Connect Square via OAuth. The moment a customer accepts a CrawlSpace quote, one click pushes a real Square invoice with the line items copied verbatim — no retyping, no reconciliation. When the customer pays, Square's webhook fires back: CrawlSpace marks the invoice paid, flips the deal to Won, and auto-converts the lead to a customer. Tied into the CRM and bundled into the same flat $29.95 per month.
Square OAuth · One-click invoice push · Webhook-driven payment status · Auto deal close
You quote in your CRM. The customer accepts. Now somebody has to retype every line item into Square (or QuickBooks, or FreshBooks) to issue an actual invoice. Three days later the payment lands. Now somebody has to find the right CrawlSpace deal and mark it Won. Then convert the lead to a customer. Then update the deal stage report. Two pieces of payment software pretending the customer doesn't exist in either of them.
Five minutes per quote, errors guaranteed. The line items have to be re-entered by hand. Decimal place wrong, line item forgotten, customer name misspelled. The invoice goes out wrong; the customer complains; the rep apologizes; somebody re-issues. All because two systems can't talk.
$20-$50 per month plus an integration. Decent accounting tools, but you still need to manually mark the CRM deal Won when the payment lands. The "sync" is usually one-way (CRM → accounting) and the payment-status feedback loop back into the CRM is somebody else's problem.
Works if you don't need a real invoice. Drop a payment link, customer pays, deal marked Won. Fine for simple transactions but no actual invoice document, no audit trail, no customer record on the payment processor side. Not workable when accounting needs the paper.
Connect Square via OAuth once. Every accepted CrawlSpace quote can be pushed to Square as a real invoice in one click — line items, prices, customer info, all copied verbatim. The customer is auto-created in Square if they're new. When they pay, Square's webhook fires back to CrawlSpace: invoice marks paid, deal flips to Won, lead converts to customer. No human in between any of those steps.
Settings → Integrations → Connect Square. Standard OAuth flow grants CrawlSpace permission to create invoices, customers, and receive payment webhooks on your Square account. Per-org connection, revocable any time from Square's developer settings.
When a quote is accepted in CrawlSpace, a "Push to Square" button appears. One click sends every line item to Square — description, quantity, unit price, line total — exactly as quoted. The Square invoice is created in draft and sent to the customer via Square's normal email flow (or held for review, your choice).
If the CrawlSpace contact isn't already a Square customer, they're created automatically with name, email, phone, and address pulled from the CRM record. Existing Square customers are matched by email so duplicates don't pile up. The two customer records stay linked by ID after the first push.
When the customer pays the Square invoice, Square fires a payment webhook to CrawlSpace. The matching invoice is marked paid in the CRM, the associated deal flips to Won, and any lead-to-customer conversion runs automatically. No human has to remember to update the deal stage; the payment itself is the signal.
If the customer pays partial, the CrawlSpace invoice reflects the partial amount with the remaining balance still due. Refunds processed in Square fire a webhook back; the CRM invoice flips to refunded and the deal stage can be optionally reset based on org rules. The CRM and Square don't drift out of sync.
The contact's timeline shows the invoice push event, the customer-paid event, the deal-Won event, and any refunds — all timestamped. The next person who looks at the account can reconstruct the payment history without opening Square at all.
The reports that track quote acceptance, deals Won, and revenue closed are the same reports that show Square payment status — because the CRM is the source of truth on both. No "let me reconcile Square against the CRM for last month's numbers." It's already done.
The Square integration isn't a separate product. The same contact record holds the quote, the contract, the invoice, the payment receipt, and every prior email and call. Open a contact and see one timeline — not "now go check Square for the payment status."
Connect Square once. The rest of the flow runs without any human intervention after the rep clicks the push button.
Settings → Integrations → Connect Square. OAuth flow takes 30 seconds. CrawlSpace requests permission to create invoices, manage customers, and receive payment webhooks. Org-level connection; the whole team uses it.
Build the quote in CrawlSpace, send it via the standard accept link, customer clicks Accept. Quote status changes to Accepted; the deal sits in the "Won — Send Invoice" stage. A "Push to Square" button appears on the deal.
Click "Push to Square." CrawlSpace creates the Square customer (if new), creates a Square invoice with every line item copied verbatim, and sends it through Square's normal customer email. Square's invoice number is stored on the CrawlSpace deal for cross-reference.
Customer opens the Square invoice email, pays by card or ACH directly through Square. Square processes the payment and fires a webhook back to CrawlSpace within seconds.
