AI-native automation
Automate work across
Litify and 
Squarewith Caddi AI Agents.
Connect Litify and Square: Create invoice in Square when new matter in Litify. Teach Caddi the job once, the way you'd train someone new, and it runs end to end. No workflow builder.
Discover, automate and govern the work between Litify and Square
Caddi AI Agents find the repetitive handoffs between Litify and Square, learn them the way a new hire would, and run them for you, with every run on the record. No workflow builder, no code.
Discover repetitive work
across all your tools.
Train an AI agent to do the work
over a video call.
Search mailMatters / Whitmore HoldingsGovern every AI agent,
every decision.
Discover repetitive work
across all your tools.
Train an AI agent to do the work
over a video call.
Search mailMatters / Whitmore HoldingsGovern every AI agent,
every decision.
Discover repetitive work
across all your tools.
Train an AI agent to do the work
over a video call.
Search mailMatters / Whitmore HoldingsGovern every AI agent,
every decision.
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 Litify and Square together
In a law firm the work between Litify 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 Litify.
Caddi watches Litify for new matter and create invoice in Square. No copy-paste, no missed records.
- 02
Create matter in Litify when new payment in Square.
Caddi watches Square for new payment and create matter in Litify so the two systems stay in lockstep.
- 03
Create customer in Square from Litify events.
When intake submitted happens in Litify, Caddi create customer in Square with the right context attached.
Actions Caddi can take across Litify and Square
- Litify
New matter
Triggers when a new matter is opened in Litify.
- Litify
Intake submitted
Triggers when a new intake clears Salesforce validation.
- Litify
Matter status changed
Triggers when a matter changes status or stage.
- Litify
Create matter
Open a new Litify matter with client and intake data.
- Litify
Create intake
Push a new intake record into Litify for triage.
- Litify
Create task
Schedule a task against a matter and team member.
- Litify
Upload document
Attach a document to a matter with metadata.
- 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 Litify and Square?
Litify 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 Litify 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 Litify and Square to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Litify + 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 Litify 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 Litify and Square?
Drop your work email and we'll show you Caddi running end-to-end against Litify, Square, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.