⏳ Winback Emails That Don’t Feel Desperate

Hey, it’s Ray.

Let’s talk about one of the trickiest types of emails to get right…

The winback.

You know the one your subscriber hasn’t opened or clicked in months, maybe even a year. 

You want them back... but you don’t want to look like you’re chasing them down the street yelling, “Please notice me!”

I used to struggle with this too.

In fact, one of my earlier winback campaigns had all the signs of desperation:

🚫 “We miss you!” subject lines
🚫 Guilt-tripping copy
🚫 A random discount that felt more like a bribe than an incentive

It didn’t work.

Worse, it felt off-brand.

So I started asking better questions:

• Why did these subscribers disengage in the first place?

• What would make me open an email after ignoring a brand for months?

• How can I re-spark interest without begging for it?

Here’s what I’ve learned (and tested) since then.

What Makes a Winback Email Actually Work?

Here’s the key mindset shift:

The goal isn’t to get everyone back.

It’s to reconnect with the right people in a way that feels intentional, not needy.

Let’s break it down 👇

1. Stop Saying “We Miss You”

It sounds sweet. But it’s been overused to the point of meaninglessness.

Plus, it’s brand-centric; it’s about you, not them.

Try this instead:

“Still interested in getting [X] from us?”
or
“Your [free shipping / member discount / VIP access] is still here…”

Make it about value, not emotion.

2. Segment Based on Behavior

Not all disengaged users are created equal.

You should separate:

• People who never opened or clicked

• Former buyers who’ve gone cold

• Window shoppers who clicked but didn’t buy
  

Each group needs a different message.

For example:

• Cold buyers → Remind them of past value and what’s new

• Clickers → Nudge them to finish what they started

• Total ghosts → Consider a “last chance” or sunset message
  

3. Use Curiosity + Personalization

Don’t just say, “Come back.” Give them a reason to open.

Try a subject line like:

“We’ve been making a few changes…”
or
“You asked, we listened.” (even if they didn’t — just use it to highlight new benefits)

In the email body, mention:

• New features or products

• Top-rated items

• Personalized picks based on past behavior
  

Even a little relevance goes a long way.

4. Offer Value (But Don’t Lead With Discounts)

Yes, discounts can work, but not first.

Otherwise, you’re training your list to ignore you until you throw money at them.

Try these first:

• Free content (guides, tips, exclusive videos)

• Limited-time early access to a collection

• Quick win or insight (example: “3 tips to get more out of [product]”)
  

If they still don’t bite?

Then roll out a discount but frame it as a “winback perk”, not a desperate plea.

5. Sunset the Ones Who Still Don’t Engage

Sounds harsh. But it’s good list hygiene and it boosts your deliverability.

I like to send a final message like:

Subject: "Should we stop emailing you?"
or
Subject: "With code GOODBYE"

Inside the email:

Let them choose. One-click to stay, or no action = remove.

This gives them control and protects your sender reputation.

Real Winback Flow Example

Here’s a flow I recently set up for a client:

• Email 1: “Still interested in [benefit]?”
  → Highlights new features + click to stay subscribed
  

• Email 2: “This is still waiting for you”
  → Personalized product picks + free shipping reminder
  

• Email 3: “Take 10% off if you’re still with us”
  → Discount offered as a “welcome back” perk
  

• Email 4: “Should we stop emailing you?”
  → One-click stay or silently remove
  

Results after 30 days:

• 18.6% of cold subs re-engaged

• $13.7K in recovered revenue

• List size reduced by 12% (but with higher engagement overall)
  

So, What’s Your Next Step?

I know re-engaging cold subscribers can feel like guesswork.

You’re writing emails, testing subject lines, segmenting your list… and wondering if any of it’s actually moving the needle.

That’s why I’m sharing these proven tactics with you.

I’ve helped brands recover thousands in revenue with smart winback strategies and the same approach can work for you, too.

When you’re ready to scale things up, I’m here to help you turn those quiet subscribers into active customers again.

Cheers,
Raymond Chen
Founder & CEO, 11 Agency

More Ways to Level Up Your Email Game

If this sounds like a lot to manage, don’t worry, I’ve got you covered.

There’s a lot that goes into building a high-converting email strategy. 

If you’re serious about optimizing your email marketing, let’s talk. 

Here’s what we can do:

✅ Done-for-You Email Strategy: If you’re ready to scale but don’t have the time, we’ll build out a full email system that maximizes your revenue. You can book a call with me here. 

✅ Or, if you just want to grab a free resource, get a FREE 10-page KPI audit and a 128-point health scorecard to optimize your email marketing. Get it here!

Extra Tips to Boost Your Email Strategy

If you’re up about boosting your email game, I’ve got a few more gems for you:

📺 Check Out My YouTube Tutorial
Want to create a high-converting popup form that actually drives results?

In my newest YouTube video, I walk you through the process of designing popups in 2025 that boost email deliverability, grow your list, and drive more conversions. Using tools like Klaviyo and platforms like Shopify, I’ll show you exactly how to optimize your forms for success. 👉 Watch it here: 

📝 Win Back Shoppers with These 10 High-Impact Abandoned Cart Subject Lines
A lot of brands lose potential sales due to ineffective subject lines that don’t grab attention.

We've compiled a list of 10 powerful subject lines that will help you win back those shoppers and boost conversions. Want to see the subject lines that work? 👉 Check out the full list here: 10 High-Impact Abandoned Cart Subject Lines to Win Back Shoppers

💡 Let’s Connect on LinkedIn
I share daily email marketing tips, behind-the-scenes insights, and strategies that actually work. If you’re looking for extra value beyond this newsletter, let’s connect!👉  Follow me here.