AI-native automation
Automate work across
Calendly and 
ShareFileby AI screensharing.
Pick any amount of tools and Caddi automates them end-to-end. No workflow builder, just show Caddi.
See it on your stack
See Caddi run Calendly and ShareFile 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.
- 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
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.
Practical ways to use Calendly and ShareFile together
- 01
Upload file in ShareFile when new event scheduled in Calendly.
Caddi watches Calendly for new event scheduled and upload file in ShareFile — no copy-paste, no missed records.
- 02
Create one-off meeting in Calendly when new file in folder in ShareFile.
Caddi watches ShareFile for new file in folder and create one-off meeting in Calendly so the two systems stay in lockstep.
- 03
Create folder in ShareFile from Calendly events.
When event cancelled happens in Calendly, Caddi create folder in ShareFile with the right context attached.
Actions Caddi can take across Calendly and ShareFile
- 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.
- ShareFile
New file in folder
Triggers when a file is uploaded to a watched folder.
- ShareFile
Shared link created
Triggers when a new shared link is generated.
- ShareFile
Upload file
Add a file to a ShareFile folder.
- ShareFile
Create folder
Create a new folder under a parent.
- ShareFile
Send file via link
Send a secure link to one or more recipients.
Common questions
How does Caddi connect Calendly and ShareFile?
Calendly and ShareFile 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 Calendly and ShareFile 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 Calendly and ShareFile to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Calendly + ShareFile 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 Calendly and ShareFile?
Drop your work email and we'll show you Caddi running end-to-end against Calendly, ShareFile, and the rest of your stack.