Life’s bigger picture is always made up of the tiniest moments of reflection earned through the wisdom-full experiences one goes through in a constantly changing reality.
The globally renowned ‘AI Thought Leader,’ Jaydeep Chakrabarty believes that life is a never-ending journey of small experiments. Whether you’re dabbling with AI prototypes, learning a new board game, or simply picking up a skill you’ve always been curious about, each attempt brings fresh insights and unexpected connections, he says.
Jaydeep joined Piramal Finance in Bangalore as its Director of AI and Tech in 2024. His role involves integrating AI into various parts of the organization, such as credit underwriting and sales enablement. He also focuses on using AI to fuel software delivery within our tech team, making processes more efficient and outcomes more impactful. “It’s been exciting to see how AI can empower traditional industries and help people achieve more,” says Jaydeep, whose personal and professional saga is made up of millions of tiny moments of such deep-rooted reflections.
A Journey of Reflections
Reflecting back on his professional journey, Jaydeep says it started at Cognizant, where he was trained as a Java developer. While he didn’t get to work on Java projects, Jaydeep found his footing in software testing through the Automation Testing Center of Excellence. “Testing was my gateway into understanding the importance of building quality into every aspect of software delivery,” he mentions. It was a foundation that taught him discipline, rigour, and how to approach problems holistically.
After four years at Cognizant, Jaydeep joined ThoughtWorks, where he spent an incredible 15-and-a-half years. ThoughtWorks gave him the chance to wear multiple hats and explore roles that he didn’t even know he’d enjoy. He started as a QA engineer, moved into Ruby on Rails development, and later took on roles like infrastructure engineer, AppSec champion, and UX designer during a stint in Atlanta.
“ThoughtWorks wasn’t just about technical roles—it also gave me the opportunity to lead,” shares Jaydeep, who served as the Head of Capabilities and Head of Communities for ThoughtWorks Bangalore and even led innovation initiatives for a brief period.
Towards the latter part of his journey, Jaydeep became the Head of AI and Generative AI for India and the Middle East, focusing on helping clients adopt AI effectively. Around 2016-17, his fascination with AI turned into something more concrete. “I discovered OpenAI’s open-source initiatives and joined their beta programs as a contributor,” he adds. It wasn’t part of his job—it was pure curiosity. He started experimenting with generative models, which sparked his passion for AI. This led Jaydeep to create GPT Wizards in 2022, an initiative within ThoughtWorks India to help businesses harness generative AI for real-world impact. What started as a small team grew quickly and became a global program, creating immense value for ThoughtWorks’ clients.
Throughout his life, Jaydeep’s take on business has been all about using creative ideas to build practical solutions that genuinely help people rather than just chasing revenue or market share. “I get a kick out of designing new ways for teams to collaborate or harness AI to tackle repetitive tasks,” he insists. For him, business is the channel to bring these innovations to life on a bigger stage, not just an end in itself.
However, here’s the real point: in his role as Director of AI, Jaydeep is not just tinkering behind the scenes. He is focused on creating genuine value for his company and clients—whether that means saving costs, boosting efficiency, or opening up new streams of revenue. He says, “When I push an AI-driven project, it’s with the mindset that we’re solving actual problems in a sustainable way.” That’s what fuels his ‘business appetite: combining technical creativity with a tangible impact.’
“I love starting out with small ideas or proofs of concept and watching them grow into solutions people can’t do without,” he adds. While he might not spend hours perfecting a sales pitch, Jaydeep does appreciate how marketing and strategy play a big role in helping them reach more customers. After all, when an inventive idea meets a real-world need, everybody benefits—colleagues, stakeholders, and customers alike.
“At the heart of it all, my approach is about building meaningful value,” he points out. Not every experiment becomes the next big product. “However, the knowledge and insights we gain always spark new breakthroughs.” That’s why he believes in constantly exploring, learning, and creating. “It’s how we stay ahead in a fast-moving industry and deliver results that actually matter to the people we serve,” says Jaydeep, whose deep-seated curiosity about how technology can genuinely improve people’s lives is what drives him. He is fascinated by that moment when someone realizes a new tool or process can make their day smoother or spark fresh ideas.
