How to Re-Engage Lost Customers [67% Reply Rate]

I used to get pretty worked up about leads slipping away early in my career, but now I know exactly how to re-engage them. In fact, our latest campaign, designed specifically for this purpose, achieved a MASSIVE 67% reply rate!

And why should you care about lost leads at all? Well, their conversion rate is 15-20%—much higher than cold leads. Plus, it’s more cost-effective to win back someone who already knows your brand.

I’ll spill all the details of this campaign + some extra tips to help you achieve the same success rate.

67% reply rate campaign to convert lost leads

I aimed to automate a process to re-engage with lost customers after a specific event, such as a ‘missing feature being added.’ 

The goal was to reach out to them, send automated connection request messages, and hopefully win them back (fingers crossed 🤞). Together with Macklin Buckler from Harochi who helped set up this campaign, we achieved the following results: 

• Connections sent: 42
• Connections accepted: 24 (57.5%)
• Messages sent: 24
• Message replies: 16 (66.7%)

The tools I integrated into this campaign were HeyReach, Fireflies, Clay, and HubSpot. The last three tools helped us pull together data on companies. 

Here’s what the full campaign setup looked like:

Now, let me take you through each step.

Step 1: Create message templates 

First, I used Fireflies transcripts to craft messages. This genius tool captures voice conversations, calls, and meetings anytime, anywhere. I’ve noticed its high accuracy in all generated transcripts. 

We’ve integrated Fireflies into our HubSpot stack, but it can also be linked with Slack, X, and other apps. I also love how Fireflies allows us to convert important parts of calls into shareable soundbite snippets right from the dashboard.

Anyway, after I reviewed and adjusted the transcript to ensure it’s accurate and relevant. I saved nearly all the transcripts to share with my team and for future reference.

And then based on the transcript, I put together a message template around the topic.

Step 2: Separating lost leads from other categories

I’ve always been a fan of audience segmentation. If your outreach isn’t targeting the right people, it’s like throwing spaghetti at the wall. 

I recommend using tools that filter out individuals who don’t meet your campaign criteria or are already engaged elsewhere. This way, your sales team can focus on those most likely to convert into customers.

For example, I excluded certain prospects from this campaign to avoid sending duplicate messages, junk leads, or targeting irrelevant groups. Take a look:

The process is quite simple. First, you select the prospects you want to target.

Then apply exclusion filters to refine your audience:

• Exclude previously messaged people from selected accounts to prevent duplicate outreach.
• Exclude all previously messaged people across your organization to ensure no one is contacted twice.
• Exclude 1st connections from selected accounts and across all organization accounts.
• Exclude profiles without a picture to focus on active LinkedIn users.

What do you get? Faster sales cycles, customers ready to re-engage, and a larger volume of quality leads. While numbers aren’t the only factor in scaling sales operations, they definitely help drive revenue.

Here are some other perks of audience segmentation I’ve seen in this campaign:

• Your message target will be focused and centralized on lost leads only.
• You will gain better insights and develop a finer strategy.
• Other members of your audience won’t be bombarded with unnecessary communication. Hence, everyone will be happier.
• You can impress your lost leads with personalized messages. 

Step 3: Send an automated connection request message

I kicked off my winback outreach campaign by automating a connection message to the lost leads I aimed to convert. I kept it brief and straightforward with these two sentences:

Hey {FIRST_NAME}, not sure if you remember meeting, but {P1}. How are things on the LinkedIn front?

For better clarity, I’ve included a contextual example to show how to use the P1 custom tag in reality:

“Hey NAME, not sure if you remember meeting, but we spoke a couple of months ago about using HeyReach for LinkedIn automation and outreach strategies at COMPANY. How are things on the LinkedIn front?”

The trick here is simple — remind the lost customer about the interaction or discussion you had recently. 

Then ask them how their professional outreach or LinkedIn account management is going on. I could ask something else too, but this direct question “forced them” to be honest in case they do reply. Simple human psychology. 😏

Step 4: Send automated follow-up messages 

Once I started getting responses, I used automation (yep, again!) to send out follow-up messages. 

Instead of the usual ‘Why didn’t you consider using our blah blah blah,’ I went with this winback follow-up message template:

BTW I maaaaayyyyy have created an integration that took our call transcript from Fireflies and our Clay to write you our last message 😋

Wanna see how?

Since the initial connection request was formal, I decided to mix it up with an emoji and some casual language this time. 

This helps reduce hesitation and makes leads more inclined to check out your offer.

I highlighted our tool stack cleverly, and by acknowledging that the previous connection request wasn't actually from me but from my integration, I showed the leads that they were being specifically targeted through this personalization. 

Finally, I invited them to take a peek at this brilliant integration.

Step 5: Assessing the results

Even though we automated most of the repetitive tasks, our campaign results were outstanding:

💪 Convert lost leads. Kickstart your first LinkedIn campaign for free and automate re-engaging lost customers.

