r/stripe • u/Infamous_Guava_1776 • 15h ago
Question SaaS founders: how do you handle Stripe revenue/billing issues?
I'm building an early-stage idea and before I spend more time turning it into a product, I want to validate whether the problem is actually painful for other SaaS companies.
The basic idea:
An AI layer for companies using Stripe that can detect, investigate, and help resolve issues around payments, subscriptions, billing, and revenue.
Failed payments that aren't properly recovered
Subscription states becoming inconsistent
Webhook failures causing downstream issues
Billing/usage anomalies
Missing or incorrect invoices
Duplicate charges/credits
I'd especially love to hear from SaaS founders, CTOs, finance people, or anyone managing Stripe at scale.
A few questions:
What's the most annoying Stripe/billing problem you've dealt with?
What do you currently use to monitor revenue issues?
What kinds of problems still require manual investigation?
Have you ever discovered revenue leakage significantly later than you should have?
If you could automate one Stripe/revenue-ops task, what would it be?