Black Friday and Cyber Monday trends: AI search, experiential pop-ups and more

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Cyber Week has kicked off and retailers are trying new playbooks to grab attention. The Modern Retail Podcast brings together reporters from Modern Retail and Glossy to dissect shopper behavior and the tactics brands are using during this peak sales window.

Key Cyber Week trends retailers are testing

Retailers are moving beyond blunt discounts. They are experimenting with experiences, exclusives, and technology to win shoppers.

  • Experience-driven offers: in-person pop-ups and early access to product drops.
  • Limited-edition collaborations: brand partnerships that create urgency without cutting prices.
  • Curated gift experiences: subscription boxes and Advent-style drops aimed at gifting.

How consumers are searching for gifts this season

Shoppers now mix traditional and digital discovery. Brand gift guides remain useful, but social search and AI tools are rising fast.

  • Official brand guides for inspiration and easy checkout.
  • Influencer and social-platform lists for trend-driven choices.
  • AI-generated prompts and chatbots for personalized gift ideas.

AI chatbots: the new test for holiday gift discovery

Brands are piloting chat features to help shoppers find gifts quickly. This is one of the first big public tests of AI in gift search.

Early signs: chat assistants can speed up discovery, but accuracy and trust still vary.

What brands need to watch with AI

  • Response relevancy and tone.
  • Seamless handoffs to human support.
  • Privacy and data handling during conversations.

Non-discount marketing strategies gaining traction

Rather than slash prices, some companies are offering perks that add value without eroding margins.

  • Exclusive product access for loyalty members.
  • Experience-based incentives like in-store events.
  • Freebies and bundled gifts to sweeten purchases.

Creative ways brands stand out beyond markdowns

Beyond discounts, brands differentiate with design-led drops and time-limited formats.

  • Advent calendars and countdown bundles that drive repeat visits.
  • Collaborations that create buzz and earned media.
  • Pop-up activations that turn shopping into an event.

Inside the podcast: voices and perspectives

The episode features Modern Retail senior reporter Gabriela Barkho and guests from Glossy. Senior fashion reporter Danny Parisi and West Coast correspondent Lexy Lebsack join the conversation.

They analyze which tactics might outlast Cyber Week and which are likely to be seasonal tests.

Where to listen and follow the conversation

The discussion is available wherever you stream podcasts. Find the episode on Apple Podcasts and Spotify.

  • Listen for tactical takeaways for retail teams.
  • Note shopper signals that brands should monitor post-Cyber Week.

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