AI-native automation
Automate work across
Box and 
Redtailby 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.
See it on your stack
See Caddi run Box and Redtail 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 Box and Redtail together
- 01
Create contact in Redtail when new file in folder in Box.
Caddi watches Box for new file in folder and create contact in Redtail — no copy-paste, no missed records.
- 02
Upload file in Box when new contact in Redtail.
Caddi watches Redtail for new contact and upload file in Box so the two systems stay in lockstep.
- 03
Create activity in Redtail from Box events.
When folder shared happens in Box, Caddi create activity in Redtail with the right context attached.
Actions Caddi can take across Box and Redtail
- Box
New file in folder
Triggers when a file is uploaded to a watched folder.
- Box
Folder shared
Triggers when a folder collaboration is added.
- Box
Upload file
Add a file to a Box folder with metadata.
- Box
Create folder
Create a new folder under a parent with permissions.
- Box
Search files
Find files or folders with advanced search filters.
- Box
Move file
Move a file between folders.
- Redtail
New contact
Triggers when a new contact is added in Redtail.
- Redtail
Activity completed
Triggers when an advisor closes a meeting, call, or task.
- Redtail
Workflow stage changed
Triggers when a workflow advances to a new stage.
- Redtail
Create contact
Add a new Redtail contact with household, address, and phone.
- Redtail
Create activity
Schedule a meeting, call, or task against a contact.
- Redtail
Add note
Append a timestamped note to a contact's history.
- Redtail
Update workflow
Move a contact's workflow to the next step or assign an owner.
Common questions
How does Caddi connect Box and Redtail?
Box and Redtail 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 Box and Redtail 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, but once the loop ships it runs deterministically — no model in the loop at runtime.
Can Caddi connect Box and Redtail to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Box + Redtail 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 Box and Redtail?
Drop your work email and we'll show you Caddi running end-to-end against Box, Redtail, and the rest of your stack.