Q2 2026 Chegg Inc Earnings Call

August 6, 2026

Speaker #1: Greetings, and welcome to Chegg, Incorporated's second quarter 2026 earnings conference call. At this time, all participants are in listen-only mode. A question and answer session will follow the formal presentation.

Operator 2: Greetings, and welcome to Chegg, Inc.'s Q2 2026 earnings conference call. At this time, all participants are on a listen-only mode. A question and answer session will follow the formal presentation. If anyone should require operator assistance during the conference, please press star zero on your telephone keypad. I would now like to turn the conference over to your host, Tracey Ford, Vice President of Investor Relations. Thank you. You may begin.

Operator: Greetings, and welcome to Chegg, Inc.'s Q2 2026 earnings conference call. At this time, all participants are in listen-only mode. A question and answer session will follow the formal presentation. If anyone should require operator assistance during the conference, please press star zero on your telephone keypad. I would now like to turn the conference over to your host, Tracey Ford, Vice President of Investor Relations. Thank you. You may begin.

Speaker #1: If anyone should require operator assistance during the conference, please press star zero on your telephone keypad. I would now like to turn the conference over to your host, Tracey Ford, Vice President of Investor Relations.

Speaker #1: Thank you. You may begin.

Speaker #2: Good afternoon. Thank you for joining CHEGG's second quarter 2026 conference call. On today's call, our Dan Rosensweig, President and CEO, and David Longo, Chief Financial Officer.

Tracey Ford: Good afternoon. Thank you for joining Chegg's Q2 2026 conference call. On today's call are Dan Rosensweig, President and CEO, and David Longo, Chief Financial Officer. A copy of our earnings press release, along with our investor presentation, is available on our investor relations website, investor.chegg.com. A replay of this call will also be available on our website. We routinely post information on our website and intend to make important announcements on our media center website at chegg.com/mediacenter. We encourage you to make use of these resources. Before we begin, I would like to point out that during the course of this call, we will make forward-looking statements regarding the future events, including the future financial and operating performance of the company. These forward-looking statements are subject to material risks and uncertainties that could cause actual results to differ materially from those in the forward-looking statements.

Speaker #2: A copy of our earnings press release, along with our investor presentation, is available on our investor relations website investor.chegg.com. A replay of this call will also be available on our website.

Speaker #2: We routinely post information on our website and intend to make important announcements on our media center website at chegg.com/mediacenter. We encourage you to make use of these resources.

Speaker #2: Before we begin, I would like to point out that during the course of this call, we will make forward-looking statements regarding the future events, including the future financial and operating performance of the company.

Speaker #2: These forward-looking statements are subject to material risks and uncertainties that could cause actual results to differ materially from those in the forward-looking statements. We caution you to consider the important factors that could cause actual results to differ materially from those in the forward-looking statements.

Tracey Ford: We caution you to consider the important factors that could cause actual results to differ materially from those in the forward-looking statements. In particular, we refer you to the cautionary language included in today's earnings release and the risk factors described in Chegg's annual report on Form 10-K for the year ended 31 December 2025, filed with the Securities and Exchange Commission, as well as our other filings with the SEC. Any forward-looking statements that we make today are based on assumptions that we believe to be reasonable as of this date. We undertake no obligation to update these statements as a result of new information or future events. During this call, we will present both GAAP and non-GAAP financial measures. Our GAAP results and GAAP to non-GAAP reconciliations can be found in our earnings press release and on the investor slide deck found on our IR website, investor.chegg.com.

Speaker #2: In particular, we refer you to the cautionary language included in today's earnings release and the risk factors described in CHEGG's annual report on Form 10-K for the year ended December 31, 2025, filed with the Securities and Exchange Commission.

Speaker #2: As well as our other filings with the SEC. Any forward-looking statements that we make today are based on assumptions that we believe to be reasonable, as of this date.

Speaker #2: We undertake no obligation to update these statements as a result of new information or future events. During this call, we will present both GAAP and non-GAAP financial measures.

Speaker #2: Our GAAP results and GAAP to non-GAAP reconciliations can be found in our earnings press release and on the investor slide deck found on our IR website investor.chegg.com.

Speaker #2: We also recommend you review the investor data sheet, which is also posted on our IR website. Now, I will turn the call over to Dan.

Tracey Ford: We also recommend you review the investor data sheet, which is also posted on our IR website. Now, I will turn the call over to Dan.

Speaker #3: Thank you, Tracey. And thanks, everyone, for joining CHEGG's second quarter 2026 earnings call. We outperformed our expectations on revenue, adjusted EBITDA, and cash, reflecting our ability to execute against our priorities while investing for future growth.

Dan Rosensweig: Thank you, Tracey. Thanks everyone for joining Chegg's Q2 2026 earnings call. We outperformed our expectations on revenue, adjusted EBITDA, and cash, reflecting our ability to execute against our priorities while investing for future growth. The goals remain the same, return Chegg to growth with high margins and strong free cash flow. Starting last fall, we embarked on our next big chapter, re-architecting the company to be AI-first, building a sustainable cost structure, and strengthening our balance sheet so we could accelerate our bigger vision. Chegg's mission to put students first and help them move from learning to earning has never wavered.

Speaker #3: The goals remain the same. Return CHEGG to growth with high margins and strong free cash flow. Starting last fall, we embarked on our next big chapter: re-architecting the company to be AI-first, building a sustainable cost structure, and strengthening our balance sheet so we could accelerate our bigger vision.

Speaker #3: CHEGG's mission: to put students first and help them move from learning to earning, has never wavered. For almost 20 years, we have evolved to meet students' most important needs, from inventing textbook rental model to make higher education more affordable, then providing 24/7 learning support through CHEGG Study, and then adding skills-based courses to help learners build the skills needed to advance their careers.

