AI-native automation
Automate work across
Dropbox Sign and 
Orionwith Caddi AI Agents.
Automate anything you do across Dropbox Sign, Orion, 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 Dropbox Sign and Orion
Connect Dropbox Sign to Caddi
Allow1Sign in to Dropbox Sign
One click with your own Dropbox Sign login. No API keys.
Connect Orion to Caddi
Allow2Sign in to Orion
The same click again. Both tools are connected.
Update household in Orion when signature request completed in Dropbox Sign.
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 Dropbox Sign and Orion together
At an RIA the work between Dropbox Sign and Orion is organized by household: the right client, the right accounts, the right advisor. Caddi carries that context through every step, so records stay tied to the household they belong to.
- 01
Update household in Orion when signature request completed in Dropbox Sign.
Caddi watches Dropbox Sign for signature request completed and update household in Orion. No copy-paste, no missed records.
- 02
Send signature request in Dropbox Sign when account opened in Orion.
Caddi watches Orion for account opened and send signature request in Dropbox Sign so the two systems stay in lockstep.
- 03
Generate report in Orion from Dropbox Sign events.
When signature request sent happens in Dropbox Sign, Caddi generate report in Orion with the right context attached.
Actions Caddi can take across Dropbox Sign and Orion
- 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.
- Orion
Account opened
Triggers when a new account is added in Orion.
- Orion
Report generated
Triggers when a client report is produced.
- Orion
Billing run complete
Triggers when a billing cycle finishes.
- Orion
Update household
Write household and account details to Orion.
- Orion
Generate report
Run a client report for a household.
- Orion
Fetch positions
Pull holdings and performance for accounts.
Common questions
How does Caddi connect Dropbox Sign and Orion?
Dropbox Sign and Orion 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 Dropbox Sign and Orion 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 Dropbox Sign and Orion to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Dropbox Sign + Orion 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.
Does this work for RIAs and financial advisors?
Yes. Caddi runs Dropbox Sign and Orion with the household as the unit of work, so plans, accounts, and activity stay tied to the right client and advisor. Firms most often start with onboarding, account maintenance, or reporting prep.
Ready to automate Dropbox Sign and Orion?
Drop your work email and we'll show you Caddi running end-to-end against Dropbox Sign, Orion, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.