There are two kinds of ecommerce shoppers in the world.
There are the planners, who buy gifts six months ahead of time, and there are the late deciders – the ones who realize today that they need a gift or a product and they need it tomorrow.
Valentine’s Day has a funny way of reminding us just how many people fall into that second camp. 😉
Every year, brands brace for the surge of last-minute shoppers rushing to buy tokens of love for their main squeezes. And every year, the same truth reveals itself: urgency doesn’t magically create conversions. It often just amplifies friction. Slow pages feel slower, too many choices create overwhelm, collections feel daunting (what do you mean, you offer these braided lanyard keychains in eighteen colors and seven different fabrics, and you're happy to throw glamour shots in as part of the deal?).
The brands that make the most of these moments aren't the ones coming up with wildly funny campaigns (as much as I love a wildly funny campaign) - they're the ones that make it easy for someone to decide what to buy at the very last second.
This issue is about designing for those moments, which will look different for every brand. I’ve got some helpful insights on the topic below that are relevant for any holiday throughout the year, because while Valentine’s Day may be seasonal, last-minute decision-making is not (I say this as a person who falls solidly into the last-minute buyer camp).
I'd sign off with an x or an o, but I don't know you like that, so let's go with cheers.
Alanna
Insights💡
Why last-minute campaigns work best when nothing feels last minute
Here are a few things from the playbook that consistently stand out as effective conversion tactics during high-volume, seasonal surges.
Clear paths outperform clever promotions. Gift guides, curated collections, and pre-built bundles work because they limit choice and help shoppers commit without second-guessing.
Delivery confidence drives action. Clear messaging around shipping cutoffs, arrival timing, and guarantees often matters more than a discount when urgency is high.
Small friction becomes expensive. Slow load times, cluttered collections, and unclear product differences may seem minor, but they quickly stop conversion when shoppers are in a hurry.
Strong systems beat scramble-mode execution. Brands that convert late deciders are not inventing offers at the eleventh hour. They are reusing existing products, content, and merchandising logic in ways that make decisions faster.
What this means: Urgent moments do not reward brands that move faster. They reward brands that have already simplified the experience. The same structures that help a last-minute Valentine’s shopper convert will quietly improve performance throughout the year.
Winning back your ex works better when you remember why you broke up
Stay AI’s winback playbook makes one thing very clear: churn isn’t a single event. It’s a collection of breakups with very different backstories. Your best bet for winning customers back is to respond to thereason the relationship ended in the first place.
Here are a few suggestions from the playbook that are worth borrowing.
Address the breakup before making the offer. Generic “we miss you” campaigns fall flat because they ignore why someone left. Winbacks work best when cancellation reasons are captured, mapped to specific responses, and triggered automatically. Examples: too much product calls for a pause, too expensive calls for flexibility, confusion calls for guidance, not incentives.
Not all churn is emotional. A meaningful share of lost subscribers never meant to leave at all. Expired cards and failed payments quietly end relationships that customers intended to keep. Treating payment failures as save moments, with simple one-click fixes, protects recurring revenue without feeling like a winback at all.
Re-engagement works best when it escalates slowly. The most effective winback flows start with a light touch. A short SMS to reopen the conversation, followed by a value-focused email, and only then a time-bound incentive if needed. Customers who re-engage should exit immediately. No one wants a love-bombing, clingy ex.
Gifts beat discounts when trust is fragile. Discounts can devalue the relationship. Thoughtful gifts, store credit with an expiration, or limited-time VIP perks feel generous without training customers to wait for markdowns. The goal is to make coming back feel special, not transactional.
Be selective about who you take back. Not all churn is worth recovering. High-value, high-trust customers deserve better incentives than known exploiters or policy abusers. Segmentation protects margins and keeps winback efforts focused on customers who are likely to stick around this time.
What this means: Winning back customers is less about grand gestures and more about emotional intelligence at scale. When brands listen closely to why customers leave, respond with intent, and remove friction from the return, they turn breakups into durable second chances, not repeat mistakes.
Events 🎉
Rebuy Partner Roundtable: what’s actually working right now Live webinar February 12th, 1pm ET / 10am PT
If you’re tired of theory and more interested in what’s actually driving results, this one’s worth your time. We’re hosting a partner roundtable with operators and agency leaders who are deep in the weeds, sharing what they’re seeing across real stores, real campaigns, and real constraints.
The conversation will cover where teams are focusing right now, what’s quietly outperforming expectations, and where common assumptions are starting to break down.Register today.
Rebuy Pool Party @ eTail February 24th, Palm Springs Surf Club, Palm Springs, California
Conference days are for learning. This is for everything else. We’re hosting an invite-only poolside hang withBear Group, Fluent,andShopify— no panels, no pitches, no name-badge small talk.
Come grab a drink, post up in a cabana, catch a wave (yes, there's a wave pool!), or just soak up the sunshine with some of the best people in ecommerce. 🌊
Ladies of Ecommerce Brunch @ eTail February 24th, 10am, Sands Hotel & Spa, Palm Springs, California
Before the hubbub of eTail kicks in, we’re starting the week the right way with sunshine, mimosas, and chill vibes. Join us at the Pink Cabana for a ladies-only brunch hosted by Rebuy, Rivo, Gorgias, and DYODE. This is a slow morning kind of gathering with women who understand ecommerce life.
Come as you are. Stay as long as you want. We're keeping this intentionally intimate so request your spot today 💕🥂 Click here to sign up.
Momentum LA: Innovation Summit March 4th, Sunset Tower Hotel, Los Angeles CA
We’re bringing Momentum to Los Angeles for a focused, one-day gathering centered on the future of beauty, wellness, and retail. Our fourth Innovation Summit brings together a small group of senior leaders from some of the industry’s most forward-thinking brands for honest conversations and meaningful connections.
Expect strategic discussions at the intersection of wellness, technology, and growth, led by executives who are actively building and scaling modern commerce experiences. This is not a trade show or a traditional conference. Momentum is designed for CMOs, digital leaders, and ecommerce decision-makers looking for practical insight, thoughtful dialogue, and long-term perspective.
YouTube and Reddit are shaping AI-powered search results
AI search tools are increasingly citing YouTube and Reddit as source material, according to recent reporting. As AI-generated answers lean more conversational and experience-driven, first-hand video content and community discussions are gaining visibility over traditional publisher pages. For brands, this means that showing up in AI search may depend less on rankings and more on whether real people are talking about you, on platforms where experience is shared openly.
AI Overviews are pulling clicks away from organic results
New data from Ahrefs suggests Google’s AI Overviews are significantly reducing clicks to traditional search listings, even when brands still appear on page one. As more answers are resolved directly in the search interface, visibility no longer guarantees traffic. For brands, this reinforces the shift echoed above: search performance is becoming less about clicks and more about presence, influence, and how your content feeds the systems shaping AI-generated answers in the first place.
LET'S STAY CONNECTED
Rebuy, Inc. 50 W BroadwaySte 333 PMB 57340 Salt Lake City, Utah, 84101-2027, USA
.jpg?upscale=true&width=1120&upscale=true&name=Touchpoint%20mid-April%202025%20(1).jpg)
.png?upscale=true&height=48&upscale=true&name=linkedin.256x244%20(1).png){kind=small}
.png?upscale=true&height=48&upscale=true&name=32px-X_logo_2023_(white).png){kind=logo}