Kalyan Chintam has spent over 24 years at the intersection of technology and business, driving digital transformation as a CIO and modern tech leader. He’s consistently leveraged technology from scaling e-commerce platforms to implementing AI-driven retail experiences to enable growth and deliver meaningful outcomes.

His journey began in India, sparked by an early fascination with computers and a push from his mother to pursue engineering. That curiosity evolved into a career spanning startups, consulting, and leadership roles at iconic brands like Macy’s, JCPenney, GameStop, Michaels, and The Container Store.

Kalyan has built a reputation for navigating complexity with resilience and remaining passionate about using new technology as the catalyst for impactful, positive change.

Speaking with Kalyan, he discusses the value in leading with a millennial mindset, prioritizing continuous learning, incorporating product thinking, and fostering your community.

Walk us through your career path. How did you decide to pursue a career in technology, and how did you get to where you are now?

I never imagined I’d become a CIO.

Looking back over the past 24 years, my path wasn’t planned; it was really shaped by my experiences, learning to stay adaptable, curious, and focused on outcomes.

It started back in India during the late 1990s.

Computers were still relatively new, and I remember the first time I used one in high school. My mother, whom I like to think was a bit of a visionary, really encouraged me to pursue computer science. At the time, in India, the big career choices were usually between medicine and engineering. I quickly ruled out medicine because I couldn’t handle the sight of blood, so engineering it was.

Thanks to my mom’s persistence, I pursued a degree in computer science and engineering, and that decision set everything in motion.

During college, I learned programming languages like Pascal and Fortran, and worked with mainframe systems, technologies that have long since been replaced, but the real takeaway from my education was a mindset of continuous learning. Even then, I was very curious about what tech was coming next, and that instinct has stayed with me throughout my career.

After graduation, I joined a startup where I spent nearly a decade, which became the foundation of everything I’ve done since.

In a startup, you do it all.

• Design

• Code

• Test

• Market

• Sell

We were responsible for everything from concept to go-to-market.

I worked directly with customers, pitched the product, got feedback, discovered gaps, and went back to fix them. We built a product that served multiple industries like retail, insurance, financial services, and telecom, which gave me a unique perspective on how tech powers different types of businesses.

That experience made me who I am today.

It taught me resilience, versatility, and how to connect technology to people, process, and purpose.

The startup grew quickly, and we had real success, but like many early ventures, we faced some challenges that led to a natural transition point. Around the same time, my wife and I had just welcomed our first child, which prompted me to look for a more stable corporate opportunity.

From there, I joined Cognizant, where I moved into retail consulting. It was a great transition. I worked with major brands like Amazon, Bass Pro Shops, and BJ’s Wholesale Club, helping them with digital engagement and advising CIOs and CTOs on where the industry was heading. That experience broadened my perspective and introduced me to the inner workings of large-scale retail.

It also positioned me to take on deeper leadership roles within the retail industry.

From there, I was able to join companies like

• JCPenney

• Michaels

• GameStop

• The Container Store

helping lead their digital transformation initiatives.

What really helped me become the leader I am today was my journey through agile transformations and technology modernization.

I’ve helped teams build agile cultures and learned from incredible leaders, peers, and team members to position technology as a growth enabler. I focus on outcomes more than systems or features.

That’s the difference I bring to the table, and it’s what defines my approach to leadership.

Can you tell us about some of the initiatives and major career accomplishments that you are proud of?

When I think about the work I’m most proud of in my career, it’s not just about launching features or fixing bugs, though those things are fulfilling too. What matters to me is how technology makes life better for the user, from customers to store associates.

One of the standout projects in my journey was the complete digital transformation at JCPenney.

This was back in 2014–2015, when digital transformation wasn’t the buzzword it is today.

We took on an end-to-end overhaul to move from legacy monolithic systems to a modern, cloud-native, open-source, microservices-based architecture. We transformed everything: our website, mobile app, call center, order management, pricing, and content platforms.

The outcomes were tangible, and we were able to dramatically reduce infrastructure costs, introduce faster and more reliable digital experiences, and double our e-commerce revenue. It was a massive initiative that positioned us ahead of the curve in retail tech.

“When you have money and people, you can solve a lot of problems in the technology space, but how do you solve in a constrained environment and deliver the same result?”

Another project I’m incredibly proud of was growing e-commerce sales from $250 million to $1.2 billion in just one year while I was at GameStop.

The timing of console launches and the pandemic played a role, but we also rolled out key innovations like dynamic bundling, same-day delivery, and dropshipping to expand assortment. We scaled the platform to handle up to 100,000 orders per hour, all while operating with a limited IT budget. It was the only way to compete against companies like Amazon and Walmart, which have custom-built systems and virtually unlimited resources.

