Descriptions:
Owen Jennings, business lead at Block overseeing Square, Cash App, and Afterpay—and former CEO of Cash App during its critical growth period—joins the a16z Show to explain the reasoning behind Block’s widely-discussed reduction in force of more than 40%. Jennings traces the foundation to 2023 and 2024, when Block built Goose (described as one of the first publicly known agent harnesses, launched in early 2024) and developed G2, an internal agentic operating system that lets any employee automate deterministic workflows.
The decisive shift came in late November and the first week of December 2025, when models including Opus 4.6 and Codex 5.3 demonstrated they could work reliably with existing complex codebases—not just greenfield projects. Jennings describes this as a binary change: the decades-long correlation between headcount and output broke almost overnight, with one or two engineers on AI tools now delivering 10x to 100x the output of larger teams. Engineering roles bore the heaviest cuts; outbound sales and account management were largely unaffected.
Jennings addresses the Jevons Paradox directly, suggesting that while individual companies will need fewer engineers for a given product roadmap, total global demand for software development may expand dramatically as AI lowers the cost of building in sectors where it was previously uneconomical. He also describes his current workflow as managing 10–20 concurrent agents running in the background, reviewing and committing their output rather than executing tasks linearly.
📺 Source: a16z · Published April 01, 2026
🏷️ Format: Interview
