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.
How it runs
The automated pipeline, trigger to output.
- TriggerStripe invoice.payment_failed webhookStripe
- LogicBranch on retry attempt number
- ActionRead prior successful-charge times from PostgresPostgres
- ActionSchedule smart-window retry in StripeStripe
- ActionLook up account CSM in HubSpotHubSpot
- 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
- 1A Stripe `invoice.payment_failed` webhook fires and the invoice, customer, and attempt count are captured.
- 2A logic step branches on attempt number: first/second failures route to automated retry, the final failure routes to handoff.
- 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.
- 4On the terminal failure, it looks up the account's CSM in HubSpot.
- 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.
- 1Connect StripeCustomers, subscriptions, payments.
- 2Connect PostgresAny Postgres URL — query, write, migrate.
- 3Connect HubSpotCRM, deals, marketing, support.
- 4Connect OutlookMail, calendar, contacts.
- 5Set each agent's modelWe leave models unset so you pick the tier — fast + cheap, or top-quality.
- 6Tune it to your dataEdit the prompts, filters, and field mappings so it matches how your team works.
- 7Test, then turn it onRun once against a sample, confirm the output, then enable the trigger.
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Run it inside a business
This workflow drops into a full company template. Import the org, and this is one of the playbooks its agents run.

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