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© 2026 Chegg, Inc. / All Rights Reserved Q3-26 Investor Presentation November 3, 2026
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2© 2026 Chegg, Inc. / All Rights Reserved Safe Harbor Statement Forward-Looking Statements This investor presentation contains forward-looking statements made pursuant to the safe harbor provisions of the Private Securities Litigation Reform Act of 1995, which include, without limitation, statements regarding customer retention, the growth of the skilling market and our skilling business, , development and customer adoption of our products, development of new partnerships and distribution channels, future expenses and profitability, future operating results including those in the “Business Outlook” section, repayment of debt, and utilization of our balance sheet, including future repurchases of debt or equity securities under our existing securities repurchase program, and our ability to utilize AI tools to enhance and differentiate our product offerings and control costs. The words “anticipate,” “believe,” “estimate,” “expect,” “intend,” “project,” “endeavor,” “will,” “should,” “future,” “transition,” “outlook” and similar expressions, as they relate to Chegg, are intended to identify forward-looking statements. These statements are not guarantees of future performance, and are based on management’s expectations as of the date of this presentation and assumptions that are inherently subject to uncertainties, risks and changes in circumstances that are difficult to predict. Forward-looking statements involve known and unknown risks, uncertainties and other factors that may cause actual results, performance or achievements to differ materially from any future results, performance or achievements. Important factors that could cause actual results to differ materially from those expressed or implied by these forward-looking statements include the following: the effects of AI technology on Chegg’s business and the economy generally; Chegg’s ability to attract new learners and retain existing learners in light of declining revenue and user traffic; Chegg's ability to innovate and offer new products and services in response to competitive technology and market developments, including AI; Chegg’s ability to diversify its revenue streams with business-to-institution programs and other enterprise offerings; the uncertainty surrounding the evolving educational landscape; Chegg’s ability to build and maintain strong brands and reputation; Chegg’s ability to develop new product and service offerings and their adoption by customers; competition in all aspects of Chegg’s business, including with respect to AI and Chegg's expectation that such competition will increase; challenges related to Chegg’s international operations; Chegg’s ability to maintain its services and systems without interruption, including as a result of technical issues, cybersecurity threats, or cyber-attacks; disruptions of services provided to us by third parties, including web hosting and payment processing services; changes in regulation, in particular those concerning privacy, marketing, and education; risks related to our ability to comply with regulations, obligations and policies related to data privacy; the outcome of any current litigation and investigations, including our litigation against Google and litigation against us; misuse of Chegg’s platform and content; the effectiveness of Chegg’s restructuring activities and disruptions related to them; changes in the education market, including as a result of AI technology; the possibility that the NYSE may delist our common stock; and general economic, political and industry conditions, including inflation, recession and war. All information provided in this presentation is as of the date hereof, and Chegg undertakes no duty to update this information except as required by law. These and other important risk factors are described more fully in documents filed with the Securities and Exchange Commission, including Chegg's most recent annual report on Form 10-K, subsequent quarterly reports on Form 10-Q and other filings with the Securities and Exchange Commission, which could cause actual results to differ materially from expectations. Use of Non-GAAP Measures To supplement Chegg’s financial results presented in accordance with generally accepted accounting principles in the United States (GAAP), this presentation contains non-GAAP financial measures, including EBITDA, Adjusted EBITDA, and free cash flow. For reconciliations of these non-GAAP financial measures to the most directly comparable GAAP financial measures, please see the Appendix to this presentation. The presentation of these non-GAAP financial measures is not intended to be considered in isolation from, as a substitute for, or superior to, the financial information prepared and presented in accordance with GAAP and may be different from non-GAAP financial measures used by other companies.
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3© 2026 Chegg, Inc. / All Rights Reserved Who Are We? We put learners first Chegg is a learning and employability platform that helps students and lifelong learners build the skills, confidence, and career readiness to succeed from learning to earning, while helping businesses develop and upskill their workforce.
