How to Automate Square

Square automates whatever it handled itself. Marketing runs recurring automatic campaigns, Loyalty applies rewards at checkout, Invoices chases with automatic payment reminders, and Appointments sends booking reminders. Totalling a day that also ran through delivery apps, a wholesaler and the bank is the part still done by hand, and where WebRun helps.

The register is the most honest record a shop keeps

Square is the card reader and the point of sale a great many small businesses actually run on: a game shop, a cheese counter, a pet store, a coffee bar, a stall in a food hall. It began as a white plastic square plugged into a phone, and Square Point of Sale grew into the whole counter.

What it holds is unusually complete for something so cheap to start with. Every sale, with the items, the modifiers, the tender type and the tip. The item library and what stock is left. The customer directory, built quietly out of the people who chose to have a receipt emailed. Team timecards. Appointments, if you book them. Payouts, and when they reached the bank.

Nobody typed any of it in. That is the point of a till. It is the one record in the business that is a byproduct of the work rather than a chore added on top, which makes it the most reliable thing an owner has.

Closing up is a second job after the doors lock

Then the shutters come down and the second shift starts.

The day's total on the Square Dashboard gets copied into a spreadsheet, because the owner wants it next to last year's. The delivery platforms get opened one at a time, since a third of the takings never went through the register and each app keeps its own dashboard. The payout that landed this morning is a lump sum covering parts of three days, and somebody works out which days.

Stock gets counted against what sold, because Square knows what left the shelf and only the supplier's portal knows what is coming. That supplier site gets checked for the price on the case you reorder every fortnight. Reviews get read. The invoice a wholesale customer has still not paid gets looked up.

Every one of those is fifteen minutes, and there are six of them, and they land at the end of nine hours on your feet.

The squareup.com homepage, the app these three jobs run in. Square
One total, every channel The register, each delivery platform and the online store added up into a single figure, waiting before the shop opens.
Payouts traced back to sales The lump sum that landed this morning split across the days it covers, with anything that does not add up flagged for you.
Reorders priced first Low stock checked against the supplier portal for availability and this week's cost, so an order is priced before it is placed.

Square's automations begin and end inside Square

Square automates a surprising amount at no extra cost, and a shop should exhaust that list before buying anything else.

Square Marketing sends recurring automatic campaigns: a welcome for a new customer, a birthday discount, a nudge to somebody who has lapsed, an abandoned cart reminder. Square Loyalty tracks points and applies rewards at checkout on its own. Square Invoices sends recurring invoices on a schedule and chases with automatic payment reminders before, on and after the due date. Square Appointments sends text and email reminders ahead of a booking, and Square Assistant handles the confirm-or-reschedule reply on its own. The Customer Directory builds itself out of transactions.

Look at what every one of those has in common. The trigger is something Square handled: a Square sale, a Square booking, a Square invoice, a Square loyalty account.

The takings on the delivery app are invisible to it. So is the wholesaler's price list, the bank statement the payout actually landed in, and the review left on a site Square has no relationship with. Square is honest about being a point of sale. It is only that a shop is bigger than its point of sale.

The whole day's takings, not just the ones on Square

Widen what can be read and the morning report stops being a Square report and starts being a business report.

Yesterday's total across everything: the register, each delivery platform's dashboard, the online store, added up and waiting before the shop opens. The payout that arrived this morning broken back down against the sales it covers, and flagged when it does not add up.

The reorder list checked twice a day against what is on the shelf, then against the supplier's portal for what is in stock and what it costs this week, so an order is priced before it goes out. Refunds from the last twenty-four hours read and anything unusual pulled out, because a run of refunds on one till at one time of day is worth seeing early.

New reviews found across the sites that carry them, with a reply drafted in your voice. Wholesale invoices still unpaid, checked against the bank rather than against hope.

Reading and comparing can run unattended all night. Anything that messages a customer or moves money should be prepared and left for a person, because a shop like this lives on its regulars.

The evening count no longer needs a person

Six dashboards, one total, and the person adding them up closed the shop an hour ago. Adding up is not the judgement here.

WebRun is an agent that works a real Chrome browser, signed in as you. It opens the Square Dashboard, the delivery platforms, the supplier portal or the bank, reads what is on the screen, and writes the result into a spreadsheet, an email or the channel your team already checks. Because it works the browser rather than an API, it reaches the systems that never built a Square integration, which is most of them.

It runs on your schedule in your own private environment, and you can watch a run and stop it partway. Anything that reaches a customer or moves money is drafted and waits for you.

The workflows below are already built, and each one names the sites it opens.

Questions people ask

Do we need the Square API or a developer account?

No. It signs into the Square Dashboard in a browser with the access you already have, so there is nothing to register and no keys to manage. The same goes for the delivery apps and supplier sites it reads.

Can it total the delivery apps as well as the register?

Yes, and that is the usual reason to run it. Each platform keeps its own dashboard behind its own login, so the day's real total is read off those screens and added to Square's before anyone opens up.

Will it message customers or issue refunds?

No. Refunds, customer emails, texts and public review replies are drafted and left for a person. Reading dashboards, comparing totals and writing them into a sheet or a channel are the parts that run on their own.

32 ready-made Square workflows

Each one names the apps it touches and the exact steps it takes. Open one to read what it will do, then turn it on.

