AI-native automation
Automate work across
Bill4Time 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 Bill4Time and Dropbox Sign. Caddi builds the loop and runs it.
See it on your stack
See Caddi run Bill4Time 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 Bill4Time and Dropbox Sign together
- 01
Send signature request in Dropbox Sign when new time entry in Bill4Time.
Caddi watches Bill4Time for new time entry and send signature request in Dropbox Sign — no copy-paste, no missed records.
- 02
Create matter in Bill4Time when signature request completed in Dropbox Sign.
Caddi watches Dropbox Sign for signature request completed and create matter in Bill4Time so the two systems stay in lockstep.
- 03
Use template in Dropbox Sign from Bill4Time events.
When new invoice happens in Bill4Time, Caddi use template in Dropbox Sign with the right context attached.
Actions Caddi can take across Bill4Time and Dropbox Sign
- Bill4Time
New time entry
Triggers when a timekeeper posts time against a matter.
- Bill4Time
New invoice
Triggers when an invoice is generated for a client.
- Bill4Time
Payment received
Triggers when a payment is recorded against an invoice.
- Bill4Time
Create matter
Open a new Bill4Time matter with client and billing details.
- Bill4Time
Post time entry
Record time against a matter and activity code.
- Bill4Time
Create invoice
Generate an invoice for one or more matters.
- Bill4Time
Add expense
Record a billable expense against a matter.
- 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 Bill4Time and Dropbox Sign?
Bill4Time 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 Bill4Time 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 Bill4Time and Dropbox Sign to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Bill4Time + 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 Bill4Time and Dropbox Sign?
Drop your work email and we'll show you Caddi running end-to-end against Bill4Time, Dropbox Sign, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.