AI-native automation
Automate work across
Clio and 
Squarewith Caddi AI Agents.
Connect Clio and Square: Create invoice in Square when new matter in Clio. 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 Clio and Square
Caddi AI Agents find the repetitive handoffs between Clio 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 Clio and Square together
In a law firm the work between Clio 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 Clio.
Caddi watches Clio for new matter and create invoice in Square. No copy-paste, no missed records.
- 02
Create matter in Clio when new payment in Square.
Caddi watches Square for new payment and create matter in Clio so the two systems stay in lockstep.
- 03
Create customer in Square from Clio events.
When new contact happens in Clio, Caddi create customer in Square with the right context attached.
Actions Caddi can take across Clio and Square
- Clio
New matter
Triggers when a new matter is opened in Clio.
- Clio
New contact
Triggers when a new contact is created.
- Clio
Time entry posted
Triggers when a new time entry is recorded.
- Clio
Communication added
Triggers when a call, email, or meeting is logged.
- Clio
Create matter
Open a new Clio matter with client, billing, and intake fields.
- Clio
Create contact
Add a person or company contact to Clio.
- Clio
Create note
Log a timestamped note against a matter.
- Clio
Create time entry
Record time against a matter with rate and activity code.
- Clio
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 Clio and Square?
Clio 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 Clio 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 Clio and Square to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Clio + 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 Clio 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 Clio and Square?
Drop your work email and we'll show you Caddi running end-to-end against Clio, Square, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.