Siddharth
Jhunjhunwala

Built for the long game

Siddharth Jhunjhunwala was in college when he started his first company. Not as a project. Not as a side hustle. As a career choice, made early and with conviction.

That was 1995. He was in Kolkata, working with network solutions while his classmates were still figuring out their first internship applications. By 2000, he had founded Web Spiders Group - an enterprise software company that would spend the next two-and-a-half decades growing into a 290-person operation across San Jose, London, Singapore, and India's 32+ cities.

Here is what makes that trajectory interesting: he did not pivot into AI when it became fashionable. He was already there. Gecko, Web Spiders' AI interview bot, was scanning candidate faces for emotional hesitation before most business executives had a clear definition of "machine learning." When BBC One's The One Show invited Siddharth to demonstrate Gecko live on air - in front of nearly 2 million viewers - the bot went head-to-head with a human recruiter, analyzing six real candidates for a consulting role. The AI and the human reached similar conclusions. The cameras loved it. Siddharth let the product do the talking.

That instinct - build the thing, show what it does, let the proof speak - runs through everything Siddharth has shipped. His framework for chatbot success is blunt: Content, Context, Intent. Three pillars. If any one is missing, the bot fails. Not a complicated philosophy, but one that most enterprise software vendors somehow still manage to miss.

The Kolkata roots matter. La Martiniere for Boys gave him the structure. St. Xavier's College gave him a Commerce degree with Honors. Then, more than a decade into running his company, he enrolled in UC Berkeley's Haas School of Business executive leadership program in 2013 - not because he needed a credential, but because he wanted the perspective. That pattern - build first, then refine the thinking - is the rhythm of his career.

SpiderX AI is the company's sharpened edge. Spun out from the broader Web Spiders Group, it focuses on enterprise conversational AI: voice agents for restaurants (DINEO), AI recruiters (Gecko), omnichannel customer service bots, and the kind of embedded AI that does not announce itself but quietly reshapes how enterprises talk to customers. In 2024, SpiderX earned Intellyx's Digital Innovator recognition. In 2025, it walked away from the CX Strategy Summit with "Best Contact Centre Experience." These are not startup awards. They are enterprise credibility markers - the kind that come from sustained delivery, not a good pitch deck.

What makes Siddharth interesting to watch is the consistency. He is not the founder who reinvented himself three times or sold one company to fund the next. He built one thing, kept building it, kept adding to it, and kept showing up - at SWITCH 2024 in Singapore, at the ABA Bank Marketing Conference in Chicago, at Retail MediaX London in May 2025, where SpiderX demonstrated how shoppers can literally talk to websites and get real answers. Twenty-five years of compounding, in a sector that has completely transformed around him while he kept pace.

The work is not finished. Voice-first AI for retail. Conversational AI for banks. AI agents for legal firms and government agencies. The ambition is broad, the execution is methodical, and the team is global. Siddharth Jhunjhunwala started with network cables in Kolkata. He is now building the infrastructure for how enterprises will communicate with their customers in the next decade. He was early then. He is still early now.