Business

AI is reshaping how Americans shop. Here’s how Target’s top tech leader says the retailer is adapting

Published

2 months ago

November 26, 2025

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.

John Kell

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NEWS PACKETS

Anthropic rolls out a new AI model. Anthropic on Monday debuted a new version of the company’s LLM that the AI startup says is better at automating coding, deep research, reasoning, and mathematics skills than its predecessors. The new Claude Opus 4.5 is Anthropic’s third major model launch in just two months, highlighting the intense race among OpenAI, Google, and other AI model makers who are competing to offer the best AI technologies for enterprise clients. The Verge, meanwhile, points out that the latest Claude model “is harder to trick with prompt injection than any other frontier model in the industry.” This comes after Chinese hackers earlier this month were suspected of using Anthropic’s AI coding tool to breach dozens of organizations, including tech companies and government agencies.

Meanwhile, Google’s Gemini 3 is getting rave reviews. The new Gemini 3 AI model has been out for less than two weeks but already generating a lot of buzz, with Salesforce CEO Marc Benioff declaring on X that after using ChatGPT every day for three years, the executive spent two hours on Gemini 3 and vowed, “I’m not going back. The leap is insane.” Tech executives have been heaping praise, including OpenAI CEO Sam Altman, who privately told colleagues in an internal memo that Google’s update would create “temporary economic headwinds” for the ChatGPT maker, according to The Information.

Tech leaders depart at Airbnb, General Motors. Last week, rental platform Airbnb disclosed that CTO Ari Balogh would step down from his role in December but remain with the company through at least February to assist with the leadership transition. The company told Bloomberg that it will share more on those transition plans soon. Prior to joining Airbnb in 2018, Balogh was VP of engineering at Google. Separately, auto giant General Motors confirmed that Barak Turovsky, who had served as chief AI officer for less than nine months, would depart. The role was created with Turovsky’s hire and GM hasn’t yet said if the company would replace him, but did tell CIO Dive that the AI team would report to the manufacturing and engineering organization.

AI bubble chatter continues to swirl. Is the hype around AI beginning to deflate? Every news outlet from Fortune to NPR to Bloomberg has been weighing in with no clear consensus, though Nvidia CEO Jensen Huang says AI companies are in a no-win situation. “If we delivered a bad quarter, it is evidence there’s an AI bubble. If we delivered a great quarter, we are fueling the AI bubble,” he told employees, according to audio of an internal all-hands meeting reviewed by Business Insider. Alphabet CEO Sundar Pichai acknowledged in a recent interview with the BBC that there was some “irrationality” in the AI boom. And some have pointed to Oracle as, well, a potential oracle of the jitters. Oracle’s stock has tumbled 40% since September, when it signed a $300 billion OpenAI deal, though one of the main issues is that the cloud-software company is borrowing a lot of cash to fund its AI ambitions.

ADOPTION CURVE

CIOs are adding new skills and feeling more confident as they adopt AI. 61% of CIOs report that they felt they were ahead of their competitors on AI as full implementation of the technology increased to 42% from 11% in 2024, according to Salesforce’s second annual study that surveyed responses from 200 global CIOs from 24 countries. These CIOs are also extremely bullish on agentic AI: with 96% saying their company either currently uses this more autonomous form of the technology or plans to within the next two years. CIOs also report that they are dedicating 30% of their budget to agentic AI. (Salesforce, it’s worth noting, has made a big push as a vendor of agentic AI technology).

With the AI boom celebrating its third birthday (ChatGPT launched in November 2022), 75% of CIOs now report feeling more confident in their role than they did a year ago. They also report that they’ve personally improved their leadership, storytelling, and communications skills, and amid the move toward agentic, report working more closely with C-suite leaders like the CEO, CFO, and COO.

Shibani Ahuja, senior vice president of enterprise IT strategy at Salesforce, tells Fortune that the role of the CIO has evolved to facilitate more strategic conversations with other C-suite leaders about what business transformation will look like when enabled with AI. “CIOs are pushing the boundaries, because they are maybe two steps ahead of where others are,” says Ahuja. These technologists, she says, are more bold in challenging their C-suite peers in saying, “you’ve come up with a use case that automates from here-to-here. That’s simple. Do you really want to challenge that a bit more?”

Courtesy of Salesforce

JOBS RADAR

Hiring:

– Hardesty & Hanover Construction Services is seeking a CIO, based in New York City. Posted salary range: $200K-$250K/year.

– Charles B Wang Community Health Center is seeking a CIO, based in New York City. Posted salary range: $180K-$210K/year.

– Atomic Machines is seeking a head of IT, based in Emeryville, California. Posted salary range: $175K-$235K/year.

– StemWave is seeking a head of IT and business systems, based in Boston. Posted salary range: $130K-$170K/year.

