How to Automate Teachworks

Teachworks automates the scheduling and billing core of a tutoring business. The Invoice Autopilot add-on raises invoices on a schedule, lesson reminders go out by email and SMS, and the Conflict Validator checks every booking as it is made. Reconciling that against Stripe, the bank and the families who stopped coming is what remains.

Teachworks is the timetable a tutoring business runs on

Teachworks is management software for education businesses that sell time: tutoring centres, test prep, music schools, language schools, driving instructors, coding and arts programmes.

A business like that is a timetable with money attached. Every hour of every teacher is either sold or it is not, half the families are partway through a block of hours they already paid for, and the whole thing rearranges itself every time a child catches a cold.

So Teachworks holds the calendar, the student and family records, teacher availability, the invoices, the packages of hours, and the wages owed to whoever taught the lesson. For a centre with fifteen tutors it is not one system among several. It is the answer to almost every question anybody asks during the day.

What it holds is what happens in the lesson. The money once it has left, the families who quietly stopped booking, and the school calendar that decides your whole timetable are all somewhere else.

The admin arrives one lesson at a time

The work around a tutoring business is never one big job. It is a hundred small ones, each attached to a single lesson.

A student cancels on Wednesday, so somebody hunts for a makeup slot with the same teacher. A family's package drops to two hours left, so somebody has to notice and ask whether they want to top up. A card declines at the end of the month, so somebody works out which lessons were already taught against it. A teacher has not confirmed next week, so somebody sends the third message. Somebody checks whether the Tuesday group class has enough students to run.

In the office it is the same shape at a larger scale: exporting a term of lessons to check the numbers, copying the families who did not come back into an email tool, matching what Stripe paid out against what the invoices said.

Almost all of it is opening one screen and comparing it with another.

The teachworks.com homepage, the app these three jobs run in. Teachworks
Package hours before they run out A family offered a top-up while there are still lessons left to book, rather than after the last one is used.
Payouts matched to invoices What Stripe actually deposited compared with what was billed, weekly, while a gap is still explainable.
Classes that will not run Group sessions counted against the head count each one needs, with time left to fill it or move a student.

Invoice Autopilot and lesson reminders already run themselves

Teachworks automates more of this than most centres switch on, and the add-ons are where it lives.

Automated lesson reminders reach students, parents and teachers before a lesson, with the wording and the lead time set per type of recipient, and SMS Lesson Reminders send the same thing to a phone. The Invoice Autopilot add-on generates invoices automatically on a schedule you choose. The Automatic Allocation add-on applies payments and credit notes to invoices without anyone matching them by hand. The Conflict Validator add-on runs the conflict checker every time a lesson is scheduled, which is the difference between catching a double booking now and catching it on Saturday morning. The Website Booking Plugin lets a family book a lesson, join an open class or enrol in a course from your own site at any hour.

That is a serious amount of automation, and all of it operates on lessons, students and invoices inside Teachworks.

It stops at the login screen. The bank is elsewhere. The payout report from the payment processor is elsewhere. So is the exam board, the local school term calendar, and the mailing list holding every family who ever enquired.

Lapsed families and half-full classes are a list, not a mystery

A tutoring centre's hardest questions all have answers on somebody's website, behind a password it already holds.

Packages running down, so a family with two hours left is offered a top-up before the last lesson rather than after it. Payments that failed at Stripe matched back to the lessons already taught against them, so nobody teaches a fourth hour for free. What a payout actually deposited set against what the invoices said, weekly, while a difference is still one week wide.

Teachers who have not confirmed next week, checked against the timetable and their own calendar, on Friday rather than on Monday. Group classes counted against the head count each needs to be worth running, with a week left to move somebody or promote it.

Families who stopped booking after March, listed with what they last studied and which teacher they had, which for a tutoring centre is the most valuable list in the building. Term dates published by the local schools, read from their own pages, because half your timetable moves when they do.

Keep the family contact supervised. A tutoring centre lives on word of mouth between parents who know each other, and one wrongly aimed message about an unpaid invoice travels through a class WhatsApp group in an afternoon.

Nobody trained as a tutor to reconcile Stripe

The teaching is the business. The judgement about a struggling student is the business. Comparing a payout report against an invoice list is neither, and it is what fills the hour after the last lesson finishes.

WebRun is an AI agent that works a real Chrome browser, signed in as you. It opens Teachworks, Stripe, the bank or the mailing tool, reads each one, and puts the comparison in front of you with the differences named.

It runs on your schedule in your own private environment, and you can watch a run and stop it. Anything going to a family is drafted and waits for a person to send it.

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

Questions people ask

Do we need the Teachworks API for this?

No. It works the browser signed in as you, using the same screens your staff use, so nothing has to be connected to your account and no developer is involved.

Will it send invoice reminders to parents by itself?

No. It prepares the message and the list, and a person sends it. Parents at a tutoring centre talk to each other, and a wrongly aimed note about money costs referrals.

We already run Invoice Autopilot. Is this the same thing?

No, and keep it. Invoice Autopilot raises the invoices. This covers what happens after: whether the payment landed, whether the payout matched, and who quietly stopped booking.

