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Automations are marketing emails that go out to subscribers and customers automatically when they meet a specific criteria,  like behavior, status, and tenure. You don’t manually send them out—you set up the templates and the sending rules and your email marketing software handles it from there. In some ways, automations are the best form of email marketing—you put in a little work up front, then just sit back (or, more likely, work on the other 50,000 things on your to-do list) and watch as your email marketing platform handles the rest, indefinitely.

In some ways, automations are the best form of email marketing—you put in a little work up front, then just sit back … and watch as your email marketing platform handles the rest, indefinitely.

Automations differ from transactional emails, which include emails like order confirmations and credit card expiration notices. While those also go out automatically, transactional emails are business-focused (they have to be, legally) with little to no selling or advertising. They’re also often required legally to fulfill a business obligation, like deliver a sale receipt. Automations, on the other hand, are often focused on selling, and not required sending according to any laws. (But it’s a good idea to send them!)

That’s why automations are marketing emails, which means they require a customer to opt-in. When someone opts in to receive emails from you, they’re fair game for automations. If they don’t, these emails shouldn’t go out to them. (However, there are a few automations that may be exceptions; check out our lesson on legality for the discussion on that topic.)

In this lesson, we’ll look at several different types of automations and offer advice on how to get the most out of them. We’ve broken them down into categories based on where they primarily occur during the customer journey: prospective, current, and lapsed customers.

Automations for prospective customers

Welcoming a new subscriber

Three-quarters of people expect to get a welcome email when they sign up for a list. (PDF)

And, as a result of that anticipation, welcome emails perform extremely well. A study found welcome emails have four times higher open rates, five times higher click-through rates, and bring in eight times more revenue than broadcast emails. (PDF) And subscribers who read a welcome message go on to read 40 percent more of your emails over the next six months.

A welcome email example.

But your welcome hook has to be good—because while some people will be engaged and ready to continue down the customer journey, one-third of people wind up unsubscribing within the first month. (PDF) That’s why it’s so important to quickly acknowledge them and kick off your relationship with them.

Setting up a welcome series

While it’s perfectly acceptable to send a single welcome email, a series of onboarding emails can help strengthen the new relationship and turn someone from a subscriber to a customer more efficiently. Start your welcome series with a general welcome, move on to education and getting to know each other, and, eventually, graduate to an ask.

Here’s a sample five-step welcome series to get you started. As with any suggested email structures or content, you should customize for your audience and then iterate and adjust based on the reactions you get.

Email 1. The first email is a welcome and thank you for subscribing. Re-introduce your brand, and reiterate what kind of emails you’re going to send. This is also a good place to set expectations on your email frequency (“Look for our weekly deals email every Friday.”)

An example of the first email in a welcome series.

Email 2. The second email should introduce your company and educate the subscriber about who you are and your values. Brand values are becoming increasingly important to millennial customers—but to older ones as well. If you can show off your values in this email, and demonstrate how they’re nicely in step with your new subscriber’s values, that’s a big step toward building a relationship and turning them into a customer.

Email 2 in a welcome series, introducing your company.

Email 3. The third email in a welcome series puts the focus on getting to know the subscriber. You want to ask how you can best serve them—which is crucial, since the decision on whether to stick with an email subscription keeps coming back to “what’s in it for me?” Extend an invitation to connect, ask the person what they want, invite them to share some info so you can send them personalized recommendations (or a piece of personal info, like their birthday, so you can send them something special in the future), and give them a number of options to chat with your team (email, social media, live chat, phone, etc.).

Email 3 in a welcome series, an invitation to connect.

Email 4. The fourth email is a good place to showcase your social media channels. Invite the subscriber to follow you and show off what different value they’ll get from following you in each place. This email from Yeti is a great example. It lays out all of the company’s social media channels, quickly states the unique value proposition of following each one, and provides call-to-action buttons to do so.

Email 4 in a welcome series, showing social options.

Email 5. By the fifth email you’ve really started to build a relationship, so you can begin to make a sales push. Show off your most popular products (and, if you have enough info about your subscriber to do so, personalized recommendations). You can offer a discount here to really try to close the deal.

Email 5 in a welcome series.

It seems like a lot, but people who read at least three emails in a welcome series are likely to become loyal subscribers, reading 69 percent of your emails going forward. You should also avoid sending a new subscriber other marketing emails while they’re receiving the welcome series, as that can overwhelm them and make it seem like you’ll be sending more often than they may’ve wanted, which can lead to a quick unsubscribe. 

A welcome email (or the first email in a welcome series) should go out immediately after a person subscribes. Real-time welcomes earn two-thirds more opens, almost three times more clicks, 10 times more transactions, and 11 times more revenue than delayed welcomes. (PDF)

Offering a welcome coupon or discount also makes a difference, and doubles the transaction rates. However, a word of caution about kicking off your relationship with a new customer by offering a discount: it can have negative effects like devaluing your brand or training customers not to ever shop at your store without a coupon. That said, it will significantly increase your chances of making the sale—so you’ll have to weigh the positives and negatives to make the choice that’s correct for you and your brand.

And one more word of caution: Welcome emails aren’t the place to use vague subject lines or other “spammy” techniques. Welcome emails receive almost three times the number of spam complaints as other emails, so keep them direct to try to blunt that number.

Cart abandonment

Roughly 70 percent of carts are abandoned. If you do some quick math, at a 70 percent abandonment rate, if your store processes 100 orders a month, that means there are about 230 abandoned carts that never make it to checkout. At, say, $50 per order, that’s $11,500 in lost sales. If you could recover even 15 percent of those carts, that would be an extra $1,725 in your pocket per month, or more than $20,000 per year.

It is possible to recover that 15 percent of abandoned carts (or more!). Believe it or not, three-quarters of people who leave items in a cart plan to return—and with abandoned cart recovery emails, you can get some of them back.

At Jilt, we’ve found that the average recovery rate is 12 percent, and with a few tweaks to the default abandoned cart content, that recovery rate can get up to 15 or even 20 percent. Some of our most successful stores have recovery rates well above that and generate hundreds of thousands of dollars in additional sales each month.

