From Cycling to C-Suite: Anand Kapoor’s Journey With ISB Executive Education’s CDO Programme
‘Dispersion’ in the roles of technology leaders is one of the key findings of Deloitte’s Global Technology Leadership Study 2023, which got everyone thinking: do tech leaders need to do and be more? The report described this as the technology function’s evolution “from seamless operations to seamless leadership.” If we were to speak more plainly and without jargon, the scope of work for technology leaders was expanding to include organisation-wide initiatives that were not traditionally in their bucket.
So, when we had the privilege to interview Anand Kapoor, who has been in the Indian tech space from its nascent stages and experienced this shift firsthand, we strived to understand it better, coupled with his upskilling journey. Kapoor, Group CIO at Straive, has completed the ISB Executive Education’s CDO Programme to further sharpen his skills in digital leadership. For him, lifelong learning isn’t just about career progression—it’s about constantly pushing the boundaries of what’s possible. Whether he’s cycling across Sri Lanka or navigating digital transformation at work, Kapoor thrives on challenges.
In this interview, Kapoor takes us through his journey, sharing his thoughts on balancing work, life, and learning, the importance of upskilling, and how his passion for cycling helps him stay focused and driven.
The Road to Upskilling
Kapoor’s educational journey didn’t follow a traditional path. He started working full-time right after high school, juggling a variety of degrees while building his career. “I didn’t have a storied educational background,” he admits. “I did a bachelor’s in commerce from Delhi University, followed by a bachelor’s in information technology from Indira Gandhi National Open University. But all the while, I was working, gaining experience in the real world.”
This hands-on approach has been a defining factor in Kapoor’s career, but he acknowledges the importance of formal learning in staying relevant. “At the end of the day, you’re always competing with someone who might have a better degree. So, it’s important to keep upskilling,” he explains.
Once he had made up his mind to do the programme, Kapoor received the requisite support of his CEO and peers to pursue this upskilling journey, which made the CDO programme the perfect next step in his journey.
Why the ISB Executive Education’s CDO Programme?
Despite already being in a technology leadership role that involved digital transformation, Kapoor felt the need to solidify his knowledge with a structured programme. “I’ve been leading digital initiatives for multiple firms, but I wanted something that would connect what I already know with new insights and strategies,” he says.
The ISB Executive Education’s CDO Programme fit the bill perfectly. With a focus on digital transformation and leadership, the programme offered a blend of practical knowledge and academic insights, which he found valuable. “It wasn’t about learning from scratch—it was about refining what I already knew and gaining new perspectives,” he explains.
The Impact of the CDO Programme
While Kapoor’s role as a digital leader meant that much of the programme content aligned with his existing knowledge, he still found immense value in the programme. “It wasn’t a life-changing epiphany,” he admits, “but it gave me new points of view and reinforced key concepts that I could immediately apply at work.”
One of the standout aspects of the programme was the real-world experience shared by the professors. “I particularly enjoyed learning from Professor Nandu Nandkishore, who had led Nestlé in Indonesia. His insights into handling real-world crises, like the Indonesian currency inflation, were incredibly valuable,” he recalls. These practical lessons, combined with academic knowledge, made the course a holistic learning experience.
Building Connections With the CDO Programme
One of the key benefits of attending a prestigious programme like ISB Executive Education’s CDO Programme is the network you build along the way. “The cohort was filled with interesting people from similar backgrounds, and it was great to connect with them on a personal level,” he shares.
While the programme was primarily online, Kapoor and his peers got the opportunity to catch up in person during the campus immersion, which was one of the high points of their learning journey. “Meeting in person added a whole new dimension to the learning experience. The immersion programme was one of my best memories from the course,” he says.
Balancing Work, Learning, and Life
As a seasoned professional, Kapoor is no stranger to managing multiple responsibilities. However, balancing a demanding full-time job, family life, and an intensive learning programme wasn’t without its challenges. “There were days when things got hectic,” he admits. “But since the programme didn’t have a steep learning curve for me, I was able to manage.”
Cycling: A Source of Focus and Discipline
Outside of work and learning, Kapoor is an avid cyclist and triathlete. In fact, his love for cycling played a key role in his decision to move to Bangalore, where many of his cycling friends and coach are based. “Cycling and other endurance sports help me stay focused and disciplined,” he shares. “It’s a great way to clear my mind and push my limits.”
Balancing his passion for cycling with his professional life has taught him the importance of time management and prioritisation—skills that have served him well throughout his career and learning journey.
The Importance of Lifelong Learning
When asked about the importance of continuous learning in today’s world, Kapoor is clear: “For the first time in history, we don’t know what the office of the future will look like. We don’t even know what skills will be needed in five or ten years.”
This uncertainty, he believes, is why lifelong learning is more important than ever. “Whether it’s structured learning through executive programmes or learning on the job, you have to keep growing. If you’re not learning, you’re falling behind,” he says.
Structured Learning vs. Learning on the Job
This obviously prompted us to ask him about his career, which has been a blend of structured learning and on-the-job experience. He believes both have their place. “Structured learning is great for everyone—it gives you a broad foundation,” he explains. “But learning on the job is where you really solidify your knowledge. It’s more practical, and you retain it longer because you’re applying it in real-time.”
For Kapoor, the ISB Executive Education’s CDO Programme was the perfect complement to his real-world experience, offering structured insights that he could immediately apply at work.
Final Thoughts
Anand Kapoor’s journey through the ISB Executive Education’s Chief Digital Officer Programme is a testament to the power of continuous learning and the importance of balancing work, life, and passion. Whether he’s cycling across countries or leading digital transformation initiatives, his drive to push boundaries and stay ahead of the curve is what sets him apart.
For those considering upskilling, he offers this advice: “Don’t wait for the perfect time. Whether you’re already in a leadership role or just starting out, there’s always more to learn. The world is changing fast, and you have to keep up.”
NOTE: The Chief Digital Officer Programme has now been revamped and enriched with AI-related modules. It is now called the Chief Digital and AI Officer Programme by ISB Executive Education.