20 ready-made Teachworks 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 Teachworks Visa Enrollment Letters
Whenever a student requests a visa enrollment or attendance letter, WebRun pulls their record from Teachworks, drafts a formatted letter in Google Docs, and prepares a Gmail draft for staff to review, sign, and send.
TeachworksGoogle DocsGmail
Automated Teachworks Tuition Installment Reminders
Every morning, WebRun finds students on installment plans in Teachworks, checks each balance in QuickBooks, and drafts a polite reminder email for every installment due soon or overdue.
TeachworksQuickBooksGmail
Automated Teachworks Teacher Availability Reminders
Every Monday, WebRun checks Teachworks and Google Calendar for teachers who have not confirmed next week's availability, and posts a reminder digest to the staff Slack channel.
TeachworksGoogle CalendarSlack
Automated Teachworks Semester Re-Enrollment Nudges
Every Monday, WebRun finds students whose semester ends within the next few weeks and who have not re-enrolled in Teachworks, drafts a personalized WhatsApp nudge for each family, and posts staff a list of who still needs to renew.
TeachworksWhatsAppSlack
Automated Teachworks Placement Test Scheduling
When a new student inquires, WebRun logs the placement test request in Teachworks, books an open slot with an available teacher on Google Calendar, and drafts a confirmation email for staff to review and send.
TeachworksGoogle CalendarGmail
Automated Teachworks Multilingual Invoice Drafts
Once a month, WebRun finds international families due to be billed in Teachworks, translates the invoice notes into each family's preferred language with DeepL, and drafts the itemized invoice in QuickBooks for staff to check and send.
TeachworksDeepLQuickBooks
Automated Teachworks Makeup Lesson Rebooking
Every morning, WebRun finds lessons that were missed or cancelled in Teachworks, finds a matching open slot with the same teacher on Google Calendar, and drafts a WhatsApp message proposing the makeup time for staff to send.
TeachworksGoogle CalendarWhatsApp
Automated Teachworks Level Progression Tracking
Every Monday, WebRun reads each student's latest assessment scores in Teachworks, logs level changes to a Google Sheets tracker, and tells the academic team in Slack who is ready to progress.
TeachworksGoogle SheetsSlack
Automated Teachworks Class Roster Balancing
Every morning, WebRun pulls every group class roster from Teachworks, flags classes that are under or over their target size in Google Sheets, and posts a balance report to the academic team on Telegram.
TeachworksGoogle SheetsTelegram
Automated Teachworks Course Completion Certificates
Every night, WebRun finds students who completed a course level in Teachworks, designs a personalized certificate in Canva, and drafts a congratulatory email with the certificate attached.
TeachworksCanvaGmail
Automated Teachworks Conversation Club Signups
Every Monday, WebRun sees who signed up for this week's conversation club in Teachworks, balances the groups by level in Google Sheets, and drafts a WhatsApp confirmation for each student.
TeachworksGoogle SheetsWhatsApp
Automated Teachworks Attendance No Show Alerts
Every morning, WebRun finds yesterday's unexcused no-shows in Teachworks, alerts the academic team in Slack, and drafts a friendly check-in email for each affected family.
TeachworksSlackGmail
Automated Trial to Enrollment Follow-Up for Tutoring
After a trial session, WebRun drafts a personalized follow-up for the family with next steps, so the momentum from the first session turns into a booking.
TeachworksGmailSlack
Automated Tutoring Session Reminders
Before each session, WebRun drafts reminder messages for the student and parent, reducing no-shows and last-minute cancellations.
TeachworksGmailTwilio
Automated Tutoring Package Hours Low Alerts
When a student's package hours drop below your threshold, WebRun drafts a personalized top-up reminder for the family so sessions never get interrupted.
TeachworksGmailSlack
Automated Tutoring Overdue Invoice Chaser
Every week, WebRun finds past-due invoices in Teachworks, drafts polite payment reminder emails for each family, and gives staff a clear aged-debt list so nothing falls through.
TeachworksGmailSlack
Automated New Tutoring Student Onboarding
When a new student is added to your system, WebRun drafts a personalized welcome email for the family, creates their onboarding checklist, and alerts the assigned tutor so the first session starts on the right foot.
TeachworksGmailSlack
Automated Tutoring Monthly Enrollment Report
On the first of each month, WebRun pulls enrollment counts, session volumes, and revenue from Teachworks and Stripe, compiles them into a clean summary, and posts it to Slack so the whole team starts the month with the same picture.
TeachworksStripeGoogle Sheets
Automated Lapsed Tutoring Family Winback
Every month, WebRun finds students who have not had a session in 30 or more days, drafts a warm re-engagement email for each family, and flags the list to staff so outreach is personal and timely.
TeachworksGmailSlack
Automated Tutoring Failed Payment Recovery
When a payment fails in Stripe or Teachworks, WebRun drafts a polite recovery message for the family and flags the account to staff so sessions continue without awkward interruptions.
TeachworksStripeGmail

Want one of these running on your own Teachworks?

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