Why digital transformation rarely goes to plan | The Digital Lighthouse

Why do so many transformation programmes fail? And what does it take to actually deliver change at scale? In this episode of The Digital Lighthouse, Zoe Cunningham speaks with Andy Burton, a technology leader with over 30 years of experience delivering large-scale digital transformation across industries including insurance, retail, and online gaming. Andy has held senior roles at organisations including Sky Betting & Gaming, The Very Group, and most recently esure, where he led a multi-year transformation to replatform the business and build a modern, digital-first insurer. They explore what transformation really looks like in practice. While many organisations begin with clear plans and ambitious timelines, the reality is far messier. External events, legacy constraints, and constant change mean even the best plans rarely survive intact. Andy shares what made the esure transformation successful, why many programmes fail before the final step, and what it really means to become “digital on the inside”. ⸻ 🔎 What you will learn • Why transformation plans rarely survive real-world conditions • Why adaptability matters more than perfect planning • Why many organisations fail to decommission legacy systems • What “digital on the inside” really means in practice • Why you can’t innovate if you can’t deliver the basics • Why technology should be embedded across the business • How to move from transformation to continuous change