AI-native automation
Automate work across
Box and 
Dropbox Signby teaching Caddi like a new hire.
Pick any number of tools and Caddi automates them end-to-end. No workflow builder. You teach it the job once, the way you'd train someone new.
Help me automate envelope generation in Box and Dropbox Sign. Caddi builds the loop and runs it.
See it on your stack
See Caddi run Box and Dropbox Sign together.
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 · 70+ tools across legal, finance, and operations
One continuous loop.
- 01Measure
Caddi watches how the work gets done today.
- 02Create
You teach it the job once. The loop ships.
- 03Improve
Caddi flags upgrades to existing loops and new automations to deploy.
Practical ways to use Box and Dropbox Sign together
- 01
Send signature request in Dropbox Sign when new file in folder in Box.
Caddi watches Box for new file in folder and send signature request in Dropbox Sign — no copy-paste, no missed records.
- 02
Upload file in Box when signature request completed in Dropbox Sign.
Caddi watches Dropbox Sign for signature request completed and upload file in Box so the two systems stay in lockstep.
- 03
Use template in Dropbox Sign from Box events.
When folder shared happens in Box, Caddi use template in Dropbox Sign with the right context attached.
Actions Caddi can take across Box and Dropbox Sign
- Box
New file in folder
Triggers when a file is uploaded to a watched folder.
- Box
Folder shared
Triggers when a folder collaboration is added.
- Box
Upload file
Add a file to a Box folder with metadata.
- Box
Create folder
Create a new folder under a parent with permissions.
- Box
Search files
Find files or folders with advanced search filters.
- Box
Move file
Move a file between folders.
- 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.
Common questions
How does Caddi connect Box and Dropbox Sign?
Box and Dropbox Sign 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 Box and Dropbox Sign 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 Box and Dropbox Sign to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Box + Dropbox Sign 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 Box and Dropbox Sign?
Drop your work email and we'll show you Caddi running end-to-end against Box, Dropbox Sign, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.