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4© 2026 Chegg, Inc. / All Rights Reserved Q3-26 Highlights We delivered a good third quarter and outperformed our expectations on revenue, adjusted EBITDA, and free cash flow,reflecting our ability to execute against our priorities while investing for future growth. AI is improving operational efficiency across the company and driving meaningful gains in profitability and cash generation. Eliminating our debt was a key objective for 2026 and marks an important milestone in strengthening our balance sheet and improving our financial flexibility. Starting last year, we embarked on our next big chapter, rearchitecting the company to be AI-first, building a sustainable cost structure, and strengthening our balance sheet so we could accelerate our bigger vision. We are combining our proprietary data, technology, AI, and deep insight into how students learn and build careers to expand into employability, helping students build the skills, confidence, and connections needed to graduate, find internships, and transition to the workforce. Chegg’s employability platform is the convergence of everything we have built - our academic platform, our skilling business, and our language learning capability - into one service that addresses one of the most pressing needs students face today. Our goal remains the same: return Chegg to growth with high margins and strong free cash flow. Our clean balance sheet and cash generation position us to invest in organic and inorganic growth. We see opportunities to acquire companies with strong technology and customer bases that can leverage our employability platform to scale faster at significantly lower costs.
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5© 2026 Chegg, Inc. / All Rights Reserved Chegg - Language Learning Uniquely designed to serve success seekers who are highly motivated learners aiming for academic and professional excellence. Busuu offers an unparalleled combination of AI-powered, self paced study and live practice with native speakers worldwide. It offers a comprehensive learning suite, combining self paced learning, live tutors and community-based interaction. The curriculum is developed by expert linguists which is validated by industry proven efficacy results. Major multinational companies choose Busuu for its engaging, results driven learnings applications which can be tailored to specific industries and job roles. Performance platform - helping people communicate with confidence and impact, in any language, when it counts
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SLIDE 6 Chegg – Language Learning and Workplace Performance Busuu helps learners perform with confidence in another language, when it counts 01 From learning to performance Built for real work moments, from meetings and presentations to client calls and negotiations 02 Language and skills in one path Workplace skills courses, taught alongside the language the learner is using for work. 03 Measured on outcomes Designed to improve how people perform at work, giving employers a clearer view of impact
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SLIDE 7 The new Busuu: built for real workplace moments Learners rehearse presentations, client meetings and negotiations with an AI speaking partner, and get feedback only people can give from expert tutors and peers.
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SLIDE 8 Chegg Language Learning - Key Product Features 01 Goal-based learning path Finds what each learner is working towards, then personalises their path 02 AI speaking partner Rehearse presentations, client meetings and negotiations with AI, available 24/7 03 Live tutoring and peer practice Expert tutors and the Busuu community add the feedback only people can give 04 Workplace skills courses Presenting, negotiating and running meetings, taught in the language learners need 05 Impact for employers Goes beyond course completion to give a clearer picture of the impact of learning
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9© 2026 Chegg, Inc. / All Rights Reserved Chegg - Skills Helps working adults and students gain practical, role-relevant skills that drive real business results. The programs bridge the gap between today’s job demands and tomorrow’s opportunities — helping employers future- proof their workforce and learners advance their careers. A learning experience designed for skill mastery & application • Hands-on practice: Engages learners with scenario-based simulations and real-world tools to build confidence and align skill growth with business goals. • Engaging, short-form learning: Delivers interactive content through videos, quizzes, and projects – paired with skills- based assessments and capstones to reinforce and validate capabilities. Drive Real Business Results
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10© 2026 Chegg, Inc. / All Rights Reserved Chegg – Skills Impact • 80% of graduates say that Chegg Skills has positively impacted their career • 71% report their future career outlook has improved • 73% of them believe that their program has prepared them to succeed in their current or future role • 67% say they begin applying their skills immediately after completing their program … and employee retention • 92% of Skills graduates remain with the same employer 6-12 months after completing their program • 62% of them say employer-sponsored education was extremely important in their decision to stay Outcomes data is calculated from the Chegg Skills survey conducted among self-reporting program graduates between January 1, 2025 and August 15, 2025. The survey was fielded between January 27, 2026 and March 3, 2026. Survey respondents were offered a $15 gift card. Respondent base (n=200) among 1,408 invites. The sample size represent s this population within a margin of error of 5% at 95% confidence. Survey responses are not a guarantee of any particular results, as individual experiences may vary. Chegg Skills development drives career growth and confidence…
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FOUNDATIONS OF MOBILITY Topic domains that open opportunity UPSKILLING RESKILLING • Technology Fundamentals • AI Fundamentals • Using Data in Business • Communication Skills for Professional Growth • Business Operations Essentials AI Upskilling • AI Fundamentals • AI Prompt Engineering • Practical AI for Clinicians • Practical AI for Healthcare Administration • Applying AI in Cybersecurity • Applying AI in Data Analytics • Applying AI in Web Development • Applying AI in Web Design • Applying AI in Customer Service Tech Upskilling • Introduction to Cybersecurity • Introduction to Data Analytics • Technology Fundamentals Data Programs • Data Analytics • Data Engineering • Data Science • Financial Analysis Tech Programs • Cybersecurity • Software Engineering (full-stack) • Web Development • Frontend Web Development • Backend Web Development • IT Professional • UX/UI Design Business Programs • Frontline Leadership • Sales Professional • Digital Marketing • Technical Project Management New… From Classroom to Career: Landing a job in a GenAI world • STEM track • Business track Programs designed expressly for college students. Chegg - Skills We deliver a technology-driven and human-supported learning experience that enhances professional growth. Our programs combine industry-aligned curriculum, personalized coaching, and AI-enabled tools to help learners stay competitive in an evolving job market.
