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Kalyan Chintam never planned to become a CIO.

His journey began in India, sparked by an early fascination with computers and a nudge from his mother to pursue engineering. That curiosity carried him from a decade in startups, where he wore just about every hat, to leadership roles at some of retail’s most recognizable names, including Macy’s, JCPenney, GameStop, Michaels, and The Container Store.

Over 24 years, Chintam has helped companies rethink their technology foundations, from spearheading a full digital transformation at JCPenney before it was an industry buzzword to growing GameStop’s e-commerce sales from $250 million to $1.2 billion in a single year.

He’s built a career thriving under constraints, proving that real leadership happens when creativity meets resourcefulness.

In this Deep Dive with The National CIO Review, Chintam opens up about the millennial mindset that drives his leadership, why continuous learning and product thinking are non-negotiables, and how he sees the next wave of retail tech reshaping the industry.

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