Why digital transformation rarely goes to plan

Why digital transformation rarely goes to plan

From The Digital Lighthouse by Softwire

May 13, 2026 · 26 min

About this episode

Zoe Cunningham interviews Andy Burton about the challenges and realities of digital transformation in organizations.

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 go awry before the final step, and what it really means to become “digital on the inside”.

People in this episode

Host: Zoe Cunningham

Guest: Andy Burton

Topics covered

  • digital transformation
  • change management
  • technology leadership
  • business strategy
  • legacy systems
  • organizational change

Keywords

  • digital transformation
  • change at scale
  • technology leader
  • business replatforming
  • successful transformation
  • legacy constraints
  • digital-first insurer

Mentioned in this episode

Organizations: Sky Betting & Gaming, The Very Group, esure, insurance, retail, online gaming

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