AI-native automation
Automate work across
Square and 
Timelywith Caddi AI Agents.
Connect Square and Timely: Create time entry in Timely when new payment in Square. Teach Caddi the job once, the way you'd train someone new, and it runs end to end. No workflow builder.
Discover, automate and govern the work between Square and Timely
Caddi AI Agents find the repetitive handoffs between Square and Timely, learn them the way a new hire would, and run them for you, with every run on the record. No workflow builder, no code.
Discover repetitive work
across all your tools.
Train an AI agent to do the work
over a video call.
Search mailMatters / Whitmore HoldingsGovern every AI agent,
every decision.
Discover repetitive work
across all your tools.
Train an AI agent to do the work
over a video call.
Search mailMatters / Whitmore HoldingsGovern every AI agent,
every decision.
Discover repetitive work
across all your tools.
Train an AI agent to do the work
over a video call.
Search mailMatters / Whitmore HoldingsGovern every AI agent,
every decision.
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 Square and Timely together
- 01
Create time entry in Timely when new payment in Square.
Caddi watches Square for new payment and create time entry in Timely. No copy-paste, no missed records.
- 02
Create invoice in Square when new time entry in Timely.
Caddi watches Timely for new time entry and create invoice in Square so the two systems stay in lockstep.
- 03
Create project in Timely from Square events.
When invoice paid happens in Square, Caddi create project in Timely with the right context attached.
Actions Caddi can take across Square and Timely
- Square
New payment
Triggers when a payment completes.
- Square
Invoice paid
Triggers when a Square invoice is paid.
- Square
New customer
Triggers when a customer is created.
- Square
Create invoice
Send a Square invoice to a customer.
- Square
Create customer
Add a customer with contact details.
- Square
Fetch payouts
Pull payouts and fees for reconciliation.
- Timely
New time entry
Triggers when a time entry is logged.
- Timely
Project updated
Triggers when a project's status or details change.
- Timely
Create time entry
Log a time entry against a project and user.
- Timely
Create project
Spin up a new Timely project with budget and team.
Common questions
How does Caddi connect Square and Timely?
Square and Timely 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 Square and Timely 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 Square and Timely to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Square + Timely 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 Square and Timely?
Drop your work email and we'll show you Caddi running end-to-end against Square, Timely, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.