Caddy

Your partner for everyday work, lives in iMessage

Y CombinatorFall 2025ActiveB2BEngineering, Product and DesignArtificial IntelligenceAI Assistant

What they do

Problem

Knowledge workers waste time switching between tools and drafting repetitive communications instead of moving work forward with consistent context and voice.

Solution

Caddy is a proactive AI operating system in iMessage that learns your workflow and creates and executes real work artifacts across tools like email, calendar, Slack, Linear, and Notion.

Who it's for

Busy professionals and teams at startups and businesses who coordinate work across multiple workplace tools.

Founders

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.

LinkedIn · X

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.

LinkedIn · X