Summary
Gabe Calabro is a seasoned enterprise architect and technology executive who shapes how platforms and teams enable business strategy, currently serving as VP of Enterprise Architecture after leading a multi-year cloud-native transformation at RLI Insurance. With two decades of hands-on software and platform engineering, he has driven Kubernetes-native, highly available, and observable foundations while aligning leadership and delivery models for sustainable change. Gabe blends deep technical execution—from custom platforms to cloud SaaS adoption—with organizational design, coaching cross-functional teams to accelerate time-to-value. Based in Peoria, Illinois, he’s now focused on embedding AI as a force multiplier across platforms, products, and operating models. An early background in music composition hints at a creative, systems-oriented approach to engineering and leadership.
5 years of coding experience
12 years of employment as a software developer
A.S., Music Theory and Composition, A.S., Music Theory and Composition at Illinois Central College
B.S., Computer Science, B.S., Computer Science at Illinois State University