AI-native automation
Automate work across
Square and 
Twiliowith Caddi AI Agents.
Connect Square and Twilio: Send SMS in Twilio when new payment in Square. 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 Square and Twilio
Caddi AI Agents find the repetitive handoffs between Square and Twilio, 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 Square and Twilio together
- 01
Send SMS in Twilio when new payment in Square.
Caddi watches Square for new payment and send sms in Twilio. No copy-paste, no missed records.
- 02
Create invoice in Square when incoming sms in Twilio.
Caddi watches Twilio for incoming sms and create invoice in Square so the two systems stay in lockstep.
- 03
Make call in Twilio from Square events.
When invoice paid happens in Square, Caddi make call in Twilio with the right context attached.
Actions Caddi can take across Square and Twilio
- 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.
- Twilio
Incoming SMS
Triggers when a message arrives on a Twilio number.
- Twilio
Call completed
Triggers when a call ends.
- Twilio
Message delivered
Triggers when an outbound message is delivered.
- Twilio
Send SMS
Text a contact from a Twilio number.
- Twilio
Make call
Place an outbound call.
- Twilio
Fetch messages
Pull the message history for a number.
Common questions
How does Caddi connect Square and Twilio?
Square and Twilio 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 Twilio 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 Twilio to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Square + Twilio 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.
Ready to automate Square and Twilio?
Drop your work email and we'll show you Caddi running end-to-end against Square, Twilio, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.