AI-native automation
Automate work across
Calendly and 
Dropbox Signby 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 envelope generation in Calendly and Dropbox Sign. Caddi builds the loop and runs it.
See it on your stack
See Caddi run Calendly and Dropbox Sign 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 Sign together
- 01
Send signature request in Dropbox Sign when new event scheduled in Calendly.
Caddi watches Calendly for new event scheduled and send signature request in Dropbox Sign — no copy-paste, no missed records.
- 02
Create one-off meeting in Calendly when signature request completed in Dropbox Sign.
Caddi watches Dropbox Sign for signature request completed and create one-off meeting in Calendly so the two systems stay in lockstep.
- 03
Use template in Dropbox Sign from Calendly events.
When event cancelled happens in Calendly, Caddi use template in Dropbox Sign with the right context attached.
Actions Caddi can take across Calendly and Dropbox Sign
- 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 Sign
Signature request completed
Triggers when all signers complete a request.
- Dropbox Sign
Signature request sent
Triggers when a request is sent for signature.
- Dropbox Sign
Signer declined
Triggers when a signer declines a request.
- Dropbox Sign
Send signature request
Send a document or template for e-signature.
- Dropbox Sign
Use template
Send a request built from a reusable template.
- Dropbox Sign
Download signed PDF
Pull the executed PDF and audit trail.
- Dropbox Sign
Send reminder
Nudge signers who haven't completed.
Common questions
How does Caddi connect Calendly and Dropbox Sign?
Calendly and Dropbox Sign 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 Sign 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 Sign to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Calendly + Dropbox Sign 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 Sign?
Drop your work email and we'll show you Caddi running end-to-end against Calendly, Dropbox Sign, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.