Chegg lost roughly 99% of its market value between its 2021 peak and early 2026, with subscribers down 31% year-on-year in Q1 2025 and two rounds of layoffs across the year (22% in May and 45% in October) cutting headcount by more than half. CEO Nathan Schultz told the May 2025 earnings call that the trends impacting the business would worsen before they got better.
Foundation-model providers and hyperscalers are now bundling AI for institutions at no marginal cost: Oxford became the first UK university to roll out ChatGPT Edu campus-wide in September 2025, and Anthropic's Claude for Education has been picked up by LSE, Northumbria, Northeastern, Syracuse and the University of Pittsburgh in the same window. Khanmigo expanded from 68,000 pilot users to over 700,000 across more than 380 districts in a single year, and MagicSchool reached six million educators by October 2025, more than the entire US K-12 teacher population.
The defensible product of 2027 is unlikely to be the one that did content delivery, homework help or generic tutoring; the moats that look most likely to hold tend to sit in the system of record, the regulated assessment layer, the proprietary curriculum, or the workflow tools that teachers and administrators actually use day to day.