- Automations
- Calendly + Clio
AI-native automation
Connect Calendly and Clio 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 Calendly and Clio together
- 01
Create matter in Clio when new event scheduled in Calendly.
Caddi watches Calendly for new event scheduled and create matter in Clio — no copy-paste, no missed records.
- 02
Create one-off meeting in Calendly when new matter in Clio.
Caddi watches Clio for new matter and create one-off meeting in Calendly so the two systems stay in lockstep.
- 03
Create contact in Clio from Calendly events.
When event cancelled happens in Calendly, Caddi create contact in Clio 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 Calendly and Clio
- 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.
ClioNew matter
Triggers when a new matter is opened in Clio.
ClioNew contact
Triggers when a new contact is created.
ClioTime entry posted
Triggers when a new time entry is recorded.
ClioCommunication added
Triggers when a call, email, or meeting is logged.
ClioCreate matter
Open a new Clio matter with client, billing, and intake fields.
ClioCreate contact
Add a person or company contact to Clio.
ClioCreate note
Log a timestamped note against a matter.
ClioCreate time entry
Record time against a matter with rate and activity code.
ClioUpload document
Attach a document to a matter with metadata.
Common questions
How does Caddi connect Calendly and Clio?
Calendly and Clio 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 Clio 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 Clio to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Calendly + Clio 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 Clio?
Drop your work email and we'll show you Caddi running end-to-end against Calendly, Clio, and the rest of your stack.




