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Chegg Inc. Slashes 388 Jobs, Reinstates Former CEO in Major Overhaul Amid AI Disruption

SANTA CLARA, 27 October 2025 – Ed-tech company Chegg Inc. has announced a sweeping restructuring initiative as it grapples with the rapid advance of generative-AI tools, which are disrupting its core homework-help and textbook-rental business model. The company will cut 388 jobs globally, roughly 45% of its workforce, and has reinstated its former CEO, Dan Rosensweig, replacing current CEO Nathan Schultz, who will assume an advisory role.

The Forcing Function: AI and Traffic Losses

Chegg cited โ€œthe new realities of AI and reduced traffic from Google to content publishersโ€ as principal reasons behind the sharp drop in usage and revenue. According to the company, these trends have challenged its business model built around step-by-step homework help, textbook rentals and tutoring services.

Costs, Impact & Strategy Pivot

The restructuring is expected to incur charges of about US$15 – 19 million in the first quarter of 2026, and US$12 – 16 million by the fourth quarter, as Chegg realigns operations and reduces its workforce.

In its public statement, the company reaffirmed it would continue as a standalone entity after concluding its strategic review, pulling back from prior speculation of a sale or privatisation.

Regional & Asian Investor Implications

Although Chegg is U.S.-based, the restructuring carries lessons and signals for Asian markets and investors:

  • Industry disruption: The move underscores how AI adoption is reshaping the ed-tech sector globallyโ€”businesses offering content, homework help and tutoring must rethink models as students turn to free or partially free AI tools.
  • Traffic & monetisation risks: Cheggโ€™s drop in traffic and demand mirrors a broader risk for firms dependent on online traffic, search referrals and subscription models, a key consideration for regional ed-tech firms in Southeast Asia.
  • Strategic leadership shifts: Bringing back Dan Rosensweig signals a return to veteran leadership during a turnaround phase, investors should note that leadership changes often accompany major shifts in strategy, business model and cost structure.
  • Cost-structure and margins: With large-scale job cuts and cost provisions, timing for profit recovery is now further out, making cash-flow, margin and runway key focus points for investors.

What to Watch Next

For Asian stakeholders, the key developments to monitor include:

  • How Chegg adapts its service offering in a world where generative-AI tools are available to students.
  • Whether the company shifts into new geographies, product lines (e.g., credentialing, career services) or partnerships that align to the changed demand dynamics.
  • Whether regional ed-tech companies emulate or diverge from Cheggโ€™s strategy, some may accelerate pivot to AI-assisted tutoring models, others may face similar headwinds.
  • The broader sentiment in ed-tech valuations, which may be under pressure if Cheggโ€™s turnaround takes longer than expected.

Author

  • Bernard is a social activist dedicated to championing community empowerment, equality, and social justice. With a strong voice on issues affecting grassroots communities, he brings insightful perspectives shaped by on-the-ground advocacy and public engagement. As a columnist for The Ledger Asia, Bernard writes thought-provoking pieces that challenge norms, highlight untold stories, and inspire conversations aimed at building a more inclusive and equitable society.

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