How to Build Loyalty Before They Even Buy

Your 2025 playbook continues with retention and lifecycle in this three-part series.

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Hey Fam,

Hope you’re kicking back, enjoying some holiday treats, and maybe ignoring your inbox just a little. But don’t ignore this one because we’re diving into part two of our three-part series to help you crush your ecommerce success in 2025.

Last week, we started with brand strategy, laying the foundation for standing out in a crowded market, building emotional connections, and creating a brand people actually care about. But strategy alone doesn’t keep the lights on—it’s what you do next that makes the difference.

Retention gets thrown around a lot as a buzzword, but let’s keep it real: most brands don’t think about it until it’s too late. They’ll focus all their energy on acquisition, then scramble post-purchase to figure out why customers aren’t sticking around. 🙈

Here’s the thing: If we start building brand loyalty at the awareness stage, before a customer even hits “Buy Now,” don’t you think retention would get a whole lot easier? (Spoiler: It would.)

This week, we’re talking about how to stop treating retention like a backup plan and start designing a customer journey that keeps people engaged, loyal, and excited about your brand.

Let’s dive in…

2025 Prediction: A Surge of Self-Serve CTV Buyers

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How to Build Loyalty Before They Even Buy

IMO, retention isn’t just about post-purchase emails and win-back campaigns. It’s about planting the seeds of connection, trust, and value from the very first touchpoint. And heading into 2025, this isn’t a nice-to-have—it’s a non-negotiable. With rising acquisition costs and saturated markets, people are choosy about where they spend their money. If you’re not giving them a reason to stick with you from Day 1, they’re swiping left on your brand.

So, how do you actually build loyalty before someone even becomes a customer? How do you get them to feel like part of your brand’s story before they’ve spent a single dollar?

Retention at Awareness: A Paradigm Shift

We’ve been trained to think of retention as something that happens after a customer buys—welcome flows, loyalty programs, win-back campaigns. Sure, those things matter, but they’re not where retention starts.

But the reality is, every single touchpoint at the awareness stage is an opportunity to start building trust and emotional connection.

And trust me, that connection matters. If someone feels like they already belong with your brand before they’ve even bought anything, they’re more likely to:

1. Say “yes” to you faster (hello, conversions).

2. Stick around longer (because loyalty doesn’t start at checkout).

3. Brag about you to their friends (your future advocates).

Take Arrae, for example. They’re in the supplement space, which is ridiculously saturated—think hundreds of brands all vying for the same health-conscious customers. But Arrae crushes it because they educate at every stage of the journey.

At the awareness stage, they’re not screaming, “Buy this!” Instead, they’re teaching people why they might need help with bloating, how their ingredients work, and what it feels like to actually see results. Through Instagram posts, TikToks, and their blog, they’re creating value before asking for a sale.

That education builds credibility—and by the time someone clicks “Add to Cart,” they already trust the brand. No brainer.

Dynamic Messaging That Meets Them Where They Are

Think of awareness campaigns as the opening scene in your retention story. Why serve generic, one-size-fits-all ads or emails when you could be setting the stage for a personalized connection?

Here’s the play:

• If someone reads a blog about sustainable materials, don’t just retarget them with a generic product ad. Instead, show them how your products align with those values.

• New email subscribers? Don’t jump straight into sales. Lead with value—offer a free guide, a how-to video, or some bite-sized education about your brand’s mission.

A challenge for you…look at your current awareness-stage messaging and ask yourself, “Would I click on this if I didn’t already know and trust my brand?” If the answer’s no, it’s time to rework it. Okkuurrrr, bestie?

Education Builds Loyalty Early

I love educating a customer on why they need what I’m slanging. Education isn’t just a retention tool—it’s an acquisition game-changer, especially in markets like sustainable clothing, where everyone is shouting about eco-consciousness and recycled fabrics. People are overwhelmed with options, so showing them why your product is worth their time—and how it fits into the bigger picture—makes all the difference.

Let’s talk about Christy Dawn, a sustainable clothing brand doing it so right. They’re not just selling dresses; they’re telling the story of how regenerative agriculture can transform the planet—and how their “Farm-to-Closet” approach is part of that solution.

