Rewiring the Founder Playbook is where founders, investors, enterprise buyers and policymakers confront the decisions reshaping the next generation of financial companies: who gets funded, what buyers will pay for, which moats survive AI, and when growth should become an exit. Flagship Founders Peak talks reveal the personal stories behind those decisions.

Corporate technology leaders are increasingly rejecting per-user subscription licenses that divorce vendor fees from measurable client performance. Research from Deloitte’s Global Chief Procurement Officer Survey indicates that 58% of enterprise procurement executives are prioritizing shared-risk, outcome-contingent commercial contracts across new software implementations to curtail budget creep. However, structuring these arrangements without triggering legal disputes requires objective measurement standards. This session explores how enterprise buyers and vendors structure verifiable performance baselines, downside penalties, and margin-protected upside mechanisms to deploy sustainable, outcome-based software engagements across mission-critical enterprise systems.

ASEAN offers significant opportunities for regional growth, but its diversity means that success in one market does not readily translate to another. For Singapore-based FinTechs, the challenge is not simply where to expand, but how to sequence that growth: build credibility with a major customer at home, or enter another market early to test whether the business can travel. Firms must also decide what to own, what to localise and where partnerships can provide faster access to customers, infrastructure and regulatory capabilities. AI may sharpen market insights and support experimentation, but its value depends on sound use cases, trusted data and effective governance. These choices ultimately determine whether expansion creates regional scale or merely complexity.