Losing a customer costs 5-7x more than keeping one. But most businesses don't know a customer is leaving until they've already gone. This recipe uses Stripe billing patterns to detect early churn signals, then automatically launches a coordinated win-back campaign across five channels — email sequences, SMS check-ins, CRM flagging, and proactively scheduled calls.
What You'll Need
- A Stripe account with recurring subscriptions or repeat customers
- Klaviyo for email marketing automation
- Salesforce for CRM record management
- Calendly for booking retention calls
- Twilio for SMS outreach
- All five integrations connected in Pipeworks
The Workflow
Identify at-risk customers from Stripe data
The agent analyzes your Stripe subscription and payment data to identify at-risk customers. It looks for warning signs: failed payment attempts, downgraded subscriptions, cancelled auto-renewals, expired cards, and customers whose usage or purchase frequency has declined compared to their historical pattern. Each customer gets a risk score based on the number and severity of signals.
Enrich with Salesforce context
For each at-risk customer, the agent pulls their full history from Salesforce — account value, support tickets, last interaction date, notes from sales reps, and any existing opportunities. A high-value customer with a recent support complaint gets a very different win-back approach than a low-tier customer with a failed payment. The agent categorizes each customer into segments: payment issue, disengagement, downgrade, or at-risk cancellation.
Update CRM records with churn risk
The agent updates each at-risk customer's Salesforce record with a churn risk flag, risk score, and the specific signals detected. It creates a task assigned to the account owner so they're aware of the situation. For high-value accounts, it sets the task priority to urgent. This ensures nothing falls through the cracks even if the automated outreach doesn't convert.
Launch targeted Klaviyo email sequences
Based on the customer's segment, the agent triggers the appropriate Klaviyo flow. Payment failures get a "we noticed an issue with your billing" email with a direct link to update payment details. Disengaged customers get a "we miss you" email highlighting new features or content they haven't seen. Downgraded customers get a value-reminder email showing what they're missing. Each email is personalized with the customer's name, account history, and specific usage data.
Send SMS check-ins via Twilio
For customers who haven't opened emails in the past 30 days (identified from Klaviyo engagement data), the agent sends a brief, personal SMS through Twilio. The message is short and conversational — not a marketing blast. It references their specific situation: "Hi Sarah, we noticed your subscription renewal is coming up. Anything we can help with?" SMS cuts through inbox noise and often gets a faster response than email.
Schedule proactive retention calls
For your highest-value at-risk customers (top 20% by revenue), the agent creates Calendly scheduling links and includes them in a personalized outreach. It checks the customer's timezone from Salesforce and creates event types with appropriate availability windows. The Calendly booking page is pre-configured with the account owner's calendar so the customer books directly with someone who knows their account.
Monitor responses and escalate
Over the following days, the agent monitors engagement across all channels. It checks Klaviyo for email opens and clicks, Twilio for SMS replies, and Calendly for booked meetings. Customers who respond positively get their Salesforce churn risk flag updated to "re-engaged." Those who don't respond to any channel within your threshold get escalated — the agent creates a high-priority Salesforce task for a manual phone call from the account manager.
What Happens
Instead of discovering churn after it happens, you catch it early and respond across every channel the customer uses. The agent handles the detection, segmentation, outreach, and follow-up — your team only gets involved for high-value accounts that need a personal touch.
Run this recipe on a weekly schedule. The earlier you catch churn signals, the higher your win-back success rate. Most customers can be saved in the first 7 days after a warning sign appears.
Be careful with SMS frequency. Twilio messages should feel like a personal check-in, not marketing. One well-timed SMS is worth more than five automated blasts. Keep messages under 160 characters and always include an easy way to respond.