AI-native automation
Automate work across
Bill.com and 
Dropbox Signwith Caddi AI Agents.
Automate anything you do across Bill.com, Dropbox Sign, and the rest of your tools. Sign in, show or tell Caddi what you want, and it runs end to end. No workflow builder.
How to connect Bill.com and Dropbox Sign
Connect Bill.com to Caddi
Allow1Sign in to Bill.com
One click with your own Bill.com login. No API keys.
Connect Dropbox Sign to Caddi
Allow2Sign in to Dropbox Sign
The same click again. Both tools are connected.
Send signature request in Dropbox Sign when new bill in Bill.com.
ScreenshareType it3Show or tell it
Screenshare the job, or type it in chat. Change it any time.
- Running
14 done1 for review
4Watch it run
Caddi does the work and flags anything unsure for review.
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 Bill.com and Dropbox Sign together
- 01
Send signature request in Dropbox Sign when new bill in Bill.com.
Caddi watches Bill.com for new bill and send signature request in Dropbox Sign. No copy-paste, no missed records.
- 02
Create vendor in Bill.com when signature request completed in Dropbox Sign.
Caddi watches Dropbox Sign for signature request completed and create vendor in Bill.com so the two systems stay in lockstep.
- 03
Use template in Dropbox Sign from Bill.com events.
When bill approved happens in Bill.com, Caddi use template in Dropbox Sign with the right context attached.
Actions Caddi can take across Bill.com and Dropbox Sign
- Bill.com
New bill
Triggers when a bill is created in BILL.
- Bill.com
Bill approved
Triggers when a bill clears its approval workflow.
- Bill.com
Payment sent
Triggers when a vendor payment is sent.
- Bill.com
Invoice paid
Triggers when a customer pays an invoice.
- Bill.com
Create vendor
Add a vendor with remittance details.
- Bill.com
Create bill
Create a bill against a vendor, with line items.
- Bill.com
Create invoice
Create and send an invoice to a customer.
- Bill.com
Look up payment status
Fetch the status of a bill or payment.
- 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 Bill.com and Dropbox Sign?
Bill.com 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 Bill.com 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 Bill.com and Dropbox Sign to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Bill.com + 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 Bill.com and Dropbox Sign?
Drop your work email and we'll show you Caddi running end-to-end against Bill.com, Dropbox Sign, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.