What’s this notification from your CRM? A brand new customer just made their very first purchase at your store! Huzzah! …But now comes the real work.

Welcome to the never-ending quest of retail success: capturing the hearts, wallets, and – the focus of this article – repeat visits of your soon-to-be loyal customers. Sure, you’ve just scored an epic win by getting that all-important first-time purchase. High fives all around, confetti, maybe even a tiny dance break if you’re a Severance fan! But after the celebrations, remember: the real journey for both your brand and the customer is just beginning right after that first transaction.

If you want a thriving brand that stands the test of time you’ve got to turn that new buyer into a repeat shopper. Why? Because research will tell you that once a customer makes their second purchase, they’re far more likely to continue shopping for the third, fourth, and five hundredth time afterward. In fact, according to smile.io, while the likelihood of another purchase after the first is 27%, the likelihood of another purchase after the second jumps up to 49% (and 62% after the third purchase). Think of it like the “gateway purchase”: that second buy is your chance to cement loyalty and kickstart a long-term relationship that’ll keep them coming back for more.

And here’s the other thing to be aware of: you only have a small window of time after the first purchase to get that second one. The rule of thumb is a 90 day timeframe to get them to make a second purchase. After that, it becomes much more difficult to get a one-time shopper to purchase again. So after that first purchase, the clock is indeed ticking.

So, what’s your move?

Unfortunately, you can’t just call up your brand-new customer and say, “I find your lack of future purchases disturbing,” in your best Vader voice. Instead, your team has to think about how to build a strategy that’s informative, personal, friendly, and yes, perhaps even in the realm of clienteling. Let’s break down some tried-and-tested tactics to master the art of the second purchase, and we’ll also show you exactly how to apply Endear’s proven engagement recipe to bring your customers back for an encore performance.

For the savvy sales rep, the groundwork for a second purchase is laid down from the first transaction. When a customer makes that first purchase, don’t let them slip away without leaving their all important contact information. You need their name, email, address, and their phone number (more on this later) in your CRM to keep the lines of communication open. This is much easier for online first purchases, of course, but great retail teams should have just as much success with in-store interactions when mining customer information.

Why is this so vital? Because outreach is impossible if you don’t know who you’re talking to or how to reach them. Relying on them to magically show up again is about as safe as betting your entire marketing budget on a single roll of dice in Vegas. Even the strongest brand awareness won’t guarantee a second purchase if the shopper rarely stumbles upon your site, or store, again. Having their info means you can gently (and sometimes not-so-gently, but politely) remind them that you exist, you have great products, and that you care about their experience.

Moreover, storing that data in a CRM like Endear ensures that you can track their history, preferences, and behavior. Because in this day and age, personalization is the alpha and omega of your brand surviving and thriving—if you want to stand out, you have to show your customers that you remember them and that you understand what makes them tick. So, step one: collect that precious customer data that is the catalyst in starting their customer journey with your brand.

Collecting their email after the first purchase is great. But getting their digits? Fantastic. When you can start up a texting relationship with the shopper, your brand has a much better chance of earning that all-important second purchase.

Why does texting work so well? First, almost everyone has their phone on them at all times. It’s our portal to memes, group chats, and simply life in general in the modern world. Second, SMS messages tend to cut through the noise more effectively than email. According to various marketing studies, open rates for texts are significantly higher than for email, and people typically see these texts within minutes of receiving them. If you’ve ever waited for a reply from a friend via text and gotten it within seconds, you’ve witnessed the power of this immediate communication.

A phone number also allows you to adopt a more personal tone. With texting, you can use your brand’s signature voice, keep messages concise, and ask for quick feedback. You might drop a personal check-in, a special discount link, or a limited-time notification about new inventory that resonates with something they previously purchased. It’s more direct and fosters that sense of “Oh, they actually remember me and aren’t just blasting generic messages to everyone.”

Just remember: with great phone numbers comes great responsibility. Be respectful of your customers’ trust. Don’t spam them, and don’t blow up their phone with mindless marketing. Keep it relevant, helpful, and entertaining, and they’ll appreciate that you’re reaching out to them in a personal way. If you’re thoughtful, your customers may even look forward to your texts, which is a huge step toward building loyalty.

Your brand is beloved, but at the end of the day people connect with people, not faceless corporations. If your brand can infuse that human touch from day one, you’ll create an experience that your customers can’t help but want to replicate. Think about how you feel when you walk into a neighborhood café and the barista says, “Hey, the usual?” or when you hear your name called out in a store by a friendly associate—instant warmth. The stronger that first connection, the more likely they will be to make a second purchase.

For online shoppers, it can be trickier, but not impossible, to create that sense of human interaction. One way is to include a personal note in the package. This could be a short, handwritten card if you’re a smaller brand, or even just a personal message typed but signed by an actual human.

