Happy Sunday fam! I am writing to you from a tiny cafe in Lisbon this week. 

The retention girly in me is SCREAMING this week to tell you this story. I recently switched from Alaska Airlines/American Airlines to United Airlines, after YEARS of being a loyal one to OneWorld. Highest tier type of loyalty. Why the switch?

They didn’t compete to keep my business. Simple as that. Service declined, and every single time I had to talk to an American Airlines representative, a piece of me died inside. 

And of course it got me thinking about how all these tiny moments where brands either win or lose our loyalty. Those micro-moments when you're deciding between two products, when you're opening that perfectly packaged box, or when you're desperately trying to reach customer service at 2 AM.

Each of these moments? They're make-or-break opportunities for brands to either strengthen or shatter customer loyalty. So today, we're diving into 5 Key Moments That Make or Break Customer Loyalty (with some data and a few examples), plus a chance to win free bars from my besties at Hormbles Chormbles! 👀

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5 Key Moments That Make or Break Customer Loyalty

1. First Impressions That Convert
Social media shouldn’t be thought of as just a place to aimlessly scroll, it’s become the new search engine. A 2023 survey revealed that 33% of shoppers discovered a new product or brand through social media in the last six months, with that number jumping to 60% for Gen Z consumers. This shift highlights how critical it is for brands to show up in searches and leverage social platforms for discovery.

Personally, whenever I’m exploring a new city or hunting for something specific, social media is my first go-to. Hate to say it, but TikTok specifically because the SEO is top notch. For brands, this means showing up with engaging, optimized content where people are actively looking.

Here are my go-to tips for this:
• Optimize those product tags. Make your products easily discoverable on platforms like Instagram and TikTok by tagging them correctly for search. Think of your SEO the same way you do your website.
• Create platform-native content. Develop content that FITS each platform’s unique format, like vertical videos for TikTok and Reels or text for X. Content by platform matters.
• Partner with micro-influencers. Collaborate with influencers in specific niches who can provide authentic recommendations to your target audience. I feel like we know this, but sometimes I see people really getting lost in the weeds going after the BIG ones. Niche down.

2. Turn Curiosity Into Consideration
Idk bout you but if an ad catches my attention, or a brand, or even just an idea of something I need….I am immediately picking up my phone to research more. And I’m not alone. 81% of retail shoppers conduct online research before buying, spending an average of 79 days gathering information prior to making a major purchase (GE Capital Retail Bank). The journey from curiosity to consideration is fast, and brands that aren’t visible during these moments risk losing potential customers.

When I research, I look for clear answers. I want comparison points, reviews, and content that builds confidence in my decision. This is where your brand can stand out by anticipating customer questions and providing the information they need.

What this means for you and your brand’s optimization:
• Build FAQ content. Create articles in your help center that directly answer the most common “People Also Ask” questions on Google. Focus on clear, concise answers and optimize each page with strong keywords and meta descriptions. This ensures your brand shows up in search results and builds trust by providing valuable, easily accessible information.
• Add social proof. Display reviews, testimonials, and ratings near price points to build trust and credibility at the moment of purchase. Seeing positive feedback near a price point can significantly reduce hesitation. It validates a buyer’s decision with real experiences and creates a seamless path to conversion.
• Us vs Them. Create clear, digestible comparison pages that highlight your product’s advantages over competitors. Use bullet points or tables to showcase key differences, focusing on the features and benefits that matter most to your audience. This The Skinny Confidential Us vs Them is giving 👌

3. The First Taste of Trust
Ever notice how we've been conditioned to expect free samples at Costco, but not at Whole Foods? It's not just about free stuff – it's about the context of the trial. Modern consumers aren't looking for handouts; they're seeking exclusive experiences and early access.

Think of a giveaway as your velvet rope moment. The difference between "free sample" and "exclusive preview" isn't just marketing speak – it's the difference between being a charity and being a curator. Smart brands know this shift in positioning can transform a simple trial into a coveted invitation.

And speaking of exclusive previews, I’ve got a little freebie for YOU from my besties at Hormbles Chormbles, the new power candy brand started by the RXBAR founders. This week, they announced insane macros for their candy bars: 10g protein, 0g sugar, and just 100 calories. Yes, a candy bar. 🤯

They’re giving away 1,000 free sample packs at launch to anyone who signs up at hormbles.com. Don’t miss your chance to get an exclusive preview of what could be the next big thing in better-for-you snacking!