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12© 2026 Chegg, Inc. / All Rights Reserved Financial Highlights: Q3 2026 Chegg Revenue Our legacy homework-help business continued to decline as expected, while we focused investment on the areas we believe offer the greatest long-term opportunity. We entered into new skilling distribution partnerships, enhanced our language offering, and continued building our employability platform, which we expect to contribute more meaningfully in 2027.
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13© 2026 Chegg, Inc. / All Rights Reserved Financial Highlights: Q3 2026 Adjusted EBITDA, Free Cash Flow, and CapEx Non-GAAP Operating Expenses, Adjusted EBITDA and Free Cash Flow are non -GAAP measures. Reconciliations of Operating Expenses to Non-GAAP Operating Expenses, Net Loss to Adjusted EBITDA and Net Cash Provided by (Used in) Operating Activities to Free Cash Flow are set forth in the appendix. Q3 non-GAAP operating expenses were $31.2 million, down 36% year over year. This reduction reflects the impact of our cost manag ement initiatives and the use of AI to streamline operations and improve productivity across the organization. Adjusted EBITDA for the quarter was $5.4 million, representing a margin of 12%. Free cash flow in the quarter was $5.5 million, reflecting our continued focus on cash generation and disciplined financial m anagement. CapEx was $1.7 million, down 71% year-over-year. For full year 2026, we are targeting a greater than 60% reduction in CapEx. $13 $5 0 2 4 6 8 10 12 14 Q3-25 Q3-26 Adjusted EBITDA $ millions ($1) $6 (2) 0 2 4 6 Q3-25 Q3-26 Free Cash Flow $ millions $6 $2 0 6 12 18 24 30 36 42 Q3-25 Q3-26 CapEx $ millions
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14© 2026 Chegg, Inc. / All Rights Reserved Balance Sheet We ended the quarter with $43.6 million in cash and investments and fully repaid our remaining convertible debt. Eliminating our debt was a key objective for 2026 and marks an important milestone in strengthening our balance sheet.
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15© 2026 Chegg, Inc. / All Rights Reserved Business Outlook (1) Non-GAAP financial measure. See appendix for reconciliation of a) Net Loss to EBITDA and Adjusted EBITDA, b) Forward -Looking Net Loss to EBITDA and Adjusted EBITDA, and c) Net Cash Provided by Operating Activities to Free Cash Flow. CapEx includes purchases of property and equipment. Q3 2026 Results Q4 2026 Guidance Total Net Revenue $46.5m $38m - $40m Gross Margin % 52% 46%-48% Adjusted EBTIDA1 $5.4m Approximately $1m CapEx $1.7m Free Cash Flow1 $5.5m
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© 2026 Chegg, Inc. / All Rights Reserved Appendix
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17© 2026 Chegg, Inc. / All Rights Reserved Reconciliation of Net Loss to EBITDA and Adjusted EBITDA
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18© 2026 Chegg, Inc. / All Rights Reserved Reconciliation of Forward-Looking Net Loss to EBITDA and Adjusted EBITDA
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19© 2026 Chegg, Inc. / All Rights Reserved Reconciliation of Net Cash Provided by Operating Activities to Free Cash Flow
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20© 2026 Chegg, Inc. / All Rights Reserved Reconciliation of Operating Expenses to Non-GAAP Operating Expenses