Sam Rea is the Chief Technology Officer at Aspire General Insurance. He leads all aspects of technology for the carrier. Sam is a technology executive with 25 years of leadership experience. His expertise spans insurance technology, M&A integration, data, and AI. He has led both small startup teams and organizations of more than 1,000 technology professionals. Sam Rea spoke at the 2025 InsurTech Spring Conference on the panel “New AI Tech Stack,” alongside Jeff Goldberg, Robert Pick, and Will Ross.
Before Aspire, Sam was Chief Technology Officer at PEAK6 InsurTech. He led technical strategy across three insurtech businesses. He also ran product and engineering for a SaaS policy administration platform. He built a proprietary platform for independent agents supporting onboarding and comparative quoting. He earlier served as CTO of National Flood Services, leading a cloud transformation there.
Sam spent nine years at National General Insurance. He served as Executive Vice President and Chief Information Officer. He led the technology transformation as the company grew from a $1 billion business to a $5 billion one. He managed a workforce of more than 1,000 people and a $200 million IT budget. He also led M&A integrations that decommissioned more than 20 enterprise systems and nine data centers. He helped facilitate the company’s sale to Allstate.
Earlier, Sam brought predictive modeling into Zurich Insurance’s North American underwriting and claims. He also spent six years at Allstate, building a web-based policy administration platform used by thousands of independent agents. He began his career as a product design engineer at Ford Motor Company.
Sam holds an MS in Mechanical Engineering from Stanford University. He also earned a BS in Mechanical Engineering from the University of Illinois. He recently completed an AI and machine learning certificate at the University of Chicago.
