The Impossible Trade-Off: How Square Built a Simple Ecosystem and Brought AI to the Corner Store

Willem Ave, Square's Global Head of Product, details the company’s evolution from a simple card reader to an entire ecosystem. He explains the complex "art and science" of keeping the platform effortless while adding sophisticated banking and software. Crucially, Willem reveals how Square is bringing accessible, trustworthy AI tools—like a virtual CMO or CFO—to small, non-knowledge worker businesses, arguing this is the best form of economic empowerment. The conversation explores balancing this innovation with the absolute necessity of maintaining merchant trust.