Head of School

UP ACADEMY Where Curiosity Thrives Head of School Location: San Mateo, CA (On-Site) Start Date: August 2026 Position Type: Full-Time, 12-Month Salary: $80,000 - $110,000 Reports To: Board of Directors School Size: TK-5, Small Micro-School About UP Academy UP Academy is a WASC-accredited, independent elementary school in San Mateo, California. We're a progressive micro-school that believes a good educational model isn't everyone getting the same thing, it's everyone getting what they need to be successful. Our core values are Respect, Innovation, Strength, and Empathy. Our small, mixed-age classrooms use deep, interdisciplinary project-based learning to help every student reach their ultimate potential. We practice universal design and differentiated instruction so that each child, whether gifted, twice-exceptional, neurodiverse, or anywhere in between, is met where they are and challenged to grow. Content isn't grade-specific; it's student-specific. We focus on competencies, not grades. We empower students of all abilities to find strength in their community, believe in the power of their ideas, and influence action in the world around them. Our students develop 21st-century skills, a global perspective, and empathetic action in an environment that nurtures creativity and encourages curiosity. The Opportunity We're looking for a Head of School who is excited to lead a small, innovative school where you can see your impact every day. This is a hands-on leadership role, you'll be the kind of leader who knows every student's name, rolls up your sleeves when needed, and deeply believes that supporting educators is the fastest path to great outcomes for kids. Our school priorities are simple and deeply held: create an incredible learning environment for students, build a wonderful experience for parents and families, and be a place where people love to work. As a leader, your role is to remove obstacles and provide resources for your team to do their best work. As Head of School, you'll oversee all aspects of the school's operations, academics, culture, enrollment, finances, and extended programming within a board-approved budget. You'll be the primary leader on campus, responsible for setting the tone, keeping our community connected, and nurturing the deep relationships with families that make UP Academy feel like home. You'll report to the Board of Directors, with coaching and mentorship available from our founder, Tanya Sheckley, who will serve as a resource during the transition and beyond. You'll also have the flexibility to build and shape your team. The Head of School has discretion to hire full-time or part-time support staff as needed, within budget, to ensure the school runs smoothly and our educators are set up for success. What You'll Do Lead, Coach, and Develop Your Team Coach, support, and develop a team of 3 full-time educators and 4 part-time staff members Coordinate and champion ongoing professional development, ensuring educators have the training, resources, and support to grow Champion a culture where educators come first, removing obstacles so they can do their best work Manage the hiring and onboarding process for new employees Foster collaboration, trust, and open communication across the team Oversee Academics and Curriculum Manage and guide the curriculum, coaching educators in its development and day-to-day use Ensure the school's approach remains rooted in project-based, competency-focused, differentiated learning Ensure universal design principles are practiced throughout the school and that all learners, including gifted, twice-exceptional, and neurodiverse students, are supported Substitute in classrooms as needed, staying connected to the student experience Maintain WASC accreditation standards and support continuous school improvement Drive Enrollment and Marketing Lead admissions and enrollment strategy, tours, outreach, family engagement, and retention Own the school's marketing presence: update the website, manage social media, and coordinate advertising Serve as the school's primary ambassador, building relationships with prospective families and the broader community Build and Sustain Our Parent Community Be the go-to relationship builder for our parent community, keeping families engaged, informed, and confident in the school Serve as the primary parent liaison, addressing concerns with warmth and care and maintaining the trust families have in UP Academy Coordinate parent volunteers and manage field trips Communicate proactively and transparently so that parents feel heard, valued, and connected to their child's experience Manage Extended Programs and Partnerships Manage and grow the specials programs, after-school programs, and external partnerships Develop and expand parent education and public outreach programming, workshops, talks, and resources that deepen the community's connection to our approach Identify opportunities to strengthen programmatic partnerships that enrich the student experience Manage Operations, HR, and Compliance Manage the daily, monthly, and annual school schedule, including staffing and arranging substitutes Handle HR responsibilities including compliance, payroll, and benefits administration Hire, assign, and manage additional full-time or part-time staff as needed within budget Educators may also take on operational roles (HR, business, admissions, marketing), coordinate and support these contributions Oversee Finances and Facilities Manage the school's finances within the board-approved budget, including paying bills, tracking expenses, and financial reporting Oversee facilities management, maintenance, upkeep, supplies, and janitorial needs Report regularly to the Board on financial health and operational status Partner with the Board Collaborate with the Board of Directors on strategic vision, planning, and school growth Provide transparent, regular updates on school performance, enrollment, finances, and culture Work alongside the founder as a thought partner on the school's evolving mission and model Who You Are We know that great leaders come from many paths. Here's what we're looking for: Required An advanced degree in business, education, or a related field Leadership experience within a startup, small school, or small business environment where you wore many hats and built things from the ground up A collaborative, mission-oriented, servant-leader approach, you're dedicated to developing your people, supporting them to do their best work, and creating an environment where people genuinely love to come to work Deep commitment to progressive, student-centered education and the belief that every child deserves to be met where they are Strong interpersonal skills, you lead with empathy, listen well, and build trust with staff, families, and kids alike A natural relationship builder who genuinely enjoys engaging with parents and creating community Resourceful and adaptable, you're not above any task and you thrive when you can see your direct impact Alignment with UP Academy's values of Respect, Innovation, Strength, and Empathy Preferred Leadership experience in an educational setting (independent, charter, or public) Experience working with twice-exceptional, gifted, and/or neurodiverse learners Familiarity with project-based learning, competency-based assessment, and/or universal design for learning Experience with enrollment management, school marketing, or community outreach Experience building or managing after-school programs, parent education, or other extended programming Compensation & Benefits Salary: $80,000 - $110,000 annually, commensurate with experience Voluntary benefits package includes: Health, dental, and vision insurance Long-term disability and life insurance 401(k) retirement plan Tuition remission policy for children of the Head of School Professional development stipend How to Apply If this sounds like the kind of work that lights you up, we'd love to hear from you. Please send a resume and a letter of interest to admin@. In your letter, tell us what draws you to UP Academy and how your experience has prepared you to lead a small, progressive school. We're interested in who you are as a person and a leader, not just your credentials. UP Academy is committed to building a diverse community. We welcome applicants of all backgrounds and do not discriminate on the basis of race, color, religion, gender, sexual orientation, national origin, disability, or any other protected status.

Created: 2026-03-10