Reimagining your tentpole moment strategy for the AI era

Back-to-School used to be more straightforward. You stocked shelves, brands ran a promotion, targeted parents and students, and waited for the sales to start. But today, brands who treat them purely transactional are missing the real opportunities.

Smaller tentpoles are no longer ‘small’

While major shopping events like Prime Day, Circle Week, and Black Friday are massive, they are open to all and category free-for-alls. All brands are vying for the same space. Back-to-School or Back-to-College are generally for supplies, snacks, meals, school clothes, etc. 

The National Retail Federation (NRF) projects K-12 back-to-school spending will reach $39.4 billion in 2025, up from $38.8 billion in 2024. And we’re seeing more and more brands leveraging this shopping moment - it’s big, and still growing. Even amid cautious budgets, shoppers are expected to spend around $570 per child, per a recent Deloitte report. 

The catch? You have to be early. Shoppers now start Back-to-School buying long before the season “officially” kicks off. By the time your campaign launches, you may already be chasing a peak that has passed.

AI is reshaping the retail landscape

At the same time, AI has become a new gatekeeper of discovery. Features like ShopGPT and Amazon’s AI-generated review summaries are changing how parents and students decide what to buy. People aren’t scrolling through endless aisles, instead they’re asking AI to “build my Back-to-School list,” and it’s pulling recommendations from articles, affiliate content, and product page reviews.

If your brand’s presence isn’t optimized for these AI-driven touchpoints, you’re invisible before you even hit the physical shelf. This isn’t just about search rankings. It’s about ensuring your brand narrative and product details are clear, relevant, and credible enough for AI to surface.

Emotional triggers still win over pure promotion

The brands winning Back-to-School aren’t necessarily the ones shouting the loudest. Stanley Cups, without any kids-specific products, tapped into college prep shopping as an emotional upsell moment. Even Uber Eats found a way to curate school essentials. This highlights that creativity and timing can open doors in unexpected categories.

These moments resonate because they tie into the feeling of transition. Parents remembering back-to-school hauls, students craving a fresh start, families wanting to mark a milestone. That emotional connection can’t be replicated by “SALE NOW” messaging alone.

We’re also seeing brands that don’t necessarily fit into the traditional back-to-school advertising mold. For example, homecare brand BISSELL, known for pet-friendly vacuums, are running a timely promotion, demonstrating they’re leveraging the moment for things like dorm cleaning essentials. 

How to win in the age of intelligence

• Be early, not reactive. Shoppers, and algorithms, move faster than your traditional campaign calendar.
• Optimize for AI curation. Ensure your content is review-rich, affiliate-friendly, and clear enough to be surfaced by AI recommendations.
• Balance performance with storytelling. Competitive targeting and ranking hacks only work if your creative earns attention and builds brand value.
• Use tentpoles as test beds. What works during Back-to-School informs your Q4 strategy and don’t waste the chance to learn.

Conclusion

Tentpole moments aren’t about who spends the most in the moment. They’re about who understands how both human and artificial intelligence shape purchase decisions. And Back-toSchool isn’t just a retail spike since it’s a proving ground for whether your brand is ready to win when the stakes are higher.