Chegg, Inc. reported continued revenue declines and operating losses in 2025 despite efforts to pivot toward a skilling-focused business model powered by AI. The company undertook significant workforce reductions and cost rationalization in response to competitive headwinds from generative AI tools offered by large technology companies. Chegg’s core Academic Services segment remains under pressure, while its growing Skilling segment targets a large market opportunity in workforce upskilling and language learning. Liquidity remains adequate with positive operating cash flow for 2025, though free cash flow was negative due to capital expenditures. The company paused share repurchases to preserve capital. Key areas for investors include execution of AI integration, growth in the skilling business, and navigating regulatory risks related to data privacy.