The high reply rate (67%) and accepted connections (57.5%) show how quickly less-digital connection turned a 'maybe' into a 'yes.' 

I showcased our stack and talked about how HeyReach could improve their LinkedIn outreach campaigns with those who responded. I also introduced our various features to address any specific challenges they mentioned.

But more than anything, I reconnected with amazing people to whom I will be talking from time to time. There is nothing better than that if you ask me. 🙂

Why it worked?

First, sending a message using a friendly tone strengthened the campaign. Most people use professional language on LinkedIn so it’s kinda refreshing if someone converses in a different, less “strict” tone.

This is how I removed the digital barrier and made our convo feel more real.

Secondly, I put a face to the company by messaging from my account (since I’m the Head of Growth @HeyReach). 

Third, I never took a salesy approach, even in my follow-up messages. Instead, I simply invited them to check out the cool tool integration I developed specifically for targeting them. This helped me stand out among all the other follow-up messages in their inbox. 

I only pitched when they shared their pain points that I could address with a solution.

Finally, our user-friendly API automated the entire process. 

With minimal effort, we could engage users through templated messages and scale the campaign effectively.

Setting up the tools stack

Here’s how our Clay table looked like. 

To import companies from your HubSpot, simply choose that option from the dropdown menu once you click on “import companies” column.

Clay connects with thousands of data sources through APIs.  By clicking on a company, we can see all of its details, like location, description, social accounts, etc.

You can import these properties into a column, but if you prefer not to use a column, you can still utilize the information. After importing the companies, you'll see the 'HubSpot ID' in the second cell. This unique identifier helps you access specific details.

Our table displays two HubSpot integrations: the native Clay HubSpot integration and the private app integration. I’ll compare these two later on. 

When we click on Clay within the HubSpot integrations, we can see the number of calls we’ve made.

With the HubSpot private app, we can check if there are any deals associated with the companies. For any deal we click on, it lists eight properties.

The system sends a GET request to retrieve deal stage labels, linking each stage to a specific number. For example, if the ID is a specific number, it automatically labels the deal as "demo."

Contacts related to deals are also pulled from HubSpot, using a custom app that matches them to their HubSpot ID. 

The magic behind the tools 🪄

I dare to say that our re-reach campaign was a masterpiece because we used the latest tools to optimize the entire process of contacting and re-engaging lost leads. 

Here’s a quick overview of what each tool accomplished:

• HubSpot: Sourced all data.
• Fireflies: Provided audio call transcriptions for customers associated with a deal.
• Clay: Functioned like a spreadsheet program (e.g., MS Excel) to display and work with all the information and numbers. 
• HeyReach: Used for selecting contacts based on defined rules. Its Unified Inbox feature helped create a single, streamlined hub for all LinkedIn conversations.

Now, I’ll walk you through the actions that led to our most successful outcomes.

The supremacy of custom app integration

Custom app integration turned out to be far better than the traditional native integration. 

Here’s why:

1. More data, less hassle: Custom app integration gave us a lot more data with minimal effort, available immediately for analysis. By using the private app, we accessed HubSpot’s APIs directly from our HubSpot account and controlled what the app could modify or request, which generated a unique access token.
2. Better deal tracking: We could create a column to show which deal was linked to each contact, making it easier to identify deals.
3. Richer information: We also set up a column to display multiple contacts associated with a deal and their transcripts. Unlike the native integration, which only provides a transcript for one person linked to a company’s deal, the custom app lets us get audio transcripts for all contacts related to a deal through Fireflies.

Using the custom or private app (as shown above), we could choose exactly which information to pull from HubSpot and integrate into Clay. 

Once we had that data, we got creative with it. This approach also enabled the audience segmentation I mentioned earlier.

Clay’s HubSpot integration 

While the native integration has its limitations, the HubSpot app in Clay allowed us to seamlessly sync companies and contacts by pulling data directly from the HubSpot CRM. 

Our team could update, create, or look up these records directly in the Clay table.

On the far left side, you can import companies from HubSpot, and on the far right side, you can look up contacts. 

These columns didn’t show whether a contact was associated with a deal, which is where our custom app came in handy.

HeyReach multiple features

And for scalability, automation, and personalization, I could rely 100% on HeyReach. 

This LinkedIn outreach tool offers brilliant performance while staying within LinkedIn’s limits. You can sync unlimited LinkedIn accounts in your campaigns, and both agencies and businesses can benefit from detailed reports and integrations with top-rated platforms.

You can send countless messages and connection requests daily. 

Here are the features that made our campaign a success:

• Native CRM Integrations: No need for manual imports, exports, or webhooks. A single click synced all our data with the free HubSpot CRM.
• Scalability: We could view profiles, send templated personalized messages, and perform all standard LinkedIn activities by connecting as many accounts as we wanted.
• Focused Inbox: The Unified Inbox combines all our LinkedIn conversations from every account into one central hub. We could add notes, tags, filters, and reminders, and manage all leads while pinning important conversations.

