Allison Eilers
Allison Eilers is an experienced educator and school leader with over two decades in the field, currently serving as the Founding Principal of Holy Cross High School in Dover, Delaware. Her career reflects a steady progression through nearly every level of education, beginning as a teenage volunteer tutor at an after-school learning center and evolving into a leader responsible for launching and shaping new schools. At Holy Cross High School, she leads the development of systems, culture, and academic programming, guiding the school from its earliest stages into a growing faith-centered institution that serves its community with a strong emphasis on individualized attention and long-term impact.
Eilers has built a strong foundation in literacy and instructional practice, holding a master’s degree in literacy from Long Island University and a bachelor’s degree in behavioral science from Mercy University. Her expertise spans literacy development, instructional coaching, classical education, and school administration. Throughout her career, she has supported both students and educators by emphasizing the importance of meeting learners where they are—whether through small-group instruction for struggling readers or differentiated professional development for teachers. Her work as an instructional coach and academic leader has contributed to measurable improvements in student engagement, achievement, and instructional quality.
Before her current role, Eilers held leadership positions including Assistant Director and Dean of Students at Bonnie Cone Classical Academy, as well as Dean of Academics, Assistant Principal, and Instructional Coach across multiple schools. She has been deeply involved in launching and sustaining startup schools, particularly within classical education models, where she helped build curriculum, establish culture, and support teacher development. Grounded in values of community, resilience, and faith, Eilers is committed to creating school environments that foster both academic excellence and character formation, ensuring that students and families feel supported, connected, and empowered.
• Literacy
• Elementary Education
• School Administration
• Long Island University - M.S.Ed.
• New York Roadrunners
• Guiding Eyes for the Blind
• Local charities
What do you attribute your success to?
I attribute my success to resilience, a strong work ethic, and a deep commitment to making a meaningful impact. I am driven by the opportunity to support both students and educators, whether by helping a teacher navigate their first year or addressing the individual needs of my students with care and understanding. Working in a close-knit community has allowed me to build meaningful relationships and contribute to systems that support long-term growth, making the work both impactful and fulfilling.
What advice would you give to young women entering your industry?
I would encourage young women entering the field to take advantage of every opportunity available, especially at a time when dedicated educators are in such high demand. Even if a role isn’t your ideal position, stepping into it—whether as an assistant or in a volunteer capacity—can provide valuable experience and open unexpected doors. Early in my career, I took on roles without pay, but those experiences gave me a strong foundation and a deeper understanding of how schools operate. Embrace each opportunity as a chance to grow, and don’t be afraid to try different paths—every experience adds value, even if it doesn’t pay off immediately.
What are the biggest challenges or opportunities in your field right now?
The field currently presents significant opportunities in recruiting and developing strong, dedicated teachers, as well as in building new schools that effectively meet evolving community needs. At the same time, key challenges include supporting overwhelmed first-year teachers, addressing the diverse learning styles of adult educators, and ensuring that strong foundational systems are established to sustain long-term school success.
What values are most important to you in your work and personal life?
The values most important to me in both my work and personal life are resilience, a strong work ethic, and a commitment to making a meaningful impact. I deeply value community and family connection, and I strive to build relationships that foster trust and support. Additionally, integrating faith into my daily life and work is central to who I am, guiding my decisions and the way I serve others.