He shares, “One of the best lessons I’ve learned from our CTO, Saurabh Mittal, is that what seems impossible today might become possible tomorrow—and you often don’t realize that tomorrow has already arrived unless you try.”
This mindset of “why not give it a shot?” has pushed Jaydeep to build multiple projects within his organization that encourage experimentation. “Whether we’re tinkering with AI prototypes or challenging conventional methods, the willingness to attempt the unthinkable leads to breakthroughs we never saw coming.”
Sure, not every idea pans out, but every single experiment teaches them something new, he believes. And when an “impossible” concept actually clicks, you can see people’s eyes light up—“It’s that spark of wonder that drives me forward,” he adds. “I’ve always believed that creativity means little if it doesn’t help someone, somewhere.” You can design the most brilliant AI model or the most elegant user experience, but if it doesn’t solve a real problem or improve someone’s routine, it’s just a fancy concept.
By keeping that end goal in mind—making life a bit easier and richer for others—Jaydeep finds the energy and passion to keep exploring new possibilities.
Ultimately, his passion springs from watching the impossible become reality and seeing how technology can bridge gaps once thought unbridgeable. “Every time I hear, “That can’t be done,” I’m motivated to ask, “But what if it can?” Because when we dare to believe in tomorrow’s possibilities, we inspire ourselves—and everyone around us—to keep pushing the boundaries of what’s possible today,” emphasizes Jaydeep.
A Personal SWOT Analysis
One of Jaydeep’s greatest strengths is his ability to connect with people from a range of technical backgrounds. Over the years, he’s worn many hats: developer, QA, UX designer, infrastructure specialist, data scientist, data engineer, and more.
“While I’m not a “master” in each discipline,” he accepts, that breadth of experience helps him rally experts around a common goal. Jaydeep loves bringing together developers, designers, and data scientists, energizing them to tackle problems that initially seem impossible to solve.
For him, it’s less about being the star player and more about building the right team and giving them the support they need to shine. Jaydeep also embraces servant leadership, where he sees himself as the person who pushes people upward rather than directing from above. He thrives on helping others discover their talents and reach new heights.
Another strength is Jaydeep’s knack for explaining complex technology in simple terms. That skill has opened doors for him, including a column in The Hindu, where he’s broken down topics like AI, security, and IoT so more people can get excited about what’s possible.
“Of course, I’m still a work in progress,” says Jaydeep, adding that his biggest weakness is saying “yes” to too many things. “I get so enthusiastic about new ideas and projects that I sometimes overextend myself.” Managing time and energy effectively has become an ongoing challenge—one he’s actively trying to address.
“It’s a double-edged sword: passion fuels creativity, but it can also lead to burnout if left unchecked,” says Jaydeep, who believes his range of skills and passion for bringing people together define his leadership style. At the same time, he’s learning to balance that enthusiasm with a realistic workload. “If there’s one thing my journey has taught me, it’s that every strength can become a weakness if not carefully managed—and I’m committed to finding that balance every day,” says Jaydeep with an innate sense of reflection.
Surfing on the Tsunami
All these strengths and weaknesses helped Jaydeep to tackle the biggest crisis time the modern world faced during the COVID-19 pandemic. Like everyone else, he felt the jolt when COVID-19 hit. In the early days, it was daunting to imagine collaborating strictly through a screen—no casual chats by the coffee machine, no face-to-face brainstorming, recalls Jaydeep. “But I soon realized that this shift wasn’t optional; it was the only way to keep projects going and people safe.”
