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Black Friday & Cyber Monday 2025: Why AI Is the New Playbook

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Black Friday & Cyber Monday 2025: Why AI Is the New Playbook

2024’s e-commerce holiday numbers broke records to the tune of billions of dollars, with $41.1 billion spent between Thanksgiving and Cyber Monday alone. The Q4 stretch from November to year-end is still the highest stakes shopping period of the year, but using last year’s playbook won’t drive the same results in 2025. 

Shopping behaviors and expectations are shifting, and top retailers are already responding with AI-enhanced assistants and shopping experiences, but you don’t have to be Amazon or Walmart to take a page from their playbook.

The Problem with Traditional Black Friday/Cyber Monday E-commerce Tactics

Most retailers are facing the most expensive and competitive landscapes to date. They depend on strong discounts and heavy ad spend to drive Black Friday and Cyber Monday (BFCM) traffic and sales. Yet these one-time discounts won’t bring a shopper back.

But before they even get to a return visit, most shoppers bounce in just a few seconds, causing retailers to lose out on nearly $14 billion on BFCM revenue alone. Shoppers can’t find what they’re looking for fast enough: products get trapped behind basic search and filtering, pages load slowly, irrelevant campaign videos and pop ups get in the way.

Customer service teams get overwhelmed by repetitive questions and struggle under the pressure of 24/7 holiday coverage across high site traffic. Chatbots can help alleviate this, but they aren’t set up to truly guide customers down a path that converts. 

It’s a chaotic experience for everyone. But it doesn’t have to be.

 
Why Retailers Are Turning to AI shopping assistants for BFCM and Beyond

Forward-thinking retailers are already turning to agentic commerce and AI shopping assistants to transform their sales and strategy—and not just during BFCM, but their year-round operations. 

Agentic commerce simplifies the “shop-for-me” journey. Consumers arrive with intent, and AI doesn’t just speed up the process, it guides them toward the right purchase. This relevance and support are key, especially during BFCM, when decisions are made in seconds.

It also ensures your storefront is connected to AI search assistants like ChatGPT, Perplexity, and Gemini, where more shopping journeys now begin. By making your catalog and brand discoverable and shoppable through these AI interfaces, you capture intent earlier, guide shoppers toward purchase, and stay visible in a landscape shifting towards AI.

How Retailers Are Getting Ready for BFCM 

AI shopping assistants are experts in the entire product catalog but go beyond basic filtering, search, and FAQs to bring up the exact results a customer is looking for and answer their specific questions—all in one place—things which dramatically improve engagement and conversion

Kendra Scott success story

Lifestyle brand Kendra Scott entered the 2024 holiday season knowing that traditional e-commerce tactics wouldn’t be enough. SVP of Digital and E-commerce, Kamanasish Kundu saw huge potential in rethinking their AI strategy by transforming their support chatbot add-on into a true sales-enabled AI shopping assistant. In little time, the brand trained the assistant “in a way that mirrors how we actually sell: emotionally, intentionally, and with brand fluency.” This clearly resonated with customers during that critical holiday sales window, contributing to impressive results across their business :

  • 160% YoY growth in AI-influenced revenue
  • 6× lift in conversion rates
  • 9× increase in shopper engagement
  • AI accounted for 6% of total sales during the season

Sideshow success story

Pop-culture collectible manufacturer Sideshow’s customers aren’t your average shopper: they’re a passionate fan base who knows every detail of their favorite characters, series, and franchises. Chatbots couldn’t go into enough detail and static PDPs were burying them. The AI shopping assistant, however, could hold its own with even the most knowledgeable superfans, surface the right key details for each individual, and make it easy to compare collectibles, driving an 8x higher conversion rate and 94% CSAT just two months after implementing it.

Get Your Storefront Ready for BFCM 2025: A Quick Checklist

Preparing For the Sale

  • Implement an AI shopping assistant now.
    You can trial and set it up in days to start testing and teaching your system. When peak traffic hits, your AI shopping assistant will already be optimized to convert high-intent shoppers, protect your margins, and capture revenue.
  • Prep your AI layer with BFCM-specific knowledge.
    Update the assistant’s knowledge base and macros with promo rules, exclusions, shipping SLAs, and returns. Make sure you have well-structured attributes, rich metadata with natural language for your product details, descriptions, and FAQs. This offloads repetitive questions from CX, keeps answers consistent, builds shopper confidence, and preserves momentum at checkout.
  • Make the site instant and mobile-first.
    48% of BFCM sales come from mobile and drive 78% of traffic. Cut heavy apps/widgets, trim pop-ups, and test on phones where the majority of BFCM traffic lands. Every second saved reduces bounce and lets your AI shopping assistant engage sooner.

The Shopping Experience

  • Don’t rely on search bars and filtering to help customers find your products.
    AI shopping assistants provide immersive experiences on the UI and UX front that showcase dynamic content as a customer browses. A PLP with an AI shopping assistant transforms from a static brochure into a tailor-made guide for each customer.
  • Show fresh social proof where shoppers decide.
    Surface recent reviews on PDPs and let the assistant summarize them (“Most buyers loved the fit and gift packaging”). In BFCM, quick confidence signals close the gap between browse and buy.
  • Merchandise urgency and clarity directly on PDPs.
    Add countdown timers, low-stock flags, strike-through pricing, and “Holiday Best Seller” tags. These on-page cues pair perfectly with AI prompts (“Only 14 left—want to grab your size now?”) to turn intent into action.
  • Get your storefront ready for agentic commerce.
    More and more shoppers are starting their search with AI instead of traditional search. To avoid missing out on qualified traffic, start preparing to integrate with leading platforms like ChatGPT or Perplexity.
  • Think beyond the sale.
    Acquisition is one thing. But how will you keep the relationship alive afterwards? An AI shopping assistant can welcome a customer back without starting from scratch to continue building on their purchase history and preferences.

The Fastest Way to Get Ready Before The Holiday Shopping Rush

iAdvize helps brands tackle the holiday shopping season with more peace of mind thanks to our AI shopping assistant. By assisting retailers in:

  • Guiding visitors to the right offer
  • Answering key questions instantly
  • Handling traffic peaks without hurting the experience
  • Keeping the connection alive after purchase

It’s an easy lever to pull that strengthens your efforts and strategies. Deploying it in days, not months, you can start getting signals and driving results before the holiday shopping season is in full swing. By refining your BFCM strategy now, you’ll drive more Q4 revenue, and be set up for a successful 2026 when agentic commerce really hits its stride.

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