Owen Jennings on Block's AI-Driven Restructuring

Jennings joined Block 12 years ago on the Square business team and moved to Cash App in 2016 when it was 25 people doing peer-to-peer payments. He describes how Cash App's differentiation was instant bank-to-bank transfers on debit rails (via Visa Direct), which gave them product-market fit that competitors like Venmo lacked. The company functionalized ~18-20 months ago, consolidating product, engineering, and design across all brands under Jennings to enable more flexible resource allocation.

On AI: Jennings says Block has been early — they launched Goose, an open-source agent harness (the first of its kind per his account), and worked with Anthropic and OpenAI on MCP. But in the last week of November / first week of December 2025, the arrival of Opus 4.6 and Codex 5.3 crossed a threshold where agentic systems could autonomously write production-quality code. The org change — which overindexed reductions in product, design, and engineering — followed directly. Block now uses small squads of 2-3 full-stack engineers running tools like BuilderBot (a Slack-integrated agent built on Goose) and G2 (an agentic operating system with MCPs into Snowflake, Tableau, Gmail, Calendar, and other tools). Customer support automation is at 75-80% of chat inquiries handled without human intervention, with no degradation in CSAT. Jennings emphasizes a risk spectrum: internal tools and prototypes are high-risk-tolerance, while financial platform infrastructure (reconciliation, treasury, card issuance) remains heavily human-reviewed.

“In like late November with the model changes, we got to the point where these agentic systems were actually able to write the code autonomously and the code was good enough to ship into prod and that was like a huge change. The org changes were mostly a reflection of that.”