 5/7/2026

Position Title: Dean of Students

Department: Administration

Reporting to: Assistant Head of School (AHOS)

FLSA Status: Exempt | Full-time

With Dr. Maria Montessori’s research-based philosophy and curriculum as our foundation, we provide infants to adolescents an authentic, individualized learning experience that cultivates an unparalleled depth of knowledge. The Dean of Students has the unique opportunity to work with an exceptional team of professionals to elevate this well-established, highly loved and respected school to heights that ensure both its longevity and continued wide-spread impact. Gladwyne Montessori is the education of the future: here, now.

This is a full-time position that boasts comprehensive benefits and a salary commensurate with experience.

Position Description:

As Dean of Students, you help lead the efforts to build and maintain a strong, positive, community-oriented school culture. You will manage the behavior programs for the school and establish strong, mutually respectful relationships with students and families. This position is a visible presence in all areas of the school and is responsible for all issues relating to the well-being of the students at school. Additionally, you will help parents echo these values in the home. This is a peer to teachers role - not supervisory.  

Primary Responsibilities:

●    Work full-time hours 

●    Support teachers to resolve differences in communication with parents and students and escalate to AHOS when necessary

●    Organize and review results of various student assessments

●    Review progress reports, including mid-semester progress and conference reports

●    Organize and execute student academic and behavior support, along with clear documentation, with input from AHOS and Student Support Team (SST)

●    Maintain student discipline and follow through with documentation and escalate to AHOS when necessary

●    Coordinate the planning and preparation for new student orientation alongside department coordinators.

●    Communicate and meet with parents regarding student performance and/or conduct. This may include time sensitive phone calls to parents as well as facilitating social concerns.

●    Support teachers in building positive relationships with parents and students

●    Coordinate student academic support intervention and action plans with support from SST and AHOS

●    Work with other members of the Student Support Team to build a culture of support and celebration

●    Lead Parent Education Workshops periodically 

●    Attend and support Department coordinator meetings

●    Participate in all faculty and staff meetings

●    Support the ex-missions process by tracking and sending schools requested information

Qualifications:

●    Bachelor's degree required, Master's degree preferred;

●    Experience working in education

●    Have a strong belief in and adherence to the Montessori philosophy

●    Have strong relationship building skills;

●    Be well read on racial literacy and be willing to continually to grow in this area.

●    Possess strong communication skills that allow you to keep AHOS in the know while also partnering with teachers in a supportive manner (not managerial);

●    Have the ability to effectively analyze data to improve student achievement;

●    Have excellent oral and written communication skills;

●    Have the ability to exercise excellent judgment and decision-making;

●    Demonstrate racial literacy and cultural competency in all interactions; 

●    Have excellent problem-solving and negotiating skills

●    Provide facilitation between teachers, parents for student support

●    Have the ability to work independently with diverse constituents while maintaining high professional standards;

●    Have exemplary organizational skills along with the ability to establish and manage multiple priorities and the ability to work under pressure;

● Have an outstanding attention to detail and accuracy;

● Have patience, flexibility and a sense of humor.

Gladwyne Montessori School is an equal opportunity at-will employer and does not discriminate against any employee or applicant for employment because of age, race, religion, color, disability, sex, sexual orientation or national origin. 

Interested candidates: Submit a cover letter, resume, and representative work samples below.

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