Caddy
A personal AI assistant that lives in iMessage and works across email, calendar, Slack, Linear and Notion, surfacing what needs attention and acting on your behalf. Built by Loom's former AI team; early access, pricing not yet public.
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Our take
Caddy is a personal AI assistant that lives in iMessage and works across email, calendar, Slack, Linear and Notion. Built by Loom's former AI team, it watches your calendars, chats and tasks and tells you what needs attention now, or just handles it. Still early access with pricing not yet public, so treat the outcome claims as the vendor's own.
Best for
Founders and operators who run their day across many tools and want a proactive assistant in a chat thread they already use.
Pros
- Lives in iMessage - almost no learning curve
- Acts across email, calendar, Slack, Linear and Notion
- Proactive: surfaces what needs you right now
- Built by Loom's former AI and product team
Cons
- Early access; pricing not public yet
- Outcome claims are vendor-reported
- iMessage-first, so non-Apple users are left out
How it compares
Against horizontal assistants in our catalog like Lindy, Caddy's bet is the messaging surface - no new app to open, just a thread you already use.
Full review
Most AI assistants ask you to live in their app. Caddy goes the other way: it sits in iMessage and treats the thread as the interface. It keeps an eye on your calendar, chats and tasks, then pings you with what actually needs a decision, and can act across email, Slack, Linear and Notion when you ask it to.
The team comes from Loom's AI and core product group, which shows in the focus on low friction. The caveats are the usual early-stage ones: it's invite-based, pricing isn't public, and the productivity numbers are Caddy's own. Worth a spot on the waitlist if you live in messages; worth waiting for real reviews before you rely on it.
Cloudkart Trust Graph
3.1/5- Actual Utility3.2/5
Source: LLM scoring pass — composite-only catalog tools (2026-06)
- Ease of Use3.8/5
Source: LLM scoring pass — composite-only catalog tools (2026-06)
- Pricing Fairness2.5/5
Source: LLM scoring pass — composite-only catalog tools (2026-06)
- Reliability2.5/5
Source: LLM scoring pass — composite-only catalog tools (2026-06)
- Differentiation3.3/5
Source: LLM scoring pass — composite-only catalog tools (2026-06)
Scored as of . Each score is versioned and auditable; vendors cannot buy it.
How this score is set
- Editorial rubric
- Primary signal — five dimensions, 3.1/5 average.
- Community reviews
- None yet.
- Pricing verified
- Not yet verified
- Independence
- Score set by our editorial team before any affiliate relationship is considered. No vendor can buy it.
Frequently asked questions
- Is Caddy free, and how much does it cost?
- Caddy has a free tier, with paid plans that unlock advanced features.
- Who is Caddy best for?
- Founders and operators who run their day across many tools and want a proactive assistant in a chat thread they already use.
- How is Caddy rated on Cloudkart.ai?
- Caddy scores 3.1 out of 5 on the Cloudkart.ai rubric, which weighs actual utility, ease of use, pricing fairness, reliability and differentiation. Scores are set editorially and can never be bought.
Community reviews
No community reviews yet. Be the first to share how Caddy works for you.
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