What Brands Get Wrong About Personalization and How to Fix it in 2026

Most brands talk about personalization like they’ve mastered it. However, personalization is still mostly smoke and mirrors. If customers click your email and land on a website that acts like it has never met them, you’re not personalizing, you’re decorating. True personalization spans the entire customer journey. Great customer experience (CX) feels like one continuous conversation. This is the shift defining 2026 — real-time, whole-journey personalization.

Imagine this: A customer clicks a retargeting ad for a running top she browsed last week. She lands on the product page and immediately sees that top in her size, styled with a matching jacket and the exact running leggings she bought three months ago. The price already reflects her VIP discount. The whole set looks like it was curated just for her because it was. No searching. No code entry. No wondering if items will work together. The experience feels personal, timely and effortless.

This is the difference between personalization as a buzzword and personalization as a living, breathing customer experience. Most brands genuinely want to improve, but it’s not obvious where to begin. Here’s a clearer way to think about it.

Step 1: Map the whole customer journey (as different customers).

Start by walking through the journey, but do it as each type of customer you serve. For example, a sports equipment store might sell to pros, casual hobbyists, parents shopping for kids, or people just getting into fitness. And their journeys never look the same. Good news: You know your audience better than anyone, allowing you to easily put on each segment’s “hat” and shop the way they would.

Map each transition systematically. Ad to website, website to email, email to SMS, and back again. At every handoff, ask three questions:

1. Does this message match what brought them here?
2. Does it address a problem they actually care about?
3. Does it feel like a continuation or a restart?

These answers will differ by segment. A pro athlete clicking through from a performance-focused ad expects technical specs and gear comparisons. A parent shopping for a child's first skateboard wants safety info and starter kits. If either lands on a generic homepage or gets a welcome email that ignores what brought them in, the journey breaks.

Maybe you browse skateboards but the welcome email pushes bikes. Maybe a retargeting ad shows outdated pricing. Maybe a SMS meant for sport pros offers a discount on kids' equipment. These small breaks add up and they kill the feeling of a consistent, personal journey

А swimwear brand, JOLYN, handles this exceptionally well. It serves two very different groups: swimmers buying training gear and customers shopping for vacation swimwear. These audiences browse differently, care about different details, and respond to different messages.

To support that, JOLYN starts segmenting immediately. As soon as a visitor lands on the site, a preference pop-up sorts them into the right group. And the data collected is used right away, shaping product recommendations, adjusting the website experience, and even changing the welcome series depending on the segment.

Step 2: Fix the disconnects one by one.

When you collect all the gaps across the customer journey, it can feel overwhelming. However, you don’t need to fix everything at once. Small improvements compound quickly. You can move through the journey step by step, starting from acquisition and smoothing out each stage. You can tackle the moments that hurt conversion the most or you can simply begin with whatever is easiest to fix.

I recommend starting with website personalization.

Here's why: brands pour enormous time, energy and ad spend into driving traffic, perfecting their emails, SMS campaigns, and paid media. Then that traffic lands on a generic, static website. The experience breaks immediately. It’s like sending someone a beautiful handwritten invitation to a party and then, when they arrive, treating them like a random plus-one.

Website personalization connected to your other channels is low-hanging fruit, and most brands aren’t picking it. JOLYN is a great example of what happens when you do. After a customer receives a promo code via email, that same code appears on the website complete with a countdown timer. The offer is clear, consistent, and easy to use.

JOLYN also launched product-matching recommendations that automatically show the right bottom in the shopper’s size to match the top they’re viewing. The same logic powers its abandoned cart emails, which now feature not just the item left behind but a complete look. These recommendations already influence 7 percent of total sales. This is the kind of continuity that turns personalization into a real experience rather than a collection of isolated tactics.

Step 3: Optimize and add complexity over time.

Once you’ve fixed the obvious disconnects, the work shifts to continuous improvement. Look for gaps, test new ideas, and gradually add more sophistication to your journeys.

For JOLYN, this meant introducing artificial intelligence-calculated discounts, creating different flow versions for different customer segments, and enabling cross-device cart recovery — i.e., the cart someone built on one device reappears when they open your email on another. The result? A 26 percent increase in campaign-driven revenue.

Ideas like this start appearing everywhere once you pay attention. A/B test your welcome series for different segments. Experiment with timing. Try new recommendation algorithms. The key is constant testing and iteration, always checking how each customer category behaves and ensuring all channels connect into one seamless, truly personalized journey.

Personalization is a Journey

Personalization isn't about individual tactics. It's about orchestrating an entire journey that feels coherent, thoughtful and human. To make it easier, you need two things: a strong marketing team and the right technology.

I personally believe in all-in-one solutions. The reason is practical: unified platforms let you see the entire customer journey without data silos. They simplify the creation of connected experiences, like syncing your website and email communications, because all the data lives in one system.

With everything in one place, you can focus on what actually matters. Start by mapping your customer journeys as different personas. Fix the disconnects one at a time. Then keep optimizing and adding sophistication. The brands that get this right don't just see better metrics (though they definitely do). They build relationships. They earn trust. They turn customers into advocates. That's what journey-wide personalization is really about.

Maryna Hradovich is the co-founder and COO of Maestra, an all-in-one marketing platform that helps scaling DTC brands personalize beyond email and SMS.