The Art of Breaking Up: Understanding and Responding to Prospect Signals

Did you know 97% of supposed buyers are not actually in a buying cycle? Keeping them in your email sequence is bound to get you blocked, which is why it might be time to break up. | Originally aired on May 17, 2022

Key takeaways.


Gifting + “breakup” email idea: Accompany your last sales email to a prospect with a gift as a way of humanizing them.


Don’t just take from sales prospects. Make sure you’re conscious and clear about what value you’re giving them.


Data-driven recommendations for sales emails: Make them 25-50 words and a 5th grade reading level for the most success.


I know I read a lot better when I’ve got my favorite cup of coffee. End with your normal breakup email, which is really a “timing’s not right” [message] and a last chance to engage there. And if they don’t, you’re actually going to send them a gift. Send them some coffee. It gives you a touchpoint. And now when they get it, it’s got a little card inside that links to the most recent article you posted. It gives them something to read in the meantime and a super casual follow-up.

Adam Pasch • Director of Alliances and Partnerships, Postal.io


Adam Pasch • Director of Alliances and Partnerships, Postal.io

Adam is the Director of Alliances at Postal, the leading offline marketing platform. As a partnership leader, Adam has broad experience supporting marketing, sales and customer success teams. Adam leads Postal’s channel sales team. Working with partners, agencies and their clients to integrate and automate offline into their marketing campaigns.

Will Allred • Co-Founder & COO, Lavender

Will is a cofounder at Lavender, an email assistant helping sellers write better emails faster. As one of LinkedIn's Top Voices in Sales in 2021, Will actively shares what it means to write better emails. He's regularly sharing the data that comes from the millions of emails running through Lavender's system. He's also quick to share the perspective gained from over a thousand coaching sessions that he's done with individual sellers.

daniel-rocheleau (1)
Daniel Rocheleau • Sr Director of Digital Marketing, Iron Horse

Daniel is a Sr Director of Digital Marketing at Iron Horse with more than 25 years’ experience in the digital marketing field. Daniel works closely with our technology-driven customers to deliver strategy and manage programs to bring the latest and greatest technologies to market. Before coming to Iron Horse, Daniel was at HP for 12 years, where he was the worldwide marketing lead. In that capacity, he launched HP’s gaming brand, HP OMEN, above the noise in a highly competitive market, establishing it as a relevant brand today.

Episode Transcript

Daniel Rocheleau: Good afternoon, everyone. My name is Daniel Rocheleau. I'm senior director here at Iron Horse Interactive. I'll be your host for today's coffee break session, The Art of Breaking Up: Understanding and Responding to Prospect Signals. Joining me here today, first guest is Adam Pasch, director of alliances at Postal, a leading offline marketing platform. And our other guest today is Will Allred, a co-founder and COO of Lavender Email Assistance, helping sellers write better emails, faster.

Daniel Rocheleau: Today's conversation, all inspired from several social media posts we had, that came up between LinkedIn and other social activities, debating the breakup emails and whether or not to use them. And what we learned is that there was a lot of opinions out there. Before we dive into that real quick, I do want to make everyone aware. We do have a polling question in today's webinar. Should you break up with unresponsive prospects? Yes, no, or not sure yet. We'll find out after the webinar. Diving in real quick, Adam, I wanted to give you a chance to talk about a give away this happening during this webinar, and then we can dive into our conversational topics here.

Adam Pasch: Yeah, absolutely. What Postal does is it makes sending a gift as easy as sending an email or even an invite to an event. And so in that light, better than seeing it and being told how it works, the best way to get it is to receive a gift. So what we're going to do is for any of the questions that folks put in the chat or that they, some folks already submitted some questions. I've given Stephanie, our great moderator behind the scenes, a magic link from us that she's going to send folks a direct message to thank them for their participation and asking that real thoughtful question. She's going to send them a little gift and hopefully we get some of them brought up live so that we can, that the questions put in so that we can answer some of them live.

Daniel Rocheleau: Thank you, Adam. With that, let's go ahead and dive in. Will, I'm going to start off with you real quick. Since we've had some conversations back and forth here. What is the breakup email? Why are we having this conversation?

