Linchpin Appoints Roy Caswell as Chief Technology Officer

Seasoned insurance technology leader to drive MSP strategy, cybersecurity, and automation for growing client base

GLENDALE, Calif. – December 2025 – Linchpin-IT, a national managed services and Insurtech firm dedicated to the insurance industry, today announced the appointment of Roy Caswell as Chief Technology Officer. Caswell will oversee Linchpin’s overall IT strategy, managed services delivery, and the integration of advanced technologies – including AI, machine learning (ML), and robotic process automation (RPA) – to support the firm’s expanding portfolio of insurance agency and brokerage clients.

Caswell brings extensive hands-on experience leading technology teams inside some of the industry’s most recognizable organizations, including Trucordia, Risk Strategies, The Liberty Company Insurance Brokers, and Insurance Office of America. Most recently, he served as CEO and Virtual CIO at CIO-Solution, LLC, where he strengthened cybersecurity frameworks and led strategic technology initiatives designed to improve business performance and resilience.

Previously, as EVP and Chief Information Officer at The Liberty Company Insurance Brokers, Caswell managed the external MSP relationship and led the integration of IT services for more than 60 agency acquisitions over a three-year period. During his tenure, he also implemented a cloud-first strategy that enabled seamless remote work and business continuity throughout the COVID-19 pandemic.

Roy has experience on both sides of business – he understands the realities of agency life, not just the theory,” said Angela Kristensen, CAO of Linchpin. “Our clients rely on us to keep their systems secure, connected, and easy for their teams to use. Roy has a strong reputation for simplifying complex environments, reducing operational friction, and driving measurable cost efficiencies. His track record in M&A integration, cybersecurity, and scalable infrastructure makes him the ideal leader to take our IT services to the next level.

I’m excited to join a company that is laser-focused on the unique technology needs of insurance organizations,” said Caswell. “Linchpin already has a strong foundation as a trusted partner to agencies and brokerages. I’m looking forward to building on that by expanding our MSP capabilities, advancing our cybersecurity posture, and helping our clients use automation and AI in practical, meaningful ways.

Outside of work, Caswell is actively involved in community service as an Assistant Scoutmaster with Scouting America’s Troop 507 and previously served as Vice President of the Lake Mary High School Band Boosters. He is an avid enthusiast of classic automobiles and motorcycles. He is passionate about mentorship, teamwork, and developing future leaders – values that mirror Linchpin’s commitment to long-term client and colleague partnerships.

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About Linchpin-IT

Linchpin is a national insurtech firm delivering technology and agency operations solutions exclusively for the insurance industry. Since 2015, Linchpin has helped insurance agencies, brokerages, clusters, and aggregators streamline operations, modernize systems, free up internal capacity, and compete at the highest level.

From accounting and IT solutions to virtual associates and agency management system optimization – Linchpin makes it easier for agencies to run their business and operate smarter.

For more information, visit linchpininsurtech.com or contact hello@linchpininsurtech.com.