Block has unveiled Managerbot, a new AI agent embedded in the Square platform that represents the most tangible evidence yet of CEO Jack Dorsey’s vision for artificial intelligence reshaping commerce. Unlike traditional AI assistants that wait for questions, Managerbot proactively monitors a seller’s business, identifies emerging problems, and proposes actionable solutions — working continuously in the background like an always-on business partner.
The Shift from Reactive to Proactive
In an exclusive interview with VentureBeat, Willem Ave, Block’s head of product at Square, described Managerbot as a decisive break from the company’s earlier Square AI assistant, which functioned as a reactive chatbot answering seller questions about sales, employees, and business performance.
“The big shift from Square AI to Managerbot is really from reactive to proactive,” Ave said. “What that means is the primary interface is not a question box. You assign tasks to Managerbot, and that could be based on data, an insight, or a signal from your business.”
Three Core Capabilities That Work While You Sleep
Managerbot operates across three core domains, continuously watching over a seller’s business and surfacing recommendations with proposed actions attached.
Inventory Forecasting: Managerbot monitors stock levels, sales velocity, and external signals such as weather patterns and local events. When an item is about to run out — or when sellers should stock up ahead of anticipated demand — Managerbot alerts them in advance. “In warmer weather, we can see that you sell more of a certain good,” Ave explained. “That’s the forecasting capability, combined with local data — weather, events — so we can help sellers manage both their inventory and cash flows.”
Employee Shift Scheduling: One of the most time-consuming tasks for small business owners, shift scheduling is now handled autonomously by Managerbot. The agent analyzes forecasted sales data and generates optimized employee schedules that balance worker preferences with coverage needs. “It turns out that frontier models are actually pretty good at it,” Ave noted.
Automated Marketing Campaigns: Managerbot identifies sales trends across a seller’s catalog and automatically drafts win-back campaigns and promotional outreach targeted at a store’s best customer segments. Block is seeing “very meaningful lift” from Managerbot-generated campaigns compared to what some sellers create manually.
Built on Frontier Models, Driven by Block’s Agent Harness
Managerbot runs on third-party frontier models — Ave specifically referenced Anthropic’s Sonnet and OpenAI’s GPT family — but Block’s competitive advantage lies in the “agent harness” the company has built around those models.
That harness draws heavily on Goose, Block’s open-source agent framework, and incorporates learnings from its consumer-facing Money Bot on Cash App. The challenge specific to Square is scale and complexity: a seller might interact with hundreds of different tools across invoicing, inventory, customer management, marketing, payroll, and scheduling.
“This isn’t like, you know, you load a skill and call it a day — think about hundreds of skills,” Ave said. “Actually, managing the context and managing the way that we progressively disclose tools, and some of the other innovation that we have at the harness layer, is I think some of the secret sauce.”
Human-in-the-Loop: Every Action Requires Approval
A critical design decision shapes every Managerbot interaction: the agent does not autonomously execute changes to a seller’s business. Every write action — whether adjusting a shift schedule, publishing a marketing campaign, or modifying inventory — requires explicit seller approval. Managerbot generates clear summaries of proposed changes, making it easy for sellers to understand and approve or reject recommendations.
Availability and Pricing
The product is beginning to roll out now, with full availability to Square sellers expected over the coming months. Block declined to say whether Managerbot would carry an additional fee or be bundled into existing Square subscriptions.
For millions of small businesses relying on Square to run day-to-day commerce, Managerbot represents the first AI agent that truly works as a proactive business partner — anticipating problems, optimizing operations, and generating growth opportunities without being asked.