Glossary
Table of contents
Why This Case Study Matters

Email marketing is still the undisputed ROI king—delivering $36+ for every $1 spent—but only when emails are seen, opened, and acted on.
For growth-stage apps like Dumpling, user acquisition is only half the battle. True scale comes from activation and retention. That’s where email comes in.
Dumpling wasn’t just another grocery app. It was built to support local business owners—shoppers who run their own delivery services through the platform.
That emotional connection mattered. But it was only effective if people stuck around long enough to experience it.
Step 1: Drive App Installs (Acquisition Strategy)
To drive installs, Dumpling partnered with growth agency Tuff and used:
- Facebook Ads (targeting grocery buyers by location + behavior)
- Google Search Ads (keywords like “personal grocery shopper,” “grocery delivery near me”)
- Paid promotions on channels like Reddit and Instagram
These efforts grew the user base, but that’s when the real challenge began—turning installs into engaged users.
Step 2: Identify Where the Funnel Breaks
Dumpling’s customer journey had clear friction points. Three core user groups weren’t making it to repeat usage:
Segment | Behavior | Challenge |
---|---|---|
Segment 1 | 1 order, then churn | Didn’t form a bond with the shopper |
Segment 2 | 1–3 orders, 60+ days inactive | Lost momentum or forgot value |
Segment 3 | Installed app, no orders | Didn’t complete onboarding or see value fast enough |
Each group needed tailored messaging—not a one-size-fits-all nudge.
Step 3: Build Behavior-Driven Winback Email Flows
This is where email became the growth lever.
Each user segment was added to a dedicated winback flow, fully personalized and built for one goal: get users to re-engage by reinforcing Dumpling’s unique value.
Segment 1: One-and-Done Users
Challenge | Solution |
---|---|
Lacked a deeper relationship with the shopper | Emphasize consistency and personalized service |
Subject Lines We Used:
- “Your Grocery Routine—Made Personal”
- “What If Your Shopper Knew Exactly What You Like?”
- “Meet Your Grocery Partner (Not Just a Driver)”
Email Content:
- Highlighted customer testimonials about ongoing shopper relationships
- Included a soft CTA: “Start your next list”
- Reintroduced the concept of relationship-based delivery, not gig work
Segment 2: Users with 1–3 Orders but Inactive 2+ Months
Challenge | Solution |
---|---|
Liked the service once but didn’t see lasting value | Reframe the offer + remind them of core benefits |
What Worked:
- Subject: “Your Shopper Misses You (and So Do We)”
- Incentive: 15% off reactivation promo
- Benefit Callout: No hidden fees, no grocery markups
- CTA: “Get Back to Easy Shopping”
This group responded strongly to “we remember you” messaging. They didn’t need a full re-introduction—just a reason to come back.
Segment 3: App Installed, No Orders
Challenge | Solution |
---|---|
Didn’t understand Dumpling’s model or unique benefit | Education, onboarding, first-order discount |
Messaging Breakdown:
- Subject: “It’s Time to Meet Your Shopper!”
- Tone: Inviting, informative
- Offer: $15 off your first $50+ order
- Visuals: Shopper headshots, local service map, testimonials
The first touchpoint assumed zero context. Each follow-up layered in more information, including how the service worked and why it was better than national competitors.
Messaging Pillars: What Made These Emails Convert
Core Message | Why It Worked |
---|---|
Convenience | Shopping gets done while you live your life |
Local Support | You’re empowering real people in your community |
Transparency | No grocery markups—just a simple service fee |
Personalization | Same shopper, every time, learns your preferences |
A/B Testing: Subject Lines, Offers, and Timing
What was tested:
Element | Variations |
---|---|
Subject Line | Offer-focused vs. relationship-focused |
Send Time | Morning vs. evening |
CTA Style | “Reorder Now” vs. “Meet Your Shopper” |
Discount Type | % off vs. $ off |
Key Learning: Relationship-driven subject lines converted 12–18% higher than offer-only ones. Personal relevance > generic urgency.
Offer Strategy: Incentives Without Margin Loss
User Segment | Offer Used |
---|---|
Never ordered | $15 off first $50+ order |
Lapsed user (1–3 orders) | 15% off + “Welcome back” tone |
Connected but never completed order | Free delivery or bonus incentive |
Dynamic codes were used to limit abuse and create urgency (24–48 hour expiry window).
Results at a Glance
Segment | Reengaged Users | Engagement Rate | Conversion |
---|---|---|---|
One-and-done | 352 of 2,084 | 17% | 14% placed new orders |
1–3 orders, dormant | 556 of 2,035 | 27% | 21% reordered within 5 days |
App download, no order | 480 of 3,455 | 14% | 10% placed first order |
Takeaways for Any Brand Building Winback Flows
1. Segment ruthlessly
Treat different behaviors differently. Generic winback = lost revenue.
2. Match message to mindset
Where are they emotionally? Confused? Disengaged? Lapsed? Speak to that.
3. Don’t over-rely on offers
Use incentives to nudge, but let your value proposition carry the weight.
4. Test, learn, iterate
Your first version won’t be perfect. Build flows, then optimize over time.
5. Use dynamic flows
Email tools like Klaviyo allow dynamic personalization for content, product recommendations, and cart links.
6. Don’t let time kill the relationship
Build re-engagement windows based on behavior, not just fixed time periods.
Suggested Visuals & Rich Content for SEO Ranking
Content Type | Description |
---|---|
Lifecycle Flowchart | User journey from install → dormant → reactivated |
Email Screenshots | Real examples of each segment’s email content |
Reengagement Funnel Graphic | Show drop-off → recapture flow visually |
Test Results Table | Side-by-side performance of A/B tests |
Comparison Table | “Spray-and-pray” email vs. segment-specific winback strategy |
Offer Impact Chart | Visualize % lift from adding discounts to email flow |
Frequently Asked Questions (FAQ)
1. What is a winback email campaign?
It’s an automated email sequence designed to re-engage inactive users by reminding them of your product’s value, offering incentives, and encouraging them to return.
2. When should I send winback emails?
Timing depends on your product lifecycle. For Dumpling, flows were triggered after 14–60 days of inactivity depending on user segment.
3. Do I need to offer a discount to win users back?
Not always. Discounts help, but clear value-driven messaging and personalized content often perform just as well—especially with loyal users.
4. How do I segment users for winback flows?
Use behavioral triggers: users who downloaded but didn’t convert, placed 1 order, or haven’t re-engaged in 30+ days.
5. How do I know if my winback emails are working?
Track open rates, click-through rates, reactivation rate (e.g., orders placed), and overall engagement per user cohort.
6. What tools do I need to build winback email flows?
Platforms like Klaviyo, Drip, or ActiveCampaign allow for automated flows, segmentation, A/B testing, and dynamic personalization.
Final Thoughts: Winback Isn’t Just Recovery—It’s Relationship
The best winback campaigns don’t feel like winback campaigns.
They feel like a friend reminding you why you liked something in the first place.
If you’re running an ecommerce brand, an app, or a service and you’re not building behavior-based re-engagement flows, you’re leaving money and loyalty on the table.
Want help building your winback flows from scratch?
At Blossom Ecom, we’ve helped 100+ brands recover lapsed customers and create email systems that scale.
Let’s talk strategy. You bring the users—we’ll bring them back.
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