Pick n Pay bets on AI chatbot to catch up with Shoprite's Sixty60

South Africa's online grocery war has moved beyond delivery speed into artificial intelligence, with Pick n Pay launching Penny — a Gemini-powered assistant that lets shoppers order via voice, text, or photo instead of browsing. It's a direct challenge to Shoprite's dominant Checkers Sixty60, which grew digital revenue 48% last year to R18.9bn. For Pick n Pay, trailing badly with its stock down 16% this year against Shoprite's 7.8% gain, Penny is part of CEO Sean Summers' turnaround push. The real question for investors: can AI-driven convenience actually shift market share, or is this a defensive move to stem further losses?.By Janice Kew.South Africa’s online grocery battle is entering a new phase where the competition is no longer just about delivering groceries faster, but rather about making shopping itself almost disappear.After years of racing to offer one-hour delivery and expand digital reach, retailers are increasingly betting that artificial intelligence will become the next front of the race. Instead of searching through thousands of products, shoppers are being encouraged to simply ask for what they need.The battle is fierce. Shoprite Holdings Ltd., Africa’s largest supermarket chain, has steadily cemented its lead in the country’s online grocery market through its Checkers Sixty60 platform. It reported 48% growth in that unit in fiscal 2025, with digital revenue reaching 18.9 billion rand ($1.2 billion) — almost 9% of its local supermarket sales and 10 times larger than in 2021. Rival Pick n Pay Stores Ltd. is now trying to gain an edge by replacing the search bar with a simple question.Cape Town-based Pick n Pay on Thursday unveiled Penny, an artificial intelligence-powered assistant embedded in its asap! delivery app that allows customers to shop using voice, text or photographs instead of manually browsing products. Whether asking for ingredients for a recipe, uploading a handwritten shopping list or photographing the contents of a fridge, customers can describe what they need and Penny builds a basket using products available at their chosen store, said Enrico Ferigolli, who heads Pick n Pay’s online business..Powered by Google’s Gemini AI models, the assistant can recommend recipes, suggest substitutions, tailor recommendations to customers’ previous purchases and budgets, and add products directly to their carts. The technology marks a move from search-led shopping to conversation-led shopping, as retailers look for ways to reduce the friction involved in ordering groceries online.For Pick n Pay, the launch is about more than introducing a new digital feature. It forms part of Chief Executive Officer Sean Summers’ broader effort to revive the retailer after years of weak performance in its core supermarket business. The stock has lost 16% so far this year, compared to Shoprite’s 7.8% rise.Summers, who returned to lead the company in 2023, has been working to restore Pick n Pay’s reputation for fresh food while rebuilding the retailer’s digital capabilities. Although it recently pushed its target for the core supermarket business to break even back by a year to fiscal 2029, it continues to invest in technology to strengthen its competitive position..© 2026 Bloomberg L.P..Sign up for your early morning brew of the BizNews Insider to keep you up to speed with the content that matters. Register here.Support South Africa’s bastion of independent journalism, offering balanced insights on investments, business, and the political economy, by joining BizNews Premium. Register here.If you prefer WhatsApp for updates, sign up to the BizNews channel here.

Pick n Pay bets on AI chatbot to catch up with Shoprite's Sixty60

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