AI-native automation
Automate work across
Square and 
TimeSolvwith Caddi AI Agents.
Connect Square and TimeSolv: Create matter in TimeSolv 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 TimeSolv
Caddi AI Agents find the repetitive handoffs between Square and TimeSolv, 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 TimeSolv together
In a law firm the work between Square and TimeSolv is organized by matter: the right client, the right matter, the right people on it. Caddi carries that context through every step, so nothing is filed against the wrong case.
- 01
Create matter in TimeSolv when new payment in Square.
Caddi watches Square for new payment and create matter in TimeSolv. No copy-paste, no missed records.
- 02
Create invoice in Square when new time entry in TimeSolv.
Caddi watches TimeSolv for new time entry and create invoice in Square so the two systems stay in lockstep.
- 03
Post time entry in TimeSolv from Square events.
When invoice paid happens in Square, Caddi post time entry in TimeSolv with the right context attached.
Actions Caddi can take across Square and TimeSolv
- 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.
- TimeSolv
New time entry
Triggers when a timekeeper posts time.
- TimeSolv
Invoice issued
Triggers when an invoice is finalized.
- TimeSolv
Create matter
Open a new TimeSolv matter with client and billing details.
- TimeSolv
Post time entry
Record time against a matter and activity code.
- TimeSolv
Add expense
Record a billable expense against a matter.
- TimeSolv
Generate invoice
Bill one or more matters in a single statement.
Common questions
How does Caddi connect Square and TimeSolv?
Square and TimeSolv 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 TimeSolv 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 TimeSolv to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Square + TimeSolv 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.
Does this work for law firms?
Yes. Caddi runs Square and TimeSolv with the matter as the unit of work, so documents, time, and communications land against the right client and matter rather than in a general folder. Firms most often start with intake, document filing, or billing prep.
Ready to automate Square and TimeSolv?
Drop your work email and we'll show you Caddi running end-to-end against Square, TimeSolv, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.