Caddy

Caddy

Fall 2025

The voice interface that works proactively for you

About Company

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.

Active Founders

Connor Waslo

Connor Waslo

Founder

Co-founder of Caddy. Building the operating system that understands your workflows and gets work done for you. Previously led product for Loom's AI Suite and Monetization team.

Rajiv Sancheti

Rajiv Sancheti

Founder

Co-founder of Caddy. Building the operating system that understands your workflows and gets work done for you. Previously led design for Loom’s AI suite, and before that, worked at Airbnb and KP Fellows.

Company Facts

LocationRemote
Team Size3
Founded2025
StatusActive