We were working with off-the-shelf platforms like Salesforce, which was often a black box to us, forcing us to get creative.

That’s something I take a lot of pride in.

As a leader, it’s one thing to deliver results with big budgets and teams. But driving transformation under constraints, using creativity and smart problem-solving, that, to me, is real innovation and leadership.

Looking ahead, what disruptive technology or trend do you see impacting the industry and society?

I’ve always had this vision of what’s coming next and how technology is going to change every 5-10 years, but now, new technology comes seemingly every year that disrupts the entire industry.

Years ago, it was the internet, then cloud computing, and more recently, artificial intelligence.

Today, generative AI has transitioned from an experiment to a productive engine. Companies are already learning how to save money and boost efficiency with AI, and I believe it’s only the beginning.

“We are all going to be forced to adapt.”

At The Container Store, when GenAI started dominating the conversation, I knew we had to approach it with intention. We had to find where it could solve real problems and not just chase the trend. We started by doing an internal assessment to identify business pain points that AI could meaningfully improve.

One of the first areas we focused on was product content.

If you shop online, you know how important the product detail page is, where customers make their decisions. For us, this was manually written content by our internal team, which was time-consuming and delayed product onboarding. So, we decided to introduce GenAI to write descriptions for the existing catalog and new items. This immediately improved our operational efficiency by cutting down the time and effort needed to create compelling content. The tool generated multiple versions that the team could refine, which sped up the process while maintaining quality. While this alone was a big win, we didn’t stop there.

We continued by feeding real, positive reviews into the AI and asking it to generate short, impactful summary statements.

Think of something like: “Customers love this product for its durability and leak-proof design.”

Simple, but powerful.

It added a level of trust and clarity for new customers, right on the product page. After implementation, we saw a 16% increase in add-to-cart rates, a strong signal of improved purchase intent. That direct lift in conversion from AI ties straight into revenue.

What made it even more impactful was how quickly the team embraced the change.

Their ability to move fast allowed us to pair creativity with experimentation, and that combination really paid off.

That smaller-scale success opened the doors for us to go bigger.

We began exploring inventory optimization, demand forecasting, and even AI-enabled support tools for store associates.

Imagine a future where a store’s team member can discreetly ask a voice assistant product questions and get real-time, AI-driven information, acting as a digital expert in their ear.

That’s not science fiction; we’re actively working toward that.

Looking forward, I believe the future lies in vertical AI.

Unlike generic AI models, vertical AI focuses on industry-specific intelligence, like tools tailored to retail for dynamic pricing, inventory planning, or customer sentiment analysis. These models are fine-tuned to understand the nuances of our space, making them far more actionable and impactful.

I’m also closely watching the evolution of composable commerce and advancements in edge-native architectures to see how they can bring digital services closer to the consumer’s in-store point of interaction.

What do you think about the current state of IT talent that’s available? And what strategies are you using to find and develop that talent?

Of course, IT talent is changing a lot with AI.

We’re now evaluating tools that can generate Jira stories for the product team, write code for developers, and write draft test cases for my tester. So the technical aspect is shifting faster than ever, and for me, that means technical skills alone aren’t enough.

What I prioritize is finding people with a growth mindset and collaborative instincts.

“Technology can be learned, but mindset is harder to teach.”

I still remember that after my first job interview, my boss didn’t ask me a single technical question. When I asked him why later, he said, “Technology anyone can learn, what I’m hiring for is a good attitude and a good mindset.”

Today, I look for people who can navigate ambiguity because in retail, uncertainty is constant. From bankruptcies to mergers to layoffs, things move fast.

I need people who can stay focused and execute in any type of environment.

To grow and nurture talent internally, we focus heavily on mentorship and individual development plans. I treat my team like a CEO would run a business. We’re accountable, we own outcomes, and we always understand the “why” behind what we do. It could be a feature launch or a major strategic shift, but I’ll make it a point to explain the reasoning behind every decision.

That openness is what builds trust and boosts morale.

My team operates with a product mindset, always thinking in terms of business outcomes. We also invest in team-building activities, continuous recognition, and peer motivation.

What advice would you give someone aspiring to be a CIO, based on your experiences and your background?

My advice to anyone aspiring to be a CIO is simple: don’t just aim to run IT, aim to lead change.

As technology leaders, we’re not just responsible for system uptime or infrastructure.