Fireflies transcripts

As I mentioned earlier, Fireflies is fantastic for tracking calls, conversations, and meetings—it really saves time. It helped us capture key information from conversations to craft effective follow-up messages.

We integrated Fireflies into our HubSpot stack, and it worked flawlessly. 

In addition to its great and accurate transcriptions, I love its ability to react—users can add pins, thumbs up, or thumbs down to any part of the call so others can revisit specific moments and know what to focus on. 

There’s also an option to write comments at different points in the call, leaving time-stamped notes.

How to scale sales ops?

Now that we’ve covered how to run a successful LinkedIn outbound campaign, let me talk a bit more about scaling sales operations to get the best results with lost customers.

Scaling your sales operations = boosting productivity and driving revenue growth. 

To do this right, use advanced tools and techniques while keeping your strategies fresh and effective.

In my experience, conversation is the secret sauce of sales operations. 

Focusing on tracking, analyzing, and improving the way your team communicates with potential customers can make a huge difference. 

Your sales reps need to do more than just chat—they need to make sure customers are really tuning in. Here are some tips on how to make that happen:

1. AI-powered note taking

Of course, you don’t have to go with Fireflies; you might find another tool that suits you better. However, I wholeheartedly recommend it. 🙋

When choosing an AI note-taking tool, focus on features that help transcribe key details and show people's reactions during the call. The smarter the tool, the easier it will be for you to take it from there.

Overall, these tools speed up the sales cycle with accurate, real-time data that improves customer engagement and retention. They also reduce the time spent sharing data between team members which is a huge plus. 

We share all the collected information automatically through our channels, so the whole team stays aligned on sales development.

2. Leveraging CRM

What keeps customers engaged? A solid relationship with the company. To stay on point, you need to make the most of your CRM system.

Take HubSpot, for instance. It uses AI to predict customer behavior, pinpoint the best leads, and even handle scheduling meetings and follow-ups on its own. This way, no lead gets overlooked and your team can give every opportunity their full attention.

When AI is integrated with CRM, it gives your team all the data, trends, and insights they need to make smart decisions. This means higher conversion rates and more personalized outreach.

3. HeyReach’s Unified Inbox

Isn't it a drag checking messages across different platforms and accounts just to keep track of leads? 

That’s a surefire way to slow things down. HeyReach’s Unified Inbox pulls all my LinkedIn conversations into one place, so I never miss an update.

It’s 1 inbox for all my accounts, no need to switch between accounts or to juggle between Sales Navigator and regular LinkedIn inbox anymore. Lifesaver, trust me.

It makes replying to customers super simple and keeps your sales reps from wearing out their welcome. I can even draft messages for teammates and keep everyone in the loop. Plus, I get a clear view of my campaigns with notifications, filters, and tags.

Sometimes, success is all about timely replies and making potential customers feel valued. When they know they’re a priority, they’re more likely to re-engage. 

4. Warming-up time

Email marketing agencies usually face a three-week warm-up period when onboarding a new client. 

During this time, you can’t just sit around waiting. Many companies use burner domains and accounts to make initial contact with prospects and keep them engaged.

While your email campaign is warming up, these burner efforts keep your customers interested—exactly where you want them. It’s a great opportunity to run parallel campaigns on other platforms or tap into existing lead sources.

If campaigns aren’t warmed up properly, they can end up in spam and lead to dead ends. You don’t want your hard work to end up in spam folders, so let’s keep customers engaged during this period.

5. Automating lead nurturing

Lead nurturing is the heartbeat of sales operations, but it can be overwhelming. Challenging. Time-consuming. 

Even top sales teams can get bogged down by the sheer volume of information they need to manage. Give them an edge by automating the routine tasks.

Using AI doesn’t mean your team’s slacking off—it means they’re working smarter. While your team focuses on managing a high volume of leads, AI handles the categorization, scheduling, and other workflow tasks. 

The result? More leads get nurtured and have a better shot at conversion.

And here’s the real kicker: automation improves your team’s productivity without needing to hire more people. It’s a smart move for any business aiming for long-term success.

Summary 

And what I tell everyone who is just starting this 'game' is: don’t write off lost customers so easily. It might seem like you can easily find new ones to replace them, but it’s time to change that mindset. 

Trust me, it’s easier to re-engage a customer who already knows about you and was once satisfied than to win over someone who has never heard of you before.

So, re-engaging lost leads should be your priority. Find out why they left. Why did they decide to say no? Do everything you can to make sure they say “yes” again. 

Be persistent, but not pushy. And of course, make things easier for yourself. Use automation in your follow-up process to free up time for the big tasks. 

A smart approach will help you focus on what really matters and bring those leads back into the fold.