Middle School Learning Specialist

Middle School Learning Specialist 2026-2027 with mid-year opening available VISION: Inspire students to achieve their dreams and reach beyond themselves to make a difference in the world. MISSION: Hillbrook provides an extraordinary educational experience that fosters a love of learning in our students and helps them develop the knowledge, skills, and confidence to achieve their highest individual potential in school and in life. At Hillbrook, students are known, respected and valued as individuals and every day is a journey of self-discovery, imaginative thinking, creative problem solving, laughter and friendship. CORE VALUES: Be kind. Be curious. Take risks. Be your best. The Hillbrook Faculty Member: Who Are YouDo our Core Values – Be kind. Be curious. Take risks. Be your best. – align with how you show up as an educator? Are you committed to building and bridging inclusive communities? Do you believe learning should be an active and relational process? Do you enjoy nurturing and maintaining best practices and continuity of programs, while also evolving programs in response to new information? Are equity and impact at the forefront of what you do? Are you entrepreneurial? Do you thrive in small collaborative environments? Do you seek opportunities for interdisciplinary, experiential learning? Do you believe that students are capable changemakers at any age and stage? A Hillbrook faculty member will emphatically say yes to each of these questions. The Position: What Will You Do & How Will We Collaborate?The Middle School Learning Specialist will be an educator who understands diverse learning needs and enjoys helping students build confidence, and independence with social, academic, and executive function skills. Joining a highly collaborative faculty and a skilled Student Support Team, the Middle School Learning Specialist will teach daily small-group Academic Prep classes and will provide individualized, small-group, and classroom support for students with mild to moderate learning differences across grades 5-8. Reporting to the JK–12 Director of Student Support, they will partner with teachers, families, outside providers, and their Student Support Team colleagues to coordinate accommodations and develop responsive learning strategies. They will also contribute to advisory programming, middle school interdisciplinary Reach Beyond experiences, and grade-level collaborations that support overall student learning and wellbeing. Specific Duties and ResponsibilitiesActively participate in a collaborative employee culture that is committed to being at the leading edge of JK-12th grade educationReport to JK-12 Director of Student SupportBe present on campus between 7:45-3:45 pm to assist with students’ learning support needs in 1:1, small-group, and classroom settingsProvide grade-level executive function and behavioral support through both systematic & dynamic / responsive advisory group programmingSupport Middle School Reach Beyond Block programming, including participating on a grade level team during the weekly RBB interdisciplinary project block and rotating on a yearly basis between travel and non travel week-long RBW experiences in the SpringParticipate in MS events such as admissions open houses, and student life eventsTeach daily “Academic Prep” classes providing support for students with a variety of mild to moderate learning differencesDesign and lead the delivery of targeted, small-group executive function coaching during office hours after school; expanding on our embedded support for students with learning differencesSupport case management for students, including, but not limited to:Partner with Director of Student Support to schedule & make student observationsCommunicate and meet with families as necessary to support student wellbeingCoordinate on-site support for MS students, including sessions with external providersPartner with Director of Student Support to review evaluation reports and translate those into accommodationsSupport the annual review of Official Teacher Notes, Accommodation Summaries, and outside support plansParticipate in Grade Level Team Meetings as availableProvide coaching or guidance to teachers as they develop curriculum and teaching strategies to meet students’ diverse learning needsActively team with Student Support Team colleagues to advance the work of learning support at the schoolOther responsibilities as assigned by the Director of Student Support QualificationsBachelor’s degree in special education or related fieldDemonstrated experience partnering with students (and their families) with a range of mild to moderate learning differences to build confidence and content/skill masteryDemonstrated ability to partner with teachers as colleagues, develop and pilot new programs, while also maintaining existing programming and structuresDemonstrated commitment to teaching and learning in a diverse, dynamic, and progressive school communityA commitment to anti-racism and demonstrated skill designing equitable and inclusive educational experiences and learning environments that incorporate themes of diversity and justiceDesire and ability to work in a collegial, highly collaborative environment Diversity, Equity, Inclusion, Justice, & ActionAs noted in our Statement of Inclusivity, we strive to reflect the extraordinary diversity of Silicon