AI

Caddy

Caddy is an AI teammate operating within iMessage that helps professionals manage daily tasks by integrating with work tools like email, Slack, and Notion. Founded by Loom's AI team and backed by Y Combinator, it brings artificial intelligence into everyday workflows.

Work at Caddy?

Team size
1-10
Founded 2025
Total raised
$500k

About Caddy

Caddy is building a personal, proactive AI teammate that operates directly within iMessage, bringing artificial intelligence into the natural flow of everyday work. Founded by the team behind Loom's AI and core product, the company is on a mission to make AI feel simple, natural, and useful for professionals managing their daily tasks. Based in SoHo, New York, the four-person team is backed by Y Combinator, Matrix Partners, and prominent angels. Currently in beta with hundreds of monthly active users, Caddy integrates seamlessly with essential work tools including email, calendar, Slack, Linear, Notion, and Stripe, enabling users to manage their workflows without leaving their messaging app.

Culture & values

Small, high-trust team where everyone has significant ownership, autonomy, and responsibility

All current team members are former founders

Culture is intense, fast-paced, and deeply ownership-driven

Strong emphasis on product craft, speed, and in-person collaboration

Team works in person from SoHo, New York office, typically six days a week

Team shares lunch and dinner together in the office

Deeply bought into the same goal: building a product and company they're proud to share with their friends, families, and the world

High standards and fast pace

Team thrives with autonomy and cares about craft

Funding

$500ktotal raised

Company at a glance

Founded2025
Websitecaddy.app
LinkedInLinkedIn

Top Benefits

  • Founding-level equity
  • Shared lunch and dinner in the office

The team at Caddy

1-10 peopleSee everyone on LinkedIn

Christian Catanese

Founding Engineer @ Caddy (YC F25)

Connor Waslo

Co-Founder @ Caddy (YC F25)

RS

Rajiv Sancheti

Co-Founder @ Caddy (YC F25)

Location

Team Composition

3 people
  • Entrepreneurship2 senior2
  • Engineering1 senior1

Life at Caddy

Frequently asked questions

Key benefits include: Founding-level equity, Shared lunch and dinner in the office.

Ask your AI about Caddy

Connect Clera once, then ask what they're hiring for.

Ask about this company

Tell me about Caddy (https://www.getclera.com/companies/caddy). Then find open roles at similar startups on Clera that fit my profile.
Not connected yet? Takes a minute
One click above pre-fills the connector. Or by hand: Settings > Connectors > Add custom connector, paste https://mcp.getclera.com. Either way, sign in with the account you use on Clera and approve the consent screen.
https://mcp.getclera.com

Sign in with your Clera account. MCP docs

Companies similar to Caddy