AI-native automation
Automate work across
Adobe Sign and 
Squarewith Caddi AI Agents.
Connect Adobe Sign and Square: Create invoice in Square when agreement completed in Adobe Sign. 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 Adobe Sign and Square
Caddi AI Agents find the repetitive handoffs between Adobe Sign 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 Adobe Sign and Square together
- 01
Create invoice in Square when agreement completed in Adobe Sign.
Caddi watches Adobe Sign for agreement completed and create invoice in Square. No copy-paste, no missed records.
- 02
Send agreement for signature in Adobe Sign when new payment in Square.
Caddi watches Square for new payment and send agreement for signature in Adobe Sign so the two systems stay in lockstep.
- 03
Create customer in Square from Adobe Sign events.
When agreement sent happens in Adobe Sign, Caddi create customer in Square with the right context attached.
Actions Caddi can take across Adobe Sign and Square
- Adobe Sign
Agreement completed
Triggers when all signers have completed an agreement.
- Adobe Sign
Agreement sent
Triggers when an agreement is sent for signature.
- Adobe Sign
Agreement declined
Triggers when a signer declines an agreement.
- Adobe Sign
Send agreement for signature
Send a document or template out for e-signature.
- Adobe Sign
Use template
Send an agreement built from a reusable widget or template.
- Adobe Sign
Download signed PDF
Download the executed PDF and certificate of completion.
- Adobe Sign
Send reminder
Nudge signers who haven't completed yet.
- 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 Adobe Sign and Square?
Adobe Sign 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 Adobe Sign 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 Adobe Sign and Square to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Adobe Sign + 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.
Ready to automate Adobe Sign and Square?
Drop your work email and we'll show you Caddi running end-to-end against Adobe Sign, Square, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.