Valley, believing that educational excellence and equity depend on the creation of a diverse and inclusive community where all students, families and employees feel a full sense of membership. To live up to our DEI Teaching Philosophy Statement, all employees contribute to developing culturally competent students and building an educational institution committed to social justice and reaching beyond. We offer a wide range of opportunities for all employees to engage in work that furthers these goals, from personal dialogues that help us understand different perspectives, to pedagogical training designed to support equitable instructional practices and build habits to disrupt bias whenever we see it. Ultimately, we hope that this work helps all of our constituents—employees, students, and families—be more aware, empathetic, globally-minded, and justice-oriented. A highly collaborative community, we use the following norms to guide our communication with each other:Assume good willCome from your own experienceBe more curious than certainHold yourself and others capable Our commitment to these norms makes it possible for us to partner meaningfully, disagree productively, and lean into conversations that are both challenging and generative.Each and every day our students will be challenged to live out our Core Values - be kind, be curious, take risks, be your best - as they engage with an exceptional team of educators committed to helping each student reach their highest potential in school and in life. Our program is also guided by the core questions of the Scott Center for Social Entrepreneurship - “What matters to you? What are you doing about it?” Simple yet provocative, these two questions inspire all members of our community as they convey two foundational beliefs: learning must be purposeful and have enduring impact, and leveraging student interest drives both engagement and success. Hillbrook, unlike any other school, not only calls on its students to make the world a better place, but also explicitly prioritizes the skills and habits that prepare them to do so, activating and empowering students to make immediate and lasting social impact during their JK-12 years while launching them into a lifetime of social impact work. To ApplySalaries are competitive. Benefits include: full medical, dental, and vision coverage; ample retirement planning; a generous holiday schedule; religious/cultural holidays following each employee’s faith and background; access to the latest state-of-the-art educational technology; and a strong commitment to engaging and personalized professional development. Hillbrook School is an Equal Opportunity Employer and seeks candidates from diverse backgrounds. Hillbrook School is committed to fostering and sustaining a learning community and does not discriminate on the basis of race, color, religion, sex, gender, sexual orientation, national origin, ancestry, age, marital status, disability, or any other characteristic protected by law. This policy applies to, but is not limited to, educational policies, admission, financial aid, hiring and employment practices, use of school facilities, athletics, and other school-administered programs and activities. The annual salary range for this role is $80,000 - $145,000 dependent on years of experience. Please apply by submitting your resume/CV and letter of intent via this. Please apply by submitting your resume/CV and letter of intent via this application form. The School: Who Are WeFor more than 85 years, Hillbrook School has been a junior kindergarten-8th grade independent school located on 14 acres of oak woodland in Los Gatos, CA. Founded in 1935, the school remains deeply connected to its historical roots as a place where children are known, learning is authentic and active, and success is measured one child at a time. Over the years, we have grown and evolved from a small boarding school serving wards of the state to one of the leading independent schools in the Bay Area, and yet our vision remains the same—to inspire children to achieve their dreams and reach beyond themselves to make a difference in the world.We are now in the midst of one of the school’s most ambitious strategic initiatives ever: the expansion to a JK-12 with the addition of a high school in downtown San José. We are driven by a foundational belief - that our 8th graders and other students deserve an extraordinary educational experience in high school that builds upon the exceptional foundation we provide our JK-8 students. The core differentiators for our current program - the placement of choice and engagement at the center of the learning experience, integrated, real world education that challenges students to reach beyond and make a difference, and a deep commitment to diversity, equity and inclusion - is being expanded one year at a time into a 9-12 environment, allowing us to extend our innovative approach into a market in need of a new model of secondary school education. LocationHillbrook has two campuses located in Los Gatos and San Jose. These locations in the heart of Silicon Valley are 35 minutes south of Stanford University, 30 minutes north of Santa Cruz, and 1 hour south of San Francisco. The Bay Area is home to world-class universities, museums and restaurants, farmers markets and wineries, and outstanding outdoor opportunities for biking, hiking, surfing and more.