How does a CIO lead a credit union from $5 billion to $10 billion in assets? In this episode of The Outlier Podcast, host Anurag Mukherjee sits down with Anil Choudary, Chief Information Officer at Keesler Federal Credit Union, to unpack the real playbook behind large-scale technology transformation in financial services. With a career that spans GE (where he helped build a digital bank), Goldman Sachs, CIBC, and Alliant Credit Union, Anil brings a rare blend of enterprise software engineering, big-bank strategy, and credit union pragmatism. Now leading end-to-end technology at one of the fastest-growing credit unions in the U.S., he shares exactly how he plans to scale Keesler Federal through core banking modernization, API strategy, data lakehouse build-out, automation, and AI. This is a candid, tactical conversation for CIOs, CTOs, banking executives, and fintech leaders trying to navigate the same transformation curve. In this episode, we cover: • Why a CIO's role is to drive both member trust and long-term growth • The 5 building blocks of a modern credit union tech stack: operating model, core banking, API strategy, data and AI strategy, and digital strategy • Why "no-regret decisions" matter most when choosing core banking platforms • How to balance buy vs. build in a vendor-heavy organization • Why data strategy must come before any AI strategy • Why automation should come before agentic AI on your roadmap • How to extract real ROI from every technology dollar invested • Why point solutions break down at enterprise scale • How regional culture and demographics shape technology strategy • What separates credit unions that will reach $10B from those that won't Standout quotes from Anil: "Culture eats strategy for breakfast, lunch, and dinner." "Without a foundational data strategy, you cannot deliver value through AI." "Digital is how you deliver a connected experience across all channels — not just web and mobile." "If you're investing a dollar, you need to extract at least 80 cents of value. Hopefully a dollar ten." About the guest: Anil Choudary is the Chief Information Officer at Keesler Federal Credit Union, leading end-to-end technology transformation. His career spans senior leadership roles at GE, Goldman Sachs, CIBC, and Alliant Credit Union, where he has built digital banks, modernized core platforms, and led enterprise-scale transformation programs. About the host: Anurag Mukherjee hosts The Outlier Podcast, a series featuring conversations with forward-thinking technology and business leaders driving real transformation across financial services, banking, and the credit union movement. Who this episode is for: Credit union CIOs, CTOs, CDOs, and CEOs; banking and fintech technology leaders; digital transformation executives; core banking modernization strategists; data and AI leaders; and anyone scaling a financial institution from $1 billion to $10 billion and beyond. If you enjoyed this episode, please leave a rating and review on Apple Podcasts. It helps more leaders discover the show. Topics: credit union technology, CIO leadership, digital banking transformation, core banking modernization, API strategy, data lakehouse, member experience, enterprise AI, agentic AI, banking automation, Keesler Federal Credit Union, Alliant Credit Union, Goldman Sachs, CIBC, buy vs build, member 360, data governance, $10 billion credit union, banking culture.