- Automations
- Box + Redtail
AI-native automation
Connect Box and Redtail with AI
Pick any two tools and Caddi runs the loop between them end-to-end — no complicated workflow builder, no IT ticket.
- 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


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.
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.
Actions Caddi can take across Box and Redtail
BoxNew file in folder
Triggers when a file is uploaded to a watched folder.
BoxFolder shared
Triggers when a folder collaboration is added.
BoxUpload file
Add a file to a Box folder with metadata.
BoxCreate folder
Create a new folder under a parent with permissions.
BoxSearch files
Find files or folders with advanced search filters.
BoxMove file
Move a file between folders.
RedtailNew contact
Triggers when a new contact is added in Redtail.
RedtailActivity completed
Triggers when an advisor closes a meeting, call, or task.
RedtailWorkflow stage changed
Triggers when a workflow advances to a new stage.
RedtailCreate contact
Add a new Redtail contact with household, address, and phone.
RedtailCreate activity
Schedule a meeting, call, or task against a contact.
RedtailAdd note
Append a timestamped note to a contact's history.
RedtailUpdate 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. 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 Box and Redtail 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 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 the screenshare. 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.