Automated Daily Food Hall Sales Log
Every morning, WebRun totals yesterday's sales across every stall from Hallpass, adds Square walk-up and event takings, and appends one clean daily line to the owner's Google Sheet with the hall total and per-stall breakdown.
HallpassSquareGoogle Sheets
Automated Slow-Mover Markdown Flags
Every morning, WebRun reads how long each cheese has been on the shelf in ShelfPerks, checks its sales pace in Square, and logs a markdown candidate list to Google Sheets so slow movers get discounted before they turn.
ShelfPerksSquareGoogle Sheets
Automated Cut-To-Order Waste Reports
Every week, WebRun reads how much of each wheel ShelfPerks logged as cut-to-order waste, compares it to the wheel's yield and Square sales, and posts a Slack report showing which cheeses are losing the most to trim and rind.
ShelfPerksSquareSlack
Automated Cheese Shrink Variance Reports
Every week, WebRun compares the weight you cut into ShelfPerks against what Square actually sold by weight, calculates the shrink per cheese, and logs a variance report to Google Sheets so you can see where product is walking off.
ShelfPerksSquareGoogle Sheets
Automated CoatingOS Deposit Scheduling
WebRun watches Square for new coating deposits, pulls the matching job from CoatingOS, holds an install slot on your calendar, and drafts a confirmation text for the homeowner to approve.
SquareCoatingOSGoogle Calendar
Automated CoatingOS Quote Follow-Ups
WebRun finds coating estimates that are still open in CoatingOS, checks whether a deposit came in on Square, and drafts a warm follow-up email for each homeowner who has not booked yet.
CoatingOSSquareGmail
Automated Square Staff Hours vs Sales Report
Every Monday, WebRun pulls Square's team timecards and sales data for the prior week, calculates your sales-per-labor-hour ratio for each day, and posts the comparison to Slack so you can see exactly where you were over or understaffed.
SquareGoogle Sheets
Automated Square Repeat Customer Win-Back Drafts
Every week, WebRun identifies Square customers who have not returned in 60 days, drafts a personalized win-back message for each, and queues them in Google Sheets for your approval before any message is sent.
SquareGoogle Sheets
Automated Square Refund Anomaly Detection
Every morning, WebRun reviews Square refund activity from the past 24 hours, flags anything that looks out of the ordinary, and posts a summary to Slack so you can investigate before patterns become losses.
SquareSlack
Automated Square Payout Reconciliation Report
Every morning, WebRun checks your Square payout details and logs each deposit against expected amounts in Google Sheets so your bookkeeper can reconcile without logging into Square.
SquareGoogle Sheets
Automated Square New Seller Onboarding Checklist
When a new seller or location is added to your Square account, WebRun runs through a setup checklist, verifies the key settings are configured, logs any gaps in Google Sheets, and notifies the team via Slack so nothing falls through the cracks.
SquareSlack
Automated Square Loyalty Campaign Drafts
Every week, WebRun checks your Square Loyalty program for members nearing a reward milestone or who have not redeemed points in 30 days, drafts targeted campaign messages for each segment, and queues them in Google Sheets for your review before any message is sent.
SquareGoogle Sheets
Automated Square Low Inventory Alerts
Every morning, WebRun checks your Square inventory levels, finds any items at or below your reorder point, and sends a low-stock alert to Slack so you can reorder before you run out.
SquareSlack
Automated Square Item Performance Report
Every Monday, WebRun pulls Square's item sales data for the past week, ranks every product by revenue and units sold, and posts the top and bottom performers to Slack so you can make smarter stocking and menu decisions.
SquareSlack
Automated Square Failed Payment Follow-Up
When a Square payment fails, WebRun logs it in Google Sheets and drafts a polite follow-up message for your team to review and send, so no unpaid transaction is forgotten.
SquareGoogle Sheets
Automated Square Daily Sales Digest
Every morning, WebRun opens Square, pulls yesterday's sales totals, top items, and payment breakdown, then posts a clean digest to Slack so you walk in knowing exactly where you stand.
SquareSlack
Automated Square Customer Feedback Routing
When Square collects customer feedback after a sale, WebRun reads the rating and comment, routes positive feedback to your marketing list and negative feedback to the manager for follow-up, all without manual monitoring.
SquareSlack
Automated Square Chargeback Dispute Evidence Drafts
When Square flags a chargeback, WebRun gathers the transaction details, compiles the available evidence, and drafts the dispute response for your review so you never miss a response deadline.
SquareGoogle Sheets
Automated Square Appointments No-Show Report
Every morning, WebRun reviews Square Appointments from the previous day, identifies no-shows and late cancellations, logs them in Google Sheets, and posts a summary to Slack so your team can follow up and fill the gaps.
SquareGoogle Sheets
Automated Hobby Shop Stock Alerts
Every morning, WebRun checks Square inventory for products below your reorder threshold, drafts a reorder email to the distributor in Gmail, and posts a low-stock alert to Slack.
SquareGmailSlack
Automated Pet Store Stock Alerts
WebRun checks Square inventory each day, flags items below your reorder threshold, drafts a reorder email for your approval, and posts a low-stock alert to Slack so your team stays ahead of gaps.
SquareGmailSlack
Automated Hobby Shop Sales Digest
Every evening, WebRun pulls the day's Square sales data, breaks it down by category, and posts a clean daily digest to Slack.
SquareSlack
Automated Pet Store Sales Digest
Every evening, WebRun pulls the day's sales from Square, breaks them down by department, and posts a clean digest to Slack so you and your team always know how the store performed.
SquareSlack
Automated Hobby Shop Review Requests
After a completed Square transaction, WebRun checks Google Business for recent review activity and drafts a review request for staff to send to happy customers.
SquareGoogle BusinessSlack

Want one of these running on your own Square?

Show WebRun the process once and it will run it on schedule, in your own private browser environment.