FINANCE

Stripe Smart-Retry Dunning Orchestrator

Catches Stripe failed-payment events, schedules retries inside the customer's most-likely-to-succeed billing window, and escalates to a CSM after the final attempt fails.

CategoryFinance
Enginesim
Difficultyintermediate
Triggerwebhook
Steps6
Setup~15 min

How it runs

The automated pipeline, trigger to output.

  • TriggerStripe invoice.payment_failed webhookStripeStripe
  • LogicBranch on retry attempt number
  • ActionRead prior successful-charge times from PostgresPostgreSQLPostgres
  • ActionSchedule smart-window retry in StripeStripeStripe
  • ActionLook up account CSM in HubSpotHubSpotHubSpot
  • OutputEmail CSM handoff via OutlookOutlook

What it does

When a Stripe subscription charge fails, this workflow opens a structured dunning sequence instead of leaving the customer to Stripe's default retry cadence. It computes a smart retry window from the customer's payment history, schedules the next attempt, and only escalates to a human when automated recovery is exhausted.

When to use it

Run this when involuntary churn from card declines is eating into MRR and Stripe's built-in retries feel blunt. Best for B2B SaaS with named customer-success owners who should step in before a subscription cancels.

How it works

  1. 1A Stripe `invoice.payment_failed` webhook fires and the invoice, customer, and attempt count are captured.
  2. 2A logic step branches on attempt number: first/second failures route to automated retry, the final failure routes to handoff.
  3. 3For retries, the workflow reads the customer's prior successful-charge timestamps from Postgres and picks the next retry slot (e.g. payday-adjacent) before scheduling the Stripe retry.
  4. 4On the terminal failure, it looks up the account's CSM in HubSpot.
  5. 5It emails that CSM via Outlook with the at-risk MRR, decline reason, and a one-click recovery link.

Set it up

What you configure once, before turning it on.

  1. 1
    Connect StripeCustomers, subscriptions, payments.
  2. 2
    Connect PostgresAny Postgres URL — query, write, migrate.
  3. 3
    Connect HubSpotCRM, deals, marketing, support.
  4. 4
    Connect OutlookMail, calendar, contacts.
  5. 5
    Set each agent's modelWe leave models unset so you pick the tier — fast + cheap, or top-quality.
  6. 6
    Tune it to your dataEdit the prompts, filters, and field mappings so it matches how your team works.
  7. 7
    Test, then turn it onRun once against a sample, confirm the output, then enable the trigger.

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