Hired:

– Intel has appointed Cindy Stoddard to serve as SVP and CIO, effective December 1, and reporting directly to CEO Lip-Bu Tan to lead the chipmaker’s global IT organization. Stoddard joins Intel from Adobe, where she spent nine years leading global IT and cloud operations. Prior to Adobe, she held senior technology leadership roles at companies including data infrastructure company NetApp and grocery retailer Safeway.

– Guidehousenamed Ron White as CIO, joining the consulting firm to lead internal IT operations, cybersecurity and cloud-first initiatives. Previously, White served as CIO at IT consultancy Avanade, CIO at glass bottle manufacturer O-I Glass, and as a managing director at consulting giant Accenture.

– FormAssemblyannounced that Bryan O’Neill has been promoted to CTO. O’Neill first joined the web form builder company in June 2024 as VP of engineering and has played a key role in expanding FormAssembly’s AI strategy. Prior to that, he served as SVP of technical operations at tech company Babel Street and held senior engineering roles at GMAC Insurance, Lowe’s, and Anheuser-Busch.

– Gallion Health appointed Mathieu Baissac as CTO, joining the health-technology company after it was spun out from the University of Maryland Medical System in July to commercialize its hospital supply chain management software. Baissac previously held senior director roles at healthcare companies Phreesia and Kyruus and as a VP of product management at software firm Flexera Software.

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Business

Crypto market reels in face of tariff turmoil, Bitcoin falls below $90,000 as key legislation stalls

Published

26 minutes ago

January 20, 2026

Jace Porter

If you don’t like the price of Bitcoin, wait five minutes, and it will change. The major cryptocurrency’s volatility has been on full display to start the year, this time dipping about 7% since last week to its current price of just under $90,000 as of mid-day Tuesday.

Other cryptocurrencies have also slid. Ethereum is down 11% in the last six days to its current price of about $3,000, and Solana is down about 14% during that time to its price of about $127.

The dip comes as President Donald Trump threatened European nations with tariffs as they pushed back against his plans to take over Greenland, causing markets to scramble. Meanwhile, crypto markets faced an additional headwind as key legislation for the industry, known as the Clarity Act, became stalled after industry giant Coinbase unexpectedly withdrew its support late last week.

“President Trump’s threat to impose tariffs on Europe has put Bitcoin under pressure,” said Russell Thompson, chief investment officer at Hilbert Group. “The postponement of the Clarity Act in the Senate committee mainly due to concerns from Coinbase eliminated a large amount of positive sentiment in the market.”

Coinbase CEO Brian Armstrong objected to the Clarity Act primarily on grounds that crypto owners would not be able to earn yield from stablecoins. The new uncertainty over the bill, which many assumed was on a smooth path towards a Presidential signature, has shaken the price not just of crypto assets but also the share price of companies exposed to digital assets.

It’s uncertain whether the current headwinds will fade anytime soon. Trump has made his intentions of taking control of Greenland clear. When a group of European nations expressed solidarity with the Danish, he threatened those countries with tariffs, saying he would not back down until Greenland was purchased. Bitcoin and other risk assets subsequently fell, along with major stock indices, while the price of gold rose.

It’s not all gloom and doom for crypto, at least according to some analysts, who view Bitcoin’s correlation with macroeconomic forces as confirmation that digital assets have finally gone mainstream.

“Bitcoin’s reactivity is another sign of its increasing integration with broader macroeconomic forces, signaling maturation rather than fragility, even as short-term volatility continues,” said Beto Aparicio, senior manager of strategic finance at Offchain Labs.

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Business

The 9 most disruptive deals of Trump’s first year back in the White House

Published

57 minutes ago

January 20, 2026

Jace Porter

President Trump lives on deals: “That’s what I do—I do deals,” he once told Bob Woodward. On the one-year anniversary of his second presidency, he’s pushing hard to make his biggest, most disruptive deal ever, one that would bring Greenland under the control of the U.S.—and the global business community is still scrambling to adapt to his approach. Here are nine of Trump’s most unorthodox deals from the past year.

Nine deals that shook the business world

April 2, 2025: Reciprocal tariffs

Trump imposes “reciprocal tariffs” on 57 countries, with each tariff understood as an opening bid in a negotiation. Several countries have since made deals. The one-on-one negotiations, unlike the multilateral system of the past 80 years, can be chaotic for companies and economies

June 13: U.S. Steel “Golden Share”

In return for allowing Nippon Steel to buy U.S. Steel, Trump requires that the U.S. receive several powers over the company, including total power over all the board’s independent directors and vetoes over locations of offices and factories.

July 10: MP Materials

The U.S. pays $400 million for a large equity share in MP and signs a contract to buy all of MP’s rare earth magnets for 10 years. The reason for the equity stake was not disclosed.

July 14: Nvidia, Part 1

JADE GAO—AFP/Getty Images

Trump reverses the U.S. ban on selling Nvidia H20 chips to China in exchange for Nvidia paying the U.S. 15% of the revenue.

