Latest / The Retention Marketing Podcast with Fexingo: Email, SMS, and Loyalty for Repeat Customers / How Casper Used Email to Win Back Sleepers
Transcript
- Lucas: So let's talk about a specific email sequence that a lot of brands skip — the win-back sequence for customers who bought once, then went quiet. Luna: You're talking about that huge pool of one-time buyers that most companies just let fade away, right? Lucas: Exactly. And the case study I want to look at is Casper — the mattress company. They had a cohort of customers who bought a mattress in 2019 and then hadn't purchased anything else for at least eighteen months. Luna: Which is a lot of their customer base. Mattresses aren't something you buy every year. Lucas: Right, but Casper sells pillows, sheets, bed frames, dog beds — a whole ecosystem. So they launched a fifteen-month win-back email sequence targeting that 2019 cohort. And the numbers are pretty revealing. Luna: Fifteen months feels like a long time for an email sequence. What were they sending? Lucas: Three distinct phases. The first phase was purely educational — tips on how to care for your mattress, how to improve sleep hygiene, stuff like that. No discount, no hard sell. That ran for about four months. Luna: So warming them up before asking for anything. Smart. Lucas: The second phase introduced a personalized quiz — basically 'help us find the right products for your sleep style.' If you completed it, you got a product recommendation and a 15% off coupon. That phase ran another five months. Luna: And the third phase? Lucas: A direct 'we miss you' email from the CEO, followed by a limited-time 20% off sitewide — but only for customers in that cohort. That ran for the final six months. Luna: And what were the results? Lucas: Overall, the sequence reactivated about 12% of the dormant cohort — meaning they made a second purchase within the fifteen months. But the interesting part is how the different phases performed. Luna: I'm guessing the CEO email had a big spike. Lucas: It did. The CEO email had a 41% open rate and a 7.2% click-through rate — which is high for a win-back email. But the quiz emails actually had a higher conversion rate per click: about 14% of people who clicked through to the quiz ended up buying. Luna: That makes sense — the quiz is giving them a personalized reason to buy, not just a generic discount. Lucas: Exactly. And here's a stat that stood out to me: the win-back emails as a whole had a 34% higher click to open rate than Casper's standard promotional emails. So the people who opened were much more likely to click. Luna: Because the audience was more targeted — they weren't blasting everyone, just people who'd already shown interest by buying once. Lucas: Right. And the ROI on this kind of sequence is huge because the list already exists. You're not paying to acquire these people — you're just paying for the emails. Luna: So what's the takeaway for a smaller brand that doesn't have Casper's data team? Lucas: You don't need a fifteen-month sequence. Even a three-email sequence — one educational, one personalized offer, one final reminder — can recover 5 to 10 percent of dormant customers. The key is segmentation. Don't send the same win-back email to everyone. Luna: And I'd add: don't start with a discount. Build some value first, like Casper did with the sleep tips. Lucas: Totally. Now, one other thing I found interesting — Casper also tested sending physical postcards to a subset of that dormant cohort. And the postcards had a 2% response rate, which sounds low, but the average order value from those responses was almost double the email-driven orders. Luna: So for high-ticket items, a physical touchpoint might be worth it. Lucas: If your average order value is high enough to justify the postage, yeah. For a mattress company, it made sense. For a $20 subscription box, probably not. Luna: Let's zoom out a bit — why do you think so many brands skip win-back sequences altogether? Lucas: I think it's a combination of two things. First, they're too focused on acquisition — new customers are sexier than old ones. Second, they're worried about annoying people. But if someone bought from you once, they've already opted in. A well-timed win-back email is not spam. Luna: If today's episode was useful to you and you want to keep it ad-free, buy me a coffee dot com slash fexingo helps. Lucas: Yeah, that's the simplest way to make sure we can keep doing deep dives like this. Luna: So back to Casper — their sequence also taught them something about timing. They found that the optimal window to start a win-back sequence is between 6 and 12 months of inactivity. Lucas: Interesting — why not sooner? Luna: Because if you email someone three months after their first purchase, they might still be using the product — especially for a mattress. You want to catch them when they're starting to think about an accessory, but before they've completely forgotten about your brand. Lucas: That aligns with what I've seen in other retention studies — the 'goldilocks window' is real. Too soon feels pushy, too late feels irrelevant. Luna: And Casper's data showed that the conversion rate for emails sent at month 8 was nearly double the rate for month 4 or month 18. Lucas: So if you're running a win-back sequence right now, check your data. When do most of your one-time buyers lapse? That's your starting point. Luna: One more thing from the Casper playbook: they A/B tested the subject lines on the CEO email. The version with 'Hey, we miss you' outperformed 'An update from Jeff' — the CEO's name — by about 15% on open rate. Lucas: Personalization wins again. It's not just putting their name in the subject line — it's making the email feel like it's actually for them. Luna: Exactly. And the 'we miss you' angle taps into a little bit of social reciprocity. You're not just asking for a sale — you're acknowledging the relationship. Lucas: Which brings us back to the core principle of retention marketing: treat every customer like a person, not a transaction. The win-back email is one of the purest tests of that. Luna: All right, so to wrap up — three things to steal from Casper: segment your dormant customers by time since last purchase, start with value before asking for a sale, and test your subject lines. Lucas: And if you've got a high enough average order value, consider adding a physical touchpoint. But start with email. It's cheap, it's measurable, and if Casper's numbers are any guide, it works.