Automated Tutoring Failed Payment Recovery
Every morning, WebRun checks Teachworks and Stripe for new failed or declined payments, drafts a courteous recovery email for each affected family, and posts a flagged list to the staff Slack channel so the team can follow up before the next session.
How do I automatically recover failed tutoring payments without awkward conversations?
Every morning WebRun checks Teachworks and Stripe for new failed payments, drafts a courteous recovery email in Gmail for each affected family, and posts a prioritized flagged list to Slack for staff. Every email is held for review before any family is contacted, keeping the recovery process warm and human.
- Failed payments are caught the morning after they occur, before sessions are affected
- Families receive a warm recovery message rather than an abrupt cancellation
- Staff have an urgency-sorted list every day so the most time-sensitive accounts get called first
Built for tutoring centers · private tutoring businesses · learning centers · test prep centers
What does WebRun do on every run?
The exact actions WebRun takes, in order - in plain language, so you can adjust anything.
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WebRun signs in and gets to work
Opens
app.teachworks.comin a real browser with your saved login - no setup, no API keys. -
1
Teachworks - find failed or overdue payments
teachworks.com
WebRun opens Teachworks to find failed or overdue payments. - Open Teachworks and navigate to the billing or payments section
- Filter for invoices with a failed, declined, or unpaid status updated since the last run
- Capture the family name, amount owed, payment method, and next scheduled session date
Done when Every new failed payment is listed with the family and session details.
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2
Stripe - confirm declined charge details
stripe.com
WebRun opens Stripe to confirm declined charge details. - Cross-reference the flagged accounts in Stripe to confirm the decline reason
- Note whether the failure was a card error, insufficient funds, or expired card
- Capture the last four digits and expiry to include in the recovery message if appropriate
Done when Each failed payment has a confirmed decline reason from Stripe.
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3
Gmail - draft recovery emails for review
gmail.com
WebRun opens Gmail to draft recovery emails for review. - Draft a warm, non-confrontational recovery email for each affected family
- Include the amount, a clear update-payment link, and reassurance that sessions continue as planned
- Save each email as a draft for staff to review before it is sent to the family
Done when One draft recovery email exists in Gmail for every failed payment.
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4
Slack - alert staff to flagged accounts
slack.com
WebRun opens Slack to alert staff to flagged accounts. - Post a summary of all flagged accounts to the staff channel, sorted by next session date
- Include family name, amount owed, decline reason, and next session for each account
- Flag any account whose next session is within 24 hours as urgent
Done when Staff have today's failed-payment action list in Slack.
How is each run configured?
Secure by default
Connect once, stays signed in
WebRun signs in once and keeps each session in a persistent environment, so every run picks up right where it left off.
Every action is checked against this policy before it runs.
Questions, answered
Will it email families about failed payments automatically?
No. Every recovery message is saved as a Gmail draft and held for staff review. No family receives a payment request until a person approves and sends it.
What if the payment was retried and succeeded overnight?
WebRun reads the live status from Teachworks and Stripe each morning. If a payment resolved before the morning run, that account will not appear in the draft list.
Will it retry the charge itself?
No. WebRun does not initiate charges or modify payment methods. It only drafts the communication and flags the account so a staff member or your payment processor handles the retry.
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