Conversational AI Becomes New Front Door for Holiday Shopping

The traditional holiday shopping journey, a linear path of keyword searches, doom-scrolling and multi-step checkouts, is being dismantled in real-time. This season is seeing the rise of agentic commerce, where AI not only suggests products but also actively intermediates transactions.

Retailers expect AI-assisted commerce to play a larger role in how consumers discover, evaluate and purchase products. To prepare, merchants reworked product data, payments infrastructure and discovery systems as conversational tools increasingly shape the path to purchase.

As Karen Webster, CEO of PYMNTS, wrote, “ Systems designed for human attention and human decision cycles are now interacting with autonomous agents that operate with far more context, speed, precision and consistency than people ever could.” That shift is forcing retailers to rethink commerce experiences that were built around search bars, scrolling and clicks, and to adapt for environments where AI intermediates the shopping journey.

Retailers are treating conversational interfaces as a new commerce surface where content, discovery and payments converge. PYMNTS Intelligence found that 42% of shoppers used AI assistants during Black Friday to find discounts, 35% to track prices and 31% to compare products.

Major retailers are already moving in that direction. Walmart, Target and Etsy have integrated with OpenAI to enable shopping inside ChatGPT, while smaller merchants are restructuring product listings to surface in AI-generated answers rather than traditional search results.

Nik Sathe, CTO of Blackhawk Network, framed the shift as spanning the entire customer journey. “When I think about AI, I really think about it in three categories: helping consumers find the right product, helping them transact, and then helping them use what they’ve purchased,” he told PYMNTS.

Retailers Brace for Peak Season

As conversational shopping scales, retailers are moving away from keyword-driven search optimization toward richer, context-aware product data. Target told CNBC that conversational phrasing now accounts for about 25% of customer searches, prompting the retailer to expand product descriptions with contextual details such as sustainability attributes, use cases and seasonal relevance.

Prat Vemana, Target’s chief information and product officer, said the company is publishing richer merchandise descriptions to improve visibility inside AI-generated responses. In November, Target announced that customers could complete multi-item purchases, including groceries, directly through ChatGPT. The company said thousands of shoppers have already used its AI-powered Gift Finder, with early results showing higher engagement and larger average cart sizes.

As reported by PYMNTS, Walmart also announced a similar partnership with OpenAI in October as part of a broader shift toward AI-native commerce. Amazon has taken a different path, developing its own proprietary AI shopping assistant, Rufus, rather than integrating with third-party conversational platforms. The company said more than 250 million customers have used the assistant this year.

Smaller brands are also adjusting ahead of the holiday rush. Michael Wieder, co-founder of baby goods retailer Lalo, told CNBC his team now structures product listings around the questions consumers are likely to ask AI assistants. Instead of emphasizing specifications alone, Lalo incorporates phrases such as “good for small spaces” to align with conversational queries that drive AI discovery.

Beyond discovery, retailers are also preparing for AI-native checkout flows that compress discovery and transaction into a single interface. OpenAI launched Instant Checkout with Etsy in September, enabling single-item purchases without leaving ChatGPT. The AI chatbot has since expanded its integrations with Shopify merchants, including Skims and Vuori, and charges transaction fees on purchases made on its platform.

Control Still Matters

As retailers experiment with AI-driven discovery and checkout, Sathe cautioned that consumer trust will shape how far automation can go during the holidays. While shoppers may welcome assistance with repeatable, low-stakes purchases, they remain wary of surrendering judgment on more personal decisions. “Consumers will want the convenience of having an agent do things for them, but they’re not going to give up control entirely,” he said. “Some purchases are objective and repeatable; others are subjective and personal.”

That distinction is already influencing how retailers deploy AI ahead of peak season. AI tools are gaining traction where speed, price comparison and replenishment matter most, while traditional browsing remains dominant for categories tied to taste, fit and preference. Sathe said the shift will be incremental rather than disruptive, with merchants layering AI into existing journeys instead of replacing them outright.

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