Working at ThoughtWorks back then helped tremendously, as distributed teams were already part of our day-to-day. That familiarity eased the technical transition to video calls, remote stand-ups, and digital whiteboards. Still, the larger world was a constant source of anxiety. Around him, friends and family members tested positive, and the daily news was full of grim statistics. He caught COVID-19 too, which added a layer of worry—yet it also reminded him to focus on what he could control: staying safe, staying connected, and doing his work as best he could under the circumstances.
“In a surprising twist, those lockdowns brought one unexpected gift: more time at home with my family. We rediscovered the joy of board games, bonding over everything from strategic epics to quick-fire card games. For someone like me—who’s always been big on creativity and problem-solving—these evenings rekindled my love for play and learning. Even though the pandemic limited our freedom to meet up with friends or travel, it gave me a deeper appreciation for the simpler moments,” remembers Jaydeep.
Looking back, COVID-19 forced him to rethink how he manages both work and life. Adapting to remote tools, supporting colleagues and clients online, and finding comfort in small joys at home were all part of surviving (and, at times, thriving). He continues, “While I wouldn’t wish a pandemic on anyone, I can’t deny the insights it offered: new ways to collaborate, greater resilience in tough times, and a chance to slow down and reconnect with what truly matters.”
Going Back to the Beginning
Jaydeep grew up in Silchar, a lively town in Assam, where his early years were filled with books, friends, and a whole lot of chess. School was in Bengali medium, so his world revolved around his native language, while English mostly stayed in the background. Chess, on the other hand, was a constant companion—it became his favourite way to unwind, compete, and sharpen my thinking. Over time, the game shaped the way Jaydeep approached challenges in life, teaching me patience, focus, and strategic thinking.
After completing his twelfth grade, he took a big leap and moved out of Silchar to join the Vellore Institute of Technology (VIT) for a degree in Computer Science. This was a huge shift—not just geographically but culturally. Suddenly, everything was in English, and Jaydeep felt like he was decoding a new language while studying computer science. The first year was tough; he flunked most subjects except mathematics (thankfully, numbers are universal). But he didn’t give up and eventually adjusted, graduated, and left VIT more confident and prepared for the next phase of life.
It was in 2014, after he had settled into his professional journey, that Jaydeep achieved one of his milestones—he became a FIDE-rated chess player. “Chess had always been more than just a hobby for me; it was a way of life. Competing at that level brought both fulfilment and valuable lessons, and it remains a big part of who I am today.”
Living in the Now
Beyond work, writing has always been Jaydeep’s passion. He regularly contributes to publications like The Hindu and Open Source For You, where he simplifies complex topics like generative AI and open-source technologies for readers. “Writing is my way of giving back to the tech community and encouraging others to explore the possibilities of technology.”
One of his most exciting projects right now is a book Jaydeep is co-authoring with Harinee Muralinath, the Business Information Security Officer of ThoughtWorks India and the Middle East. “Harinee is not just a colleague but a very close friend, and together, we’re writing about the journey of bringing an idea to production in generative AI,” he informs. The book, which is set to release in mid-February through a renowned publisher, is all about bridging the gap between imagination and execution in the world of AI and Generative AI. “It’s a labour of love, and I can’t wait to see how readers respond to it.”
When he’s not working, Jaydeep usually indulges in his other great passion: strategic board games. These aren’t your typical roll-the-dice games—his favourites include Dungeons & Dragons, Warhammer, and other complex games that make you plan every move. Whenever he visits Singapore, he makes it a point to join local gaming communities for long and competitive sessions. Jaydeep’s collection of board games is massive, built over years of collecting from India and across the globe. “Every trip abroad means I return with a suitcase full of new games, much to my family’s amusement.”
Another creative outlet for Jaydeep is painting. “Miniature painting, in particular, is something I love—there’s a unique joy in adding tiny details to figures. I also enjoy bottle painting and experimenting with colours on larger canvases. On quieter days, I might even hum a tune or record songs for my YouTube channel.”
