Executive Director Search
Cypress School of San Francisco selects Nichole Sullivan to be the Executive Director
February 6, 2026 - Letter from the Board of Trustees
Dear CSSF Community,
The Board of Trustees is thrilled to share that, following a comprehensive search process, Nichole Sullivan has been selected as our next Executive Director, starting May 26, 2026.
This decision reflects months of listening to faculty, staff, and families through surveys, onsite candidate presentations and interviews. We’re grateful to everyone who shared their perspective. The feedback we received reinforced the importance of finding a leader who is deeply aligned with our mission and values, while also bringing the operational strength needed to steward the school forward.
Nichole possesses a rare combination of administrative expertise and pedagogical vision, grounded in more than fifteen years of experience as a progressive early childhood educator and senior leader within Reggio/inquiry-based school communities. Most recently, she served as Director of Admissions, Multicultural Recruitment, and Sliding Scale Tuition at La Scuola International School, a Reggio Emilia Italian immersion and International Baccalaureate school serving students from preschool through eighth grade.
Earlier in her career, Nichole led full-site operations for a multi-classroom early childhood program, overseeing budgets, staffing, fundraising, and family engagement as Site Director for Marin Day Schools. She later served as a field education and training specialist with Bright Horizons and as Deputy Director of Operations at Five Keys Charter School.
A highly relational leader, Nichole is very active in the Bay Area education community and currently serves as President of the Bay Area Directors of Admissions, a network of more than 70 independent schools.
Across roles, Nichole is known as a collaborative, thoughtful leader who brings clarity, steadiness, and care to complex systems, while keeping children, educators, and families at the center of decision-making. Our community’s feedback echoed the Board’s own impressions; highlights from what we heard:
She has a vision for aligning more closely with Reggio principles while celebrating the legacy of our school, and she highly values the educators that make up its backbone. She also has a background in making admission accessible to all which aligns with my personal values as well!
Nichole brings a rare and powerful combination of deep experience, clear values and forward-thinking leadership that feels especially well-suited to Cypress.
She has amazing experience in the early childhood realm, Reggio, and beyond and is incredibly well networked. I felt so inspired listening to her every word - and felt a deep sense that she will be an incredible mentor and leader for our school.
In support of a smooth transition, Nichole will partner closely with school leadership through the end of the academic year. Our Interim Head of School, Molly Huffman, will transition off this summer. An eternal thank you to Molly for her steady leadership and devotion to the school during this period.
Many thanks to everyone who participated in this process and helped shape this important decision. Please join us in warmly welcoming Nichole Sullivan to our community.
We’re excited for the leadership, care, and vision she will bring as we move into this next chapter together!
With gratitude,
The CSSF Board of Trustees
Nichole Sullivan brings more than fifteen years of experience as a progressive early childhood educator and senior enrollment leader deeply grounded in Reggio, inquiry-based school communities. Her work spans classroom teaching, site-level leadership, and institution-wide strategy.
Most recently, Nichole served as Director of Admissions, Multicultural Recruitment, and Sliding Scale Tuition at La Scuola International School, a Reggio Emilia, Italian immersion and International Baccalaureate school serving students from preschool through eighth grade.
Nichole also serves as President of the Bay Area Directors of Admissions, a professional network representing more than 70 independent schools across the region.
As a senior leader at La Scuola, Nichole partnered closely with pedagogical and operational leadership to ensure that enrollment practices, family engagement, and external storytelling authentically reflect the school’s child-centered philosophy. She also worked closely with the CFO and leadership team to steward the school’s Sliding Scale Tuition model, balancing economic diversity, enrollment health, and financial viability across multiple campuses.
Earlier in her career, Nichole served as a Site Director with Marin Day Schools (Sherith Israel), later acquired by Bright Horizons Family Solutions, where she led full-site operations for a multi-classroom early childhood program. In this role, she oversaw budgets and staffing, strengthened family partnerships, and guided program quality. Notably, she led a campus playground remodel, established a Parent Association and led curriculum restructuring, staff transition, and professional development initiatives. She later served as a field education and training specialist with Bright Horizons, and held the role of Deputy Director of Operations at SFSD Five Keys Charter School.
Nichole holds a Master’s Degree in Early Childhood Studies with a focus on Administration, Management, and Leadership from Walden University and a Bachelor’s Degree in Child and Adolescent Development from San Francisco State University. A San Francisco native and longtime Bay Area educator, Nichole enjoys exploring and staying connected to the vibrant early childhood education community.
Message from Nichole Sullivan
Dear Cypress Community,
I am profoundly honored to be stepping into the role of Executive Director at Cypress. From my earliest conversations with the Board and Search Committee and during my time on campus, I felt a genuine sense of welcome and purpose that affirmed just how special this community is.
I’ve long admired Cypress, both as a parent and educator, for its inquiry and play-based approach to learning. The school’s home in the Presidio is magical and spending time with your students, teachers and families only strengthened my desire to be a part of this community.
My career in education began in the preschool classroom, where I learned that early childhood education is both simple and complex. At its core, it is about honoring children as capable, curious, and relational beings while thoughtfully designing environments and systems that allow their potential to flourish. I believe childhood itself is sacred, and that schools carry a responsibility not only to educate young children, but to protect the joy, wonder, and dignity of their early years. These beliefs are deeply aligned with the heart of Cypress.
I am inspired by Cypress’s commitment to child-centered learning, meaningful relationships, and a culture of belonging. Strong relationships are the foundation of meaningful learning and enduring school communities: when children feel known, when educators feel supported, and when families feel connected – schools flourish. My hope is to lead in a way that nurtures those relationships, strengthens collaboration, and ensures that Cypress remains a place where every member of the community feels valued and inspired.
I’m so grateful to the Board and the Search Committee for the care, trust, and intention they brought to this process, and for welcoming me so warmly. I look forward to listening, learning, and growing together as we steward Cypress into its next chapter.
Thank you for the gift of this opportunity. I cannot wait to begin this journey with you.
Warmly,
Nichole