We’ve also found that for every abandoned cart recovery you send, you’ll bring in an average of $4.80. That’s not based on emails opened or clicked—it’s based on emails sent. So if you send 100 abandoned cart emails in a week, that can mean an extra $500 in revenue—and $26,000 per year.

Why people abandon carts

It’s important to know why people are abandoning your carts—it can help you fix problems with your pricing and website interface to reduce the number, and can help guide the strategy you use for your cart abandonment emails.

Here are the results from a study of more than 2,500 people on why they recently abandoned a cart.

  • The extra costs were too high (shipping, taxes, fees), 55 percent.
  • The site wanted me to create an account, 34 percent.
  • The checkout process was too long or complicated, 26 percent.
  • I couldn’t calculate the total order cost up front, 21 percent.
  • I didn’t trust the site with my credit card information, 17 percent.
  • The website had errors or crashed, 17 percent.
  • The delivery times offered were too slow, 16 percent.
  • The returns policy wasn’t satisfactory, 11 percent.
  • There weren’t enough payment methods offered, six percent.
  • My credit card was declined, four percent.

Another study found fairly similar results.

  • Unexpected shipping cost, 28 percent.
  • I had to create a new user account, 23 percent.
  • I was just doing research, 16 percent.
  • I didn’t trust the site’s security, 13 percent.
  • The checkout process was long and confusing, 12 percent.
  • I couldn’t find coupon codes, eight percent.

There are some common themes here, but there’s also a clear number one reason: Unexpected costs. We’ll keep that, and all of the other reasons, in mind as we plan out a possible cart abandonment recovery email series.

Capturing an email address

You can’t send an abandoned cart email unless you have a person’s email address. Here are the four primary ways to get that email address so you can start the recovery sequence:

  • If a returning customer or email subscriber is logged in, you have their email.
  • If the person enters an email during the checkout process but leaves before they complete the transaction, most sophisticated email marketing tools (including Jilt!) will capture the email.
  • You can attempt to capture an email address earlier using the methods we discussed in the growing your email list lesson—promote your list around your site and its value proposition to try to get people to sign up before they become customers.
  • You can use early email capture. We also discussed this in the growing your email list lesson; essentially, it’s a pop-up that prompts a person to enter their email as soon as they add a product to their cart.

Regardless of how you capture the email address, your cart abandonment sequence should kick off quickly to try to revive the potential sale.

Setting up a cart abandonment series

At Jilt, we’ve found a three-email sequence is the most effective way to recover abandoned carts. All three emails should be focused entirely (or overwhelmingly) on recovering the cart, not making other sales—so consider the reverse pyramid email model with a headline, limited copy, and one strong call-to-action.

Email 1. The first email should go out within an hour or two of the cart abandonment. Our default is a one-hour delay, and data shows the best success comes from recovery emails sent within one- or two-hours. The email should ask the person what’s wrong, offer support options to help fix what was wrong, and remind them of what’s in their cart. The call-to-action should direct them to finish checking out, and take them back to the checkout page to complete the transaction.

This cart abandonment email from StackSocial came about 15 minutes after I left two items in my cart. It shows me what those items are and gives me a call-to-action to resume checking out. The subject line is designed to create a sense of urgency: “Hurry, your cart expires in 24 hours!” That urgency is backed up subtly in the body copy, which lets me know they aren’t holding the items for me and someone else might snatch them up if I don’t come back quick to purchase them myself.

Email 1 in a cart abandonment series.

Email 2. If the first email doesn’t work, the second should go out 24 to 30 hours after the cart was abandoned. You’ll again want to remind the person what was in their cart and you may want to offer a discount. (We’ll get into the pros and cons of abandoned cart discounts shortly.) 

Email 3. The third and final email should go out within 48 hours. If you offered a discount, reiterate it here. This email should create a sense of urgency or scarcity—if they don’t act now, their cart is going away and the products could go out of stock. You can also use this email to address some potential reasons a person abandoned the cart: Offer links to support to answer questions, clarify your return policy, and if you have a satisfaction guarantee, mention it.

The third email in a cart abandonment series.

If, after all three emails, the person still hasn’t finished the purchase, then it’s fair to say they aren’t going to—a fourth or fifth email most likely won’t get the job done, but could irritate them to the point where they develop a negative feeling about your brand.

Should you offer discounts to recover abandoned carts?

There are very good cases for both sides on the discount/no discount debate. First, the reasons to discount:

  • The runaway top reason for cart abandonment is unexpected costs, including shipping, tax, and fees. By giving a discount, you eliminate that sticking point and, therefore, get rid of the thing that was stopping a large percentage of people from completing their transaction.
  • Discounts are proven to help recover carts. A study found 54 percent of customers will buy something they left in a cart if they’re offered it again with a discount. That jumps to 72 percent among millennials.
  • As we said in our lesson on building your email list, discounts close the deal. 57 percent of first-time customers say they would not have made the purchase without a coupon.

Now, the reasons not to discount:

  • It can devalue your brand, creating a permanent perception in a customer’s mind of lower quality.
  • It might make people question ever purchasing something from you at full price since it was that easy to get a quick discount out of you.
  • As we said back in our lesson on building your email list, one study found that new customers who use a coupon on their first purchase are 50 percent less likely to make a subsequent purchase from your store.

It all comes down to your priorities (and whether you have the margins to play with to offer repeated discounts to customers). This could also be a good case for an addition-not-subtraction discount; rather than offering money off a product, offer something additive instead like free shipping if they hit a certain cart value threshold, a free gift with purchase, a free upgrade with purchase, or points toward a loyalty program. 

Browse abandonment

Browse abandonment occurs when a potential customer leaves your eCommerce site before they add anything to their cart. To that end, they’re not quite as hot of a lead as someone who abandoned a cart—that person was, at least, strongly considering making a purchase—but it’s still someone who was interested enough in what you’re selling to visit and explore your site.

