- Automations
- Box + Calendly
AI-native automation
Connect Box and Calendly with AI
Pick any two tools and Caddi runs the loop between them end-to-end — no complicated workflow builder, no IT ticket.
- Doesn't break. Caddi reads intent, so when fields move or UIs change, your loop keeps running.
- Screenshare to set up, chat to improve. Show Caddi once on a screenshare. Tweak it later by chat — no workflow builder to re-architect.
SOC 2 attested · Human-in-the-loop · Full audit trail · 70+ tools across legal, finance, and operations

Practical ways to use Box and Calendly together
- 01
Create one-off meeting in Calendly when new file in folder in Box.
Caddi watches Box for new file in folder and create one-off meeting in Calendly — no copy-paste, no missed records.
- 02
Upload file in Box when new event scheduled in Calendly.
Caddi watches Calendly for new event scheduled and upload file in Box so the two systems stay in lockstep.
- 03
Update invitee in Calendly from Box events.
When folder shared happens in Box, Caddi update invitee in Calendly with the right context attached.
One continuous loop.
- 01Measure
Caddi watches how the work gets done today.
- 02Create
You screenshare it once. The loop ships.
- 03Improve
Caddi flags upgrades to existing loops and new automations to deploy.
Actions Caddi can take across Box and Calendly
BoxNew file in folder
Triggers when a file is uploaded to a watched folder.
BoxFolder shared
Triggers when a folder collaboration is added.
BoxUpload file
Add a file to a Box folder with metadata.
BoxCreate folder
Create a new folder under a parent with permissions.
BoxSearch files
Find files or folders with advanced search filters.
BoxMove file
Move a file between folders.
- Calendly
New event scheduled
Triggers when an invitee books a meeting.
- Calendly
Event cancelled
Triggers when a scheduled meeting is cancelled.
- Calendly
No-show recorded
Triggers when an invitee is marked as a no-show.
- Calendly
Create one-off meeting
Spin up a one-off meeting link with custom configuration.
- Calendly
Update invitee
Modify an existing invitee's details or registration.
Common questions
How does Caddi connect Box and Calendly?
Box and Calendly just run together. All it takes is showing us how you use them — one screenshare, no workflow builder to wire up. Caddi turns the demo into a verified loop and runs it against Box and Calendly end-to-end.
Do I need engineering help?
No. Whoever does the work today shows it once on a call. Caddi builds the loop. No code, no IT ticket.
Is my data safe?
Yes. Caddi is SOC 2 attested. The AI watches and builds the automation, but once the loop ships it runs deterministically — no model in the loop at runtime.
Can Caddi connect Box and Calendly to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Box + Calendly loop is live, Caddi suggests other tools and other workflows to fold in.
How fast can it go live?
Typical first loops ship within a week of the screenshare. The Caddi team reviews every loop before it runs in production.
Ready to automate Box and Calendly?
Drop your work email and we'll show you Caddi running end-to-end against Box, Calendly, and the rest of your stack.