July 23: Columbia University

The Trump administration restores $400 million of canceled federal research funding for the university under an unprecedented multipoint deal. For example, Columbia must supply data to the federal government for all applicants, broken down by race, “color,” GPA, and standardized test performance. A few other schools later make similar deals.

August 6: Apple

At a public appearance with Trump, CEO Tim Cook announces Apple will invest an additional $100 billion in the U.S. over four years; Trump announces Apple will be exempt from a planned tariff on imported chips that would have doubled the price of iPhones in the U.S.

August 22: Intel

Intel trades the U.S. government a 9.9% equity stake in exchange for $8.9 billion that might already be owed to Intel under the CHIPS and Science Act. The deal is unusual because the company was not in immediate danger or significantly affecting the economy.

December 8: Nvidia, Part 2:

Trump reverses the U.S. ban on selling powerful Nvidia H200 chips in exchange for Nvidia paying the U.S. 25% of the revenue. Both Nvidia deals are unusual because the payments to the U.S., based on exports, appear to be forbidden by the Constitution.

December 19: Pharma

Nine pharmaceutical companies make deals with Trump that are intended to lower drug prices. This is unusual because Trump negotiated separate deals with each company, and the terms have not been released.

All eyes this week will be watching President Trump at the World Economic Forum in Davos, where the president has hinted he’ll announce some high-stakes agreements. Expect the unexpected.

A version of this piece appears in the February/March 2026 issue of Fortune.

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Business

Microsoft CEO Satya Nadella’s biggest AI bubble warning yet is a challenge to the Fortune 500

Published

1 hour ago

January 20, 2026

Jace Porter

Microsoft CEO Satya Nadella has been leading the charge on artificial intelligence (AI) for years, owing to his long alliance with OpenAI’s Sam Altman and the groundbreaking work from his own AI CEO, Mustafa Suleyman, particularly with the Copilot tool. But Nadella has not spoken often about the fears that rattled Wall Street for much of the back half of 2025: whether AI is a bubble.

At the World Economic Forum annual meeting in Davos, Switzerland, Nadella sat for a conversation with the Forum’s interim co-chair, BlackRock CEO Larry Fink, explaining that if AI growth spawns solely from investment, then that could be signs of a bubble. “A telltale sign of if it’s a bubble would be if all we are talking about are the tech firms,” Nadella said. “If all we talk about is what’s happening to the technology side then it’s just purely supply side.”

However, Nadella offers a fix to that productivity dilemma, calling on business leaders to adopt a new approach to knowledge work by shifting workflows to match the structural design of AI. “The mindset we as leaders should have is, we need to think about changing the work—the workflow—with the technology.”

Growing pains

This change is not wholly unprecedented, as Nadella pointed out, comparing the current moment to that of the 1980s, when computing revolutionized the workplace and opened up new opportunities for growth and productivity and created a new class of workers. “We invented this entire class of thing called knowledge work, where people started really using computers to amplify what we were trying to achieve using software,” he said. “I think in the context of AI, that same thing is going to happen.”

Nadella argues that AI creates a “complete inversion” of how information moves through a business, replacing slow, hierarchical processes with a view that forces leaders to rethink their organizational structures. “We have an organization, we have departments, we have these specializations, and the information trickles up,” Nadella said. “No, no, it’s actually it flattens the entire information flow. So once you start having that, you have to redesign structurally.”

That shift may be harder for some Fortune 500 companies as structural changes could be accompanied by uncomfortable growing pains. Nadella says that leaner companies will be able to more easily adopt AI because their organizational structures are fresher and more malleable. On the other hand, large companies could take time to adopt new workflows.

Despite widespread adoption of AI, the 29th edition of PwC’s global CEO survey found that only 10% to 12% of companies reported seeing benefits of the technology on the revenue or cost side, while 56% reported getting nothing out of it. It follows up on an even more pessimistic finding about AI returns from August 2025: that 95% of generative AI pilots were failing.

PwC Global Chairman Mohamed Kande spoke to Fortune’s Diane Brady in Davos about the finding that many CEOs are cautious and lack confidence at this stage of the AI adoption cycle. “Somehow AI moves so fast … that people forgot that the adoption of technology, you have to go to the basics,” he explained, with the survey finding that the companies seeing benefits from AI are “putting the foundations in place.” It’s about execution more than it is about technology, he argued, and good management and leadership are really going to matter going forward.

“For large organizations,” Nadella told Fink, “there’s a fundamental challenge: Unless and until your rate of change keeps up with what is possible, you’re going to get schooled by someone small being able to achieve scale because of these tools.”

New entrants have the advantage of “starting fresh” and constructing workflows around AI capabilities, while larger firms will have to contend with the flattening effect AI has on entire departments and specializations.

To be sure, Nadella says that large organizations have kept an upper hand, especially when it comes to relationships, data, and know-how. However, he maintains that firms must understand how to use those resources to their advantage to change management style, then that could pose a major roadblock.

“The bottom line is, if you don’t translate that with a new production function, then you really will be stuck,” he said.

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