Webhook arrives → CRM invoice marks paid → deal flips to Won → lead converts to customer → revenue reports update. The contact timeline shows the whole sequence, timestamped. Total human effort after the push click: zero.
Process a refund in Square → refund webhook fires → CRM invoice flips to refunded → optional deal-stage reset per your org rules. Partial payments tracked accurately. The two systems stay in agreement without manual reconciliation.
Most CRM-to-payments setups are duct-tape: CSV export, Zapier hop, accounting silo. Native Square in CrawlSpace is the same database telling the same story.
| Capability | CrawlSpace + Square | CRM + QuickBooks | CRM + Stripe Payment Link |
|---|---|---|---|
| One-click quote → invoice push | ✅ Native button | ⚠️ Paid Zapier or middleware | ⚠️ No invoice doc, just a link |
| Line items copy verbatim | ✅ Native | ⚠️ Sync-dependent | ❌ N/A |
| Customer auto-created in payment system | ✅ Yes | ⚠️ Sync-dependent | ⚠️ Per Stripe flow |
| Payment status flows back to CRM via webhook | ✅ Real-time | ⚠️ Manual or paid sync | ⚠️ Custom webhook |
| Deal auto-flips to Won on payment | ✅ Native | ❌ Manual | ⚠️ Requires custom rule |
| Lead auto-converts to customer on payment | ✅ Native | ❌ Manual | ❌ Manual |
| Partial payment + refund mirroring | ✅ Yes (both directions) | ⚠️ One-way most setups | ⚠️ Custom |
| Real invoice document for accounting | ✅ Yes — Square invoice | ✅ Yes — QuickBooks invoice | ❌ Just a payment receipt |
| Additional monthly cost | $0 — bundled in CrawlSpace | $20-$50/mo (QB) + sync fees | Stripe fees only |
| Includes the rest of the CRM | ✅ Deals, quotes, dialer, more | ❌ Separate products | ❌ Just a payment hop |
| Starting price | $29.95/mo total | CRM + $20-$50/mo QB + sync | CRM + Stripe processing fees |
Native Square invoicing. Real webhook close-loop. Bundled into the same flat $29.95 a month.
The gap between "customer accepted the quote" and "deal marked Won" is where deals die. Manual reconciliation between the CRM and the payment system is the most common reason revenue reports are wrong and AEs get paid late commissions. Closing the loop in the data, not in the rep's head, fixes both.
Line items copy verbatim from quote to Square invoice. No decimal-place mistakes, no missed line, no misspelled customer name. The invoice that goes out is what the customer agreed to, exactly.
Payment lands → webhook fires → deal flips to Won. The AE doesn't have to remember to update the deal stage at end-of-quarter. The pipeline report is accurate the moment money arrives.
The same webhook that flips the deal to Won also auto-converts the lead to a customer record. Welcome emails, onboarding tasks, customer-only newsletter audiences — all triggered without anyone clicking anything.
Compared to running CRM + QuickBooks + a sync tool, you're saving $30-$80/month in subscriptions plus the rep time it takes to keep them aligned. We'll add Stripe and other processors similarly over time — same model.
The Square integration is built for the "quote → accepted → paid → won" cycle that most service businesses live on.
Consultant quotes a $4,000 engagement. Customer accepts in CrawlSpace. Consultant clicks Push to Square; Square emails the invoice to the customer. Customer pays by card the next day. Square webhook fires; CrawlSpace marks the invoice paid, flips the deal to Won, converts the lead to a customer, and triggers the onboarding-kickoff task. The consultant did one click in this whole sequence.
Project deal requires a 50% deposit upfront. First quote pushed to Square as the deposit invoice; customer pays; deal stage advances to "Deposit Paid, In Progress." Second quote pushed as the final invoice on delivery; customer pays; deal flips to Won. Partial-payment tracking makes the two-invoice workflow trivial without any custom logic.
Customer requests a refund on a recently-closed deal. Refund processed in Square fires the refund webhook; CrawlSpace invoice flips to refunded; per the org's rule, the deal stage resets to "Closed Lost — Refunded" and the lead-to-customer conversion is reverted. Revenue reports update automatically; no manual cleanup, no quarter-end surprise.
CrawlSpace CRM gives you a native Square integration, plus deals, quotes, contracts, calendar, the dialer, meeting recordings, email sequences, lead search, inventory, invoicing, and 27+ reports. Same flat $29.95/month. No paid sync layer, no QuickBooks subscription, no manual reconciliation.
$29.95/month · Cancel anytime · Works on day one · Square OAuth setup in 30 seconds