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Caddy: AI assistant voice interface that automates tasks across work apps by understanding user intent for professionals, focused on hands-free productivity.
Key people at Caddy.
Caddy was founded in 2025 by Connor Waslo (Founder) and Rajiv Sancheti (Founder).
Based in San Francisco, California, Caddy develops a voice-activated interface that controls business applications by interpreting user intent and screen context to automate background tasks. The business-to-business productivity software functions as a proactive AI assistant, targeting professionals who require hands-free automation across their daily workflows. Users can issue verbal commands to execute complex, multi-step processes across third-party platforms such as Slack and Linear without interrupting their primary desktop activities. Operating with a current scale of two to three employees, the seed-funded startup is actively participating in the Fall 2025 batch of its lead investor, Y Combinator. The company receives additional advisory support from Y Combinator partner Aaron Epstein as it expands its engineering operations. Caddy was founded in 2025 by Rajiv Sancheti and Connor Waslo, who previously directed product and design for the AI suite at Loom.
Caddy was founded in 2025 by Connor Waslo (Founder) and Rajiv Sancheti (Founder).
Caddy is a desktop voice interface designed to streamline productivity by allowing users to control and automate tasks across their work apps—such as Slack, Linear, Gmail, Calendar, and Notion—using only their voice. The product is built for founders, operators, and productivity power users who spend their days switching between tools and performing repetitive tasks. Caddy solves the problem of context switching and workflow fragmentation by enabling users to stay in flow, offloading routine actions to a voice-powered assistant that understands both intent and context. The company has gained early traction through a private beta and is backed by Y Combinator, signaling strong momentum and market interest.
Caddy was co-founded by Connor Waslo and Rajiv, both of whom led the AI suite at Loom, where they witnessed firsthand how natural language and automation were transforming the way people work. Their experience at Loom exposed them to the pain points of fragmented workflows and the limitations of existing voice assistants, which inspired them to build a more powerful, context-aware voice interface for the desktop. After leaving Loom, they moved to San Francisco to join Y Combinator, where they refined their vision and began building Caddy. Early feedback from productivity-focused users and a growing waitlist have validated their approach, setting the stage for broader adoption.
Caddy is riding the wave of AI-driven productivity and the shift toward voice-first interfaces. As work becomes increasingly distributed across apps and platforms, the need for seamless, context-aware automation is growing. Caddy’s timing is ideal, as organizations seek ways to reduce friction and boost efficiency in hybrid and remote work environments. The company is also part of a broader trend toward ambient computing, where technology recedes into the background and responds to natural human input. By making voice a primary interface for work, Caddy is helping to shape the future of how people interact with their digital tools.
Caddy is poised to become a foundational layer in the next generation of productivity software. As AI and voice technology mature, the demand for tools that can automate complex workflows across apps will only increase. Caddy’s focus on context, flow, and ease of use gives it a strong edge in a crowded market. The company is likely to expand its integrations, deepen its AI capabilities, and potentially move into new verticals or enterprise use cases. For investors and users alike, Caddy represents a compelling bet on the future of work—one where voice is not just a novelty, but a powerful, everyday interface.
Key people at Caddy.