The Rooted In Knowledge Leadership Course
A transformational program to help women in education turn their experience into evidence, their strengths into strategy, and their goals into action.
Meet Your Mentor
Heidi O'Leary, Superintendent of Schools and leadership coach dedicated to helping women in education step confidently into leadership roles.
With experience spanning from the classroom to the central office, Heidi understands firsthand the complexity of navigating leadership pathways in education. She has led district-wide initiatives in special education, strategic planning, and school administration—always with a focus on clarity, collaboration, and meaningful impact.
But more importantly, Heidi knows this to be true:
Many women are already leading—they just haven’t been given the language, structure, or support to recognize it.
Through Rooted in Knowledge, Heidi helps women turn their everyday leadership into clear, evidence-based confidence. Her work focuses on helping educators define their leadership readiness, articulate their unique story, and take intentional steps toward their next role.
She leads with respect, listens with intention, and creates spaces where women feel seen, supported, and capable of stepping forward.
Superintendent with 30+ years in education
Leadership across classroom, coaching, and district roles
Led district-wide initiatives in special education & strategic planning
Creator of the Leadership Readiness framework
Here’s why you should trust her:
Join me and fellow educators to explore how this transformative experience empowers women in education. At the core of this journey is the belief that you already possess the knowledge and leadership skills needed to thrive. With the right support and structure, you’ll confidently harness your strengths, fostering growth in both yourself and your community.
The Rooted In Knowledge Course
Women are already leading in schools every day—yet far fewer hold formal leadership roles.
The Reality of Women in Education Leadership
The higher the leadership level, the fewer women are represented.
The gap isn’t about capability—it’s about clarity, visibility, and support.
Many women are already doing the work of leadership, but lack the structure to define, articulate, and advance it.
That’s exactly what Rooted in Knowledge is designed to change.
