AI-native automation
Automate work across
Docusign and 
Gmailby 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 inbox triage to CRM in Docusign and Gmail. Caddi builds the loop and runs it.
See it on your stack
See Caddi run Docusign and Gmail 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 Docusign and Gmail together
- 01
Send email in Gmail when envelope completed in Docusign.
Caddi watches Docusign for envelope completed and send email in Gmail — no copy-paste, no missed records.
- 02
Send envelope from template in Docusign when new email in Gmail.
Caddi watches Gmail for new email and send envelope from template in Docusign so the two systems stay in lockstep.
- 03
Reply to email in Gmail from Docusign events.
When envelope sent happens in Docusign, Caddi reply to email in Gmail with the right context attached.
Actions Caddi can take across Docusign and Gmail
- 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.
- Gmail
New email
Triggers when a new email arrives in your inbox.
- Gmail
New email matching search
Triggers on new emails matching a Gmail search query.
- Gmail
New label applied
Triggers when a new label is applied to a message.
- Gmail
Send email
Send a new email from your Gmail account.
- Gmail
Reply to email
Reply to an existing email thread.
- Gmail
Send email with attachments
Send an email with one or more attached files.
- Gmail
Apply label
Add a label to a message or move it between folders.
Common questions
How does Caddi connect Docusign and Gmail?
Docusign and Gmail 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 Docusign and Gmail 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 Docusign and Gmail to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Docusign + Gmail 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 Docusign and Gmail?
Drop your work email and we'll show you Caddi running end-to-end against Docusign, Gmail, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.