With the right effort, some of those people can become customers. The primary method is through retargeted ads—if you’ve ever gone to an eCommerce site and suddenly seen ads for that site showing up on other websites you visit and on Facebook and Instagram, it’s because of retargeting. It works, too—75 percent of marketers who do browsing retargeting say it’s effective. (PDF)

In this lesson, however, we’re going to focus on using email to target people who abandoned your site while they were browsing.

Who you should target with browse abandonment campaigns

Not everyone is a great target for your browse abandonment campaigns. First, you’ll need an email address. You have the same options to grab it as we just discussed in the cart abandonment section however, in this case, you won’t be able to use early email capture as that only pops up when someone adds an item to a cart.

When you’re setting up targeting rules for browse abandonment, experts recommend you don’t send to everyone—rather, just people who’ve shown some signs of a more serious interest. That includes:

  • People who visited more than once.
  • People who spent a certain amount of time on your site or on a specific product page.
  • People who looked at several items in a specific category.
  • People who used your search feature to hunt for products.
  • People who viewed a product that’s out of stock.
  • People who viewed expensive items and have potential to be a very valuable customer.

You also should avoid sending a browse abandonment email to someone who opened a preview browse abandonment email from you in the past 60 days, or someone who made a purchase from you in the past 30 days. In those cases, you’d be overwhelming the person’s inbox and quite possibly looking too greedy and pushy in the process.

One advanced way to use browse abandonment is to incorporate the results into your other emails. For instance, if you send a weekly broadcast email to your subscribers and include personalized product recommendations, you can include the products a person was browsing to try to bring them back to make the purchase.

Setting up a browse abandonment series

A two-email sequence is recommended for browse abandonment.

Email 1. The first email should go out quickly but not immediately. Delay the send by at least a half hour—your site is still fresh in their mind, but you don’t come off like a stalker who was remotely watching their every move. Don’t wait more than 24 hours to have the email go out. In the email, feature the product they were looking at, offer to answer any questions they might have, and, if the stock of those products is low, create a sense of urgency by noting how few items remain. Use a clear call-to-action that invites the person back to the site, something along the lines of “Come back and shop again.”

Email 1 in a browse abandonment series.

Email 2. The second email should go out one day after your first and, again, include the products they looked at and possibly create a sense of urgency. If the second email doesn’t work, it’s time to end your pursuit—they’ll either come back when they’re ready, or they just aren’t interested.

As for offering discounts, check out the pros and cons in the cart abandonment section above—the same principles apply. 

It’s important to stop the series if the person makes a purchase. That purchase could happen before or after the first email—just make sure your sending rules are set up so that person doesn’t receive a browse abandonment email anyway.

Automations for active customers

Thank you/post-purchase email

There’s a difference between a thank you email and a receipt/order confirmation. The latter is a transactional email, designed to deliver the straight details and (by law) little to nothing else. A thank you email is different. It’s a marketing automation that’s all about building and growing the customer relationship.

The thank you email can be the first part of a larger welcome series. It’s similar to the welcome series we described earlier in this lesson for new subscribers—but with this series, you’re not trying to turn a prospect into a customer, you’re trying to turn a customer into a repeat customer. 

Your thank you email should go out immediately after the purchase is completed and should aim to accomplish all (or at least some) of these objectives:

  • Thank the customer for making the purchase.
  • Get the customer excited about the purchase.
  • Give all the key info (even if they’ll also get that in a transactional receipt email) like what they paid, shipping estimates, important links, and customer support contact methods.
  • Introduce your brand’s voice and personality.

On that last point, the thank you email doesn’t have to be dry or just feature straight facts—in fact, it shouldn’t do that. Think of a hypothetical pet toy company’s thank you email—rather than a headline like “Thank you for ordering” it would say “Your best friend’s new friend is on the way!” After all, this email’s main purpose is to make a customer feel good about their purchase and kick off their new relationship with your brand—you need to show them why you’re a cool brand with which to form a relationship.

Setting up a welcome series for new customers

Again, since the thank you email goes out to a new customer (and not just a new subscriber you want to turn into a customer, like the welcome series we described earlier), that changes the sequence of emails and the goals you’re attempting to achieve with each one.

Here’s a possible six-email welcome series for a customer after their first purchase.

Email 1. The first email is a thank you email that goes out immediately after the purchase, as we’ve discussed above. Thank the customer, get them excited about the purchase, give the key info, and introduce your brand’s voice.

Email 2. The second email should come within the next few days. Here’s where you introduce your company—show the people behind the company, introduce your philosophy and values, and share your story. You can also include your social media channels here. It’s also good to include a link to the key info about the customer’s purchase—they’ll probably want to click on a link to see the shipping status of their order.

A "get to know us" email in a welcome series.

Email 3. The third email can go out before the customer’s order arrives or concurrently. It’s a product education email, a guide to help them get the most out of the product they ordered.

A welcome email to a new customer with product education.

Email 4. The fourth email should go out a few days after the customer has received their product to check in on how they’re enjoying it and to offer customer service if they have any questions or problems. You can also include some related products here (we’ll cover that more in our section below on cross-selling), as this is a ripe time to sell an accessory or add-on. In lieu of cross-sells, you can also use this email to ask for a product review.

Email 5. The fifth email is where you really flip the switch and begin trying to convert the customer into a repeat customer. In this email, which should go out about five days after the previous email, present a time-sensitive offer to the customer, preferably one that’s personalized based on their previous purchase. You can even present it as a thank you to the customer for purchasing—a special “thank you” coupon code that’s only good for the next two days.

An exclusive discount in a welcome email.

Email 6. The sixth and final email in the welcome series should go out a day after the previous email and reiterate the time-sensitive offer (“Only 24 hours left!”)

The final email in a welcome series.

Setting up a thank you series for repeat customers

The above email sequence won’t work for returning customers making their second (or third, fourth, fifth, etc.) purchase from you. They don’t need an introduction to your company like a new customer. They are your most valuable asset—return customers spend 120 percent more than first-time customers. (It also costs seven times more to acquire a new customer than to retain an existing one, which means they’re bringing in far more revenue at a far lower cost.)

