Decades of enterprise technology and data leadership — packaged by Hoosiers for the Indiana business owner. Here’s who you’ll be walking the fairway with.
Portraits below are branded stand-ins for now — drop in real headshots whenever they’re ready and they’ll slot right in.
Ryan is a husband, father, and grandfather, and a longtime member of the Westfield community. 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, that means building the plan and making sure the work gets delivered.
On every piece we publish, Ryan writes Following Through — the practical blueprint and checklist an owner can act on the same week.
Caleb is a proud Hoosier — a husband, brother, dad, and grandfather. Growing up near the Country Club of Terre Haute, he 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 20 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, 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, is co-inventor on a U.S. patent for hospital revenue-cycle forecasting, and is studying agentic architectures through MIT Professional Education.
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.
On every piece we publish, Caleb writes The Local Take — explaining the week’s enterprise AI news in plain terms, and why it matters for a Hamilton County business.
Two operators, one simple promise: enterprise-grade thinking, sized for a business that knows its customers by name.
Plan. Aim straight. Then swing. We cut the jargon and focus on the next clear shot.
We’re Hoosiers. We work shoulder-to-shoulder with central Indiana owners, not from a far-off tower.
We prioritize the few places AI and data move the needle for your margins right now.
Humans play golf. Our customers are humans. Tell us about your business and, if it’s a fit, the round’s on us.