Presently, Jaydeep lives in Bangalore with his family. His wife, Dr Anindita Chatterjee, is a dentist. “She keeps us all smiling—literally and figuratively. We have two wonderful kids, Saanvi and Aadrit, who bring much energy (and questions!) into our lives. My mom also lives with us, adding her warmth and care to our home,” informs Jaydeep.
Jaydeep reflects, “Life for me is about balancing all these passions—chess, board games, painting—and creating meaningful moments with family. It’s about finding joy in small things, like rolling dice late into the night or perfecting a miniature’s tiny cape, and letting those moments add up to a life well-lived.”
A Magical Mantra
Jaydeep’s biggest piece of advice to future leaders is to focus on growing the strengths of the people around you. When you help others uncover their hidden talents, you’re not just building a stronger team—you’re creating an environment where each individual feels valued and motivated to excel. As a leader, you’ll often switch roles: sometimes, you’re an enabler, working hands-on with your team to guide them through challenges; other times, you’re an ambassador, leveraging your experience and credibility to champion their work to the wider organization.
A crucial part of leadership is recognizing that everyone—regardless of their title or experience—has something to teach you. “I’ve learned countless lessons from colleagues who were technically “junior,” and it’s shaped my perspective on what true collaboration should look like.” By actively seeking out and appreciating different viewpoints, you grow as a leader alongside your team.
He also believes in delegating authority, not just tasks. When you only delegate tasks, you might build a group of skilled followers, but you risk stifling real ownership and creativity. On the other hand, giving team members the authority to make decisions and innovate transforms them into leaders in their own right. That sparks a chain reaction of shared accountability, higher confidence, and a sense of true partnership within the team.
Lastly, never lose sight of the human element behind every project or goal. Being there to support, mentor, and celebrate your team’s successes will pay off far more than simply issuing directives. Over time, this approach creates a network of empowered leaders, each capable of driving initiatives forward—often in ways you never expected. If there’s one lesson I’ve learned, it’s that the more leaders you help create, the more your own leadership evolves organically.
Jaydeep’s mantra for growth is simple: help others succeed, and you’ll grow alongside them. Stay curious, especially in a world where Gen AI and other new technologies emerge daily. Tools like YouTube can guide you to cutting-edge knowledge. Learning is an ongoing process, and if you keep your mind open, success will follow naturally. It’s not just about personal wins—it’s about creating an environment where everyone thrives. Embrace everyday changes with confidence. Don’t be afraid to fail—those detours often spark the best ideas. Just remember: growth isn’t a solo sport. The more you uplift others around you, the richer your own path becomes. Keep your enthusiasm alive, stay open to new possibilities, and continue challenging yourself to move beyond your comfort zone. That’s where the most meaningful transformations happen.
Awards & Accolades
- Jaydeep Chakrabarty was honored with the Global Technology Influencer of the Year award in Dubai, presented by Mr Hanif Shaikh, founder of Emirates. This moment affirmed Jaydeep’s commitment to advancing AI and tech innovation on a global stage.
- At ThoughtWorks, he was selected for their Global Leadership Training, an exclusive program designed to cultivate top talent.
- Around the same time, he contributed to the 2021 FOSS Report on the state of open source in India, spotlighting his passion for open-source advocacy and the value it can bring to organizations nationwide.
- At ThoughtWorks, he led the GPT Wizards initiative in 2023, helping teams across India and the Middle East explore and implement generative AI solutions.
- Beyond corporate settings, he’s written for ‘Open Source For You, The Hindu, and DataQuest, breaking down complex tech topics—like AI, security, and IoT—into something people can digest and get excited about.
- On the personal front, becoming an Arena FIDE Master in chess back in 2019 was a proud milestone that connected Jaydeep’s love for strategic thinking with a globally recognized accomplishment.
His Social Media Links:
- FB – https://www.facebook.com/jaydeep.chakrabarty/.
- Twitter – https://x.com/jchakrabarty.
- LinkedIn – https://www.linkedin.com/in/jchakrabarty/.
- YouTube – https://www.youtube.com/@jaydeepchakrabartysings.