Scaling Up · 2025-09-07 · 49 min
Owen Jennings, the head of product at Block Inc(NYSE:XYZ) and a key person around the executive table of what is now by market cap, one of the largest 500 companies in the world. Block (formerly known as Square) is really several powerful ecosystems under one roof: Square serving millions of merchants; Cash App, the consumer super app that's become the financial home for tens of millions of people; and of course, Australian founded Afterpay, the global buy-now-pay -later platform that connects these two bringing shoppers and sellers together. Owen is one of the rare executives that has truly grown up inside acompany over the past 13 years. Owen has worn just about every hat from early roles in ops to becoming the COO of Cash app where he helps scale it from a scrappy side project into a FinTech powerhouse that now generates c$6 billion in annual gross profit. Today Owen leads product across all of Block. He's widely credited for the new sense of product velocity inside the company and the ability to ship faster, to experiment at scale, and to embed AI as a multiplier in everything they do. Most importantly, this is a story about scaling culture.
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