• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia

Exclusive

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

TechAI

Marc Benioff blasts Microsoft’s Copilot AI tool as the next ‘Clippy’

Sasha Rogelberg
By
Sasha Rogelberg
Sasha Rogelberg
Reporter
Down Arrow Button Icon
Sasha Rogelberg
By
Sasha Rogelberg
Sasha Rogelberg
Reporter
Down Arrow Button Icon
September 23, 2024, 3:12 PM ET
Marc Benioff speaks and gestures with both his hands in front of him.
Salesforce CEO Marc Benioff said Microsoft's Copilot does not hold high value for its users.David Paul Morris/Bloomberg—Getty Images

During the PC boom of the 1990s, Microsoft introduced Clippy as a friendly face to help users hone their word-processing skills. An animated paper clip with round cartoon eyes and expressive eyebrows floating over a sheet of yellow legal paper, Clippy would frequently and spontaneously pop out of the corner of the screen to provide advice and tips on saving files and using good grammar. Clippy was also almost universally hated, his shifting eyes and unsolicited feedback providing more irritation than comfort.

Recommended Video

Salesforce CEO Marc Benioff believes Microsoft is on its way to a repeat act of creating a loathsome program meant to assist users in Copilot, the tech company’s foray into AI-powered assistance.

“We all know now that Microsoft Copilot is basically the new Microsoft Clippy, that customers have not gotten value from it,” Benioff said in a Bloomberg interview Thursday during Salesforce’s Dreamforce conference in San Francisco.

Microsoft has invested over $13 billion into OpenAI, the large language model powering Copilot. Launched in November 2023, Copilot promised to help expedite menial office tasks like summarizing Teams meetings and draft emails. Chemical company Dow plans to introduce the assistant to its 35,900 employees by the end of the year after a successful pilot test, but others aren’t sold on the program’s $30-per-month costs—particularly after Microsoft has had to iron out Copilot Designer’s issue of generating inappropriate images and its Recall feature that took excessive screenshots, jeopardizing user privacy.

Of course, Benioff’s criticisms of Copilot are in Salesforce’s best interest. The software giant announced a “hard pivot” to Agentforce, its own AI assistant program. The program, introduced last week, promises to integrate with hundreds of other applications to streamline business operations. It’s part of a growing movement of implementing AI agents over copilots to take tech assistance one step further.

“This is like we’re selling science projects to companies, and they’re tired of it. They have not gotten the value, which is why you see these customers so excited they’re coming here,” Benioff said. “And they’re getting immediate value, and they’re able to use this next generation platform to do everything that they’ve heard that’s possible.”

Benioff is banking on Agentforce’s success, which is already being piloted by a few dozen companies like Wiley, Open Table, and Fossil. It hasn’t been all smooth sailing for the program so far. Andreessen Horowitz challenged Salesforce’s ability to create a compelling AI assistant, saying in a July blog post, “We believe AI will so fundamentally reimagine the core system of record and the sales workflows that no incumbent is safe.”

Salesforce and Microsoft did not immediately respond to Fortune’s request for comment.

AI skepticism

AI skeptics are bracing themselves for the future of tech assistants. With upwards of $200 billion expected to be invested into AI by 2025, according to Goldman Sachs, some in the industry fear AI will not be able to keep its promise of revolutionizing how people engage with tech, threatening the lofty valuations of many tech startups.

Beyond a potentially muted moment in the AI hype cycle, firms also have to contend with mounting concerns over privacy and safety.

“Tech companies are putting this deeply flawed tech in the hands of millions of people and allowing AI models access to sensitive information such as their emails, calendars, and private messages,” Melissa Heikkilä wrote in the MIT Technology Review last October.

After introducing updates and AI agent features to Copilot last week, Microsoft doubled down on its promise of privacy when using Copilot’s chatbot feature. Jamie Teevan, Microsoft’s chief scientist, said Copilot customers will see greater value in the product once they optimize how to use it. She added the company is keen to avoid the pitfall of a nagging assistant like Clippy when continuing to develop its AI agents. Benioff isn’t convinced.

“Microsoft has deceived customers with their AI strategy, they don’t need to DIY it,” he said. “We build it into our platform, customers shouldn’t be forced to train and retrain their models.”

Join our exclusive webinar on May 28, featuring tech leaders from Orange, Mars, Reckitt, and Saint-Gobain. Apply to attend and receive Fortune’s editorial takeaways.
About the Author
Sasha Rogelberg
By Sasha RogelbergReporter
LinkedIn iconTwitter icon

Sasha Rogelberg is a reporter and former editorial fellow on the news desk at Fortune, covering retail and the intersection of business and popular culture.

See full bioRight Arrow Button Icon

Latest in Tech

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Tech

altman
CommentarySam Altman
Musk vs. Altman: AI safety cannot be one man’s job
By Stavros GadinisMay 18, 2026
7 hours ago
Pope Leo launches an AI commission days before he releases a papal letter alongside Anthropic cofounder Christopher Olah
AIPope
Pope Leo launches an AI commission days before he releases a papal letter alongside Anthropic cofounder Christopher Olah
By Catherina GioinoMay 18, 2026
8 hours ago
John Ketchum, CEO of NextEra Energy, speaks during BlackRock's 2026 Infrastructure Summit in Washington, DC, on March 11, 2026. Photographer: Daniel Heuer/Bloomberg via Getty Images
EnergyNextEra Energy
NextEra’s $67 billion Dominion takeover creates the world’s largest utility—just in time to win the AI data-center power surge
By Jordan BlumMay 18, 2026
8 hours ago
Harvard University banners hang in front of a building
CryptoCryptocurrency
Harvard sold off its entire $87 million Ethereum stake just one quarter after buying it
By Jack KubinecMay 18, 2026
8 hours ago
Not the Allbirds effect: Japan’s top bidet maker Toto has been quietly making chip supplies for decades, and the stock market finally noticed
AIChips
Not the Allbirds effect: Japan’s top bidet maker Toto has been quietly making chip supplies for decades, and the stock market finally noticed
By Catherina GioinoMay 18, 2026
9 hours ago
monet
CybersecuritySocial Media
6.7 million people thought they were ripping apart an AI-generated Monet painting. But it was real
By Nick LichtenbergMay 18, 2026
10 hours ago

Most Popular

The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
Politics
The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
By Jake AngeloMay 12, 2026
6 days ago
Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI
AI
Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI
By Jake AngeloMay 16, 2026
3 days ago
While Trump insisted the Iran war would end ‘soon,’ an account in his name was buying millions in oil, defense and gold
Economy
While Trump insisted the Iran war would end ‘soon,’ an account in his name was buying millions in oil, defense and gold
By Eva RoytburgMay 18, 2026
10 hours ago
EXCLUSIVE: An hour in the Oval Office with the CEO-in-Chief, President Trump
Politics
EXCLUSIVE: An hour in the Oval Office with the CEO-in-Chief, President Trump
By Alyson ShontellMay 18, 2026
22 hours ago
The top foreign holders of U.S. debt may soon dump Treasury bonds and bring their money back home, potentially spiking borrowing costs
Economy
The top foreign holders of U.S. debt may soon dump Treasury bonds and bring their money back home, potentially spiking borrowing costs
By Jason MaMay 17, 2026
1 day ago
Current price of oil as of May 18, 2026
Personal Finance
Current price of oil as of May 18, 2026
By Joseph HostetlerMay 18, 2026
15 hours ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.