What Happened?
Shares of online study and academic help platform Chegg (NYSE:CHGG) jumped 6.2% in the afternoon session after its CEO and President, Daniel Rosensweig, disclosed a significant purchase of company shares, which was viewed as a strong vote of confidence in the firm’s future. Rosensweig bought 100,000 shares on the open market. Such a move by a top executive was often interpreted by investors as a signal that leadership believed the company was on the right track. Adding to the positive sentiment, Chegg also announced it had repurchased $20 million of its convertible senior notes due in 2026 for $19.4 million in cash. This action was seen as a prudent financial step that helped to strengthen the company's financial position.
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What Is The Market Telling Us
Chegg’s shares are extremely volatile and have had 98 moves greater than 5% over the last year. In that context, today’s move indicates the market considers this news meaningful but not something that would fundamentally change its perception of the business.
The previous big move we wrote about was about 21 hours ago when the stock dropped 4.4% on the news that investor fears over artificial intelligence disrupting the software industry sparked a broad sell-off. The anxiety stemmed from the rapid adoption of new 'agentic AI' tools, which some investors believed could dismantle traditional Software-as-a-Service (SaaS) business models. This 'AI Panic' led to indiscriminate selling across the sector. The market move reflected growing concerns about the downside of the AI boom for established software companies.
Chegg is down 40.5% since the beginning of the year, and at $0.58 per share, it is trading 68.3% below its 52-week high of $1.84 from September 2025. Investors who bought $1,000 worth of Chegg’s shares 5 years ago would now be looking at an investment worth $5.52.
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