Member of Technical Staff

Caddy is building the next interface for AI — a personal, proactive AI teammate that lives in iMessage and works on your behalf across the tools you use every day. Instead of requiring complex prompts or technical setup, Caddy learns how you work and acts autonomously, handling everything from drafting email responses to managing your calendar, Slack, Notion, and more.

Their mission is to make AI feel simple, natural, and useful in the flow of everyday work. While most AI products today still feel like tools for the technical 1%, Caddy is building software that's accessible to everyone — from startup founders to people in theater — without downloading an app or learning a new interface.

Culture

Caddy is a small, high-trust team where everyone has significant ownership, autonomy, and responsibility. All current team members are former founders. The culture is intense, fast-paced, and deeply ownership-driven with a strong emphasis on product craft, speed, and in-person collaboration.

The team works in person from their SoHo, New York office, typically six days a week. They're deeply bought into the same goal: building a product and company they're proud to share with their friends, families, and the world.

Caddy is backed by Y Combinator, Matrix Partners, and prominent angels. The founding team previously built Loom's AI and core product.