SMS Win-Back Campaigns: How to Re-Engage Cold Leads with Automated Workflows

Ignoring company messages has become second nature to consumers.

You spend hours crafting reminders, consumers spend a second ignoring them.

I've got 300+ unread promo emails on my phone, most from brands I interacted with once.

Sure, personalization helps.

But is personalization the only way to re-engage cold leads?

Not quite.

How to Create SMS Win-Back Campaigns that Actually Convert

Leads don't ghost you without a reason. They stop responding when your texts feel irrelevant, badly timed, or demanding without delivering value. So before you hit "send" on that next SMS, take a moment to audit these common mistakes and fix them with smarter workflows.

1. Be hyper-specific in personalization

81% of users ignore irrelevant messages. Clearly, your audience is tired of generic pings that sound like you don't know them.

The key is to personalize meaningfully. (And not just with a name!)

Instead of "Hey [Name], Sign up for our bonus templates!"

Try:

"Hey [Name], noticed you were exploring our CRM tools last week. Still weighing your options? If you sign up today, you'll unlock 7 bonus templates to help you get started!"

You can get this kind of granularity going with Mobile Text Alerts. Our solutions help you send messages triggered by what people actually do, so you're not just guessing. (We'll dive into the "how" later in the article!).

2. Send the messages at the precise time of peak engagement

What happens when your texts arrive at moments when people just aren't ready to engage? Like Monday mornings, late nights, or during Sunday chaos? You lose them even without making them aware of your services/promotions.

Your best bet is usually mid-morning (around 10–11 AM) or early afternoon (1–2 PM).

It's best to avoid:

• Monday mornings
• Late evenings
• Weekends

💡 Pro Tip: Use timezone-based segmentation in your campaigns so no one gets a 2 AM ping. When users sign up, include a field in your opt-in form to capture their location or time zone information. Based on the collected data, create separate subscriber lists for each time zone and schedule messages accordingly. You can also use the phone number area codes to help determine timezones.

3. Be highly intentional about the purpose of the message

Sending a message just to "stay on their radar" isn't enough. If you want someone to click, respond, or buy, give them something useful.

This is true with all of marketing, but is especially so with SMS, even more than other channels, because of how personable it is to receive a text message.

Example:

Instead of:

"Hey! Just checking in. We miss you!"

Try:

"We just launched a free guide on how to get the most out of your marketing budget. Want a copy?"

Even better if the value aligns with what they previously showed interest in.

4. Provide offers that are hyper-personalized to the recipient

Everyone loves to feel like they're getting a special deal, especially if it's just for them.

Example:

Instead of:

"10% off sitewide this week!"

Try:

"Hey [name], because you browsed our skincare range last month, we're giving you early access to our new serum launch, plus 15% off (valid for 24 hrs only)."

For example, a campaign by Sephora showed that sending early access offers based on browsing history resulted in a 3x increase in conversion rates compared to generic promotions.

5. Don't leave ‘em guessing at next steps (CTA)

A good CTA doesn't leave a user guessing. Period.

Example:

Instead of:

"Let us know what you think."

Try:

"Click to redeem your 15% discount now" or "Book your free demo today."

Understand the different types of CTAs and when to use them, so you can craft messages that match your audience’s intent and move them closer to conversion.

💡 Pro Tip: Always test your CTA placement, wording, and urgency triggers. "Act now" might work better for a flash sale, while "Get started" is ideal for SaaS trials.

6. Nurture leads over time with SMS drip automations

Don't rely on one-off messages. Create automated drip campaign workflows of timely, relevant texts that guide leads through their journey to build trust, address objections, and nudge them toward conversion without being pushy.

Let's go through a few campaign examples.

1. Incentive-based SMS campaign

This approach targets inactive customers by offering them a compelling incentive to return.

Trigger: Identify customers who haven't purchased in a specified period (e.g., 60 days).

Action: Send an SMS offering a limited-time discount or special offer.

Follow-up: If there's no response, send a reminder SMS after a few days.

Example message:

"We miss you! Here's 20% off your next purchase. Use code WELCOME20 at checkout. Offer valid for 48 hours!"

Why it works: It creates a sense of urgency and provides a tangible benefit to encourage return.

2. Personalized reminder SMS campaign

This strategy focuses on reminding customers of the value they previously found in your products or services, similarly to cart abandonment reminders.

Trigger: Detect customers who have shown interest but haven't completed a purchase.

Action: Send a personalized SMS referencing their past interactions or viewed products.

Follow-up: Offer assistance or additional information to facilitate the purchase.

Example message:

"Hi [Name], noticed you were interested in [Product]. Need help deciding? We're here to assist you!"

OR

"Hey [Name], noticed you left [Product Name] in your cart. It's still waiting for you 👀 Need help or want 10% off to seal the deal? Use code FINISH10 – valid for 24 hrs!"

Why It Works: It's personalized, which increases engagement and demonstrates attentiveness to customer needs.

3. Automated win-back drip campaigns

Many modern businesses depend on subscription models for steady revenue. While the goal is always to retain every subscriber, cancellations are inevitable. That's where automated win-back drip campaigns come in.

These campaigns help re-engage churned subscribers by gradually rebuilding interest, often using timely incentives or exclusive offers.