Will Allred: I think the reason why we're having a conversation is this notion of, is a breakup email... People view this breakup email as this controversial idea. And in reality, what a breakup email is, it's an end cap on a series of outreaches that you do where ideally you're stating to the person on the other end that you're stopping the outreach. So everybody knows what it's like to be in a cadence. And so this is the note where you say, it's over. Now you can do that better and you can do that worse, which I think is what the conversation today is about. I think everybody knows, I'm not going to come up here and be like, I love when people say, press one, if you've been eaten by an alligator. Nobody should send that email. But I do think within a proper cadence strategy and with a thoughtful, clear message, a breakup email can be a really effective thing to add to a cadence. And it's something I didn't believe for the longest time until I saw the reply rates from it.

Daniel Rocheleau: Why? Why are we doing a breakup email? Why don't we just let them just trail off and they didn't respond and just throw them back into the marketing pool.
Will: Yeah. I think for a seller it's important for your outreach to have a start and a conclusion, because I think it's important for a seller to have a specific reason for reaching out. So if I'm thinking about my outreach and I'm comparing it to the classic sales email. Classic sales email, I'm going to show up and I'm going to keep pitching my product, my services without really any context for why it's relevant for them in that dialogue. I'm going to do it over and over. And in that scenario, whether or not you break up or not is really irrelevant. By the time that you do, they can't wait for you to be done.

Will Allred: But if I reach out with a thoughtful message and I say, Hey, given the following thing I'm observing, it makes me believe that you've got this problem. And I reiterate that across three to max five emails and that fifth email, that max fifth, or even maybe the third or the fourth, I'm saying, Hey, I reached out a couple times. This clearly wasn't of interest. Let me know if I got it all wrong, but given the following scenario, I thought this would be a useful conversation. I'm going to stop my outreach. That's a very different breakup than what I think a lot of us are normalized to when it comes to breaking up.
Daniel: Adam, what are your thoughts on this?

Adam Pasch: Yeah. So this is the nice place to start, where we're all holding hands, where I think we all agree that we've got to stop the outreach at some point from a sales perspective. And I think where we all also agree is in this space where the relationship between a, I'm going to just say a SAS company, but really a business selling company. The relationship with that prospect exists between multiple departments, whether it's marketing, sales, maybe even partnerships. It's a longer term relationship. And I think what we're really talking about here is the sales cadence and the sale in this idea of ending that specific sprint. And so with that, that's from thinking the sales rep has to stop at some point to not burn that prospect out and instead have that retreat back to another engagement.

Adam Pasch: But I think to the point about, why does it get replies? I can say it for myself as a buyer, I get emails, I've been reading them, I'm busy, we're all busy. I meant to reply because they hit on something on that second email. It resonated, it's in the back of my mind, but I'm going to get to it later because it's not the top of my priority. It worked. They got me, but I haven't acted yet. And so when they do come to the, not press one if you were eaten by an alligator, that's just going to irritate me. We don't have a rapport enough yet. If Will sent me that email now, it'll work because we have enough rapport. But it gives me that moment to say, oh, this person's being respectful.

Will Allred: They're saying, Hey, it's not the right time. They hit one last time on what they think that pain point really might be. And if it resonates, I'm like, look, oh, they're not going to follow up with me again. I need to act now. Or I know that I'm just never going to follow up on it, and now I'm going to reply. Now that's speaking as me when I'm on the buyer's side. So that's why I think this breakup is important. It's all about tonality. But then I think where we might start to diverge is where, what I think we should do there is think about that marketing relationship and use that as the seller's opportunity to pass back to marketing in the form of, whether it's a newsletter or some other passive inbound strategy.

Daniel Rocheleau: So that's the question I have is on the whole intent, the whole transition from marketing to the sales cycle, did we miss-intent a customer. Did we see that they did something or saw behavior and we acted on them and said, Hey, we need to get them in the sales funnel. We think this is a good prospect. And then ultimately we see, they fall off the other side, we did this breakup email. That was an, I call it unsuccessful, attempt and engaging in the sales cycle. Do we just play this by the numbers game? Is this just part of sales where we just run this many through the mix and see who takes the hook? Or are we missing something on the intent signal cycle where we were premature in maybe pulling someone into the sales mix?

