Caddy
Caddy is a YC Fall 2025 (F25) company. Team of 3.
About Caddy
Summary
Caddy builds a proactive personal AI assistant that works across email, calendar, Slack, and other everyday tools to handle tasks and communications on the user's behalf. It monitors schedules, messages, and to-dos, then acts without waiting to be asked, drafting replies, booking appointments, and updating documents in the user's own voice. It replaces the manual coordination and context-switching that fills a knowledge worker's day.
Business model
Paid subscription plans accessed after a free sign-up flow.
Go-to-market
Caddy targets individual professionals and is accessed entirely through text or voice messages, with no app to download, lowering the barrier to getting started.
From the Y Combinator listing
The voice interface that works proactively for you
Caddy is the operating system that works proactively for you. It learns how you work and acts on your behalf, keeping work moving while your context and voice stay intact. Instead of producing generic AI output, Caddy creates real work artifacts that sound like you and fit how you actually work. Today, it operates across the tools you use every day, including email, calendar, Slack, Linear, and Notion. Caddy is built by the team behind Loom’s AI and core product. We believe the next era of computing is software that understands intent, handles ambiguous work, and quietly gets work done in the background.
Facts
- B2B / B2B -> Engineering, Product and Design
- 3
- Active
- Early
Founders (2)
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