AI-native automation
Automate work across
ClickUp and 
Dropbox Signwith Caddi AI Agents.
Automate anything you do across ClickUp, 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 ClickUp and Dropbox Sign
Connect ClickUp to Caddi
Allow1Sign in to ClickUp
One click with your own ClickUp 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 task in ClickUp.
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 ClickUp and Dropbox Sign together
- 01
Send signature request in Dropbox Sign when new task in ClickUp.
Caddi watches ClickUp for new task and send signature request in Dropbox Sign. No copy-paste, no missed records.
- 02
Create task in ClickUp when signature request completed in Dropbox Sign.
Caddi watches Dropbox Sign for signature request completed and create task in ClickUp so the two systems stay in lockstep.
- 03
Use template in Dropbox Sign from ClickUp events.
When status changed happens in ClickUp, Caddi use template in Dropbox Sign with the right context attached.
Actions Caddi can take across ClickUp and Dropbox Sign
- ClickUp
New task
Triggers when a task is created in a list.
- ClickUp
Status changed
Triggers when a task moves to a new status.
- ClickUp
Task due
Triggers when a task reaches its due date.
- ClickUp
Create task
Add a task with fields, assignee and due date.
- ClickUp
Update task
Change status, fields or assignee on a task.
- ClickUp
Add comment
Post a comment on a task.
- 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 ClickUp and Dropbox Sign?
ClickUp 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 ClickUp 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 ClickUp and Dropbox Sign to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first ClickUp + 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 ClickUp and Dropbox Sign?
Drop your work email and we'll show you Caddi running end-to-end against ClickUp, Dropbox Sign, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.