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Explore the challenges and lessons learned from leading a major platform rewrite at a high-growth fintech company managing £15 billion in assets through this 26-minute conference talk. Discover how commercial debt—the non-scalable business decisions made during early growth phases—often poses greater risks than technical debt when scaling an organization. Learn about the critical decision-making process for convincing boards to invest in technology transformation when existing systems that built a successful business won't support the next decade of growth. Gain insights into the personal evolution required when transitioning from a senior technology leader to an executive team member, including mastering stakeholder management, strategic communication, and balancing high-level executive perspective with deep technical problem-solving. Understand practical approaches to handling legacy data challenges and discover how to build compelling business cases for complex, expensive transformation projects using agile methodologies applied to seemingly waterfall-style initiatives.