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The trends that will dominate Black Friday and Cyber Monday, from AI search to experiential pop-ups

Modern Retail Podcast · with Danny Parisi and Lexy Lebsack · November 29, 2025 · 45 min

Summary

This episode breaks down crucial Black Friday and Cyber Monday trends for ecommerce operators. It highlights how brands are leveraging AI for gift discovery and moving beyond discounts with experiential retail, exclusive access, and unique collaborations to engage shoppers and drive sales during the most competitive shopping period of the year. Implement these strategies to stand out from the noise.

Key takeaways

Themes

ai in retailcustomer engagementholiday commerce strategynon-discount marketing

Topics covered

advent calendarsai chatbots for giftsblack friday trendsbrand gift guidescyber monday trendsexclusive product accessexperiential retaillimited-edition collaborationspop-up shopsshopper behavior analysis

Episode description

Cyber Week is here and the Modern Retail Podcast is breaking down the biggest shopping and trends to watch during this all-important shopping period. This week, Modern Retail senior reporter Gabriela Barkho is joined by staff from our sister site, Glossy, including senior fashion reporter Danny Parisi and Glossy West Coast correspondent Lexy Lebsack. Now that the sales week has officially begun, the trio discusses a number of brand strategies and shopper behavior they have spotted this season, including the first big test for AI chatbots assisting with gift search. On this week’s show, the staff’s roundtable covers topics such as: The modern gift guides and where shoppers are looking for holiday gift ideas, from brands’ own gift guides to ChatGPT suggestions.  The non-discounting marketing strategies, in which brands are instead offering shoppers perks like exclusive access to products and in-person pop-ups.  Other ways brands are standing out beyond traditional marketing sales, including limited-edition collaborations and even advent calendars.

Frequently asked about this episode

What does this episode say about ai in retail?
Explore integrating AI chatbots for personalized gift recommendations on your site to enhance customer experience and drive conversions.
What does this episode say about customer engagement?
Shift marketing spend from deep discounting to creating exclusive product access, limited-edition collaborations, or unique experiential pop-ups to build brand loyalty and perceived value.
What does this episode say about holiday commerce strategy?
Develop comprehensive, curated gift guides (both on-site and potentially AI-assisted) that cater to diverse customer needs, moving beyond generic product listings.
What does this episode say about non-discount marketing?
Consider innovative engagement tactics like advent calendars or early access programs to build anticipation and drive pre-holiday sales without relying solely on price reductions.
What does this episode say about ai in retail?
Analyze current shopper behavior to identify emerging trends in gift discovery and adapt your marketing and product strategies accordingly.

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