In 2023, Dan Rosensweig had been president and CEO of Chegg, Inc. (NYSE: CHGG), for over a decade, and had successfully led the company from near bankruptcy to a multi-billion-dollar valuation. But Chegg, an American education technology (EdTech) company based in California, had several current challenges to address. First, the stock price had dropped significantly, erasing 90% of its market capitalization gains. Second, the rise of artificial intelligence (AI) tools like ChatGPT, created by OpenAI, had started to show new possibilities for disrupting many industries, including the EdTech market. Third, college enrollment was declining, a trend that could threaten Chegg’s business. This case sets up a changing EdTech landscape for Rosensweig, who had been a tech executive for 30 years, to tackle. Students can explore the IPO and stock price performance, evaluation of subscription models, growth through acquisition, company financing, and the future of higher education, all through an executive leadership communication lens.