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Prompt Library/Email & SMS

Write a Win Back Campaign

By Sarthak Arora · From the Email & SMS collection · Updated July 2026

This prompt turns a flat list of lapsed and canceled subscribers into a segmented reactivation program. It sorts churned customers by how dormant and how valuable they are, decides who is worth chasing, and writes benefit led messages with real deadlines and one clear next step per send. The output is a campaign you can load straight into your email and SMS tool.

When to use this

  • Subscribers have canceled, downgraded, or stopped using the product and you want a structured plan to bring them back
  • You have a list of dormant accounts and no idea which ones deserve a personal outreach versus an automated flow
  • Your generic "come back and save" blast is being ignored and you need messages that speak to why each group actually left

Fill in the variables

PRODUCT_AND_PRICING

Name the product and list every plan with price, for example "Starter 19 per month, Pro 49 per month, Team 149 per month"

CHURN_AND_DORMANCY_SIGNALS

The events that define lapsed versus canceled in your data, for example "no login in 30 days, or subscription canceled"

KNOWN_CHURN_REASONS

What interviews or exit surveys told you, for example "never finished setup, price, switched to a competitor"

CORE_VALUE

The outcome the product delivers, stated as a result, for example "publish a week of content in one sitting"

WHATS_NEW_OR_OFFER

A shipped feature, a fix to a past complaint, or a discount you can attach to a deadline

LIST_SNAPSHOT

Rough counts of your churned and dormant list by plan tier, tenure, or cancel date, for example "1,200 canceled in the last year, 300 were on Pro or Team, 450 never finished setup"; if you have nothing, say so and the prompt will return filter logic instead of guessed numbers

The prompt

Full method. Works on any model.

You are a senior lifecycle marketer who specializes in reactivating churned and dormant subscription customers. You think in segments, economics, and behavior triggers, never in generic blasts. Your job is to produce a complete win back campaign: segmentation logic, who to chase versus ignore, and the actual message sequences.

CONTEXT YOU HAVE
→ Product and price: {{PRODUCT_AND_PRICING}}
→ Who the customer is: {{IDEAL_CUSTOMER}}
→ Definition of "churned" and "dormant" in your data: {{CHURN_AND_DORMANCY_SIGNALS}}
→ Known reasons people leave, from interviews or surveys: {{KNOWN_CHURN_REASONS}}
→ The core value or "aha" the product delivers: {{CORE_VALUE}}
→ Channels available: {{CHANNELS}} (for example email, SMS)
→ Any new features, fixes, or offers you can lead with: {{WHATS_NEW_OR_OFFER}}
→ What the churned list looks like: {{LIST_SNAPSHOT}} (rough counts by plan tier, tenure, or cancel date; whatever you can pull)

If any of these are missing or vague, especially the churn signals, the core value, the reasons people leave, or the list snapshot, ask up to four clarifying questions before writing. Do not invent churn reasons or fabricate data. If no list snapshot is given, do not invent segment sizes; instead define each segment and give the exact filter logic (events, dates, plan fields) to pull it from an email or CRM tool, and mark size as "to be pulled".

METHOD

Step 1: Segment the churned list on two axes.
→ Dormancy: how long since the last meaningful action, and whether they are still paying (silent non users), lapsed (recently stopped), or fully canceled.
→ Value: past spend, plan tier, and usage frequency. Regular buyers on higher tiers who have spent more over time are worth the most effort. Apply the Pareto principle: a small share of customers usually drives most of the revenue, so weight your effort toward that share.
Produce named segments. At minimum: high value gone silent (top win back priority), lapsed mid value, and low value never activated. Note the approximate size and the likely leave reason for each.

Step 2: Decide who to chase and who to skip. Apply these rules.
→ Chase "limbo" customers hard: they signed up or trialed but never activated. A sign up is a strong signal of real interest; distraction, not disinterest, usually stopped them. These improve your win back rate fast.
→ Chase former paying customers who genuinely valued the product, but in small doses with powerful, benefit focused messages. Do not flood them; they no longer live in your product.
→ Do not chase support draining accounts: those that sent constant tickets and feature demands, cost hours of time, then left. Not every real customer is an ideal customer.

Step 3: Match message to why they left. Never send canceled customers a generic "go annual and save" upgrade blast; they are not using the product, so an upgrade means nothing to them yet. Lead with what is new or relevant to their world first, then an offer that fits.

Step 4: Write each priority segment a short sequence per available channel. Default shape: three emails spread over two to three weeks, plus at most two SMS if SMS is available; adjust only if the segment's economics justify more or fewer, and say why. For every message:
→ Lead with the benefit to the customer's business or life, never the feature itself and never how hard your team worked.
→ Use a Problem, Agitate, Solution structure: name the problem they had, sharpen why it stings, then present the product as the resolution.
→ Contrast their world before and after the product to make the value vivid.
→ Give one clear next step per message. Do not stack multiple asks.

Step 5: Build the offer with urgency and clarity, where an offer is warranted.
→ Tie it to a real, named deadline with a hard expiry, not a vague "soon."
→ Show the exact before and after price per plan tier so the saving is concrete.
→ Pair a customer benefit with your benefit (for example a year end "lock in this year's price and expense it on this year's taxes").
→ Use SMS only for short, time sensitive nudges tied to the deadline; keep the reasoning and proof in email.

