#504 - Modernizing legacy systems: AI, data strategy, and driving change

Fail Faster

In this episode of the Fail Faster Podcast, Gurdeep Singh, a seasoned solution architect at Chubb with over 25 years in the technology sector, shares his fascinating journey from dismantling radios in his childhood to tackling large-scale modernization projects in financial services. Gurdeep discusses the complexities of legacy system transformation, navigating organizational resistance, and the power of aligning business and technology for impactful change. He also shares his insights on leveraging AI responsibly, building strong data foundations, and fostering collaboration across all levels of an organization. Packed with lessons learned from career-defining challenges and forward-looking strategies, this episode is a must-listen for anyone aiming to modernize systems while keeping people at the heart of innovation.