AI-native automation
Connect Dropbox Sign and Expensify with AI
Pick any two tools and Caddi runs the loop between them end-to-end — no complicated workflow builder, no IT ticket.
- Doesn't break. Caddi reads intent, so when fields move or UIs change, your loop keeps running.
- Screenshare to set up, chat to improve. Show Caddi once on a screenshare. Tweak it later by chat — no workflow builder to re-architect.
SOC 2 attested · Human-in-the-loop · Full audit trail · 70+ tools across legal, finance, and operations
Practical ways to use Dropbox Sign and Expensify together
- 01
Create expense in Expensify when signature request completed in Dropbox Sign.
Caddi watches Dropbox Sign for signature request completed and create expense in Expensify — no copy-paste, no missed records.
- 02
Send signature request in Dropbox Sign when new expense report in Expensify.
Caddi watches Expensify for new expense report and send signature request in Dropbox Sign so the two systems stay in lockstep.
- 03
Create report in Expensify from Dropbox Sign events.
When signature request sent happens in Dropbox Sign, Caddi create report in Expensify with the right context attached.
One continuous loop.
- 01Measure
Caddi watches how the work gets done today.
- 02Create
You screenshare it once. The loop ships.
- 03Improve
Caddi flags upgrades to existing loops and new automations to deploy.
Actions Caddi can take across Dropbox Sign and Expensify
- 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.
- Expensify
New expense report
Triggers when an expense report is submitted.
- Expensify
Report approved
Triggers when a report is approved for reimbursement.
- Expensify
Create expense
Add an expense with amount, category, and receipt.
- Expensify
Create report
Open a new expense report for an employee.
- Expensify
Submit report
Submit an expense report for approval.
Common questions
How does Caddi connect Dropbox Sign and Expensify?
Dropbox Sign and Expensify just run together. All it takes is showing us how you use them — one screenshare, no workflow builder to wire up. Caddi turns the demo into a verified loop and runs it against Dropbox Sign and Expensify end-to-end.
Do I need engineering help?
No. Whoever does the work today shows it once on a call. 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, but once the loop ships it runs deterministically — no model in the loop at runtime.
Can Caddi connect Dropbox Sign and Expensify to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Dropbox Sign + Expensify 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 the screenshare. The Caddi team reviews every loop before it runs in production.
Ready to automate Dropbox Sign and Expensify?
Drop your work email and we'll show you Caddi running end-to-end against Dropbox Sign, Expensify, and the rest of your stack.