Caddy

High-Level Overview

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.

Origin Story

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.

Core Differentiators

• Context-Aware Voice Control: Caddy understands what’s on your screen and what app you’re in, enabling it to act on nuanced commands like “follow up on this email” or “create a ticket for this Slack message.”
• Action and Dictation Modes: Users can either automate tasks (Action mode) or replace typing entirely (Dictation mode), making Caddy a comprehensive voice-first productivity tool.
• API-Based Integration: Caddy works behind the scenes via APIs, so it doesn’t take over your computer but instead executes tasks in the background, requiring only an approval step.
• Focus on Flow: The product is designed to minimize interruptions, keeping users in their workflow while offloading repetitive tasks.
• Early Access and Community: Caddy has cultivated a strong early user base through a private beta and waitlist, with active engagement from founders and productivity enthusiasts.

Role in the Broader Tech Landscape

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.

Quick Take & Future Outlook

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.