Here’s a possible three-email sequence to send to repeat customers after a purchase.

Email 1. The first email should still be a thank you—everyone likes being thanked. It can be the same as the thank you that goes out to new customers.

Email 2. The second email should go out a few days after the customer received their product to check in on how it’s going and offer customer service. This is the time to ask for a review as well.

Email 3. The third email can go out a few days after the previous email. Here, though, you don’t need to give a time-sensitive offer—your recurring customers will (hopefully) keep coming back without an offer to buy things, and buy them at full price. Instead, this email should be highly personalized and feature products you can predict the customer will like based on their purchase history.

Feedback and review requests

You want to get reviews on your eCommerce site. More than nine out of 10 people will hesitate to buy something from a site if there are zero reviews. Just one review for a product can lead to an 18 percent increase in sales, and at five reviews that jumps up 270 percent.

But even with the importance of reviews, it can be tough to ask for them. After all, the primary action you want your customers to take is buying more stuff. If you also ask them to take their time to review their purchases, now you have to worry about appearing too demanding of their time and erasing some of the goodwill you’ve accrued.

In the previous section of this lesson, we recommended asking for reviews during a post-purchase welcome series—generally a few days after the customer received their product when, ideally, they’re most excited about the new, amazing thing they got. In this section we’ll cover some approaches to the review email to help avoid overreaching or overasking.

Tips for a feedback or review request

Keep it simple and focused. This is another time where it’s good to use the reverse pyramid design strategy: A simple email that makes just one ask. No one wants to read a ton of words when they’re doing you a favor.

That said, this is a situation when a plain text or limited text appeal could work well. Rather than using lots of images and a complex design, a review request plays well as a straightforward email coming from a real person.

An example of a review request.

Personalize based on what they bought. Even though you’re not asking someone to buy something, personalization strategy is still at play. Show a picture of the item they bought when asking for a review on it.

Then link directly to the page where they can leave the review. You’ll cut down on friction that way—and since this is a scenario where you’re asking for a favor, the more friction you can eliminate, the better. Don’t worry about selling things in the email; after they leave the review, then you can get back to selling to them.

Tell the customer why you want a review. There’s a psychological principle that found people are more willing to help someone out if you tell them why you want the help. There’s a famous psychology study from the 1970s where researchers asked to cut in line at a Xerox machine; sometimes they’d just ask to jump ahead, sometimes they’d give a reason. And regardless of the reason, people were more likely to say ok—even if the reason was something nonsensical like, “May I use the Xerox machine because I have to make copies?” We want to justify things in our brains, and the “because” helps us do so.

So how does that apply to asking for review requests? If you don’t just ask for a review but give a reason—any reason—why you need reviews, it should help the customer justify the favor in their mind. There are any number of reasons why you could need reviews:

  • Help us improve the product.
  • Help us come up with future products.
  • Help spread the word.
  • Help guide other customers looking for advice.
  • Every time we get five reviews our boss gives us all cookies. (If this is true where you work… are you hiring? 🍪)
A review request with a reason.

Should you offer an incentive for leaving a review?

Incentivized reviews is a major gray area, and one that some giant companies are firmly against. Amazon has cracked down hard, banning companies from offering free or discounted products in exchange for reviews and even suing people who sell fake review-writing services. Google and Yelp have worked hard to fight fake or incentivized reviews from appearing on their sites as well.

But… if talking about your own site, then the rules are yours to make. And while you’d never want fake reviews, offering an incentive to leave a review might work for you; one study found 58 percent of people had no problem trusting incentivized reviews.

If you do want to offer people something to leave a review, here’s what to keep in mind.

  • Don’t only incentivize good reviews. You have to allow people to leave honest reviews, good or bad.
  • Rather than discounting the product pre-review, offer a discount code on future products for someone who left a review.
  • But if you do give out free or discounted products in exchange for reviews, make sure that is fully disclosed in each review. (Amazon does do this, with its Vine program for top reviewers—with very strict rules.)
  • Know that you’re walking into a minefield and an area that some major online retail players (and the Federal Trade Commission) are heavily against. Translation: It might affect your rank on Google or your multichannel presence on Amazon if they know you’re trading in incentivized reviews. 

It’s probably best to try to get reviews without offering incentives at first, and only go down the incentives route if you’re really struggling to get reviews without.

Upsell and cross-sell emails

An upsell is when you get a customer to buy an upgraded or premium version of a product—like an airline offering to upgrade you to a first-class seat “for only $319 more” when you buy a ticket, or any company getting you to pay for an extended warranty. A cross-sell is when you get a customer to buy a related product—like a screen protector and case for the new phone you just bought.

Upsells and cross-sells don’t necessarily have to come in stand-alone emails; you can incorporate them into other emails as well, from welcome emails to personalized broadcasts. In this section, we’ll focus on emails that are only designed to upsell or cross-sell; however, you can apply the principles here to any section of any email that’s upselling or cross-selling.

The 60×60 rule

The 60×60 rule is a sales principle that sets the price threshold for upsells and cross-sells: Your customers will buy an upgraded or related product 60 percent of the time for 60 percent of the original purchase price (on cross-sells) or a 60 percent increase over the original price (for upsells).

For example, on an upsell, let’s say you’re selling a software-as-a-service product and you have three plans: Basic, premium, and pro. Basic is $5-a-month. The 60×60 rule says you can probably convince a good number of people to upgrade to premium—if it’s $8 or less. You’ll have a tougher time getting them to upgrade straight to pro for, say, $12. But… down the road, you may be able to convince users to upgrade from premium to pro because, again, it’s a 60 percent price jump.

For a cross-sell example, let’s look at how Apple prices the iPad—and the iPad accessories people are most likely to buy. An entry-level iPad is currently $329. The smart cover is $49—well under the 60 percent price threshold. So let’s throw in the Apple Pencil for $99, and a screen protector for $40. That adds up to $188—just under 60 percent of the product price (which would be $197).