One example is a campaign by MH Digital, a subscription-based online magazine. Their SMS drip sequence is designed to bring lapsed users back by offering them a discounted re-subscription.

Trigger: User cancels their subscription.

Action: Send an SMS offering a discount if they resubscribe within 3 days.

Follow-up: Remind them of the offer's expiry and send a final incentive to sweeten the deal.

Example messages:

Day 1 SMS: "We noticed you’ve canceled your subscription. We’d love to have you back, here’s 15% off for the next 3 days."

Day 3 SMS (if no response): "Still thinking it over? Just a reminder, your exclusive discount expires tonight!"

Day 7 SMS: "Want full access again? Here's one final offer: 20% off if you re-subscribe this week."

Why it works: This approach builds urgency while showing appreciation for the customer's previous interest. By spacing messages out and escalating the offer, the brand maximizes the chances of re-engagement without being intrusive.

How to Automate Campaign Triggers with Our Workflow Builder

1. Go to the Workflows tab and click "Add Workflow"

Select whether you'd like this workflow to be a single use flow, or whether you'd like it to be a permanent ("recurring") flow on your account.

2. Select your trigger

The next thing you need to do is select what you'd like to be the event that triggers the workflow to begin for your subscribers.

Your trigger options are:

• When a subscriber sends you a text message
• When a subscriber opts in
• When a subscriber joins a group
• Important dates
• Using a Zapier action

3. Implement your actions

You'll then be taken to the Workflow Builder canvas. From here, you need to drag "actions" into the canvas as desired.

You can mix and match these actions in your workflow however you'd like.

Example:

4. Save and start your workflow

When you're done making edits to the workflow, save your changes.

Then click "Options->Start" to make the workflow live.

Your workflow will then start triggering whenever your designated trigger conditions are met.

Measuring Success: Tracking Key Metrics

Re-engaging cold leads means going beyond vanity metrics and digging into what's driving behavior. Here's how to make your metrics work harder for you:

Segmented click-through rates (CTR)

Simply tracking general CTR won't help. Segment it by message type, time of day, and audience persona. For instance, you might find promotional messages work better in the evening, while educational ones perform best during work hours.

Well-defined conversion rates that are trackable through SMS:

Does conversion mean a sale, a signup, or a reply?

If lots of people click but don't buy, the issue might be a clunky checkout or unexpected shipping costs. Or if you're pushing a free trial, and users click your SMS but don't sign up, maybe your landing page isn't communicating value or has too many steps, or not enough social proof!

SMS unsubscribe rates:

With SMS in particular, a high unsubscribe rate may signal that you're messaging too often, being irrelevant, or failing to provide value.

For instance, Khris Steven, who works with creators and coaches online, witnessed a rise in engagement after switching to RCS messaging.

"We were running a pre-sale for a digital course and started with basic SMS. Click-through sat at 6.1%, and replies were short and cold. Once we flipped to RCS, we baked in a product walkthrough carousel, a video testimonial preview, and smart reply buttons like 'I'm ready' or 'Need more info?' Engagement jumped fast. Click-through went to 17.4%, and reply rates more than doubled."

Understand why users are opting out, and tweak your campaigns accordingly. (Ask us about RCS messaging here.)

💡Pro tip: Marketers who regularly A/B test their landing pages have seen a 37% increase in conversions by optimizing elements like headlines, CTAs, and visuals. But even beyond A/B testing, use A/B/C and A/B/C/D tests to uncover even more insights with your SMS.

Ready to Curate SMS Win-Back Campaigns that Convert?

Tools like mobile text alerts make that easier. You can craft timely, personalized messages that get noticed, analyze their performance, and tweak your SMS win-back campaigns accordingly. Get a complimentary strategy session to see how Mobile Text Alerts could fit in your own tech stack today.

FAQs

1. When is a lead considered cold?

In most industries, a lead is considered cold when there has been no engagement for 30–90 days, depending on the sales cycle and customer journey. For B2C, it could be as short as 14–30 days, while for B2B or high-consideration purchases, the window may stretch longer. The key signal, however, is a noticeable drop in opens, clicks, replies, or interactions.

2. Why do leads go cold in the first place?

Leads get cold for several reasons:

Message fatigue: Too many emails, push notifications, or ads can overwhelm users. When every ping feels like noise, they tune out, even from brands they liked initially.

Lack of personalization: Users notice if you're still sending generic content. Today's users expect communications that reflect their behavior, interests, and lifecycle stage.

Irrelevant offers: Misaligned offers make users feel misunderstood, and they disengage.

Off timing: If texts land when users are busy, asleep, or offline, there's a good chance they'll be ignored or deleted without a second glance.

3. How to reengage cold leads?

To re-engage cold leads, send personalized SMS campaigns with relevant offers, updates, or reminders. Use drip sequences to build interest gradually, and A/B test your messages for better timing and content.

Author Bio:

Parita Pandya writes long-form, SEO-friendly B2B content that sounds human. She works with SMEs in digital marketing, telecom, and e-commerce—turning complex stuff into content people actually want to read.

Visit her LinkedIn for a peek at her frequent dose of humorous (self-proclaimed!) one-liners, marketing takes, and occasional existential crises.