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Rob Grigg

Rob Grigg

Group Chief Technology Officer, Holiday Extras

Rob Grigg — AI Augmented CTO | Architect | Technologist  Rob is a CTO and technologist, drawing on more than thirty years of experience building scalable platforms, nurturing high performing teams, and navigating the ever shifting tides of technology. From the rise of the internet and open source, through cloud computing, mobile, and now AI, he has consistently adapted to and helped others embrace each new wave of innovation with clarity, pragmatism, and curiosity.  A lifelong software engineer and hands on leader, Rob blends technical depth with cultural awareness to drive real world impact.

He is now exploring the next transformation: the era of AI native development. His current work focuses on how tools like Copilot, Claude, and Cursor are changing how we think, collaborate, and build — turning engineers into editors, shaping code with intent, not syntax.  He is known as much for his storytelling and bad analogies as his systems thinking, looking to bring some humour, insight, and a human touch to complex topics.  Currently Group CTO at Holiday Extras, Rob spends less time behind the console and more time shaping systems, growing teams, and helping engineers thrive in this new hybrid world.

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