EP46: The Hidden Risk in Fleet Tech: Are You Still Running Legacy Systems?

In this episode of The Future of Ground Transportation, Daniel Perez welcomes Will Waller, Director and Partner at Kyndryl, for a conversation that bridges transportation, IT resilience, and digital transformation.With decades of experience across public and private sectors, Will shares insights on how aging transportation infrastructure can be modernized through IT innovation, and how organizations can prepare for cyber risks, vendor complexity, and technology debt.The episode highlights how Kyndryl helps clients stabilize, optimize, and transform mission-critical systems, and explores what it takes to make long-standing IT environments truly future-ready.⚡️ Here are some power takeaways from today’s conversation:• Infrastructure modernization is essential• Technical debt slows innovation• Stability comes before transformation• Resilience enables operational readiness• AI needs strong foundations⚡️ Episode Highlights: [03:15] Modernizing Legacy SystemsWhy so many transportation networks still run on outdated infrastructure—and how to fix it?Will Waller explains why legacy systems remain in use across public and private transit agencies, and what makes modernization so complex yet unavoidable. From old software to hardware dependencies, this segment explores the reality on the ground.[08:40] From Break/Fix to ResilienceThe mindset shift from reactive support to proactive IT planning.Here, the conversation shifts to how organizations can escape the endless cycle of “putting out fires” and start investing in systems designed for long-term resilience, stability, and growth.[13:10] Cybersecurity in TransportationWhy outdated systems increase cyber risk—and what to do about it?Will outlines how old, patchwork systems leave critical infrastructure exposed to threats, and what a modern, risk-aware cybersecurity approach looks like for fleet operators and transit agencies.[18:25] Creating Operational ReadinessWhy innovation only works when systems are stable?Before you launch automation or AI, you need solid infrastructure. Will walks through how Kyndryl helps clients build operational maturity—layering innovation only after core systems are secure and dependable.[24:50] Future-Forward TechnologiesExploring the real potential of AI, automation, and observability.What’s hype and what’s real? Will offers a practical perspective on which emerging tools are already helping transportation operators—and which still have a long way to go.📚 Resources Mentioned:🔗 Learn more about Kyndryl: https://www.kyndryl.com🔗 Connect with Will Waller: https://www.linkedin.com/in/willwaller🗣️ About the GuestWill Waller is a Director and Partner at Kyndryl, where he helps lead digital transformation initiatives across industries. With a deep background in IT modernization, infrastructure resilience, and public sector consulting, Will works closely with organizations navigating complex technical environments.Transportation, Fleet Management, Digital Transformation, Public Transit, IT Infrastructure, Legacy Systems, Resilience, Cybersecurity, Smart Mobility, Kyndryl