
Just because a prospect went cold doesnโt mean the deal is dead. In this episode of Pipeline Playbooks, we dig into the art of spotting when lost opportunities come back to life. When a previously silent prospect starts revisiting your siteโespecially high-intent pages like pricing, case studies, or feature overviewsโthatโs your window to re-engage. The best part? Youโre not starting from scratchโthey already know you.
We walk through how to track those digital signals using tools like Dealfront and Leadfeeder, how to connect CRM history with real-time behavior, and how to personalize outreach without sounding desperate. With real-world examples and proven outreach templates, this episode is your guide to turning yesterdayโs โnoโ into tomorrowโs closed-won.
Expect to Learn:
- How to identify returning lost opportunities
- Which website behaviors signal renewed interest
- How to set up real-time alerts via Slack or email
- The CRM data to cross-reference before reaching out
- Messaging strategies for pricing, features, or use case changes
- Why timing and personalization are everything
- What results teams have seen by reactivating cold leads
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Alicia Morgan
at Dealfront
Ethan Cole
at Dealfront
00:02 We've all been there, right? You think you've got a hot lead, maybe even gone through a couple rounds of calls, sent over a proposal, but then nothing. Crickets. Total ghost town. Exactly. It feels like the deal just vanished into thin air. Poof. Gone. Well, for this deep dive, you sent over some really interesting stuff from Dealfront. A bunch of articles, actually, all about what happens when those prospects, the ones you thought were long gone, suddenly reappear. They're back. Checking out your website again.
00:32 Yeah, it's like, wait a minute, hold on. You're interested again. I thought we were done here. I know. So that's what we're digging into today. These website revisits from lost prospects. I mean, think about it. What if those deals weren't actually dead? What if they were just dormant? Waiting for the right moment to come back to life. We're going to figure out how to spot these second chances and how to actually use them to, you know, maybe even revive those deals. Bring them back from the dead. I like it. Exactly. Now.
01:01 I'm sure we've all had those deals that just seemed to stall out and disappear. But when someone who basically told us no thanks is suddenly browsing our pricing page again, that's got to be a sign, right? What's the big deal about a return visit like that? Why should we get excited? OK, so think about this. These folks, they've already gone through some level of evaluation with your company, right? At some point, they were interested enough to engage, to learn more.
01:30 So they have some awareness of who you are, what you do. When they come back, it's a pretty strong indicator that whatever their initial hesitation was, maybe it was budget, maybe timing, maybe a feature you didn't have, well, that barrier might not be there anymore. Maybe their budget has freed up or they tried another solution that didn't quite work out. The fact that they're coming back to your website specifically, well, that tells me they're actively reconsidering what you have to offer. Right, right, makes sense. It's like they're giving you a second look. Exactly. And you know what?
01:58 That existing familiarity that you have with them is a huge advantage. It's way better than trying to start from scratch with a brand new prospect. Oh, absolutely. It's like you're picking up where you left off instead of having to introduce yourself all over again. OK, that makes sense. But how do we even know it's that specific lost opportunity? Websites get a ton of traffic every day. How can we cut through all that noise and zero in on those valuable return visits? That is the million dollar question, isn't it? And the answer is technology. The articles you sent.
02:28 they really stress how important it is to have website tracking tools that work hand in hand with your CRM. CRM, meaning? Your customer relationship management system. It's where you keep all your customer data. So platforms like Dealfront, they have some really powerful tools for this. They can give you real time visibility into which companies are on your website right now and what they're looking at. So we're not just talking about seeing like an anonymous visitor hit our homepage. These tools can actually flag a specific company.
02:58 Let's say Global Innovations Inc. pops up on our site. The tool could say, hey, remember these guys? You marked them as lost three months ago, and guess what? They're back. That's exactly it. And it goes even deeper. You can see specific behavioral signals that tell you just how interested they are. For instance, are they jumping right to your pricing page? OK, so if they're spending time on pricing. That could mean they're seriously considering Ludge It and want to see if you're a good fit now.
03:24 Or maybe they're comparing your pricing to what your competitors are offering. What about your features pitch? Are they looking at that? That tells me they're reevaluating what you can do, seeing if you have what they need. And case studies, especially the ones in their industry, that's huge. That means they want to see how you've helped other businesses just like theirs. Right. They want proof. Exactly. Proof that you can deliver. So the pages they visit are a big clue. What other online behaviors should we be looking for?