We need to deeply understand our customers, whether that’s the end consumer or our internal business partners, and think like product leaders. Speak the language of the business, and become a translator between business needs, customer expectations, and technology.

I often say the modern CIO is also a Chief Relationship Officer because we influence trust by showing how technology can solve real business problems.

We have to bridge the gap between what the business wants and what technology can enable. Ultimately, unless you’re at a tech-native company, technology isn’t the product; it’s the enabler.

“Don’t just aim to run IT, aim to lead change.”

In retail, for example, revenue comes from selling products, not from the tech stack. So if what we build doesn’t drive top-line growth or improve the bottom line, then we’re missing the mark.

As a CIO, you have to keep that business-first mindset at the core of everything you do.

Beyond the organization, I’ve also realized how important it is to contribute to something larger than yourself.

A few years ago, I began asking, “What am I doing outside of work to give back to the community?”

That question led me to get involved with nonprofit organizations like C5, which supports leadership development for students from seventh to twelfth grade. It’s incredibly meaningful to be part of that journey to help shape future leaders while also learning from others.

For me, community involvement and constant learning go hand in hand.

I see myself as a modern leader with a millennial mindset. One who leads with clarity, embraces continuous learning, and isn’t afraid to say, “I don’t know.”

I’ve also learned that 24 hours is never enough time. You have to prioritize ruthlessly.

I try to lead by example, even at home with my kids, teaching them the importance of balance and physical well-being. When they say, “Dad, I don’t have time,” I remind them that it’s not about having time, it’s about making time for what matters.

That’s how I approach leadership, both at work and in life. It’s all about building the right ecosystem and staying grounded in what really matters.

Who would you say has been the biggest influence on your career path, either in school or in a previous role? And why?

There have been two key individuals and two companies that have profoundly shaped my career.

• The first was someone I worked with early on at my startup, who helped lay the foundation for how I think and operate today. That startup experience taught me how to wear multiple hats; I had to handle everything from marketing and consulting to product development and sales. It gave me a 360-degree view of both technology and business, which still influences my leadership style.

• The second major influence was a leader I worked with at JCPenney, and continued to work with through GameStop and The Container Store. He was a mentor as well as a boss, guiding me from a senior manager role all the way to the C-suite. He taught me that in retail, relationships are everything, and technology should always be a growth enabler.

I also picked up important lessons from my time consulting at Amazon, particularly their relentless customer obsession, which left a lasting impression on me.

Beyond those two key individuals, I’ve gained valuable insights from every leader I’ve worked with, and I truly believe there’s something to learn from everyone, as long as you’re paying attention.

My peers and team members, especially, have taught me lessons through continued challenges and inspirations.

Across all these roles, I learned to balance scale with speed, stay calm under pressure, build credibility in any room, and lead with clarity. One thing I’m very fortunate and thankful for is that those above me have taken me with them, and that those under me have followed me wherever I go.

That speaks a lot to me.

How do you decompress from the challenges of being a CIO? What do you like to do for fun?

For me, family time is everything. It’s what keeps me balanced and grounded.

I have two kids, a 10th grader and an 8th grader, and they keep me busy in the best way. We love traveling together, exploring new places, and trying different cuisines. We’re all self-declared foodies.

I also come from India, where movies are a big part of the culture, so watching films with friends is one of my favorite ways to unwind.

Whether it’s family trips, new food experiences, or movie nights, these are the things that recharge me and help me show up as my best self at work.

Are there any books that you recommend, that you give to others, or that have shaped you as a leader?

One book that really resonated with me is The Alchemist. I found it deeply inspiring, especially in how it speaks to purpose and resilience, two qualities that I believe are essential in both life and leadership.

I also come back to a couple others that reflect the way I lead, Siddhartha, for its simplicity and perspective, and Principles: Life and Work by Ray Dalio, which has some great frameworks around decision-making and leadership.

I’m also drawn to the story of Buddha, which offers valuable lessons in perspective and simplicity.

I tend to gravitate toward books that go beyond strategy or management and convey deeper life lessons or a sense of meaning. Those kinds of stories really shape how I lead and stay grounded.

Anything else you’d like to add before we wrap up?

I always emphasize that technology leaders are more than just system and platform experts.

We’re in a unique position to bring people together, understand the real business problems, and act as agents of change.

We have the power to enable growth and drive meaningful outcomes.

A lot of times we are seen solely as tech implementers when the reality is more about aligning technology with business goals, without ever losing sight of the customer.

In retail, where the customer truly is king, every decision we make needs to center around their experience.

If we stay grounded in purpose, in people, and in progress, everything else tends to fall into place.