Woolworths taking on Checkers and Pick n Pay at their own game

Woolworths has joined Checkers and Pick n Pay in launching an artificial intelligence (AI)-powered assistant on its on-demand delivery app.

Called ‘My Woolies Chef’, Woolworths’ AI tool will allow customers to ask questions, find meal ideas, plan dishes, and shop for ingredients more seamlessly.

My Woolies Chef will be available to a small group of existing MyDifference loyalty programme members from September 2026 as part of an ongoing beta testing phase. Woolworths intends to roll out the service more broadly in early 2027.

“Unlike general-purpose AI tools, My Woolies Chef is built specifically around the Woolworths food ecosystem,” the retailer said in a press release on 13 July. 

“The assistant combines local recipe content, product information and shopping functionality to deliver recommendations that are relevant to the South African customer context and directly connected to the Woolworths shopping experience.”

My Woolies Chef will use generative and conversational AI to interpret customers’ questions and return relevant suggestions.

The AI tool has been trained on thousands of Woolworths TASTE recipes and, unlike a traditional search function, it is designed to understand the context behind a request.

“The system has been trained to interpret natural language prompts related to meal planning, cooking preferences, and household needs,” the retailer explained.

This allows customers to interact with the platform in a more intuitive and conversational way. 

“Conversational AI allows customers to engage with Woolworths’ food content and digital shopping experience in a more intuitive way,” Woolworths’ group data and AI officer, Jose Rodrigues, said. 

“Instead of navigating multiple searches, they can describe what they need in everyday language and receive suggestions that are relevant to the context of their request.” 

“Our focus is on developing the technology responsibly, testing it through a phased rollout and improving the experience through customer feedback.”

South African retailers go all-in on AI

The announcement of My Woolies Chef comes shortly after Pick n Pay and Checkers have launched their own versions of an AI-powered chatbot integrated into their on-demand delivery apps.

Checkers was first to the punch, announcing its AI-powered shopping assistant, named ‘Pixie’, on its Sixty60 delivery platform in April 2026.

Described as a “trusted personal butler with a PhD in shopping”, Checkers’ tool learns from customers’ buying habits and generates personalised grocery baskets and product recommendations.

Pick n Pay responded to Checkers’ move in early July 2026, introducing ‘Penny’, an AI-powered, multimodal shopping assistant on its asap! platform.

Penny can assist asap! users with building shopping baskets, answering questions, and helping with “smart shopping”.

With Woolworths, Pick n Pay, and Checkers now having announced their AI-powered upgrades to their delivery platforms, it is becoming clear that the new retail battleground has shifted to convenience shopping.

All of South Africa’s major retailers have been investing heavily in their on-demand delivery platforms over the past few years, looking to capture more market share through these convenience options.

Currently, Checkers’ Sixty60 platform is the clear market leader and was the first to launch major upgrades that the other market players soon followed.

As South African shoppers increasingly prioritise convenience and the online shopping experience, retailers will need to differentiate themselves through their on-demand platforms.