From Instagram posts showing their regenerative cotton farms in India to beautifully written blog posts about why deadstock fabric matters, Christy Dawn educates their audience on the impact of their clothing. They help customers see their purchase as part of a bigger movement, not just a cute outfit. By the time someone’s eyeing their signature Dawn dress, they’re already emotionally invested in the mission behind it.

When you position your brand as an expert or problem-solver, customers see you as more than a product—they see you as a trusted resource.

Think about the biggest questions or challenges your audience has. How can you create content that educates and solves those problems upfront? That’s the kind of value that earns trust before the sale.

Emotional Connection From Day One

People don’t buy products—they buy into the stories, values, and emotions behind them. This is why your mission should shine loud and clear from the jump.

This is especially powerful for brands in competitive spaces. If someone feels emotionally connected to your values, they’re less likely to be swayed by a competitor’s price or flashy promotion.

Here’s an idea: Take a quick audit of your awareness content. Is your brand’s story front and center? If not, brainstorm three ways to share it this week—whether it’s a founder video, a heartfelt email, or a simple Instagram post.

What about measurement tho?

Great question, bestie. Talking about retention at the awareness stage is all well and good, but how do you actually know it’s paying off? Let me break it down—these are my favorite ways to measure if your efforts are hitting the mark:

• Engagement Rates: Are people clicking on your ads, engaging with your quizzes, or responding to your emails? High engagement is your green light—it means your content is resonating and drawing people in.

• Repeat Visits: Are they coming back for more? Whether it’s revisiting your website, watching your Instagram stories, or liking multiple TikToks, a repeat interaction signals curiosity. And curiosity is the first step toward conversion.

• Conversion Quality: When someone does buy, are they doing it faster and spending more after engaging with your awareness-stage content? If yes, congrats—you’ve built trust before they even clicked “Buy Now.”

Metrics like these are your north star. They’ll tell you what’s working, what’s not, and where to refine your approach. The goal? Build awareness that doesn’t just drive clicks—it builds a brand people can’t quit.

Retention and lifecycle marketing are the engine that keeps your business moving forward. They turn first-time buyers into lifelong fans, create consistent revenue, and give your brand the chance to stand out in a crowded marketplace. When done right, they’re the secret sauce that makes your brand unforgettable.

And that’s my take on retention and lifecycle. Maybe some of this was already on your radar, or maybe you’re walking away with fresh ideas to implement. Either way, the goal is to help you take that next step toward building a customer journey that doesn’t just sell products—it builds relationships.

This is just the middle—2 of 3 in our series about crafting your 2025 playbook. Next week, we’ll close things out with customer experience, the final pillar that ties everything together. Because when your customers can’t stop talking about how good it feels to shop with you, success takes care of itself.

If this week’s newsletter got you rethinking your retention game (or you’re ready to tackle lifecycle marketing like a pro), call the crew at OLC. Whether it’s retention strategy, marketing, or CX, we’re here to help you turn one-time buyers into lifelong fans.

Same time, same place next week?

Have a Marketing and/or CX-related question for me?

UPCOMING EVENTS

  1. Headed to NRF in January? Empath Club (Eli and I’s lovely community) and Midcoast (Dillon and I’s founder community) are teaming up to host a fun AF event at 12 Chairs on January 13th. If you are a brand operator or founder either attending NRF or just in the NYC, join us!

    RSVP HERE

  2. The Sheinnovates Girl Gang and I are plotting and planning for Sheinnovates 3 (LA) and Sheinnovates 4 (NYC) next year. Sign up here to be alerted when tickets are available!

More IRL events coming in 2025!
Interested in working together? Hit me up.

👐 BONUS CONTENT 👐

This week, I released a very fun episode with Jai Patel, Founder of JUV, is a compact, blender-based juicing tool designed to easily separate juice from pulp by pressing blended fruits and vegetables. We talk about finding a problem, inventing a solution, the woes of entrepreneur life and even share a QVC like demonstration. It’s fun, it’s juicy and packed with so many good tid bits!

and if you are an earbud bestie, listen here.

If you are a brand operator or founder, I’d love to have you on Above The Fold in 2025! Fill out this form and let’s get you on!