Upselling with physical products  

Upselling a physical product via email can be a bit tricky from a logistics standpoint. It makes sense to try to upsell a physical product before someone leaves your eCommerce store (either right before checkout, or right after). Upselling on a completed order via email isn’t as smooth—your email would, basically, have to convince the person to amend the order they just completed in order to buy something more expensive. That can also be difficult to pull off with your eCommerce platform—you’ll need to be able to have someone go back into their order and edit what they purchased (and fast enough that it hasn’t already been packed and shipped!).

That being said, it’s not impossible—and could be lucrative if your upsell emails are successful. You’ll need to send the upsell email almost immediately after the purchase, though—maybe even incorporate it into your thank you email—and make it clear the customer has a short amount of time to edit their order before it ships. You can also use this tactic for cross-sells—a quick email offering some complementary products they can add to their order if they act fast.

Here’s an upsell email I got after ordering custom cups for an event. DiscountMugs quickly sent a follow-up email putting the same logo on other products that I could add to my order before it shipped out.

An upsell email example.

Another strategy for upselling with physical products is to attempt a pre-emptive upsell by emailing strategic coupons. For instance, sending out a coupon that offers a free gift when someone spends a certain amount (“Spend $30 and get this necklace—a $9.95 value—free!”) With that kind of offer you’re coaxing people to spend more than they might without the offer—thus making it a backdoor upsell.

Upselling with digital and subscription products

Digital and subscription products are natural fits for upselling as there’s always a more premium version or a new add-on someone can buy. You can use a series of emails to convert people who’ve downloaded free or lower-priced items or subscription plans into higher-tier customers. And it’s important that you do—one study found that more than 90 percent of revenue for software-as-a-service companies comes after the initial sale from renewals, upsells, cross-sells, and usage charges. 

Email 1. The first email goes out early, even on the first day someone’s using a digital product. Once they’ve had a little bit of time with it, your first email details the benefits of upgrading, purchasing an add-on, or buying a companion product (like an eBook) and all the extra benefits they’ll get.

Email 2. Within a few days of the first email, send out another email—there just so happens to be a limited time sale right now if you upgrade.

Email 3. If those emails still haven’t worked, you’ll need to work harder to convince the person how much they need to upgrade. In this third email, share a case study of a person or company that’s had great success with the upgraded version. 

Email 4. Remember that upgrade deal from before? This email lets the person know it expires in 24 hours, so they’d better act now.

Email 5. In the fifth email, you’ll do something unexpected—you won’t try to upsell. Instead, you’ll let the person know the discount has expired, they really missed it, and there’s not another discount available right now. That sends the message that when you say there’s a limited time offer, you actually mean it—so next time one comes around, they’d better take it seriously and jump on it. This email can also offer links to guides and support for your product—you want them to keep using it, fall in love with it, and get to the point where they feel like they need to upgrade.

Remember to make sure you set up your campaign rules so that customers stop receiving your upsell email series once they upgrade.

Cross-selling email strategies

Cross-selling is a great way to increase your average order value—and to turn your one-time customers into recurring customers. 

The ideal products to cross-sell fall under the 60 percent threshold we discussed earlier—with a $100 product, your cross-sells should be $60 or less. If you cross-sell something that’s under 10 percent of the main product’s price (so under $10 in this example), then you stay under the just noticeable difference threshold—our brains don’t really start seeing a difference at that level, so $100 and $109 feel about the same. Which means: If you offer a relevant, quality add-on for less than 10 percent of the purchase price, it should be an easy call for the person to add it to their order. (The key there is relevance and quality, though—people won’t just give you money for fun!)

Here are a few strategies for cross-selling emails you can employ:

Send an email recommending related products. Think of Amazon’s “people who bought this also bought” feature. You want your email to feel like that. Use your sales data to determine which products are frequently purchased together. There are also some products that are just natural add-ons—like selling batteries to someone who bought a product that needs batteries, or selling a matching belt to someone who bought a pair of shoes.

A cross-sell example.

Cross-sell other products the customer was looking at. If you’re tracking browsing data for customers, you can cross-sell them products they looked at but didn’t wind up purchasing.

Cross-sell your most popular products. While you want to always target and personalize your cross-sells, it’s also worthwhile to offer up your most popular products as well. They’re popular for a reason and might connect with the customer in a way their purchase history data doesn’t currently indicate.

Limit the number of options. Based on all of the suggestions above, it’s tempting to put together an email with tons of cross-sell possibilities… but show restraint. Too many choices is overwhelming; three products is a good number.

Retention and loyalty

Retention and loyalty emails are one of the top ways to turn customers into recurring big spenders who advocate for your brand. You want to make sure customers at that level feel loved, respected, and valued. Customer retention and loyalty emails keep customers happy and coming back for more.

After a person makes 10 purchases from a store, they’ll refer an average of seven customers, according to one study. (PDF) Those new customers then spend around 75 percent of what the initial customer spent. Loyal customers recruit other loyal customers. 

Here are some emails you can send for the purchases of retaining customers and building loyalty that can help you build high-quality, lucrative relationships.

Milestone emails

Milestones are good opportunities to send emails. They make customers feel like you’re paying attention, and they offer an organic trigger for a relevant email, so you don’t have to worry about seeming pushy. (We discussed emails needing to be “anticipated, personal, relevant” in our lesson on email content. Milestone emails easily hit all three criteria.)

You can send milestone emails for a number of reasons…

  • Happy birthday, almost always with some kind of offer or freebie (your “birthday gift” to your customer)
  • Anniversary of subscribing, becoming a customer, making a first purchase.
  • Congratulations on hitting a milestone with your product. (E.g., “It’s been one month since you purchased your new treadmill and started on this exercise journey!”) 
  • A week or year in review.
An example of a milestone email.

Holiday emails are a subset of milestone emails. While you won’t want to send a happy holidays email for every holiday (“Happy National Chocolate Donut Day” is probably only appropriate for chocolate donut shops), a note during the winter holiday season thanking the person for being a customer is a nice touch.

