Counter to typical scaling patterns, Square reverted from a business-unit model back to a functional one. They believed the General Manager structure diluted deep domain expertise, and a functional organization better preserves the "craft and excellence" within disciplines like product and engineering.
The Directly Responsible Individual (DRI) model is not just for accountability. Its primary purpose is to eliminate product slowdowns caused by "silent vetoes" from cross-functional teams. It empowers a single person to cut through bureaucracy and drive decisions across the entire product lifecycle.
Historically, organizational structures existed to manage information flow. AI can now encode that institutional knowledge into agents that democratize data and decision-making. This enables small, autonomous teams to execute faster without the need for traditional management layers for communication.
The core value of AI for SMB owners isn't just automation; it's providing an "intelligent thought partner." It helps with the isolated, difficult decisions like menu pricing or marketing strategy, directly addressing the loneliness entrepreneurs face when they have no one to consult.
Moving beyond simple Q&A, the next wave of AI must perform real work. Instead of just text answers, users expect AI to synthesize data and generate sophisticated "artifacts"—like complete menu analyses or labor forecasts—that provide immediate, actionable value for decision-making.
Instead of being constrained by a predefined Total Addressable Market (TAM), Square believes great products create new markets, making the potential almost infinite. To maintain focus within this vast space, they use a strategic "forcing function"—their "neighborhood network" concept—to guide product decisions.
Platform teams risk building generic solutions that don't truly solve anyone's problem. Square avoids this by having its platform organization also own and be responsible for specific product surfaces. This structure forces them to stay close to customer outcomes and build practical tools.