AI-native automation
Automate work across
Datadog and 
Docusignwith Caddi AI Agents.
Automate anything you do across Datadog, Docusign, 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 Datadog and Docusign
Connect Datadog to Caddi
Allow1Sign in to Datadog
One click with your own Datadog login. No API keys.
Connect Docusign to Caddi
Allow2Sign in to Docusign
The same click again. Both tools are connected.
Send envelope from template in Docusign when monitor alert in Datadog.
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 Datadog and Docusign together
- 01
Send envelope from template in Docusign when monitor alert in Datadog.
Caddi watches Datadog for monitor alert and send envelope from template in Docusign. No copy-paste, no missed records.
- 02
Post event in Datadog when envelope completed in Docusign.
Caddi watches Docusign for envelope completed and post event in Datadog so the two systems stay in lockstep.
- 03
Send envelope from document in Docusign from Datadog events.
When alert recovered happens in Datadog, Caddi send envelope from document in Docusign with the right context attached.
Actions Caddi can take across Datadog and Docusign
- Datadog
Monitor alert
Triggers when a Datadog monitor fires.
- Datadog
Alert recovered
Triggers when a monitor returns to OK.
- Datadog
New event
Triggers when an event is posted to the stream.
- Datadog
Post event
Send an event to the Datadog stream.
- Datadog
Mute monitor
Silence a monitor for a maintenance window.
- Datadog
Fetch metrics
Pull metric values for a report.
- 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 Datadog and Docusign?
Datadog and Docusign 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 Datadog and Docusign 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 Datadog and Docusign to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Datadog + Docusign 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 Datadog and Docusign?
Drop your work email and we'll show you Caddi running end-to-end against Datadog, Docusign, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.