User Acquisition Strategy for Loyalty Programs: How Creative Director Jonathan Hildebrand Helps Brands Drive Sign-Ups

Senior Creative Director Jonathan Hildebrand understands the value of first impressions. After nearly 20 years working in brand and experience design, Jonathan knows that every touchpoint with your brand — physical or digital — has to extend beyond a surface-level interaction. Each instance (especially that first moment) has to deliver a felt experience to keep customers coming back.

Take loyalty programs: many new customers go online to research before signing up, and those online experiences have to wow. In Jonathan’s opinion, brands must make user acquisition strategy a core part of their landing page designs.

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I caught up with Jonathan to ask how he helps brands grow their loyalty programs by weaving user acquisition strategy into their design process. “Think of your landing page as the invitation to your party,” he replied, with a buzzing, infectious energy mellowed by warm Southern charm. “It’s not just about getting people to show up. It’s about promising them an experience so good they can’t resist signing up.”

Jonathan Hildebrand’s Approach to User Acquisition for Customer Loyalty Programs: An Interview

You liken loyalty programs to parties. Can you expand on that idea?

Think of a loyalty program as the ultimate gathering you're hosting. You can throw the best party in the world, but people will only come if they're sold on the idea of a good time. It’s the same with loyalty programs. Your acquisition experience, that first touchpoint, is essentially your invitation. If it’s compelling, they’ll come. If not, all your efforts are wasted.

I love creating great experiences, and I consider myself an expert in that. In fact, I even got the license plate [pointing to his personalized NC plate that reads ‘UXPRT’]. When you ride around with a label like that, you better deliver on that promise.

Personalization plays a big part in creating a good experience. Always think about your guests’ (i.e., customers’) expectations. Where are they coming from? What did they see before they arrived on your landing page? Your social media profile? An email marketing campaign? A referral program?

Then you look at your content marketing. Even if you can’t personalize the acquisition experience using first-party data, you can curate their experience by automating the headline and primary hero imagery to reflect their geolocation or repeat the visuals they saw at their previous click. Things like this are a low-lift way to make the experience feel tailor-made from the start.

How do you approach user acquisition strategy when designing for loyalty programs?

Looking at your competition is a great place to start. You can learn a lot about what customers expect by seeing the landscape of what others are saying. That landscape includes everything from paid advertising to influencer partnerships to the keywords from your SEO research. You can get a feel for what might be working, but you never know how your competitors’ efforts are actually performing, so don't over-index on what they’re doing.

From there, we can discuss the content hierarchy of the page (e.g., deciding when to show key features of the app versus moments of joy and lifestyle enhancement when using the app itself).

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Next, we involve the user, either by pulling insights from research done during app development or by doing our own hallway-style user testing. Finally, we'll craft our strategy for the page itself.

A well-crafted acquisition page should allure and inform. It should paint a vivid picture of what to expect. For instance, stating what the user gains upfront — a discount or a premium feature — acts like the headline of your party invitation. It’s about creating that intrigue and excitement from the get-go.

With such emphasis on creating an inviting experience, how do you ensure reaching a diverse audience, including globally?

I’ve traveled all over the world and experienced different cultures, cuisines, and continents. One thing that remains the same regardless of location is communication. Presenting the details of your event, product, or program in a way that your prospects can clearly understand the benefits is the key to getting that sign-up.

For instance, in our study on Global Credit Card Rewards Programs, you can see how things like cultural norms, spending habits, and overall attitudes towards money change around the world. But one thing that stays the same is the demand for transparency. People want clarity on the value they’re getting, and their options for maximizing that value based on what matters to them.

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So, globalization is more than just changing your go-to-market language for a specific region. It's about personalizing your loyalty program to each market so it represents the diverse audiences you want to reach. It means understanding dialects like a local, promoting the benefits that matter most to each market, using inclusive imagery, and maybe even trying out different color schemes. It’s about making everyone feel welcome at your party.

You mentioned accessibility. How does this factor into loyalty acquisition?

In the South, we say “Y’all means all.” It means no one is excluded. If you’re leaving folks out, you’re not only being a bad host — you’re shrinking the guest list. In business, why would you turn away anyone ready to hand you their money? You wouldn’t. Accessibility and inclusivity aren’t just the right thing to do from a moral standpoint, they’re also good business.

This starts visually with your design’s color palette. Roughly 300 million people worldwide have some form of color blindness, and it impacts their digital experience because they can’t see contrast between certain colors. So if your color palette doesn’t work for everyone, you tweak it. We developed a design system with color combinations that work well together, removing the guesswork for future projects. For example, rather than just changing colors, we might design entire modules using accessible color contrasts.

In fact, we care so much about this at WillowTree that we developed a Figma plug-in called Contrast to make it even easier. It’s a free tool that helps designers test and implement color combinations so web experiences are accessible to vision-impaired users. We’ve surpassed 220,000 downloads and are adding 1,000 to 2,000 new users per week.

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Plus, Contrast was just one of 10 Figma plug-ins featured at Config, Figma’s annual global conference. I’m so proud to be part of the Contrast team.

What’s the importance of “moments of delight” in your user acquisition strategy?

Think of moments of delight like this wedding invitation [holding up an invitation from the corner of his desk]. It’s not just on a random piece of white paper. The stock is heavier. It’s got a beautiful satin ribbon, letterpress that leaves a brilliant impression, and a prestamped return envelope. Everything is laid out clearly so that RSVPing is a breeze; adding your plus-one is easy. Every detail is designed to make the receipt of this invitation feel special. That’s what great design should do.

Consider showing what it’s like to earn rewards and what it feels like to cash those in. Add in animations to celebrate any steps the user takes closer to becoming a member. Or you could incorporate auto-fill into your sign-up form, so instead of endless forms to fill out, boom, you’re in.

The little things, those delightful touches, turn transactional moments into something fun, easy, and worth sharing. That’s why people make unboxing videos now. The packaging and exploration of new physical things can be a delightful experience. We want to do that in a digital form, the delight of unpacking your invitation to this loyalty party.

Finally, how else can you increase the chances of someone joining a loyalty program?

It’s good to remember that good design solves user problems. It’s about more than aesthetics and metrics — it’s about functionality and removing barriers. For example, ensuring buttons are large enough to be easily clickable, and links are underlined to differentiate them are practical aspects that enhance usability. Small but consistent positive experiences like those mean more long-term customers, higher conversion rates, and lower customer acquisition costs.

The bottom line: user acquisition strategy in loyalty program design is about making the customer’s journey enjoyable and effortless. It's like ensuring your party guests have such a good time that they can't wait to come back. Whether through seamless navigation, engaging content, or delightful surprises, the goal is to create an experience that users value enough to return to time and again. That builds lifetime value.

Go from User Acquisition to Customer Retention with the Right Loyalty Strategy

Jonathan’s philosophy is deceptively simple: Make joining your loyalty program as easy and exciting as saying yes to a weekend bash. But what excites people about joining financial services loyalty programs isn’t the same as what makes them sign up for DQ Rewards at Dairy Queen. Fiscal responsibility and frozen treats speak to different parts of the brain.

WillowTree helps you discover what resonates with your target audience based on deep audience and market research. We then help you identify the program structure, tech stack, digital marketing strategy, and acquisition channels needed to successfully take your loyalty program to market.

Learn more about our loyalty strategy and customer experience consulting.