And lastly, here’s how you can recreate this for your own brand:
• Frame trials as exclusive access, not desperate discounts. Position trials as a VIP opportunity, like “early access” or an “exclusive preview,” to create excitement and avoid devaluing the product.
• Create FOMO through limited quantity drops. Use scarcity to drive urgency with phrases like “only 500 available” or “limited time offer.” Exclusivity motivates action.
• Build anticipation with behind-the-scenes content. Share behind-the-scenes content or teasers to generate excitement and emotional connection before your launch.

4. Usage Moments
The magic of your product isn’t just in unboxing—it’s in that first “aha” moment. This is when your customer transitions from feeling unsure to becoming a confident, empowered user. Think about Apple’s seamless tutorials (yes, I use these) or Duolingo’s perfectly timed encouragement. Loyalty starts here, in the moments where your product proves its value.

What this means for your brand’s experience:
• Create short-form tutorial content. Help customers quickly understand how to get the most out of your product with bite-sized, engaging how-to videos. Everything is a content moment these days.
• Build moment-of-success triggers. Celebrate milestones or wins, like completing a task or achieving a goal, to reinforce value and build confidence.
• Design intuitive onboarding flows. Guide users step-by-step with simple, clear instructions that reduce friction and encourage their exploration of your product. I am a TSC stan these days and the email flows are GIVING. Everyone should take note. This snippet of their onboarding flow for a night routine 👇

5. The Echo Effect
Your best marketing doesn’t come from you, it comes from your customers. It’s the viral TikToks, the glowing reviews, and the posts that make people say, “I need that.” Brands like Stanley and Trader Joe’s thrive because they nail the experience, making it impossible for customers not to share.

What this means for your brand’s advocacy:
• Create shareable moments in your journey. Design delightful experiences that customers can’t help but talk about, whether it’s unique packaging or a memorable unboxing.
• Build community-driven content engines. Encourage customers to share their stories by featuring their content or creating spaces where they feel part of something bigger.
• Reward organic advocacy. Recognize and celebrate loyal customers who champion your brand authentically, without transactional incentives that feel forced.

Alright, bestie, bottom line…loyalty isn’t won with grand gestures. It’s built in the moments where you show up and deliver. Whether it’s nailing that first impression, turning curiosity into action, or creating those “aha” moments, the brands that pay attention to the details are the ones that win.

So, what’s your next move? Take one of these strategies and run with it. Test it, iterate on it, and make it your own. Because the brands that stay ahead are the ones that never stop improving.

That’s it from me this week. If you need help turning ideas into action, you know where to find me and the OLC crew.

See ya next week! I hope you absolutely CRUSH this week.

-Jess
Founder of Open Late Collective

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UPCOMING EVENTS

1. Headed to Shoptalk in March? Midcoast has something extra FUN and special planned for the eve of March 24th. Reply to this email to get the deets.
   

2. The Sheinnovates Girl Gang and I are plotting and planning for Sheinnovates 3 (NYC) and Sheinnovates 4 (LA) next year. Sign up here to be alerted when tickets are available!
   
   And if you are a brand interested in doing an activation with us, or being a part of our goodie bags, reply to this! We are seeking baddie brands to highlight and partner with.
   

3. On Feb 10th, I am hosting an AfterHours Live on Linkedin with my friends at MixMix. We are breaking down customer journeys, and commerce in the cannabis industry. RSVP HERE
   
   Whether you are in cannabis or not, there will be LOTS for you to learn on this one! Don’t miss it.
   

4. Empath Club is bumpin’ already this year with our 2nd dinner and planning our 3rd! Feb 20th, Eli and I are hosting a dinner at Port Sa’id in New York. RSVP HERE. (shout out to Gorgias for supporting us)
   
   March details coming soon!

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

   LET’S CHAT

BONUS CONTENT

This week, I dropped a new epi with Kenzie McAndrew of Jacksepticeye’s brand Top Of The Mornin’ Coffee. Kenzie is the marketer behind Akira Coffee and Top of the Mornin’, to unpack the highs, lows, and creative chaos of building creator-led brands.

For my earbud folks, listen here. Or click the link below to watch on YT!

A WORD ON THIS WEEK’S SPONSOR

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