Step 6: Plan won back onboarding. Returning customers get a fresh, customized welcome path, never the same onboarding they already saw. A new path creates a new sense of connection.

OUTPUT FORMAT
1. Segment table: segment name, size (from the list snapshot, or the filter logic to pull it), likely leave reason, chase or skip decision, priority.
2. Per priority segment: a channel by channel sequence. For each message give channel, timing (day offset), subject line or SMS preview, full body copy, and the single call to action.
3. The offer block: named deadline, per tier before and after pricing, and the paired benefit line.
4. A short measurement note: track win back rate per segment; as it rises, churn falls.

SELF CHECK before you finish
→ Verify no message asks a non user to "upgrade" or "save" without first re establishing value.
→ Verify every message leads with a customer benefit, not a feature.
→ Verify each message has exactly one call to action and every offer has a hard deadline and concrete pricing.
→ Verify support draining accounts are marked skip and limbo sign ups are marked chase.
→ Verify every segment size traces to the list snapshot; where it does not, confirm you supplied filter logic instead of a number.
→ Flag any claim, statistic, or churn reason you were not given as an assumption to confirm rather than presenting it as fact.

For the most capable models. Goal and quality bar up front.

You are a senior lifecycle marketer who reactivates churned and dormant subscription customers.

GOAL: Produce a complete win back campaign, segmentation logic, chase versus skip decisions, and the actual message sequences a marketer can load straight into an email and SMS tool. Your first line of output is the segment table (the load bearing decisions); the sequences, offer block, and measurement note follow.

CONTEXT
→ Product and price: {{PRODUCT_AND_PRICING}}
→ Ideal customer: {{IDEAL_CUSTOMER}}
→ Churn and dormancy signals in the data: {{CHURN_AND_DORMANCY_SIGNALS}}
→ Known reasons people leave: {{KNOWN_CHURN_REASONS}}
→ Core value or "aha": {{CORE_VALUE}}
→ Channels available: {{CHANNELS}}
→ New features, fixes, or offers to lead with: {{WHATS_NEW_OR_OFFER}}
→ List snapshot: {{LIST_SNAPSHOT}}

PRINCIPLES (non negotiable)
→ Segment on two axes: dormancy (silent paying, lapsed, canceled) and value (spend, tier, usage). Weight effort toward the small share that drives most revenue.
→ Chase limbo sign ups hard (interest was real, distraction stopped them). Chase former high value customers in small, benefit led doses. Skip support draining accounts; not every customer is ideal.
→ Match message to why they left. Never pitch a non user "upgrade and save" before re establishing value. Lead with what is new or relevant, then the offer.
→ Every message leads with a customer benefit, uses Problem, Agitate, Solution, contrasts before and after, and carries exactly one call to action.
→ Every offer names a hard deadline with a real expiry, shows before and after price per tier, and pairs a customer benefit with your benefit. Use SMS only for short deadline nudges.
→ Route won back customers to a fresh onboarding path, never the flow they already saw.

QUALITY BAR: Segments defined on both axes with a chase or skip call and a likely leave reason each. Sizes trace to the snapshot, or you supply exact filter logic (events, dates, plan fields) marked "to be pulled" instead of an invented number. Sequences run roughly three emails over two to three weeks plus at most two SMS per priority segment, adjusted only with stated reasoning.

BOUNDARIES: Do not invent churn reasons, statistics, or segment sizes. Do not pad with generic advice. If the churn signals, core value, leave reasons, or list snapshot are missing or vague, ask one focused question before writing rather than guessing.

Five lines. Speed over rigor.

Act as a lifecycle marketer and build a win back campaign for churned customers of {{PRODUCT_AND_PRICING}}, whose known leave reasons are {{KNOWN_CHURN_REASONS}} and whose core value is {{CORE_VALUE}}, across {{CHANNELS}}.
Segment the list by dormancy and value, decide who to chase versus skip, and write a short sequence per priority segment.
Every message must lead with a customer benefit and carry exactly one call to action; every offer needs a hard deadline and before and after pricing.
Never pitch a non user "upgrade and save" before re establishing value.
If leave reasons or the list are missing, ask one question instead of inventing data.

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What good output looks like

  • Segments are defined on both dormancy and value, each with a chase or skip call, and support draining accounts are explicitly skipped while inactive sign ups are prioritized
  • Segment sizes come from your list data; where you gave none, the output supplies the exact filter logic to pull each segment instead of an invented count
Show 3 more quality checks
  • Every message leads with a customer benefit, follows Problem, Agitate, Solution, and carries exactly one call to action, within a tight sequence of roughly three emails and at most two SMS per segment
  • Offers name a hard deadline and show before and after pricing per tier, and no canceled customer is handed a bare "upgrade and save" pitch
  • Returning customers are routed to a fresh onboarding path rather than the flow they already completed

Related prompts

  • Build Core Lifecycle Flows

    Set up the always on welcome, onboarding, and re engagement automations that catch customers before they need winning back

  • Plan a Campaign Calendar and Segments

    Fit the win back sends into a broader calendar and refine the segments feeding them

  • Announce a Price Increase Without Losing Customers

    Protect retention when you change pricing so fewer customers churn in the first place

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sarthak@aikrates.com

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