AI-native automation
Automate work across
Calendly and 
Rocket Matterwith Caddi AI Agents.
Automate anything you do across Calendly, Rocket Matter, 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 Rocket Matter
Connect Calendly to Caddi
Allow1Sign in to Calendly
One click with your own Calendly login. No API keys.
Connect Rocket Matter to Caddi
Allow2Sign in to Rocket Matter
The same click again. Both tools are connected.
Create matter in Rocket Matter 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 Rocket Matter together
In a law firm the work between Calendly and Rocket Matter is organized by matter: the right client, the right matter, the right people on it. Caddi carries that context through every step, so nothing is filed against the wrong case.
- 01
Create matter in Rocket Matter when new event scheduled in Calendly.
Caddi watches Calendly for new event scheduled and create matter in Rocket Matter. No copy-paste, no missed records.
- 02
Create one-off meeting in Calendly when new matter in Rocket Matter.
Caddi watches Rocket Matter for new matter and create one-off meeting in Calendly so the two systems stay in lockstep.
- 03
Post time entry in Rocket Matter from Calendly events.
When event cancelled happens in Calendly, Caddi post time entry in Rocket Matter with the right context attached.
Actions Caddi can take across Calendly and Rocket Matter
- 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.
- Rocket Matter
New matter
Triggers when a new matter is opened in Rocket Matter.
- Rocket Matter
Time entry posted
Triggers when a new time entry is recorded.
- Rocket Matter
New invoice
Triggers when an invoice is generated.
- Rocket Matter
Create matter
Open a new Rocket Matter matter with client and billing details.
- Rocket Matter
Post time entry
Record a time entry against a matter.
- Rocket Matter
Add expense
Record a billable expense against a matter.
- Rocket Matter
Add note
Log a timestamped note against a matter.
Common questions
How does Caddi connect Calendly and Rocket Matter?
Calendly and Rocket Matter 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 Rocket Matter 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 Rocket Matter to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Calendly + Rocket Matter 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.
Does this work for law firms?
Yes. Caddi runs Calendly and Rocket Matter with the matter as the unit of work, so documents, time, and communications land against the right client and matter rather than in a general folder. Firms most often start with intake, document filing, or billing prep.
Ready to automate Calendly and Rocket Matter?
Drop your work email and we'll show you Caddi running end-to-end against Calendly, Rocket Matter, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.