Winback Campaign

This drill builds targeted campaigns to re-engage customers who have cancelled or gone inactive. It segments churned users by reason and timing, delivers personalized winback messaging through email and in-app channels, and tracks reactivation through to retention.

Input

• Attio with churned customer records including churn reason and date
• PostHog with historical usage data for churned accounts
• Loops configured for broadcast and triggered emails
• Intercom configured for in-app messaging
• At least 30 churned customers to segment meaningfully
• Output from the churn-signal-extraction drill (churn reasons and pre-churn behavior data)

Steps

1. Segment churned customers

Using attio-lists, pull all churned customers. Using posthog-cohorts, enrich each record with pre-churn behavior. Classify into segments:

• Price churners: Cancelled citing cost. Billing-related events in last 30 days before churn.
• Missing feature churners: Cancelled because the product lacked something they needed. Feature request tickets or support conversations mentioning specific capabilities.
• Competitor churners: Switched to a competitor. Mentioned competitor in exit survey or abrupt usage stop.
• Poor experience churners: Cancelled due to bugs, poor support, or frustration. High support ticket volume or error events before churn.
• Inactive churners: Never fully activated or gradually stopped using the product. Low feature breadth, declining sessions for 8+ weeks.
• Business change churners: Company closed, role changed, or project ended. Exclude from winback — mark as do-not-contact.

Sub-segment by recency: Fresh (0-30 days), Mid (31-90 days), Stale (91-180 days), Cold (180+ days). Sub-segment by value: High (top 25% by previous MRR), Standard (middle 50%), Low (bottom 25%).

2. Design segment-specific campaigns

Each segment gets a different approach and offer:

• Price churners: Lead with a discount, extended trial, or a new lower-tier plan. "We launched a Starter plan at $X/mo — everything you used, at a price that works." Include specific features they used.
• Missing feature churners: Only contact when the requested feature has shipped. "You asked for X — we built it. Here is a 14-day free pass to try it." Link directly to the feature.
• Competitor churners: Lead with differentiation. Share what has improved since they left. Include a comparison or case study.
• Poor experience churners: Acknowledge the issue directly. Explain what was fixed. Offer a personal walkthrough.
• Inactive churners: Re-educate on value. Share a case study from a similar company. Offer a new onboarding experience.

3. Build email sequences

Using loops-sequences, create a 3-email winback sequence per segment:

• Email 1 (trigger: segment assignment or 30 days post-churn): Acknowledge their departure. Share the most relevant improvement for their segment. No hard sell. Single CTA.
• Email 2 (7 days after Email 1, if no engagement): Social proof from a similar customer. Specific results or testimonial relevant to their churn reason.
• Email 3 (14 days after Email 1, if no engagement): Direct offer with 14-day expiration. Discount, free trial, or personal demo depending on segment.

Exit conditions: User reactivates (exit immediately). User unsubscribes (exit and mark do-not-contact). User engages with Email 1 or 2 (continue sequence but skip hard-sell Email 3).

For Smoke level, use loops-broadcasts for manual one-time sends instead of automated sequences.

4. Add in-app touchpoints for returning users

Using intercom-in-app-messages, set up welcome-back messages for churned users who return to the site or log into an expired account:

• Detect returning churned users via PostHog cohort: users with churned lifecycle stage who trigger a new session_started event
• Show a personalized banner: "Welcome back, [name]. Here's what's new since [churn date]: [2-3 bullet points based on their segment]."
• One-click reactivation CTA. Pre-fill their previous plan. Offer data and settings restoration.
• If eligible for a discount, apply it automatically on reactivation.
• Frequency cap: Show once per user per 14 days.

5. Route high-value winbacks to personal outreach

For High Value sub-segment churned accounts, create Attio tasks for the account owner. Include:

• Churn reason and date
• Pre-churn usage summary from PostHog (features used, engagement level)
• What has changed since they left (product improvements relevant to their churn reason)
• Recommended offer and talking points

Automated email sequence still runs, but personal outreach is the primary channel for high-value accounts.

6. Track winback metrics

Using posthog-custom-events, track the full lifecycle:

• winback_email_sent: Properties: user_id, segment, email_step, offer_type, days_since_churn
• winback_engaged: Properties: user_id, engagement_type (opened, clicked, replied, logged_in), channel
• winback_reactivated: Properties: user_id, segment, offer_type, days_to_reactivation, reactivated_plan
• winback_retained_30d: Properties: user_id, segment, reactivated_plan
• winback_rechurned: Properties: user_id, segment, days_to_rechurn, original_offer_type

Calculate reactivation rate per segment, per email step, and per channel. Target: 10-15% overall reactivation rate. If a segment consistently fails to reactivate (<3% for 8+ weeks), stop spending resources on it and focus upstream on the churn-prevention drill.

Output

• Segment-specific winback email sequences configured in Loops
• In-app welcome-back messages configured in Intercom
• High-value winback tasks routed to account owners in Attio
• Full lifecycle event tracking in PostHog
• Reactivation funnel: email_sent -> engaged -> reactivated -> retained_30d

Triggers

• Smoke: Run once manually with a batch of 30-50 churned users
• Baseline: Automated: new churners enrolled in sequences within 24 hours of churn
• Scalable: Automated with multi-channel escalation for non-responders and A/B testing
• Durable: Autonomous optimization of offers, timing, and messaging