AI-native automation
Automate work across
Bill4Time and 
Microsoft Outlookby 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 Bill4Time and Microsoft Outlook 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 Bill4Time and Microsoft Outlook together
- 01
Send email in Microsoft Outlook when new time entry in Bill4Time.
Caddi watches Bill4Time for new time entry and send email in Microsoft Outlook — no copy-paste, no missed records.
- 02
Create matter in Bill4Time when new email in Microsoft Outlook.
Caddi watches Microsoft Outlook for new email and create matter in Bill4Time so the two systems stay in lockstep.
- 03
Reply to email in Microsoft Outlook from Bill4Time events.
When new invoice happens in Bill4Time, Caddi reply to email in Microsoft Outlook with the right context attached.
Actions Caddi can take across Bill4Time and Microsoft Outlook
- Bill4Time
New time entry
Triggers when a timekeeper posts time against a matter.
- Bill4Time
New invoice
Triggers when an invoice is generated for a client.
- Bill4Time
Payment received
Triggers when a payment is recorded against an invoice.
- Bill4Time
Create matter
Open a new Bill4Time matter with client and billing details.
- Bill4Time
Post time entry
Record time against a matter and activity code.
- Bill4Time
Create invoice
Generate an invoice for one or more matters.
- Bill4Time
Add expense
Record a billable expense against a matter.
- Microsoft Outlook
New email
Triggers when a new email arrives in your inbox.
- Microsoft Outlook
New event
Triggers when a new event is added to your calendar.
- Microsoft Outlook
Flag set on email
Triggers when you flag a message for follow-up.
- Microsoft Outlook
Send email
Send a new email from your Outlook account.
- Microsoft Outlook
Reply to email
Reply to an existing email thread.
- Microsoft Outlook
Forward email
Forward an existing email to one or more recipients.
- Microsoft Outlook
Create event
Add a new calendar event with attendees and reminders.
- Microsoft Outlook
Move message
Move an email between folders.
Common questions
How does Caddi connect Bill4Time and Microsoft Outlook?
Bill4Time and Microsoft Outlook 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 Bill4Time and Microsoft Outlook 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 Bill4Time and Microsoft Outlook to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Bill4Time + Microsoft Outlook 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 Bill4Time and Microsoft Outlook?
Drop your work email and we'll show you Caddi running end-to-end against Bill4Time, Microsoft Outlook, and the rest of your stack.