Addressing Payment Failures with Automated Follow-Up: Building a Simple Monitoring Tool

In the world of subscription-based services and online payments, even small oversights can lead to significant revenue loss. Recently, I encountered a situation that highlighted a common but often overlooked challenge: what happens after a failed payment?

The Incident: A Missed Opportunity

While working on one of my projects, I observed a scenario where Stripe, our payment processor, attempted to charge a user. The payment failed—possibly due to insufficient funds, expired card, or other reasons. Stripe’s automated email notification was dispatched to the customer, informing them of the issue. Unfortunately, neither the customer responded nor did we take additional follow-up action.

As a result, the subscription quietly churned—$200 in Monthly Recurring Revenue (MRR) vanished without recovery. It was a wake-up call highlighting a potential blind spot in our customer retention process.

Identifying the Problem

This experience made me realize that relying solely on automated emails and passive monitoring isn’t enough. When a payment fails, a quick manual intervention could lead to customer retention. However, manually tracking failed payments across multiple accounts or customers is tedious and prone to oversight.

Proposed Solution: A Minimalist Monitoring Tool

To address this, I am considering building a straightforward, lightweight tool that:

• Listens for failed Stripe payment webhooks
• Waits for 24 hours to allow the customer time to resolve the issue
• Checks if the customer has rectified the payment
• If not, sends a Slack notification to the team for manual follow-up

This approach emphasizes simplicity:

• No OAuth authentication required
• No complex API integrations
• Just a webhook listener and some logical checks

Your Input: Is This Worth Building?

Before investing development time, I’d value insights from the community:

• Have you encountered similar issues with failed payments slipping through the cracks?
• Would a tool like this be beneficial in your workflow?
• Are there other best practices or tools you recommend to proactively manage failed payments?

Conclusion

Proactively addressing payment failures can save revenue and improve customer relationships. A lightweight, automated follow-up system might be a worthwhile addition to your payment management toolkit. I’m curious whether others see this as a viable solution or if it’s a solution to a problem I might be alone in facing.

Would love to hear your thoughts and experiences!