Prat Vemana, the chief information and product officer for Target, this week experienced something brand new as a shopper. He bought sleepwear through the retailer's app in OpenAI's ChatGPT.

The C-suite executive's new shopping behavior reflects a seismic shift happening for retailers as they head into Black Friday and a holiday season that's projected to surpass $1 trillion in spending for the first time in the U.S. Shoppers who have spent the past few decades migrating to web-based shops, then to mobile commerce, and shopping and discovery on TikTok and other social media platforms, are evolving again. They are now beginning to embrace artificial intelligence, including AI web browsers like ChatGPT Atlas from OpenAI and Comet from Perplexity, as yet another new way to shop.

“Whether it's ChatGPT, Perplexity, or Gemini, we want to be there to help answer a question that the guest has,” says Vemana, who joined Target in 2022 with digital retail experience from big-box retailers The Home Depot and Staples. “The minute Target comes to their mind, we want to be there.”

By integrating with ChatGPT, Target is angling to get in front of the chatbot's 800 million weekly active users with personalized recommendations from the retailer. Another generative AI bet that Target placed this month was the debut of an AI-powered gift finder that's now on the company's website and app, allowing shoppers to ask questions like “what's a good present for my mother-in-law” and get a natural-language response.

While Target, which is ranked 41 on the Fortune 500, has already signaled to investors that it expects its ongoing sales struggles will continue through the holiday season, digital sales have been a bright spot. When Vemana joined the company from healthcare giant Kaiser Permanente, where he served as chief digital officer for three years, he was given a clear mandate from Target CEO Brian Cornell. “He said 'Just get us to positive comps,'” recalls Vemana with a laugh.

By the fiscal first quarter of 2024, digital comparable sales were on the upswing and have increased for seven consecutive quarters, including a 2.4% gain for the fiscal third-quarter results that were reported last week.

With wind behind his sails, Vemana's responsibilities have also expanded to include CIO duties following the retirement of Brett Craig earlier this year. Vemana now oversees enterprise product technologies, engineering, infrastructure, and cybersecurity.

Internal applications of AI include ChatGPT Enterprise, which has been rolled out to about 18,000 employees who are using the tool to ask questions, upload spreadsheets, and for summarization. Last week, OpenAI's team visited Target's corporate office, where 4,300 employees participated in ChatGPT-focused training sessions. Vemana says that 92% were satisfied with the experience.

In its stores, Target has rolled out a generative AI chatbot called Store Companion, which can help answer questions to make store operations run smoother or address a shopper's questions. Vemana says he's continuing to field input from associates to make improvements to Store Companion.

“Ultimately, we want to make sure that their experience in store is fully assisted with tech so that they can focus on the guest,” he says.

Target has already deployed several agentic AI use cases, with early areas of focus on handling customer service requests and improving IT workflows. Vemana is also rolling out a data science-led inventory management system that triangulates the complexity of a network of 2,000 Target stores with hundreds of thousands of products to more precisely match inventory levels with anticipated demand.

“The models are evolving and learning,” says Vemana, noting that the early focus on this project are “frequency items” like cereal or a pack of underwear.

Target told investors this month that it would increase capital expenditures for the next fiscal year by an additional $1 billion, bringing the planned spending to about $5 billion on new store openings, remodels, and technology advancements. Tech's core focus areas will be on supporting merchandising, supply chain, and store operations, though Vemana says he will share more details about his spending priorities in March 2026.

But he vows that technology will play a critical role in lifting Target's overall sales.

“Not a single minute goes by without me thinking about growth,” says Vemana.