You don’t need to vary up the templates too often on your milestone automations—however, we do recommend switching them up annually so, at the very least, customers are getting a different-looking birthday email from you every year.

VIP or loyalty program emails

A VIP program works on a win-win level for both your customers and your business: It makes recurring customers feel properly appreciated and incentivized—and, to your benefit, it encourages them to keep on spending more. Customers want a VIP program—61 percent say it’s frustrating when they aren’t rewarded for their loyalty.

Here’s a sample email sequence you can use to invite a customer to join your VIP or loyalty program. There are many ways to initiate the invitation: You may want to let customers know they can join if they hit a certain spending threshold during a year, you may want to wait until they’ve made one purchase or multiple purchases, or you may want to invite everyone. Regardless of the membership requirements, the key with these emails is to make it clear to people how it works and why they should join.

Email 1. The first email introduces the person to the club, gets them excited about it, and invites them to join. It should very clearly lay out all the benefits without getting too bogged down in the details like the terms and conditions (you can put those on your website). This email should focus on just one call-to-action: Joining the club. 

Email 2. The second email should get more in depth into how the program works—how to earn more points and what kind of rewards they can expect. You can also offer some free welcome points for someone who joins.

Email 3. The third email should focus on the exclusivity of your club. Here you can use what is almost “reverse” social proof—rather than showing all the people who are using your club, talk about how few of your customers get an invitation to take part in all these great benefits.

Emails to send to members of a VIP or loyalty program

Once a person joins a VIP program, you’ll want them to keep having reasons to spend, engage, earn points, and feel like they’re on an exclusive level that other customers aren’t. Here are some of the emails you can send to your VIP list to achieve those objectives.

Exclusives and early access. Offer your best customers exclusive products or, at least, early access to buy your newest products before anyone else. The latter works especially well when you have a limited quantity of the new product—you’ll trigger the scarcity mentality to increase the chances of the purchase while also giving the feeling of exclusivity.

An offer of early access.

Advisory council. People who love a brand’s products, most likely, would love to give their own opinions on what the brand should make next. Invite your VIPs to be part of an advisory council where they can share ideas, discuss products in development—maybe even receive prototypes or pre-release versions to test themselves.

An invite to an advisory group.

Progress toward reward status. You should regularly update your VIPs on their progress toward earning different rewards. These emails can also showcase new products at your store—the goal being to bring the person to your store to buy the newest thing you’ve got to hit their next reward tier in the process.

An email with progress toward reward status.

Referral incentives. Since the goal is to turn your best customers into brand advocates, you can help move that process along by incentivizing your VIPs to recommend your store to their friends. Offer them bonus reward points for doing so—and points for their friends’ purchases as well.

Gamification. Gamification turns the shopping process into some kind of game, which can keep your VIP customers engaged, entertained, and interested. Games are also a great way to drive helpful behaviors, like more buying or more sharing with friends.

An email gamifying a VIP program.

You can also use a game as a way to reveal a big new product or announcement. Litmus, for instance, used a game to announce the location of a conference and saw a 60 percent increase in email engagement over the previous year.

Referral bonuses

While we covered referrals in the VIP section, VIPs aren’t the only ones who will recommend you to their friends. You want every customer recommending your brand to friends—84 percent of people say they trust recommendations from people they know, which is the highest score for any form of advertising. So even if you don’t set up a VIP or loyalty program, you can still offer benefits for referrals.

Your referral emails should encourage customers to recommend their recent purchase to a friend and, in some cases, you can offer a coupon or other incentive in exchange for every referral. 

A referral request email with an incentive.

Perhaps the pinnacle of referral emails came from Tesla in 2015. It’s a nearly-plain-text text email, sent by Elon Musk, that uses a wide variety of techniques to encourage people to recommend Tesla to their friends. We’ve broken them down below.

A classic referral request from Tesla.
Via: Reddit.

[wptb id=24111]

Tesla was trying to get people to recommend $75,000 cars to their friends. And the email was so effective that tons of people did—the company did about 5,000 sales from referrals, accounting for one-third of all the cars sold in the quarter.

And while you likely won’t be able to incorporate all of those strategies in your referral emails (also, you’re probably not pushing $75,000 items), you can use at least some of them to make your referral emails perform. At the very least, making the referral request come off as a personal, transparent email from the founder of the company is a good place to start. 

For lapsed customers

Replenishment and expiration reminders

A replenishment reminder is an email or series of emails that reminds a customer to reorder a consumable product that’s on the verge of running out. An expiration reminder is related; it’s a reminder that a subscription renewal is coming up.

Replenishment reminders are an effective sales tool. One study found they have the highest click-to-open rate of any email—more than 50 percent of people were opening replenishment emails, then clicking through to the website. Another study found similar results:  Replenishment reminders had an average open rate of 50 to 60 percent, and an average click-through rate of 40 to 50 percent.

Replenishment and expiration reminders perform so well because they hit all three elements of “anticipated, personal, relevant.” For “anticipated,” they’re actually doing a service for customers—helping them remember when to reorder to remove that task from the customer’s mental load. For “personal,” they’re emails tailored to the exact product a person bought. And for “relevant,” the emails go out at the perfect time—when the product is close to running out, so by reordering now there won’t be any time without the product.

On top of that, replenishment reminders inherently create a sense of urgency—just another reason why these emails hit the marketing sweet spot.

Figuring out when to send replenishment reminders

Expiration reminders are easy to figure out: You know the date when the person’s subscription expires and you can work backwards from there. 

Replenishment reminders can be a bit trickier because people might go through a product at different speeds. Some people wear a new pair of daily contact lenses every day; some people might only put in contacts a few times a week. So the first step is to look through your sales data at other reorders to see how frequently the average person is reordering. You can send your first replenishment email, as we’ll discuss shortly, at the point where you’d expect the person to be about 75 to 80 percent of the way through their supply.

You should also base your timing on the quantity the person bought. If you sell protein bars, the replenishment reminder is different for someone who bought one box versus a case of 12 boxes.

For some products, you may be able to simply ask the customer at checkout how long they expect their supply to last.