Will Allred: So I think it's an interesting idea of, how do we keep the conversation going? Are you suggesting that the cadence ends and then they're automatically put into a marketing funnel or are you trying to get them to opt into a marketing funnel?

Adam Pasch: So I think there's one part of this is me just recognizing what the world of these B2B companies are just doing anyways. When sales ends a cadence, they're going back into a marketing funnel. They're still in HubSpot, they're still in Marketing Cloud. They're going to get another email in the future unless they opt it out. The sad truth of, we're never letting go, unless the buyer or prospect says, we're breaking up and now we're going to be GDPR and whatever else compliant.

Daniel Rocheleau: Right.

Adam Pasch: So just recognizing reality there. So with that understanding of that's how it's going to work, what I'd rather do is offer this last chance at the direct pain. I still want my rep to hit on, is this relevant? We did some research, maybe I used Lavender and I saw the careers page. And I wrote about that they're hiring in this area and this is a key need that relates to what I do. I've made it really relevant. I hit on a problem and if it's not right, or the timing is off, then I want to offer bringing them into some other regular piece of content that I have that continues to hit on and solve that pain through education and content until they're ready to be in an active buying cycle. But that way they're still getting educated and we're still hitting on that pain point.

Will Allred: Yeah. And I think one of the key distinguishing factors here is the typical B2B outreach process versus what I outlined in a cadence above where, if your approach to cadence with a very pointed reason for showing up, I think having that ask makes a ton of sense. If you just approached it with, here's a bunch of information about me, let's find 30 minutes. And then you're like, Hey, I'm going to stop sending you emails, but do you want to sign up my marketing newsletter? Who the heck are you? If you even get the open. In which case, you're better off just going the old school way of not even asking them to opt in because you're just not going to get it. But it's an interesting touch. I hadn't thought about that. It could be an interesting, this is an interesting idea.

Will Allred: What if you made it a breakup bump, where you followed up to the breakup and you said something like, oh, apologies one last note. By the way, recognize that usually the case is just timing was off. If you want to stay up to date with what we're doing, subscribe here. But I think the problem is it's too tempting to subscribe them to something regardless. And so it's really a question for marketers of, do you have the one, the content in place and two, the segmentation in place to create two different types of subscription for that individual post-breakup. Because there's the engaged breakup where it's like, I actually want them to be getting marketing emails because they've opted in, versus the non-engaged where I'm like, if I start emailing them, I'm running the risk of just getting my entire domain blocked from this account.

Daniel Rocheleau:
Right, right.

Adam Pasch: That's exactly, a hundred percent. So, that's where I'm thinking where you do have this second route that goes into this opt-in area where it is more highly targeted. This is where it does take more than just one team's acceptance of this. Sales needs to buy in, but marketing needs to buy in as well. So that way, if we are saying, now we're targeted around a certain persona or around a certain pain point that we're going to continue the content follow up. But that means that you're going to have to have relevant content related to that.

Daniel Rocheleau: Yes.

Will Allred: Rare to see.

Adam Pasch: So, and that's a fair point. And so there might be a middle place here where what we're really trying to do through all of this is create some sort of value for customers, I think. For prospects.

Daniel Rocheleau: Specifically on the marketing side of things. So, follow up question here from someone online. It says, what if they have the problem? What if they have a need for our products or services, but they don't have the budget or the timing isn't right? Wouldn't it be better to put them in the nurture cadence, monthly touch points, so you can stay on the radar and when they're ready, you are staying on top of mind. So it feels like this is what we were just discussing. It feels like if we could almost pull for them, like, Hey, and I've seen some emails like this. If the timing isn't right, let me know. And then I can get you into a different nurture stream versus just the generalized marketing stream. This is where we might be able to qualify them better and keep them a little closer to that sales funnel without quite going after them yet, until they're ready.

