Harshender Singh Chhabra

Most enterprise AI initiatives fail not because of technology, but because organisations layer AI onto operating models never designed for scale, risk, or accountability. With 26+ years across global enterprises, I work as an Enterprise Architect on complex transformation and commercial pursuits, partnering with CIOs, CTOs, boards, and founders where technology decisions carry long-term commercial, operational, regulatory, and risk consequences. I lead solution strategy across large-scale deal pursuits, shaping AI-enabled enterprise solutions for commercial wins that scale. To date, I have contributed to $300M+ in won deals, working directly with CXOs and senior stakeholders across prospective and existing customers. My work sits at the intersection of enterprise architecture, AI transformation, and deal strategy, helping organisations move beyond isolated use cases to AI-native operating models that deliver growth and resilience under real enterprise constraints, with accountability built in. I advise leaders on where AI creates durable leverage, where it introduces hidden risk, and how platforms, operating models, and decision structures must evolve to support sustainable outcomes. Connect to discuss scaling AI-native architecture or follow for deal-tested frameworks that help leaders make fewer, better decisions under uncertainty.