AI-native automation
Automate work across
Rocket Matter and 
Squarewith Caddi AI Agents.
Automate anything you do across Rocket Matter, Square, 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 Rocket Matter and Square
Connect Rocket Matter to Caddi
Allow1Sign in to Rocket Matter
One click with your own Rocket Matter login. No API keys.
Connect Square to Caddi
Allow2Sign in to Square
The same click again. Both tools are connected.
Create invoice in Square when new matter in Rocket Matter.
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 Rocket Matter and Square together
In a law firm the work between Rocket Matter and Square 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 invoice in Square when new matter in Rocket Matter.
Caddi watches Rocket Matter for new matter and create invoice in Square. No copy-paste, no missed records.
- 02
Create matter in Rocket Matter when new payment in Square.
Caddi watches Square for new payment and create matter in Rocket Matter so the two systems stay in lockstep.
- 03
Create customer in Square from Rocket Matter events.
When time entry posted happens in Rocket Matter, Caddi create customer in Square with the right context attached.
Actions Caddi can take across Rocket Matter and Square
- 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.
- Square
New payment
Triggers when a payment completes.
- Square
Invoice paid
Triggers when a Square invoice is paid.
- Square
New customer
Triggers when a customer is created.
- Square
Create invoice
Send a Square invoice to a customer.
- Square
Create customer
Add a customer with contact details.
- Square
Fetch payouts
Pull payouts and fees for reconciliation.
Common questions
How does Caddi connect Rocket Matter and Square?
Rocket Matter and Square 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 Rocket Matter and Square 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 Rocket Matter and Square to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Rocket Matter + Square 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 Rocket Matter and Square 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 Rocket Matter and Square?
Drop your work email and we'll show you Caddi running end-to-end against Rocket Matter, Square, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.