Retention for subscription businesses declined in Billing. What is your analysis plan

Problem Statement Description

Product context: Stripe is financial infrastructure for internet businesses; its products include payments, Checkout, Billing, Connect, Radar, Issuing, Terminal, and tax tools.

Stripe Billing supports subscription businesses that rely on recurring invoicing, payment collection, plan management, retries, tax handling, and reporting to retain their customers and grow revenue. You are told that retention for subscription businesses using Billing has declined, and you need to lay out how you would investigate the issue.

This is a root-cause analysis question. Focus on how you would frame the anomaly, validate whether the decline is real, segment the impact, generate hypotheses, and determine what evidence you would need before recommending action. The problem may involve merchant churn from Stripe Billing, end-customer subscription retention for merchants, payment success, pricing or packaging changes, product reliability, integration friction, compliance requirements, or competitive pressure.

Your analysis should reflect Stripe’s context: financial reliability, developer experience, merchant growth, conversion optimization, and global payment complexity. Assume multiple teams may be involved, including Billing, Payments, Risk, Support, Data, Engineering, and Go-to-Market.

The experience should consider:

- How you define “retention” precisely, including numerator, denominator, time window, cohort, and whether it refers to merchants or their subscribers.

- How you would verify the anomaly through instrumentation checks, metric lineage, data freshness, tracking changes, and seasonality.

- Which segments you would cut by, such as merchant size, geography, industry, subscription model, payment method, integration type, tenure, pricing plan, and acquisition channel.

- What hypotheses you would explore across product changes, payment failures, dunning performance, API or dashboard reliability, onboarding quality, support issues, pricing changes, fraud/risk interventions, and competitor switching.

- What evidence would confirm or reject each hypothesis, including quantitative trends and qualitative signals from support tickets, sales notes, merchant interviews, and incident reports.

- How you would distinguish between leading indicators, lagging indicators, and guardrail metrics such as payment success rate, invoice recovery rate, involuntary churn, voluntary churn, API errors, dispute rates, and support contact rate.

- How you would prioritize investigation paths based on business impact, reversibility, affected customer value, and confidence.

- How you would communicate findings, near-term mitigation, and longer-term prevention without jumping prematurely to a solution.

Your goal is to present a structured analysis plan that would help Stripe quickly determine whether the retention decline is a measurement artifact, a product or reliability issue, a merchant lifecycle issue, a payments performance issue, or an external market shift, and to identify the next decision points for action.