AI-native automation
Automate work across
Calendly and 
Docusignwith Caddi AI Agents.
Automate anything you do across Calendly, Docusign, and the rest of your tools. Sign in, show or tell Caddi what you want, and it runs end to end. No workflow builder.
How to connect Calendly and Docusign
Connect Calendly to Caddi
Allow1Sign in to Calendly
One click with your own Calendly login. No API keys.
Connect Docusign to Caddi
Allow2Sign in to Docusign
The same click again. Both tools are connected.
Send envelope from template in Docusign when new event scheduled in Calendly.
ScreenshareType it3Show or tell it
Screenshare the job, or type it in chat. Change it any time.
- Running
14 done1 for review
4Watch it run
Caddi does the work and flags anything unsure for review.
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 · 150+ tools across legal, finance, and operations
Practical ways to use Calendly and Docusign together
- 01
Send envelope from template in Docusign when new event scheduled in Calendly.
Caddi watches Calendly for new event scheduled and send envelope from template in Docusign. No copy-paste, no missed records.
- 02
Create one-off meeting in Calendly when envelope completed in Docusign.
Caddi watches Docusign for envelope completed and create one-off meeting in Calendly so the two systems stay in lockstep.
- 03
Send envelope from document in Docusign from Calendly events.
When event cancelled happens in Calendly, Caddi send envelope from document in Docusign with the right context attached.
Actions Caddi can take across Calendly and Docusign
- 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.
- Docusign
Envelope completed
Triggers when all signers complete an envelope.
- Docusign
Envelope sent
Triggers when an envelope is sent for signature.
- Docusign
Recipient signed
Triggers when a single recipient completes signing.
- Docusign
Envelope declined
Triggers when a recipient declines an envelope.
- Docusign
Send envelope from template
Send a pre-built template out for signature with merged fields.
- Docusign
Send envelope from document
Send an arbitrary document out for signature.
- Docusign
Void envelope
Cancel an in-flight envelope with a reason.
- Docusign
Download signed PDF
Pull the executed PDF and certificate from a completed envelope.
- Docusign
Move envelope
Move a completed envelope to a specified folder.
Common questions
How does Caddi connect Calendly and Docusign?
Calendly and Docusign 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 Docusign 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 Docusign to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Calendly + Docusign 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 Docusign?
Drop your work email and we'll show you Caddi running end-to-end against Calendly, Docusign, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.