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