Head of Learning Support

gogunn.org | Washington, CT 

The Frederick Gunn School, founded in 1850, is a co-ed boarding and day school for students in grades 9-12 as well as a post-graduate year. Mr. Gunn had a deep appreciation for the natural world, believing that in nature students understand themselves as humans and their place in the world. He took a principled stand against slavery and spurred students (and the town at large) to examine their beliefs. In addition to the habits and skills students will need in college and life beyond, we teach them to follow Mr. Gunn’s example: to cultivate wisdom, to be trailblazers, to act with conviction, and to value character as highly as intellect and achievement. 

Our continuous focus on moral character development intentionally engages all members of our school in the work of creating an inclusive and equitable living and learning ecosystem.  Community and citizenship are at the heart of our aspiration to both social justice and academic excellence, with individual diversity integral to the strength of that community. When we embrace difference and pursue school life with respect, equity, and compassion, we build a foundation for engaged citizens.

In keeping with the tenets of our founder Frederick Gunn, who was himself a prominent abolitionist and progressive educator, The Frederick Gunn School seeks to provide a pluralistic learning environment for all inclusive of (but not limited to): culture, ethnicity, gender identity or expression, national origin, learning differences, physical difference, political affiliation, race, religion, sex, sexual orientation, and socioeconomic differences.  

We invite applicants who resonate with our mission and who will foster an environment of cultural and intellectual richness and an active participant in advancing equity and inclusion.

Summary

The Head of Learning Support plays a pivotal role in supporting student success by leading a dedicated team of learning specialists, overseeing individualized academic support, and ensuring the effective delivery of services for students with diverse learning needs. This role involves collaborating closely with faculty, families, and school leadership to create and maintain comprehensive Learning Profiles, coordinate accommodations and testing services, and guide students in building essential academic and executive functioning skills. The Director also contributes to admissions decisions, manages departmental operations, and fosters a supportive, student-centered learning environment grounded in empathy, growth, and high expectations.

Responsibilities

• Lead, support, and supervise Learning Center Specialists while fostering a collaborative, student-centered environment
• Provide individualized academic coaching in executive functioning, study skills, and self-advocacy
• Develop and maintain Learning Profiles by interpreting neuropsychological evaluations and coordinating with faculty
• Collaborate with the Student Success Team, Health Center, and school psychologists to ensure holistic student support
• Oversee accommodations processes, including applications for College Board/ACT and management of distraction-free testing spaces
• Partner with Admissions to review academic/testing histories and recommend appropriate support for incoming students

Necessary Skills

• Instructional Leadership – Ability to mentor and support teachers, provide meaningful feedback, and foster professional growth
• Expertise in Learning Differences – Deep understanding of neurodiverse learning profiles and the ability to interpret and apply psychoeducational evaluations
• Communication & Collaboration – Strong interpersonal skills to work effectively with students, families, faculty, and external partners
• Organizational & Administrative Skills – Ability to manage scheduling, documentation, testing logistics, and multiple student support plans
• Commitment to the unique learning environment of a boarding school

Full Responsibilities 

Leadership & Team Management

• Oversee the Learning Support Program and manage a dedicated team of Learning Specialists and Learning Center teachers
• Observe learning support sessions and provide constructive, strengths-based feedback
• Contribute to the hiring, onboarding, and ongoing professional development of Learning Center faculty
• Organize and lead regular department meetings
• Communicate departmental needs and priorities to school leadership

Student Support & Instruction

• Provide individualized support in executive functioning, study skills, and academic strategies
• Help students develop lifelong learning habits, including a growth mindset, goal-setting, and self-advocacy
• Create and update Learning Profiles based on neuropsychological evaluations
  Read and interpret testing reports to evaluate student needs and recommend appropriate support levels
• Sit on the Student Success Team to collaborate with teachers, Health Center staff, and school psychologists for holistic student support

Accommodations & Testing Coordination

• Apply for accommodations through the College Board and ACT
• Manage distraction-free testing environments and scheduling
• Coordinate with Region 12 for local services, PPTs, and neuropsychological evaluations

Admissions & Family Communication

• Review academic and testing histories; meet with families to support admissions decisions and ongoing student success
• Collaborate with the Admissions Office to recommend appropriate support levels based on evaluations and learning needs
  Communicate with families about accommodations, testing, and student progress

Operations & Scheduling

• Manage and schedule all learning support sessions

Other

• Contribute to the broader school community, including potential opportunities for coaching and involvement in residential life

Desired Qualifications

• Advanced degree in special education or a comparable teaching resume
• 7+ years administrative or managerial experience

Job Details 

This is a 10-month, full-time position opening for the 25/26 school year. The offer of employment will be contingent upon a successful background check. 

Compensation and Qualifications 

The Frederick Gunn School offers an attractive compensation package that includes a salary commensurate with experience, school-provided housing, medical and dental insurance, and retirement plan contributions. 

To Apply 

Please submit the following materials in PDF format to hr@frederickgunn.org

• Resume 
• Cover letter 
• Transcript(s) 
• Two to four letters of recommendation

The Frederick Gunn School is an Equal Opportunity Employer. Except in cases of a bona fide occupational qualification or need, or except as otherwise permitted or required by law, The Frederick Gunn School does not discriminate against applicants for employment on the basis of race, color, religious creed, age, sex, marital status, pregnancy, sexual orientation, national origin, ancestry, present or past history of mental disorder, intellectual disability, learning disability or physical disability, gender identity or expression, genetic information, or any other protected class status under applicable law with respect to hiring, compensation, promotion, discharge from employment or other terms and conditions of employment. Position announcements are intended to describe the general nature and level of work performed by employees assigned to the job title and the education and skills required. Descriptions are not intended to be a complete list of all responsibilities, duties and skills that are required or may be required in the future. 

BACKGROUND SCREENING: The Frederick Gunn School conducts background checks on all job candidates upon acceptance of a contingent offer, which includes using a third-party administrator to conduct the checks. 

Core Values 

Integrated Humans 

Thriving people learn to integrate the intellectual, the physical, the spiritual, and the emotional through an examination of the place of each, discernment about their relative role, and a commitment to balance and flourishing. 

Hopeful Faculty 

We prize faculty who believe resiliently, optimistically and with good humor in the students’ and faculty’s collective ability to grow and learn; know their discipline and practice, and understand character development. A faculty oriented around these principles will earn the confidence of students and create a place of purpose and fun where faculty and students want to be. 

Learning Ecosystem 

Thriving communities recognize the interdependent nature of their parts. Therefore, The Frederick Gunn School is a school that champions the interdisciplinary and inter-experiential nature of life and learning - one that incorporates the outdoors, athletics, and arts, as well as academics, into everyday life. 

Moral Character Development 

We are a school that nurtures Mr. Gunn’s belief in character as the driving force in a life well-lived, and that character emerges through the intentional pursuit—in knowledge and practice—of what is good, right, true, sustainable, and beautiful. 

Engaged Citizens 

The Frederick Gunn School is a school that, despite growing cultural apathy, cynicism, consumerism and distraction, produces people who care deeply - who become wise, engaged, active citizens.

About The Frederick Gunn School

Connections working at The Frederick Gunn School