item Wants to Bury the CRM and Replace It With an AI Sidekick

The customer relationship management category is one of the oldest and most lucrative in enterprise software, but it is also one of the most hated. Sellers complain about pipeline hygiene, support managers complain about data drift, and operations teams complain about the dozens of integrations required to make any of it useful. item, a Y Combinator Fall 2025 startup based in San Francisco, is betting that the entire shape of the CRM is wrong for an AI-native era – and that the right replacement looks less like a database with forms and more like a colleague.

item connects to all of a company’s customer-facing tools, gathers and enriches context automatically, and becomes the single source of truth from which both human teams and AI agents can act. At the center of the experience is the Assistant – described by the company as a “sidekick for daily work” – which can send follow-ups, research leads, or add deals on a simple prompt rather than through a labyrinth of dropdowns, custom fields, and required workflows. For repeatable processes, item users build Agents trained the way a manager would train a new hire: by writing documents that describe how the work should be done. Once trained, item Agents run sales, support, and account management workflows autonomously, with humans stepping in for judgment calls rather than data entry.

The pitch lands at a moment of unusual tension in the CRM market. The dominant incumbents have spent the last two years scrambling to bolt generative AI onto fundamentally form-driven products, and many customers are skeptical that the resulting features amount to more than expensive copilots draped over an old paradigm. item argues that the database-and-forms abstraction is the problem, not the absence of an AI sidebar – a stance that puts the company in direct philosophical opposition to nearly every legacy vendor. By treating the CRM as a context layer rather than a system of record that humans must constantly feed, item aims to flip the relationship between user and software: instead of the user serving the CRM, the CRM serves the user.

Founded in 2024 by Andres Santanilla, a second-time founder, and Akshay Guthal, item is a six-person team operating out of San Francisco. The company is hiring its first product engineers and is squarely positioned as AI CRM software for the B2B, Automation, and AI Assistant categories – a wedge that could prove decisive if it converts even a small fraction of the disenchanted Salesforce or HubSpot user base. The market opportunity is enormous: CRM is a multi-billion-dollar category and the lifecycle workflows around it – outbound sales, customer support, account management – represent a meaningful share of every B2B company’s labor budget.