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Ryan cunningham

will dible

2019 Speakers

Blurring the boundaries

School district boundaries provide great benefits to communities across our nation. The pride we feel in our local schools is evident, powerful, and provides a sense of identity for our greater school communities, but these district boundaries also place unintended limits on the learning possibilities for our students. In the name of deeper and powerful learning, we think it’s time to blur the boundaries.


As the Teaching and Learning Director of Okoboji Schools, Ryan Cunningham seeks ways to shift systems in order to create learning environments that will empower students for their future. Spending 18 years as a middle school teacher and principal before moving into his current role, his educational mindset has been refined through collaboratively-led changes to increase engagement and deeper learning for students and educators.  


As Spencer School’s Director of School Improvement, Will is obsessed with innovation in education. He received his B.A. and M.A. from the University of Iowa.  Starting his career as a teacher in a rural Iowa school, he realized the need for change and began initiating unique practices. As a lifelong learner, Will has spread his innovation at conferences, workshops, and the National AP Conference.  His passion for education reform guided him to administration where he now aims for systemic reform. Presently, Will develops personalized structures and programs through collaboration for the betterment of the student experience.