AI-native automation
Automate work across
Docusign and 
SimpleLegalby AI screensharing.
Pick any amount of tools and Caddi automates them end-to-end. No workflow builder, just show Caddi.
See it on your stack
See Caddi run Docusign and SimpleLegal 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.
- 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
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.
Practical ways to use Docusign and SimpleLegal together
- 01
Keep Docusign and SimpleLegal in lockstep.
Caddi listens for changes on either side and writes the matching update to the other — your team stops keeping two systems in sync by hand.
Actions Caddi can take across Docusign and SimpleLegal
- Docusign
Envelope completed
Triggers when all signers complete an envelope.
- Docusign
Envelope sent
Triggers when an envelope is sent for signature.
- Docusign
Recipient signed
Triggers when a single recipient completes signing.
- Docusign
Envelope declined
Triggers when a recipient declines an envelope.
- Docusign
Send envelope from template
Send a pre-built template out for signature with merged fields.
- Docusign
Send envelope from document
Send an arbitrary document out for signature.
- Docusign
Void envelope
Cancel an in-flight envelope with a reason.
- Docusign
Download signed PDF
Pull the executed PDF and certificate from a completed envelope.
- Docusign
Move envelope
Move a completed envelope to a specified folder.
Common questions
How does Caddi connect Docusign and SimpleLegal?
Docusign and SimpleLegal 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 Docusign and SimpleLegal 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 Docusign and SimpleLegal to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Docusign + SimpleLegal 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 Docusign and SimpleLegal?
Drop your work email and we'll show you Caddi running end-to-end against Docusign, SimpleLegal, and the rest of your stack.