platoseed
← All companies
Caddy logo

Caddy

Active

Your partner for everyday work, lives in iMessage

Fall 2025Founded 20254 peopleNew York City, NY, USA
Generate ideas →

About

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.

Founders · 2

Connor Waslo
Connor WasloFounder

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 SanchetiFounder
Airbnb

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.

B2BEngineering, Product and DesignArtificial IntelligenceAI Assistant

Related startups

Also in Fall 2025