And beware of sending to someone who left a negative review—or returned the product. That’s a good way to have a very angry customer and, possibly, one who’ll mark your email as spam.

Replenishment reminder email series

A three- or four-email replenishment reminder series is recommended. Always include an image of the product in these emails, in case it’s something the person ran out of a while ago or need a reminder about.

Here’s a sample of how a replenishment series might go.

Email 1. The first email should go out in advance of the person running out, when you expect they’d be approximately 75 to 80 percent of the way through their supply. Your call-to-action should take them directly to the product page to reorder—you could take them directly to a filled-in shopping cart, but that could hurt the chances of upsells and cross-sells. 

You don’t need to include a discount with the first email—the ticking clock on the person’s supply is already enough of a built-in incentive for them to come back to buy more. You should definitely put a few potential cross-sell products in this email as well—while the main call-to-action is replenishing the supply, it’s good to give the customer a look at some of the other products they might want to pick up while they’re buying from your store. A pro move might be to offer some pre-built “packages” (their original product with some recommended add-ons), and link directly to pre-filled carts.

The same thing applies for expiration reminders here—the first reminder should go out when the subscription is about 80 percent of the way done to create a sense of urgency but also give a window where they can renew without any interruption in service.

Email 2. Your second email should go out on the day you expect the product to run out. This is a good chance to offer a coupon for free shipping or a discount on expedited shipping—yes, the product is out, but you’re helping them get more of it as quickly as possible.

Email 3. You can send another email, or another few emails, after the supply has run out. Just make sure to stop sending once the person has re-ordered.

Win-back emails

Win-back campaigns go out to lapsed customers in an effort to make them active again. They’re very important for the health of your email list—as we discussed in our lesson on list maintenance, you don’t want a big list, you want an active list. Win-back emails are the crucial “final step” to take before you remove someone from your email list.

It’s sad, but a study found roughly two-thirds of the average email marketer’s list is inactive. Win-back campaigns can reactivate some of those inactive subscribers—in fact, possibly a surprisingly high number. The study found that 92 percent of win-back emails made it into inboxes and had a 12 percent open rate. That open rate sounds low, but considering you’re dealing with inactive subscribers, 12 percent is a massive improvement from zero percent. And 75 percent of the re-engaged subscribers read at least one more email within three months.

What constitutes an inactive customer? You can use any number of criteria, from email opens to purchases. At Jilt, our win-back default is anyone who hasn’t purchased from a store in 90 days; however, depending on the nature of your business and your email strategy, you may want a threshold more or less aggressive than that.

Sending a win-back email series

A win-back email series shouldn’t be long—it will seem desperate if you send someone five “please come back” messages. Plus hammering an uninterested lapsed customer with emails is a good way to get yourself a spam complaint. Here’s an example of a two-email win-back series.

Email 1. The first email should use an emotionally-charged subject line that doesn’t blame the customer—but makes it clear they’re missed. Things like “It’s been a while” or “We miss you” tend to work well. 

You should also offer some kind of incentive for the customer to come back in the first email. That can be a monetary discount (or free shipping)—or you can offer a solution to a problem in that customer’s life. Discuss the new products or features you’ve developed recently and demonstrate how and why your customer would want to come back to buy them.

A win-back email example.

Email 2. The second email is the “this is it” email. Reiterate the incentive for coming back and let the customer know that if they don’t, they’ll be removed from your email list. 

If, after those two emails, the customer still hasn’t engaged, you can safely and confidently purge them from your list.

A win-back email that tells a subscriber they'll be cut.
Another last chance win-back.

Summary and implementations


Automations are marketing emails that go out to customers based on their behavior, status, and tenure. By and large they’re “set it and forget it”—you create templates, set up sending rules, and your email marketing platform handles all the sending. To that end, they’re a great form of email marketing—one that can bring in lots of revenue without much of a time commitment on your end.

Automations are different than transactional emails in that they’re focused on marketing and selling, not just business.

For prospective customers, your automations can include a subscriber welcome series, cart abandonment emails, and browse abandonment emails.

Your welcome series goes out to a new subscriber to your list, beginning immediately after they join, and is aimed at turning an interested subscriber into an active customer.

  • Start with a general welcome and thank the person for subscribing.
  • Introduce your brand, the people behind it, and your values.
  • Get to know the subscriber.
  • Showcase your social media channels.
  • And make a sales push at the end.

Cart abandonment emails go out to people who’ve put items in the shopping cart on your site but didn’t finish the checkout process. Roughly 70 percent of carts are abandoned—but with a good abandoned cart recovery strategy, stores can recover 12, 15, or even 20 percent of those orders.

The cart abandonment series serves to bring the customer back and eliminate some of the potential issues that kept them from finishing the purchase. A series can look like this:

  • A reminder of what they left in their cart asking what went wrong.
  • A second reminder the next day about the abandoned cart, possibly with a discount. Discounts are very effective for cart abandonment, but can also devalue your brand and hurt your goal of cultivating repeat customers.
  • A third reminder the day after that to create a sense of urgency that the cart will be deleted—and scarcity that the product could run out.

A browse abandonment series goes out to someone who visits your site and demonstrates a legitimate interest—either by their duration and activity on the site or frequency of visiting—but leaves without buying anything. A browse abandonment series can look like this:

  • An email a little while after the person visited featuring the product they looked at, offering to answer questions, and creating a sense of scarcity around the product.
  • A second email the next day, once again showing the product and giving a feeling of urgency.

For active customers, your automations can include a customer welcome series for new customers, a thank you series for repeat customers, feedback and review requests, upsell and cross-sell emails, and retention and loyalty emails.

Your welcome series for new customers thanks the customer for making the purchase, gets them excited, and aims to turn them into a recurring customer. The sequence can look something like this:

  • Thank you email right after purchase.
  • Introducing your company and values.
  • A product education email to help the customer get the most out of what they just purchased.
  • A check-in a few days after the customer received the purchase to see how they’re enjoying it, offer customer service, and cross-sell related accessories.
  • A time-sensitive offer personalized around the customer’s purchase.
  • An email reiterating that the time-sensitive offer is about to expire.

