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A.I. can kill your business overnight. Just ask the CEO of Chegg

By
Rachel Shin
Rachel Shin
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By
Rachel Shin
Rachel Shin
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July 12, 2023, 4:41 PM ET
Dan Rosensweig discusses CheggMate.
Dan Rosensweig at Fortune’s 2023 Brainstorm Tech conference.Fortune Brainstorm Tech Conference 2023

On May 2, Chegg’s stock plummeted 48% after the company released an earnings report saying that A.I. posed a major risk to its business. “Since March we saw a significant spike in student interest in ChatGPT. We now believe it’s having an impact on our new customer growth rate,” said the report that set off a stunning stock wipeout. The edtech company is working hard to bounce back by creating its own educational chatbot that it thinks can rival ChatGPT, CEO Dan Rosensweig said at Fortune’s Brainstorm Tech conference on Wednesday.

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“The reason I was invited on is I’m the poster child for getting your ass kicked in the public markets by A.I. since I lost 40% of value in five minutes,” Rosensweig said. “So for those of you who didn’t want to take that, I took it for you,” Rosensweig said with apparent sarcasm. “My pleasure.” 

Chegg’s new A.I. tool, called CheggMate, will be a personal learning assistant for students that creates bespoke lesson plans. Trained on a set of 100 million correct answers to 17 million new questions posed by students each year over the past decade, the A.I. will create a tailored learning experience for students, taking into account their learning style, the date of their exam or deadline, and even how they’re feeling that day, among other factors. It will also connect students to remote study groups and help them find job opportunities. 

“Just imagine the following scenario,” Rosensweig said, “you start to have a conversation with somebody that knows you, knows how you’re feeling that day, knows what you’re studying, knows when your midterm is, knows what you’re good at, what you’re bad at, builds you a personalized plan, advocates for you.”

Right now, general large language models such as OpenAI’s ChatGPT, Microsoft’s Bing, and Google’s Bard are prone to “hallucinations,” presenting false or fabricated information as fact. Rosensweig said Chegg is trying to build a chatbot that can be trusted to always provide correct answers. 

CheggMate will also incorporate various wellness metrics into a student’s learning plan. It will be able to track how much sleep the student gets and can recommend meditation exercises. It will also provide professional guidance, such as data on the top positions that alums from the student’s school with the same major landed.

“It takes a look at all of your tests that you upload, tells you what professional skills you could develop, offers you the opportunity to learn skills you don’t have, and ultimately connects you to a job and ranks you,” Rosensweig said.

‘Deprioritizing really engaging curiosity’

At Brainstorm Tech, a Harvard graduate named Nadya Okamoto questioned whether Chegg would really be used for learning rather than as an easy way for students to cheat. Okamoto, who founded the menstrual equity nonprofit Period, admitted to using Chegg to complete her problem sets at Harvard, saying she didn’t care about learning and had a “C’s get degrees” mindset.  

“I am concerned in talking to a lot of the people that I meet in my day-to-day work about the level that ChatGPT is being used to complete essays, to do homework and problem sets,” Okamoto said. “A concern of mine as a Gen Z elder is feeling like these sorts of tools are making it easier and easier to just get the answers, and deprioritizing really engaging curiosity.”

Chegg is used so frequently by students to cheat that, according to a Forbes article, it’s been coined as a verb: “chegging.” To “chegg” homework means to quickly search for answers in the site’s massive database, or to pose questions to Chegg experts who stand by 24/7 to respond to student subscribers. During the pandemic, when most schools went remote and exams were online, Chegg’s stock price more than tripled. Chegg officials have said in the past that the vast majority of its users are honest and use the platform to supplement their learning, and that the company invests heavily to prevent the misuse of its service. Update: Chegg provided the following statement after the story was published: “No matter how or where one chooses to advance your education, Chegg believes that academic integrity is fundamental to learning.” 

Rosensweig took issue with Okamoto’s description of Chegg as a way to cheat. “The truth is, you can only cheat if the professor doesn’t do any work. If the professor doesn’t write their own question, doesn’t change the question, gives you a take home test. That’s on the schools. We need people that know how to learn,” he said.

Rosensweig also responded by saying that the Harvard population composes a tiny portion of the U.S. population, and Chegg was concerned with less privileged students who don’t already have access to an elite education.

“What the kids at Harvard did, I don’t give a shit. I care about the kids who are trying to make their life better,” Rosensweig said at the conference. “We are being built for the student that is self-initiated, that wants to learn, that needs to understand, that needs to graduate with a skill.”

Join us at the Fortune Workplace Innovation Summit May 19–20, 2026, in Atlanta. The next era of workplace innovation is here—and the old playbook is being rewritten. At this exclusive, high-energy event, the world’s most innovative leaders will convene to explore how AI, humanity, and strategy converge to redefine, again, the future of work. Register now.
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