Square's public roadmap serves a dual purpose. While it informs customers, its primary internal function is to create accountability. Committing to features publicly forces the organization to deliver on its promises with speed and quality, preventing internal delays.
While competitors focus on software, Square believes designing hardware "from the chip up" is a key advantage. This control allows for a superior, integrated experience for both customers and staff at the physical counter, making the technology feel seamless and delightful.
AI will fundamentally change user interfaces. Instead of designers pre-building UIs, AI will generate the necessary "forms and lists" on the fly based on a user's natural language request. This means for the first time, the user, not the developer, will be the one creating the interface.
Square views its role as taking complex technology, from financial tools to AI, that is usually only accessible to large corporations and making it simple and available to small businesses. The ultimate goal is to improve their survival rate and help revitalize local economies.
Instead of a rigid framework, great decisions come from "terroir"—the right mix of ingredients. This includes deep customer empathy, market knowledge, and an intuitive grasp of constraints. This foundation allows a leader's gut instinct to function as a highly trained model.
Block restructured from divisional GMs to a functional organization (Engineering, Product, Design) across all brands. This creates a single shared roadmap and forces alignment, enabling cross-unit collaboration that was difficult when incentives were siloed in separate P&Ls.
To avoid AI hallucinations, Square's AI tools translate merchant queries into deterministic actions. For example, a query about sales on rainy days prompts the AI to write and execute real SQL code against a data warehouse, ensuring grounded, accurate results.
To serve its largest customers, Square's open platform is crucial. It allows enterprises to integrate their preferred third-party tools with Square's core services. This flexibility prevents churn by allowing customers to customize their tech stack instead of being locked into a closed ecosystem.
Square's product development is guided by the principle that "a seller should never outgrow Square." This forces them to build a platform that serves businesses from their first sale at a farmer's market all the way to operating in a large stadium, continuously adding capabilities to manage growing complexity.