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As remote work became immediate, customer interactions moved online, and supply chain pressure intensified, leaders had to decide whether to slow down transformation to protect operations or use it to keep the business moving through disruption and beyond. In this CIO Talk Network conversation, Rajeev Ravindran, Senior Vice President and Chief Information Officer at Ryder System, Inc., joins host Sanjog Aul to share how Ryder navigated digital transformation during the pandemic with a focus on preparedness, customer experience, measurable execution, and human-centered leadership. The discussion explores how Ryder’s business continuity foundation enabled a rapid shift to remote work, how digital products like the RyderGuide app were extended quickly to support touchless service and safer customer interactions, and how leadership teams used dashboards, project health metrics, and continuous communication to sustain productivity while managing burnout risk. Topics Covered • 00:00 Why digital transformation became a survival decision • 01:00 Business continuity readiness and the rapid shift to remote work • 03:10 Customer experience changes and RyderGuide as a digital foundation • 03:55 Touchless check-in and modular delivery during disruption • 06:40 Digital is a mindset shift, not a technology project • 07:15 Customer expectations rising through supply chain disruption • 09:38 Remote work as a long-term shift and its productivity impact • 13:42 Measuring productivity: dashboards, Power BI, Planview, ServiceNow, agile delivery • 16:27 The leadership layer: empathy, communication, and keeping morale intact • 18:58 The hidden cost: burnout in a world without decompression time • 20:33 Innovation from the front lines, not the “ivory tower” • 24:48 Infrastructure strategy: accessibility, cloud adoption, and safety-first decisions • 29:43 Analytics through disruption: visibility, mapping, and decision support • 36:22 Performance expectations during COVID and what changes materially • 41:13 The security surge and why IT workload increased, not decreased • 42:40 Leadership takeaways: emotional intelligence and putting people first Prefer a different format? ► Watch on Vimeo ► Listen on Apple Podcasts, Spotify, and iHeartRadio ► Full transcript and episode details available on ciotalknetwork.com About CIO Talk Network CIO Talk Network is a global, peer-led platform where enterprise leaders think out loud, without pitch or fluff, and share real experiences that challenge conventional thinking. Follow CIO Talk Network LinkedIn: / cio-talk-network X (Twitter): / ciotalknetwor Website: https://www.ciotalknetwork.com Official Website: https://www.ciotalknetwork.com Connect with us on: LinkedIn: / cio-talk-radio X: / ciotalknetwork Facebook: / ciotalknetwork Apple Podcast: https://www.ciotalknetwork.com/apple/ Don’t forget to like, share, and subscribe for more insightful discussions.