Will Allred: A part of me it's like, why does it have to be marketing, though, that does the nurture? If I think about cadence strategy and I think about how you could put together a cadence. Marketing's not just sitting there doing nothing of course, but sales has an opportunity to support marketing outside of that cadence, where I'm looking at three to five emails is that cadence. So this assumes you're doing it a good directional way. But you say marketing is hosting an event. I'd be like, Hey Daniel, I'm not sure if you saw the email from marketing, but Adam and Will are doing a session on XYZ. Did you check it out? It's an easy touch point where you're not going back towards what the original cadence was about. It's a new thread, it's a new conversation. But it's a light touch, where you're using marketing to your advantage to keep the conversation top of mind.

Daniel Rocheleau: So when this topic first broke, that's the first thing went through my head is, in old school agencies you had your marketing side, they had their nurture programs. They had their email programs. And then you had your sales side. And obviously if someone's got any kind of qualification or intent, we'd lob them over the wall and then the sales team takes them and runs with them. And then what we're talking about here, a breakup email, feels like, okay, didn't work, I'm lobbing them back. And I think about our rev op conversations that we have. But for me, it's like, pretend there wasn't a marketing and sales team. Pretend it's just a revenue operations team.

Daniel Rocheleau: We wouldn't be having this discussion because you would just subtly change the nature of your communications and if they didn't bite, just suddenly change it back. And they'd never know. And the customer would not even be aware that they went from marketing to sales and back to marketing because they're just basically paying attention to your emails. So I wonder how much of this is an artificial construct based upon the way we're used to doing things, versus maybe if we look at it from a more customer-centric standpoint. There may not even be a breakup, it may just be like, Hey, we'll just try and lob some content at them that we're fishing to see if they're interested in buying a product yet. If not, we back off and go back to supplying them with just some educational content.

Will Allred: Yeah. And Daniel, what you're talking on is actually what I used to believe which, I say used to because we've run the numbers and they work. I run these emails and they get a 12% plus response rate and they're typically positive and it's never like, I was never interested. Leave me alone. It was like, you know what? Appreciate the touch, it was just a bad timing thing. But my belief used to be that you would just vanish into the night and you'd come back at another moment. And they'd probably forget about you in the meantime, which is probably still true. But having that closure moment seems to work from a reply rate standpoint, even if it's just them saying, in a couple weeks, this will be a better time. Now I've got a reason to reach out in a couple weeks that's specifically tied to something they told me, as opposed to me just being in the dark, trying to figure it out.

Daniel Rocheleau: So there's something about making them aware of that change in dialogue that can actually self prompt a response. And even if it's not, I'M buying now, it's like, okay, but now I've started a two-way dialogue where before I was sending emails off and seeing if they were opening them or not.

Will Allred: Yeah. I think also there's some consumer psychology at play there where it's like, I can give or I can take it away. And so if it's just lingering out there and there's no urgency of me pulling it back, I think there's something to be said for doing that within an email cadence, which is like, cool, we're done. I'm out.

Adam Pasch: So it's interesting. You're moving me off my spot a little bit. Where, in my mind I was trying to do both things in the same email and part of it also is because I'm very much a person of my word. When I say, Hey, I'm going to stop emailing you now. Which is why I try to bring in that secondary opt in for specific, low-touch, inbound information signal in the newsletter or some other piece of content, because it gives me a signal as to what the real pain point is. If you're not ready to talk actively, maybe you are ready to consume specific oriented information. But I liked something you said a little bit earlier around this Colombo, oh, oh wait, one more thing. Truly last thing. But now you've got to really earn it. Because now, you said one thing, you did the other, so the skeptic ears are way up.

Adam Pasch: One way to lower that down is to say, in this case, if it's reading a newsletter, something else. I know I read a lot better when I've got my favorite cup of coffee. And so maybe that's the idea here is, end with your normal breakup email, which is really this, timing's not right. Gives them that chance to really engage there. And if they don't, this very last moment, you're actually going to send them a gift. Send them some coffee. It gives you a touch point. Maybe it's a coffee subscription. So there's three bags of coffee that come over the next three months. And now when they get it, it's got a little card inside that links to the most recent article that you posted. Gives them something to read in the meantime, super passive follow up.

