AI-native automation
Automate work across
Calendly and 
Dropboxby teaching Caddi like a new hire.
Pick any number of tools and Caddi automates them end-to-end. No workflow builder. You teach it the job once, the way you'd train someone new.
Help me automate classify-and-file inbound in Calendly and Dropbox. Caddi builds the loop and runs it.
See it on your stack
See Caddi run Calendly and Dropbox together.
What Caddi is and how it works
An AI teammate that runs your back-office loops.
- Doesn't break. Caddi reads intent, so when fields move or UIs change, your loop keeps running.
- Taught like a new hire. Walk Caddi through the work once. Tweak it later by chat, with no workflow builder to re-architect.
SOC 2 attested · Human-in-the-loop · Full audit trail · 70+ tools across legal, finance, and operations
One continuous loop.
- 01Measure
Caddi watches how the work gets done today.
- 02Create
You teach it the job once. The loop ships.
- 03Improve
Caddi flags upgrades to existing loops and new automations to deploy.
Practical ways to use Calendly and Dropbox together
- 01
Upload file in Dropbox when new event scheduled in Calendly.
Caddi watches Calendly for new event scheduled and upload file in Dropbox — no copy-paste, no missed records.
- 02
Create one-off meeting in Calendly when new file in folder in Dropbox.
Caddi watches Dropbox for new file in folder and create one-off meeting in Calendly so the two systems stay in lockstep.
- 03
Create folder in Dropbox from Calendly events.
When event cancelled happens in Calendly, Caddi create folder in Dropbox with the right context attached.
Actions Caddi can take across Calendly and Dropbox
- 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.
- Dropbox
New file in folder
Triggers when a file is added to a watched folder.
- Dropbox
New shared link
Triggers when a new shared link is generated.
- Dropbox
Upload file
Add a file to a Dropbox folder.
- Dropbox
Create folder
Create a new folder under a parent.
- Dropbox
Create shared link
Generate a shareable link for a file or folder.
- Dropbox
Move file
Move a file between folders.
Common questions
How does Caddi connect Calendly and Dropbox?
Calendly and Dropbox just run together. You teach Caddi the way you'd teach a new hire: walk it through how you use them today, with no workflow builder to wire up. Caddi turns that walkthrough into a verified loop and runs it against Calendly and Dropbox end-to-end.
Do I need engineering help?
No. Whoever does the work today walks Caddi through it on a call, the same way they'd train a new hire. 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, and once the loop ships it runs as deterministic code, repeatable and logged, with any model step scoped and reviewable.
Can Caddi connect Calendly and Dropbox to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Calendly + Dropbox 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 that first walkthrough. The Caddi team reviews every loop before it runs in production.
Ready to automate Calendly and Dropbox?
Drop your work email and we'll show you Caddi running end-to-end against Calendly, Dropbox, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.