ABOUT ME
Roy 'Caz' Caswell
Roy Caswell is a transformational technology leader with more than 25 years of experience helping insurance organizations turn IT from a necessary expense into a strategic advantage. As Chief Technology Officer at Linchpin, Roy leads technology strategy with a sharp focus on scalability, security, and real-world results for agencies navigating growth, change, and complexity.
Throughout his career, Roy has guided enterprise-level IT transformations for leading insurance organizations including Trucordia, The Liberty Company Insurance Brokers, Insurance Office of America, Marsh & McLennan Agency, and through his consultancy, CIO-Solution, LLC. His expertise spans M&A technology integration, cloud-first infrastructure, cybersecurity, and governance – with a focus on simplifying operations and reducing risk.
Roy is known for building high-performing teams, strengthening vendor partnerships, and designing resilient technology ecosystems that actually work the way agencies work. He brings a pragmatic, data-driven approach to every challenge – balancing innovation with stability and security.