Will Allred: What I like about what you just put out there is when I see folks talk about using gifts, I see them almost think about it as a bribe. Meet with me and I'll send you coffee. You're shaking your head. You're like, oh, please don't do that. And I'm like, that's such a clever way to introduce the gift into the process. And it's like, Hey, coffee with a newsletter. It's like, I'm going to give, and I'm going to give some more on top of that. It's making me rethink how we're approaching breakups. Because then marketing and sales are working together because they're still within our frame of thought. They're still seeing what we put out there and if they stay engaged with that content, maybe then they go back into the sales side. It could be an easy way to pull them back over, you refer to it as lob them over. I love that. Lob them back over to sales again, using some, the old beta term would be lead scoring.

Daniel Rocheleau: Right. We've got a couple questions here. Let's pull these up real quick. Interesting thought. What about a countdown to let them know they're reaching the end of the sequence? I'll try reaching out two more times. Sometimes we'll be going through online activities and it will count down for you, how many more pages you have until you're done. What do we think about this for email?

Will Allred: So it depends on where it sits in the email. If it starts the email off, I'm immediately getting a giant red flag that says, someone's trying to sell to me. Whereas, if it's at the end, I might not think as much about it. And when I say think as much about it, I mean basically the way we read email is essentially one giant categorization process. And so you're just trying not to raise giant red flag that says, Hey, I'm here to pitch you. So I'll try reaching out two more times. Back to Adam, your point, sticking to your word. I think that's pretty key there.

Daniel Rocheleau: This is a new one for me. Thoughts on any thoughts follow up email? I've heard many who love it and hate it. Would love your takes on it. What is this any thoughts email and should we be doing this?

Adam Pasch: Is that like a bump up, circling back, putting it on your radar?

Daniel Rocheleau: Yeah.

Adam Pasch: That sounds like a great way to extract value from them to you. It's the fly buzzing around the picnic, reminding me if I don't eat faster, it's going to eat my lunch. I'm a big proponent of, if you're emailing someone that was not expecting you to email them, you're innately taking. And so you have to be very specific in how you are going to give them. And, ostensibly, you're doing this because you know that you have a solution that is going to alleviate a pain of theirs, open up a new opportunity, help them hit their goals, help unblock some problem. So it is valuable that you're reaching out to them. And if that's true, then share why. But any thoughts doesn't add anything to the conversation.

Will Allred: Yeah. It was something that was popularized in 2020 and particularly sales leaders have caught on. I mentioned waving that red flag of, I'm trying to pitch you. You see thoughts, question mark in your inbox, you get a feel for what's about to happen. I don't dislike the idea of a bump. Everyone's inboxes are flooded. And so pushing something to the top is not a bad thing. It's just the way you go about it can be done more carefully, more thoughtfully to hammer on the word thoughts. But the way I would approach it is I'd say, Adam, given the original reason I reached out, wanted to see if he had any feedback on my note. Or did you have thoughts on my note? If I want to be more curt or direct. And the reason for that is I think it's good to just remind them of the context for why you're showing up in the first place.

Will Allred: It's something that should be prevalent in your first email, even your bump emails, as well as your breakup email. The reason you're reaching out, that should be woven throughout the entire cadence. So it touches on breakup emails. It touches on first touch emails and it should be even included within those second touch bump emails. SalesLoft actually did some data across the cadence where if you looked at every touchpoint along the way, introducing an angle of personalization. So if you just adjusted the template some, the worst thing that you would have happen is you boosted your response rate by 50%. And I'm like, okay, that's a no-brainer. You can just take that thoughtless thoughts, bump, and just add a little bit of context. Here's why I'm bumping it. Hey, given you're hiring, thought this would be relevant, any thoughts? Just takes that thoughts bump to the next level.

Adam Pasch: Yeah. I think that's exactly right, is that you've got to go, again, it's any thoughts on. Make it remind me what it was about. I'm going to see the email string below it and I'll go read it, but categorize it for me. Give me some semblance of context.

