Ryan Kreag
Ryan is a husband, father, brother, and grandfather who has called Westfield home for thirty years. A true Hoosier, he grew up in Granger, Indiana, around the fairways of Knollwood Country Club — and he still believes the best business gets done walking eighteen holes.
For more than 25 years, he has led enterprise IT strategy and digital transformation across manufacturing, healthcare, SaaS, and enterprise services — guiding organizations through growth, acquisitions, and modernization. His wheelhouse is the practical end of technology: infrastructure and cloud, ERP and enterprise platforms, cybersecurity and compliance, data governance, and large-scale systems integration, always tied back to real business outcomes.
Known for a collaborative, no-jargon style, Ryan partners with leadership teams to turn ambition into a roadmap a team can actually run. At fairway advisors he leads operations: when an idea proves itself in our Labs group, Ryan is the one who walks it out of the practice green and into production — the standards, support, and guardrails that let a business run on it Monday morning.
On every piece we publish, Ryan writes Following Through — the practical blueprint and checklist an owner can act on the same week.
Caleb Decker
Caleb is a curious and proud Hoosier — a husband, brother, dad, and grandfather. Caleb grew up near the Country Club of Terre Haute, and now enjoys golf and spending time outside. He’s a builder at heart, and he believes the best data systems, like a great golf swing, come down to precision, rhythm, and a strong foundation.
His career in enterprise analytics and AI leadership spans more than 25 years, including nearly two decades at Strategy (formerly MicroStrategy) serving Fortune 100 financial and healthcare organizations with business intelligence services. He’s seen every major software shift — from digitizing paper, to mobile apps & cloud, bitcoin and crypto, and now to the generative frontier — and how a precise data foundation can change the trajectory of a billion-dollar balance sheet. He holds a BS in Computer Science and is co-inventor on a U.S. patent for hospital revenue-cycle forecasting. The newest club in the bag is his agentic architectures certification from MIT Professional Education — the craft of designing systems where AI agents actually do the work, not just talk about it.
In 2026 he brought that expertise home, founding Fairway Advisors to give central Indiana businesses the same high-impact strategies once reserved for the global elite — cutting through the AI hype to build practical roadmaps that turn data into a real competitive advantage. Among other things, Caleb leads our Labs group acting as chief engineer, for now.
On every piece we publish, Caleb writes Reading the Green — the local take, explaining the week’s enterprise AI news in plain terms, and why it matters for a Hamilton County business.