Learning Specialist | Academic Success Coach

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.

Position Summary

The Learning Specialist & Academic Success Coach provides individualized academic support to students with diverse learning profiles, helping them develop the skills, strategies, and self-awareness necessary for success in a rigorous college-preparatory environment. The Learning Specialist partners closely with students, families, faculty, and the Center for Academic Excellence (CAE) team to foster independence, resilience, self-advocacy, and lifelong learning habits.

Primary Responsibilities

• Provide individualized and small-group instruction in executive functioning, study skills, academic strategies, organization, time management, and self-advocacy.
• Support students in developing lifelong learning habits, including goal-setting, self-monitoring, growth mindset, resilience, and metacognitive awareness.
• Collaborate with students to establish personalized goals and monitor progress throughout the academic year.
• Assess and document student growth through ongoing progress monitoring, data collection, and communication with students, families, and faculty.
• Support students in understanding and effectively utilizing approved accommodations and assistive technology.
• Partner with teachers through ongoing communication to support student success, implement accommodations, and promote inclusive instructional practices.
• Serve as a resource to faculty regarding learning differences, executive functioning, and evidence-based instructional strategies.
• Communicate with families regarding student progress, challenges, and areas for growth.
• Utilize Highlander Nation, Google Workspace for Education, and other learning management and productivity tools to support student learning and program operations.
• Engage in ongoing professional learning and remain current with research and best practices in learning support, neurodiversity, executive functioning, and adolescent development.
• Uphold confidentiality and professional standards in accordance with school policies and ethical guidelines.
• Participate fully in the life of the school community, including meetings, professional development, and other school responsibilities as assigned.

Preferred Knowledge and Skills

• Bachelor's degree in Education, Special Education, or a related field required; Master's degree preferred.
• Minimum of three years of experience supporting adolescents in educational settings.
• Demonstrated knowledge of learning differences, ADHD, executive functioning challenges, and learner-centered instructional practices.
• Strong understanding of adolescent development and the various factors that influence learning.
• Excellent interpersonal, organizational, and communication skills.
• Ability to build productive relationships with students, families, faculty, and administrators.
• Experience using assistive technology and digital tools to support diverse learners and foster academic success.
• Commitment to ongoing professional growth and reflective practice.
• Passion for creating learning environments that promote independence, self-awareness, confidence, resilience, kindness, and academic success.

Job Details 

Opening to be filled as soon as possible. Offer of employment will be contingent upon a successful background check.

Compensation

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

To Apply

This position is a 10-month, full-time, exempt opening, paid on a salary basis. Compensation is competitive, and the employment package includes excellent benefits, including outstanding health and dental coverage and a retirement plan. To apply, please complete our online application and upload a cover letter- including the response to the below prompt, resume, and three professional references (references will not be contacted without notifying you). Application materials are being accepted now, and qualified applicants will be invited to interview on a rolling basis.

Please submit the following materials: 

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, victims of domestic violence  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.