Another angle: after the customer checks out, send a personalized “thank you” email introducing them to the brand story, the people behind it, and perhaps some behind-the-scenes photos. Show them the hands that packed their order, or highlight the person who crafted the item they purchased.

You can also spark a conversation via your CRM right after the purchase. Endear excels at letting your staff talk to customers directly, guiding them to the best use of the product, or simply inquiring about their experience. If the shopper feels that someone on the other side genuinely cares about how they’re enjoying their new purchase, the stage is set for brand loyalty. And guess what loyal customers do? They come back for more.

First impressions can make or break any relationship, from meeting the in-laws to that initial experience with a new brand. Remember, every touch point matters. Was your store team attentive and helpful? Was their desired item in stock and ready to go? Was the checkout process smooth and efficient? These moments set the tone for your ongoing relationship. 

But your responsibility doesn’t stop once they leave the store. The first month of ownership is a prime time to win someone’s heart. Encourage them to actually use the product (it’s surprising how many people buy stuff only to let it gather dust). Offer tips via email or text for product care or usage. Did they buy a fancy gold necklace? Send them your expert guide on keeping it sparkling for years to come. Did they grab a pair of running shoes? Share some workout playlists or local running trails. This kind of value-added communication shows that you’re not just a company that sells; you’re a brand that cares about the customer’s lifestyle, well-being, or personal style.

When the first-month experience is delightful, you become the brand that gave them that jolt of happiness. Much like how people form emotional connections with movies or music that define memorable moments, they’ll associate positive vibes with your products. And next time they need something you offer, they’ll think, “That brand totally took care of me last time—count me in.”

Alright, let’s talk about irresistible deals. If you want them back, sometimes you need to pull a little “Godfather” move and give them an offer they can’t refuse. But remember the golden rule: no one likes a discount that feels phony. A meager 5% off might not be enough to entice a second purchase unless your product is astronomically priced to begin with.

Craft your discount so it feels special and exclusive to them. Consider a unique code that includes their name, like “JANE15” if their name is Jane. Attach a sincere thank-you note, and let them know that you value them so much you’re giving them this single-use, limited-time code. After all, a break-even transaction on their second purchase is still a net benefit since it increases the likelihood of future purchases.

Tying the discount to their initial purchase can also be a smart move. For example, if they bought a pair of jeans, maybe offer them a deal on a matching jacket or belt. Or if they grabbed your best-selling skincare item, offer a bundle deal on related products that complement their original purchase. Personalization is huge here: if the discount is relevant, they’ll be more likely to redeem it than if it looks like you’re just hurling random promotions at them with no real thought.

Time sensitivity is also your ally. Giving them a short window to redeem might light the needed fire under their feet. “Use this code within the next 10 days to get 20% off your next order” provides a sense of urgency. The potential risk? If the window is too narrow, they might not have the chance to buy; if it’s too long, it loses the “act now” excitement. So find a balance: not so short that they feel rushed, not so long that they procrastinate.

Now that you have a sense of the essential strategies to woo that second purchase, let’s talk about timing and the power of a structured follow-up flow. Endear has a proven engagement recipe that goes beyond random acts of outreach. It’s a tried-and-true timeline that helps keep you from dropping the ball with your new customers. Think of it like a meal plan, but for retail customer relationships. You want a healthy mix of gratitude, follow-ups, check-ins, and brand updates to keep them well-nourished on the path to that second purchase. Let’s break it down:

In the grand scheme of building a retail empire, the first purchase is merely Act One. You’ve piqued your customer’s interest enough for them to take a chance on you, but to truly convert them into a repeat buyer—and hopefully a loyal champion of your brand—you need to deliver the goods: personal interactions, consistent communication, and genuine value beyond just the product. Remember, the window to secure that second purchase is surprisingly narrow, so time is of the essence.

Start by following Endear’s proven engagement recipe like it’s a family cookbook you’ve inherited from the marketing gods. That consistent, time-based plan for outreach—two days, two weeks, two months, four months, six months, and beyond—will keep your brand at the forefront of your new customer’s mind in an unobtrusive but effective manner. If all goes well, you’ll see them pop up for that second purchase, forging the path to a long-term relationship.

Ultimately, the journey to get that first-time shopper to come back for more is a perfect storm of genuine connection, strategic communication, and well-timed incentives. Nail these elements, and you’ll see your repeat purchase rates climb like a hero’s arc in your favorite blockbuster. Remember, you’re not simply selling products; you’re offering an experience—a chance for your customers to feel seen, understood, and delighted with every interaction.

This is part 1 of 5 in Endear’s new customer journey series. Subscribe to our newsletter to be the first to see the next articles!