Caddy: Your Personal AI for everyday work. Lives in your texts.

Caddy

Your Personal AI for everyday work. Lives in your texts.

Fall 2025

Active

Artificial Intelligence

Automation

AI Assistant

https://caddy.app/

Your Personal AI for everyday work. Lives in your texts.

If you’ve got a lot to do, we believe AI can make things feel doable. Caddy is our core product: a Personal AI that helps you stay on top of everything going on. All you have to do is text. On overwhelming days, it’s super simple to just drop any task in a text thread, and Caddy will help you handle it. Caddy also keeps an eye on your calendars, chats and tasks to make sure you stay focused on what matters. If something needs you, Caddy will nudge you, or can just do it if you don’t have time. The best part is, no two Caddys are alike. The more you use Caddy, the more it learns your vibe, how you work, and what you care about.

Active 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.

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

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.

Rajiv Sancheti

Founder

Company Launches

Caddy: The Voice Interface for Your Computer

See original launch post

Hey everyone, we’re Connor and Rajiv.

We led Loom’s AI suite and saw firsthand how natural language was changing how people work. Now we’re building Caddy, the voice interface for your computer that lets you automate work across all your apps.

Join the waitlist at trycaddy.ai

Launch video: https://www.youtube.com/watch?v=v1HwM9mBYHU

The problem

Work today happens across a maze of apps. Slack for messaging. Linear for tickets. Gmail for communication. Calendar for scheduling. Every task requires jumping between tabs and tools.

Even with AI everywhere, we are still using the same old interfaces. Voice assistants like Siri or Alexa can answer trivia but cannot do real work. They do not understand what is on your screen, what app you are in, or what you mean when you say “follow up on this.”

The result is constant context switching, lost flow, and hours wasted on work that should happen automatically.

What we are building

Caddy lives on your desktop and lets you operate your computer with your voice. It has two simple modes.

Action mode: You speak your intent, and Caddy takes action.

Ask Caddy to create a ticket in Linear, send a message in Slack, or schedule a meeting in Calendar. Caddy sees what is on your screen and connects it to your apps, so you can stay focused on the work that matters.

Dictation mode: Never type again

Write emails, respond to messages, or leave comments anywhere text input exists. It is a direct replacement for typing that works globally across your computer.

Together, these two modes let you automate work and control your computer completely with your voice.

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Who Caddy is for

We are starting with founders, operators, productivity power users and the voice first generation who spend their days moving between tools and losing time to repetitive work. If that sounds like you, we would love to get you early access.

To join our waitlist add your email at trycaddy.ai or shoot us a message founders@trycaddy.ai

The team

Before starting Caddy, Connor and Rajiv spent four years at Loom where they led product and design for Loom’s AI suite and core product.