October 10, 2025
AI Takes the Reins as Retailers Prep for a Tough Holiday Season
Last year’s Black Friday rush exposed a few cracks in the system. Some online retailers ran out of stock too soon, while others couldn’t keep up with orders or saw their AI tools fail at the worst possible time. According to a new Swap Commerce report, e-commerce leaders don’t plan to make the same mistake twice.
Many are now rebuilding their digital foundations ahead of the 2025 shopping season with the help of smarter automation and better customer support. About 60% of executives say they’ll roll out AI-powered chat or AI shopping assistants, while nearly half plan to tighten up personalisation through better use of customer data. As we’ve reported before, AI is no stranger to helping people pick outfits or start a new hobby.
Juan Pellerano, Chief Marketing Officer of Swap, said: “Brands need to start thinking agentic first, as that’s what consumers will come to expect in their shopping experiences. The consumer dollar has become increasingly hard to earn, especially under current market conditions, so brands should start planning now to position their tech infrastructure for the increased wave of shoppers this holiday season.”
Black Friday in October?
This year, retailers are doing it early because shoppers are, too. The report notes that almost 25% of customers will start buying before the official Black Friday–Cyber Monday weekend, and more than half say they’ll use some form of AI help, from comparison tools to automated deal trackers. This means the “holiday season” now begins weeks earlier than it used to, and brands have less time to prepare.
Eighty-seven percent of executives admit that tariffs and supply-chain issues are still disrupting planning. Many have had to rethink how they manage suppliers or stock levels, and half are already investing in stronger, more flexible operations to handle sudden changes.
Even with those hurdles, confidence is creeping back. Just over half of respondents expect stronger revenue this year, thanks to earlier preparation and a clearer sense of where technology can actually make a difference. After years of rushing into AI without much strategy, leaders now seem to be treating it as part of long-term infrastructure, not a quick fix.
On the customer side, the numbers are modest but promising. Fourteen percent of Americans have used AI shopping assistants, yet nearly half know what it is and think it could be useful. That gap between awareness and use gives retailers a narrow but valuable opportunity to lead, if they can make the experience smooth and genuinely helpful.
If 2024 was a season of lessons, 2025 may be one of maturity. Retailers aren’t simply chasing trends this time; they’re trying to rebuild trust, efficiency, and consistency.