03:54 Well, how long are they spending on each page? Are they really digging into the content? Are they coming back to your website over and over again in a short amount of time? These are all signs that their interest is more than just casual. They're actively engaging with what you have to offer. Oh, and don't forget about downloadable content. Are they requesting demos, downloading white papers, or even reading blog posts that are relevant to their pain points?
04:20 Those are gold mines of information because they tell you what they're struggling with and what they're looking for right now. see. I see. It paints a picture of what's on their mind at this moment. Exactly. And speaking of painting a picture, the Dealfront material actually had this really cool example of how to use their lead feeder tool with the CRM. Can you break down how that works? Yeah, sure. So lead feeder is all about helping you create custom feeds that track those lost opportunities that are coming back to your site.
04:49 The first thing you have to do is make sure your CRM and Leadfeeder are talking to each other. You've got to connect them. Integrate them. Right. Integration is key because it lets you take all that past context you have from your CRM, you know, past conversations, the reasons the deal stalled and combine it with their current website activity. It's like having a super detailed picture of what's going on. Once that connection is made, you can set up a filter in Leadfeeder to find all the companies where that CRM opportunity status is marked lost. Got it.
05:17 So we're filtering for all our past lost opportunity. And you can even get super specific and filter by the salesperson who originally handled that deal. That way they can keep tabs on their own lost opportunities and be ready to jump back in when the time is right. Makes sense. The salesperson who worked that deal probably has the best relationship with that prospect. Right. They've got all that history. And here's another cool thing. You can set up automatic notifications that go straight to Slack. So let's say a company that you marked as lost suddenly visits your pricing page.
05:46 Boom, the salesperson gets a Slack alert. They know right away that something's up and can reach out. Real-time intel. Exactly. And the example even talks about how you can fine-tune those alerts even further. Like, maybe you've noticed that whenever a prospect spends a lot of time on your pricing page, they're usually pretty serious about buying. OK, so we can set up an alert that only triggers when? When a lost opportunity is hanging out on the pricing page. It's like a VIP notification for your sales team, letting them know that this one is worth a closer look.
06:16 Love it. OK, so now we've got these companies, these lost opportunities, showing renewed interest. Do we just send them the same pitch we used before? No, no, no. That's a recipe for disaster. Yeah, that makes sense. This is where you have to really analyze what they're doing on your website. What's different this time around? What pages are they looking at? Remember those high intent pages we talked about? Pricing, features, demo request forms, those are the ones to watch.
06:42 That recent activity gives you a snapshot of what they care about right now. OK, so we're looking at their current activity. But how do we connect that with the reasons why they said no in the first place? That's where your trustee CRM comes in again. You've got to cross-reference their recent activity with the notes you have in your CRM about why the deal went cold. Was it budget? Were they missing a feature they needed? Did something change on their end, like their timeline?
07:10 Ah, so was like piecing together a puzzle. Right. We're taking what they're doing now on the website and combining it with what we know about them from the past. You got it. That's how you figure out what's changed and how to tailor your re-engagement strategy. So we can make our outreach super targeted and relevant to their current situation. Exactly. Your message should basically say, hey, we know you weren't ready before and here's why. But guess what? Things have changed. We've addressed those concerns. And now we might be a perfect fit.
07:38 and it shows that you're not just blindly reaching out, you've actually been paying attention. Right, you're not just sending a mass email blast, this is personal. I like it. So the Dealfront material actually talks about how their own sales team does this exact thing. I always love hearing real world examples. Me too, it's like, okay, this isn't just theory, this is actually working for people. So Dealfront, they set up those custom feeds we talked about. They're specifically...
08:04 tracking when lost opportunities go back to their pricing page or even log back into their product. And get this, they've hooked this whole system up to Slack and their CRM, which is Pipe Drive. OK, so when a lost opportunity does something interesting on the website. Their sales team gets a notification in a dedicated Slack channel instantly. They can jump right in, look at what's going on, and decide whether it's worth pursuing again. If it looks promising, they add it to a special pipeline in Pipe Drive for re-engagement.
