AI-native automation
Automate work across
Square and 
Surepointwith Caddi AI Agents.
Automate anything you do across Square, Surepoint, 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 Square and Surepoint
Connect Square to Caddi
Allow1Sign in to Square
One click with your own Square login. No API keys.
Connect Surepoint to Caddi
Allow2Sign in to Surepoint
The same click again. Both tools are connected.
Create matter in Surepoint when new payment in Square.
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 Square and Surepoint together
In a law firm the work between Square and Surepoint 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 Surepoint when new payment in Square.
Caddi watches Square for new payment and create matter in Surepoint. No copy-paste, no missed records.
- 02
Create invoice in Square when new time entry in Surepoint.
Caddi watches Surepoint for new time entry and create invoice in Square so the two systems stay in lockstep.
- 03
Post time entry in Surepoint from Square events.
When invoice paid happens in Square, Caddi post time entry in Surepoint with the right context attached.
Actions Caddi can take across Square and Surepoint
- 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.
- Surepoint
New time entry
Triggers when a timekeeper posts time against a matter.
- Surepoint
Invoice generated
Triggers when an invoice is finalized.
- Surepoint
Create matter
Open a new SurePoint matter with client and billing details.
- Surepoint
Post time entry
Record time against a matter and activity code.
- Surepoint
Generate invoice
Bill one or more matters in a single statement.
Common questions
How does Caddi connect Square and Surepoint?
Square and Surepoint 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 Square and Surepoint 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 Square and Surepoint to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Square + Surepoint 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 Square and Surepoint 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 Square and Surepoint?
Drop your work email and we'll show you Caddi running end-to-end against Square, Surepoint, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.