SHOW NOTES
GUEST INFO
Episode Guest:
James Cryan, Founder of Willow Education PBC & Former CEO of Rocky Mountain Prep
Connect with James on LinkedIn
Website:
EPISODE SUMMARY
What happens when a charter school leader takes a hard look at the data—and doesn’t look away? In this episode, The Charter School Insider Podcast host Daniel Casselli welcomes James Cryan, founder of Willow Education and former CEO of Rocky Mountain Prep, for a deeply reflective conversation on the power (and pitfalls) of data-driven leadership.
From jaw-dropping statistics about post-secondary outcomes to the tough calls that come with mission-driven leadership, James opens up about what it takes to move beyond surface-level metrics and drive meaningful, lasting change for students. You’ll hear why 100% college acceptance may not be the win you think it is, how to connect KPIs with real student stories, and why having “bathroom goals” might just revolutionize your school culture.
If you’re a charter school executive grappling with how to make data work for you (instead of overwhelming you), this episode is your playbook.
EPISODE TAKEAWAYS
RESOURCES
Willow Education — Learn more about James Cryan’s work
National Student Clearinghouse — For post-secondary data
Four Disciplines of Execution (aka 4DX) — The leadership framework book
Charter School Growth Fund – Early Alumni Outcomes Report — Research on student outcomes post-graduation
Jobs for the Future (JFF) — On credential value and workforce readiness
CHAPTERS
00:00 Introduction and Background
02:54 Post-Secondary Success and Challenges
05:57 Data-Driven Leadership in Education
08:56 The Importance of Asking the Right Questions
11:49 Connecting Data to Student Experience
15:07 Identifying Relevant Data Points
18:00 Data Storytelling and Accountability
20:58 Translating Data into Action Plans
23:55 Change Management in Education
26:49 Key Takeaways for Data-Driven Leadership
ABOUT OUR GUEST
James Cryan is the founder and former CEO of Rocky Mountain Prep – one of Colorado's most successful public charter school networks – James carries with him over 15 years of experience in the education sector. James believes all learners deserve support to navigate their post-secondary education journey with confidence. Growing up, his mother, Fredrica, instilled in him a simple yet powerful belief: with hard work, anything is achievable. He is painfully aware that promise is not true for everyone today; and is steadfast in that mission to shape a world where every individual has the opportunity to fully realize their potential.
ABOUT OUR HOST
Daniel Casselli is a life-long learner whose passion for education has driven his professional endeavors. He is a former classroom teacher and youth ministry director whose entrepreneurial spirit landed him in the world of education technology. At EVERFI Inc., Daniel helped run the business development efforts for EVERFI’s Financial Education Program and the company was eventually sold to Blackbaud for $750M in 2021. Shortly before EVERFI’s acquisition, Daniel joined Class Technologies as one of the earliest sales hires and went on to lead K12 Enterprise Sales and helped the company land its first 100+ K12 customers across public, charter, and private schools. Daniel brings his unique experiences to BuyQ where he is focused on growth, operational excellence, business strategy, and client satisfaction. He is a graduate of Grove City College where he studied Religion and History.
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