AI-native automation
Automate work across
HotDocs and 
Squarewith Caddi AI Agents.
Automate anything you do across HotDocs, 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 HotDocs and Square
Connect HotDocs to Caddi
Allow1Sign in to HotDocs
One click with your own HotDocs login. No API keys.
Connect Square to Caddi
Allow2Sign in to Square
The same click again. Both tools are connected.
When something new comes in to HotDocs, update 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 HotDocs and Square together
In a law firm the work between HotDocs 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
Keep HotDocs and Square in lockstep.
Caddi listens for changes on either side and writes the matching update to the other, so your team stops keeping two systems in sync by hand.
Actions Caddi can take across HotDocs and Square
- 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 HotDocs and Square?
HotDocs 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 HotDocs 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 HotDocs and Square to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first HotDocs + 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 HotDocs 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 HotDocs and Square?
Drop your work email and we'll show you Caddi running end-to-end against HotDocs, Square, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.