Automated Lapsed Tutoring Family Winback
Every month, WebRun opens Teachworks, identifies students with no completed session in the past 30 or more days, drafts a warm re-engagement email for each lapsed family, and posts the winback list to Slack so staff can follow up with a personal call or message if appropriate.
How do I automatically re-engage tutoring families who have stopped booking sessions?
Once a month, WebRun opens Teachworks, finds every student with no session in the past 30 or more days, and drafts a warm re-engagement email in Gmail for each family. It posts a priority-sorted winback list to Slack so staff can decide which families to call personally. Every email awaits staff review before it is sent.
- Lapsed families hear from the center before the relationship goes cold
- Staff have a priority-sorted call list every month for high-value winback conversations
- Re-engagement happens consistently without relying on anyone to remember who has been quiet
Built for tutoring centers · learning centers · private tutoring businesses · academic coaching practices
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 students with no recent sessions
teachworks.com
WebRun opens Teachworks to find students with no recent sessions. - Open Teachworks and navigate to the student records or session history
- Filter for active or recently active students whose last completed session was 30 or more days ago
- Capture the student name, parent contact, subject, last session date, and any notes about why they stopped
Done when Every lapsed student is identified with their last session date and contact details.
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2
Gmail - draft re-engagement emails for review
gmail.com
WebRun opens Gmail to draft re-engagement emails for review. - Draft a warm, no-pressure re-engagement email for each lapsed family
- Reference the subject and the time since their last session to make it personal
- Include a soft call to action such as a link to book a session or a note to reply if schedules have changed
- Save every email as a draft for staff to review before it is sent to any family
Done when One draft re-engagement email exists in Gmail for every lapsed student.
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3
Slack - post winback list to staff
slack.com
WebRun opens Slack to post winback list to staff. - Post the lapsed student list to the staff channel, sorted by days since last session
- Flag students who lapsed after a long enrollment as higher priority for a personal call
- Note the total count of lapsed students and any common patterns such as end-of-term gaps
Done when Staff have this month's winback list in Slack with priority flags.
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 lapsed families automatically without staff approval?
No. Every re-engagement email is saved as a Gmail draft for a staff member to review before any family is contacted. Nothing sends on its own.
What counts as lapsed? Can I set my own threshold?
The default threshold is 30 days with no completed session. Tell WebRun your preferred threshold when you set it up and it applies that consistently every month.
What if a family intentionally paused for summer or a school break?
The staff reviewer sees the list before any email goes out and can remove seasonal or intentional pauses. The Slack list also shows last session date so context is easy to read.
Related templates
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