08:33 And they shared some pretty impressive results too, right? Something like a 9 % win rate from re-engaged opportunities. 9%. Can you believe that? I mean, we're talking about deals they had essentially written off. It just goes to show you how much potential there is in re-engaging those lost opportunities. It's like finding hidden treasure. Totally. Plus, they said that those re-engaged deals tend to close faster because remember, those prospects already know something about your company. They're not starting from scratch. It's like a shortcut through the sales cycle. Yeah.
09:03 Awesome. They also talked about how they're trying to do even more of this, like with their Salesforce instance. Yeah, they're always looking for ways to improve, to automate more, to get deeper insights. That kind of constant optimization, that's the key to making this whole strategy work even better over time. Love that. Always be improving. Okay, so we've identified these returning prospects. We've analyzed what they're up to. Now for the big question. How do we reach back out to them without it being awkward?
09:32 How do we make sure it doesn't feel like we're just desperate for their business? The key is personalization. You can't just blast out a generic email and hope for the best. You have to use what you've learned about their recent activity and your past interactions. First things first. Address the elephant in the room. Acknowledge why the deal didn't work out before. So if it was a budget issue before, for example, you might say something like, hey, we understand that budget was a concern last time. We've since introduced some new pricing options that might be more flexible for you. Got it.
10:02 So we're showing them that things have changed, that we've listened to their feedback. Exactly. And don't just focus on email. DealFront recommends a multi-channel approach. Reach out on LinkedIn. Give them a call if it makes sense. Use whatever channel you think will work best based on your past conversations. The more touch points you have, the better your chances of getting their attention.
10:23 And guess what? They even gave us some templates for those outreach messages. Amplets. Nice. Yeah. They've got one for new feature release so you can highlight new stuff you've added. That's perfect for those prospects who said no because you were missing a feature. Then there's a pricing update template, which is great for addressing budget concerns. And finally, there's the use case spotlight template. What's that one for? It's all about showing how other companies, similar to theirs, have successfully used your product. It's social proof. It's like saying, look,
10:53 We've helped companies just like yours achieve amazing results. Maybe we can do the same for you. Those are some great tools. So we've got our templates. We're ready to reach out. What about timing? When's the best time to make contact? Timing is crucial. When a loss prospect comes back to your website, that's your window of opportunity. They're thinking about you. They're checking you out. Don't wait. Strike while the iron is hot. Yes. Those real-time notifications, like the Slack alerts we talked about, are so valuable here.
11:22 They let your sales team reach out immediately, right when that prospect is most engaged. And Dealfront actually walks you through exactly how to set those notifications up. You go into their platform, edit the feed for your lost opportunities, and then you can choose where you want those notifications to go. Slack, email, you name it. So whether it's a Slack message popping up or an email landing in their inbox, the point is to know as soon as possible that a lost prospect is back. Yep. The faster you can reach out,
11:50 the better your chances of re-engaging them and getting that deal back on track. This is all great stuff. But I have a feeling this isn't a one and done kind of thing. It's got to be an ongoing process, You're absolutely right. Continuous improvement is key here. You've got to track how well your re-engagement efforts are working. Are people opening your emails? Are they clicking on your links? What kind of responses are you getting? So we're looking at the data and figuring out what's working and what's not. Exactly. Maybe you notice that people are going crazy over your case studies.
12:18 But no one's clicking on your pricing page links. Well, that tells you something. You might want to focus more on those success stories and maybe tweak your pricing message. The point is to keep learning and adjusting your strategies based on what you see. Make it a feedback loop. Exactly. OK, so this deep dive has been a real eye opener. I think the main takeaway here is that just because a deal goes cold, doesn't mean it's gone forever. When a prospect comes back to your website, they're giving you a second chance.
12:48 a second chance to show them what you've got and why they should choose you. And we've talked about some pretty powerful tools and strategies to make the most of those second chances. Website tracking, CRM integration, personalized outreach, and those real-time notifications. This is all about being proactive and turning those lost opportunities into wins. I love it. Turn those no's into yeses. Exactly. So for you, dear listener, think about this.
13:14 What lost accounts might be lurking on your website right now, just waiting for you to reach out? Maybe it's time to go on a little treasure hunt. Thanks for diving deep with us. Happy hunting.