Caddy YC Application

Fall 2025Active

Caddy went through Y Combinator in the Fall 2025 batch as a B2B company. Below: what the company does, who founded it, and its application to YC, reconstructed question by question in the real YC form.

YC batch: Fall 2025
Industry: B2BEngineering, Product and Design
Team size: 4
Status: Active
Launched: 2025

Founders

Connor WasloFounder
Rajiv SanchetiFounder

What Caddy does

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.

Caddy's YC application, reconstructed

Y Combinator application

Caddy, Fall 2025 batch. The real form questions, answered from public data.

Founders2
Company7
Progress7
Idea4
Equity3
Curious2
Batch Preference1

Company

Company name

Caddy

Describe what your company does in 50 characters or less.

Your partner for everyday work, lives in iMessage

What is your company going to make? Please describe your product and what it does or will do.

Caddy is an AI assistant that proactively helps you get work done across your existing tools - email, calendar, Slack, Linear, Notion - without interrupting your flow. It learns how you work and produces real work artifacts that sound like you, keeping context and voice intact.

Where do you live now, and where would the company be based after YC?

We live in New York City and plan to base the company there after YC.

Explain your decision regarding location.

We're based here because that's where we live and work, and it's where we've built our initial product and user base. Staying in NYC lets us keep momentum and access local talent.

21 more answers in the full application

Founders, Progress, Idea, Equity, Curious, Batch Preference are in the full version. Create a free account to open it in YC Insights, next to every other YC batch.

See full application

Frequently Asked Questions

Is this the real Caddy YC application?

No. Y Combinator keeps submitted applications private. This is a reconstruction: the real YC form questions, answered from Caddy's public data (launch notes, founder backgrounds, product description). It shows how a company like Caddy would present itself to YC, not the text they submitted.