What does a history major who taught himself to code have to teach CIOs about innovation? Quite a lot, it turns out.In this episode of The Outlier Podcast, Anurag Mukherjee sits down with Jonathan Cilley, CIO of Mid Hudson Valley Federal Credit Union, for a wide-ranging conversation on technology leadership, calculated risk-taking, and what the next five years could look like for credit union tech.Jonathan traces his career from C-sharp developer at a Maryland credit union — a job he took because it paid more and had a shorter commute — to managing enterprise-scale technology operations at Visions Federal Credit Union, and ultimately to his current CIO role in the Hudson Valley. His secret? A disciplined framework for taking calculated risks, and a developer's belief that if you can dream it, it can be built.