Will Allred: Yeah. Adam, I loved your point on this idea of you're inherently taking, I've always viewed it as you're interrupting. But it is. You're you're taking, you're trying to get a response. You're extracting that reply. One of my favorite follow ups is actually, I don't ask for anything and it doesn't get a ton of replies. It gets good click-through, but it actually bolsters the performance across the entire cadence. It was something I picked up from the same person who taught me that breakup emails are actually something that can work, Kristina Finseth, where she has a follow-up she calls the value-add follow-up. And as sellers we're often taught to add value, but we're not actually told what that means and how to do it. And every email should have a very specific purpose.

Will Allred: It's why I even referenced the, subscribe and get a gift thing. I reference that as like a follow-up to the breakup, because I'm anal about, every email has a specific purpose and a specific why behind it. And so with this email, you're adding value and that's the only thing that you're going to do. And so you might say, Hey, do you read outreaches blog? They brought in XYZ to talk about how they scale to ZYX and they did it without ever using a canned template. Thought you'd find it interesting, given the original reason I reached out. And then just link to it and just throw that into your cadence. And people will be bewildered that you didn't ask for anything.

Daniel Rocheleau: I'll open your next email. One last question here and we'll wrap it up. I have a question. What's your opinion on a breakup email that lists the different products you offer to spark interest in something else that you can do or provide for them. Mainly for ending a cadence that's directly targeting just one of your products.

Will Allred: Yeah.

Adam Pasch: So, to me, I feel like it's the kitchen sink approach that I might, if anything, if it's a team that's doing it regularly, I would argue let's AB test it. If you're using something like an outreach, we're going to turn this into a promo for outreach, which is okay. I love outreach. So that you end it with an A versus B, one where you throw the kitchen sink at it. But I think another one, if you did better targeting, and if you instead try and pivot to, if this one product wasn't right, maybe there's this other one that is more likely than those other 12. If it's going to convert at all, specificity in email when it's being scanned, is still going to be better. But yeah, I don't think that the kitchen sink goes is an approach that's really going to convert highly.

Will Allred: Yeah. I'm going to lean on Lavender's data here and that's informative tones are a direct corollary to you not getting a response. So you adding all of those extra details, it's you trying to inform them about other things that you do outside of the original reason that you reached out. And so what happens is you give them extra information and they don't have a reason to reply. Whereas, if you lean into the element of curiosity, a better way to approach it would just say, there's tons of other things that we can do on top of that, related to X. But I didn't think those would be relevant for this conversation. Now I'm like, I've got more behind the scenes that you don't get to see and you have to respond if you want it.

Daniel Rocheleau: Got it. We're coming up on end of time here guys. Any final thoughts before we exit our session today?

Will Allred: Did you just thoughts about me?

Daniel Rocheleau:
I was.

Will Allred: You just thoughts about me at the end there.

Adam Pasch: The things that work in live sessions, but not in email sequencing.

Daniel Rocheleau: Exactly.

Will Allred: Exactly.

Adam Pasch: There's a channel for every strategy. They don't all work in email. That's how I'll wrap up my end.

Daniel Rocheleau: There you go. Will, any thoughts?

Will Allred: Yeah. So if I had any last notes on this, it would be, keep it short and keep it simple. We see the best emails are that are performing are between 25 and 50 words. And they're written at a fifth grade reading level.

Daniel Rocheleau: Absolutely. Absolutely.

Adam Pasch: Oh, Daniel, one last thing. Only because everybody loves a good callback humor, except for when you explain the joke. I just want to make sure if Stephanie was able to get the folks that asked the great questions, I up the gift limit to 10 so that she can get those out. If there is any issue, then we'll make sure that the right folks get the right stuff.

Will Allred: Love it.

Daniel Rocheleau: It looked like it. I think so here. We'll follow up otherwise. But again, coming up on time. Thank you gentlemen, for spending time with me today. Very informational and we look forward to our next conversation.

Will Allred: Awesome. Thank you Daniel. Thank you, Adam.

Adam Pasch: See you guys.

Daniel Rocheleau: Adam.