AI-native automation
Automate work across
MoneyGuidePro and 
Squarewith Caddi AI Agents.
Automate anything you do across MoneyGuidePro, Square, and the rest of your tools. Sign in, show or tell Caddi what you want, and it runs end to end. No workflow builder.
How to connect MoneyGuidePro and Square
Connect MoneyGuidePro to Caddi
Allow1Sign in to MoneyGuidePro
One click with your own MoneyGuidePro login. No API keys.
Connect Square to Caddi
Allow2Sign in to Square
The same click again. Both tools are connected.
Create invoice in Square when new client added in MoneyGuidePro.
ScreenshareType it3Show or tell it
Screenshare the job, or type it in chat. Change it any time.
- Running
14 done1 for review
4Watch it run
Caddi does the work and flags anything unsure for review.
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 MoneyGuidePro and Square together
At an RIA the work between MoneyGuidePro and Square is organized by household: the right client, the right accounts, the right advisor. Caddi carries that context through every step, so records stay tied to the household they belong to.
- 01
Create invoice in Square when new client added in MoneyGuidePro.
Caddi watches MoneyGuidePro for new client added and create invoice in Square. No copy-paste, no missed records.
- 02
Create client in MoneyGuidePro when new payment in Square.
Caddi watches Square for new payment and create client in MoneyGuidePro so the two systems stay in lockstep.
- 03
Create customer in Square from MoneyGuidePro events.
When plan updated happens in MoneyGuidePro, Caddi create customer in Square with the right context attached.
Actions Caddi can take across MoneyGuidePro and Square
- MoneyGuidePro
New client added
Triggers when a new household is added to MoneyGuidePro.
- MoneyGuidePro
Plan updated
Triggers when a plan's inputs or scenarios change.
- MoneyGuidePro
Create client
Open a new MoneyGuidePro client with household details.
- MoneyGuidePro
Update goals
Push new retirement, education, or insurance goals into a plan.
- MoneyGuidePro
Generate plan PDF
Render the latest plan as a client-ready PDF.
- 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.
Common questions
How does Caddi connect MoneyGuidePro and Square?
MoneyGuidePro and Square 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 MoneyGuidePro and Square 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 MoneyGuidePro and Square to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first MoneyGuidePro + Square 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 RIAs and financial advisors?
Yes. Caddi runs MoneyGuidePro and Square with the household as the unit of work, so plans, accounts, and activity stay tied to the right client and advisor. Firms most often start with onboarding, account maintenance, or reporting prep.
Ready to automate MoneyGuidePro and Square?
Drop your work email and we'll show you Caddi running end-to-end against MoneyGuidePro, Square, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.