Your thank you series for repeat customers is shorter and eliminates some of the education aspect—and the discount.

  • Thank you email right after purchase.
  • An email a few days after the customer receives the product to check in and offer customer service. This email can also ask for a review.
  • An email a few days later with personalized recommendations for other products the customer would like.

Your feedback and review requests are important, as reviews are a huge part of a customer’s decision to make a purchase—but asking for them is tough. Your review requests should be simple and give a good reason why you want the review (improve the product, spread the word, help other customers, or anything else). You can offer an incentive for leaving a review, but that begins to tread into a thorny area and might bite you long-term.

Upsell emails aim to get a customer to upgrade a product they purchased; cross-sell emails aim to sell related products to the customer. Both fall under the 60×60 rule, which states that customers will buy an upgraded or related product 60 percent of the time for 60 percent of the original purchase price.

The process of upselling physical products can be tricky, since it’s easier to do while someone’s on your site. Send an upsell email immediately after a purchase, giving the customer a chance to amend their order quickly. Or you can pre-emptively upsell by emailing offers that give a customer an incentive to spend to a certain threshold to get a free product or upgrade.

With digital or subscription products, an upsell email series can help push a customer to upgrade to a higher tier.

  • The first email goes out early, often on the first day a customer is using the product, detailing the benefits of upgrading.
  • The second email goes out shortly after, offering a limited-time sale on upgrading.
  • The third email features a case study of a person or company that had great success with the upgraded version.
  • The fourth email lets the customer know the upgrade deal expires in 24 hours.
  • And the fifth email tells the customer they missed out on the deal—you weren’t bluffing. Now they know that the next time you offer a deal, they should jump on it.

Your cross-selling techniques can be incorporated into lots of emails, not just specific cross-sell ones. Whether part of another email or stand alone, you should cross-sell three main things:

  • Products related to the one the person bought.
  • Products the customer also considered buying (what they looked at on your site).
  • Your most popular products.

But limit your number of cross-sells in an email to around three, so you don’t overwhelm the customer.

Retention and loyalty emails are win-win: They make loyal customers feel valued, and they drive those customers to make more purchases more often. And since people who make multiple purchases from a store often become brand advocates—whose friends also go on to be great customers—they’re definitely worth your time.

Milestone emails go out for different occasions, like a customer’s birthday or when they hit a milestone with your product. These emails show a customer you’re paying attention, plus they’re relevant, personal emails that your customers will like.

A VIP or loyalty program for top customers is a good way to incentivize them to keep buying. You can invite someone to a loyalty program with this sample email series:

  • Introduce the club and all its benefits, and invite them to join.
  • Go in depth about how the program works.
  • Focus on the exclusivity of your club.

And once someone joins your program, you need to regularly send them emails to get the most out of it.

  • Exclusives and early access to products.
  • An invitation to be on an advisory council to help test and shape future products.
  • Updates on their reward progress.
  • Referral incentives.
  • Gamification to turn the shopping process into a game.

Referral emails can go out to non-VIPs too. You ideally want all your customers making referrals, because people trust recommendations from friends more than any other marketing channel. Ask your customers to recommend products they purchased to a friend, and consider offering a coupon or incentive for them to do so.

For lapsed customers, you’ll send out replenishment reminders and win-back emails.

Replenishment reminders go out when a customer’s supply of a product is on the verge of running out. They’re similar to expiration reminders, which go out in advance of a subscription ending. Studies have found replenishment reminders perform better than all other emails—they’re anticipated, personal, relevant, and timely. A sample replenishment series can look like this:

  • The first email goes out when you estimate the person is 75 to 80 percent of the way through their supply. It doesn’t need to offer a discount, as the sense of urgency is enough of an incentive.
  • The second email goes out the day the person’s supply runs out, and can offer a discount on expedited shipping.
  • And future emails can go out after the supply has run out—just make sure the sequence stops when the customer makes the purchase.

Win-back emails go out to lapsed subscribers and customers as a last-ditch attempt to save the relationship before you purge them from your list. You can use a two-email series to try to reactivate the customer that goes like this:

  • The first email uses an emotionally-charged (but blame-free) subject line like “We miss you” and offers the customer an incentive to come back. That can be a discount, or an update on your new products that can meet a need in the customer’s life.
  • The second email lets the person know you’ll be unsubscribing them if they don’t come back.

After the second email, if the customer still hasn’t re-engaged, it’s safe to purge them from your list.


Step 1: Set up the “minimum viable” automations

  • Create a welcome email for new subscribers.
  • Set up a simple cart abandonment series, as that can start bringing in revenue immediately.
  • Create a welcome email for new customers.
  • Create a thank you email for repeat customers.
  • If you sell a digital or subscription product, set up your upsell series, as that can start bringing in significantly more revenue immediately.
  • If you sell a consumable product, set up a replenishment series.
  • Create a win-back campaign to send before purging inactive customers from your list.

Step 2: Begin working on next-level automations

  • Turn your welcome email for new subscribers into a welcome series to work on turning them into customers.
  • Turn your welcome email for new customers into a welcome series to work on turning them into repeat customers.
  • Turn your thank you email for repeat customers into a thank you series.
  • Create a review request email, either as part of your series to new and repeat customers, or as a stand alone.
  • Incorporate cross-sells into your email series, or as a stand alone email.
  • Create a referral incentive program and send referral requests to your customers.

Step 3: Set up the most complex automations

  • Create a loyalty or VIP program, craft an email series, and invite your best customers.
  • Set up browse abandonment emails to go out based on a person’s behavior on your site.
  • Set up an upsell email to try to get customers to upgrade the order they just placed.

Step 4: Update, test, and iterate your automations

  • Iterate on your automations, for example, sending different cart abandonment emails based on the value of the cart.
  • A/B test your automations to maximize performance.
  • While automated emails are primarily “set it and forget it,” don’t forget to update them occasionally to give your customers a fresh look.