Block's Managerbot: Square's Proactive AI Business Agent

Block has launched Managerbot, an AI agent embedded in its Square platform that proactively monitors seller businesses, identifies problems, and proposes solutions without requiring user prompts. It marks a significant shift from Square's earlier reactive chatbot model. The product represents CEO Jack Dorsey's most concrete AI bet yet, signaling how Block believes artificial intelligence can reshape operations and product development. Square head of product Willem Avé describes the core change as moving from a question-and-answer interface to an agent that takes initiative on behalf of small business owners.