Dan Rosensweig: For almost 20 years, we have evolved to meet students' most important needs, from inventing textbook rental model to make higher education more affordable, then providing 24/7 learning support through Chegg Study, then adding skills-based courses to help learners build the skills needed to advance their careers. Each transition has opened up a new chapter of growth for Chegg. The foundation we have built across our products, technology, and data now positions us to expand our focus on employability. We will help students build the skills, confidence, and connections needed to graduate, find internships, and transition into the workforce. Higher education continues to evolve, but one thing will never change. After completing whatever path they pursue, students need a job. For the nearly 20 million students entering today's job market over the next few years, that transition is filled with challenges and uncertainty.

Speaker #3: Each transition has opened up a new chapter of growth for CHEGG. And the foundation we have built across our products, technology, and data now positions us to expand our focus on employability.

Speaker #3: We will help students build the skills, confidence, and connections needed to graduate, the workforce. Higher education continues to evolve, but one thing will never change: after completing whatever path they pursue, students need a job.

Speaker #3: For the nearly 20 million students entering today's job market over the next few years, that transition is filled with challenges and uncertainty. Beginning in Q3, we are soft-launching the next generation of CHEGG by combining our proprietary data AI and deep insight into how students learn and build careers we will reduce the friction for students to get internships and then jobs.

Dan Rosensweig: Beginning in Q3, we are soft launching the next generation of Chegg. By combining our proprietary data, AI, and deep insight into how students learn and build careers, we will reduce the friction for students to get internships and then jobs. The new Chegg will help automate job search and matching while adding coaching that will help students pick the right major, the right courses, and evaluate the right skills. Our plan is to automate the search, the match, and coaching so students can build the right skills, take the right courses, and make the right connections. Chegg will handle the hard parts of applying, tailoring the resumes, drafting cover letters, auto-filling and submitting applications, and even initiating alumni outreach on behalf of the students.

Speaker #3: The new Chegg will help automate job search and matching, while adding coaching that will help students pick the right major, the right courses, and evaluate the right skills.

Speaker #3: Our plan is to automate the search, the match, and coaching so students can build the right skills, take the right courses, and make the right connections.

Speaker #3: CHEGG will handle the hard parts of applying, tailoring the resumes, drafting cover letters, auto-filling and submitting applications, and even initiating alumni outreach on behalf of the students.

Speaker #3: We will then add the ability for students to get company-specific interview prep, personalized feedback, and targeting skill-building courses to close any gaps standing between them and the job.

Dan Rosensweig: We will add the ability for students to get company-specific interview prep, personalized feedback, and targeting skill-building courses to close any gaps standing between them and the job. The result is the platform that takes students from, I need a job, to, I am prepared, applied, and connected, all in one place. It's this 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. We have already had more than 10,000 students use the beta and provide feedback, we will begin rolling out the new service across both Chegg and our site, internships.com, starting in Q3 and all throughout 2027.

Speaker #3: The result is the platform that takes students from "I need a job" to "I am prepared, applied, and connected," all in one place. It's this conversions 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: we have already had more than 10,000 students use the beta and provide feedback, and we will begin rolling out the new service across both CHEGG and our site internships.com starting in the third quarter and all throughout 2027.

Speaker #4: As we expand our focus on employability, our skilling business remains an important part of the opportunity ahead. By helping organizations build workforce capabilities and helping learners develop and apply relevant skills, we are creating a platform that connects learning, skills development, and career outcomes.

Dan Rosensweig: As we expand our focus on employability, our skilling business remains an important part of the opportunity ahead.

Dan Rosensweig: By helping organizations build workforce capabilities and helping learners develop and apply relevant skills, we are creating a platform that connects learning, skills development, and career outcomes. Chegg Skills has been built as a multi-channel platform spanning enterprise, institutional, employer, and marketplace channels to create a more diversified foundation for growth. We have already signed six new partners this year, including OpenSesame and Dale Carnegie, those launches will take place over the H2 of the year. We will continue to expand into enterprises and schools over the next few years using AI and data to dramatically expand and personalize our catalog while making our courses even more affordable. Our language skills are an important component of employability, helping people expand career opportunities and communicate more effectively in an increasingly global workforce.

Speaker #4: CHEGG Skills has been built as a multi-channel platform, spanning enterprise, institutional, employer, and marketplace channels, to create a more diversified foundation for growth. We have already signed six new partners this year, including OpenSesame and Dale Carnegie.

Speaker #4: And those launches will take place over the second half of the year. We will continue to expand into enterprises and schools over the next few years, using AI and data to dramatically expand and personalize our catalog while making our courses even more affordable.

Speaker #4: Our language skills are an important component of employability, helping people expand career opportunities and communicate more effectively in an increasingly global workforce. As a result, we are transforming our language offering from a language learning app into a performance platform, helping people communicate with confidence and impact in any language when it counts.

Dan Rosensweig: We are transforming our language offerings from a language learning app into a performance platform, helping people communicate with confidence and impact in any language when it counts. Our new agentic coach, which understands each learner's goals and the context of each interaction, helps you prepare for the moments that matter, like a client call, a presentation, or an interview. Early next year, we plan to have a seamless integration of our agentic coach into the learner's actual workflow. Learning that shows up exactly when and where you need it. We are also expanding our skills offering into Europe, combining language learning with broader workforce capabilities. Underlying all of this has been the restructuring of our workforce to becoming AI first.

Speaker #4: Our new agentic coach, which understands each learner's goals and the context of each interaction, helps you prepare for the moments that matter, like a client call, a presentation, or an interview.

Speaker #4: Early next year, we plan to have a seamless integration of our agentic coach into the learner's actual workflow, learning that shows up exactly when and where you need it.

Speaker #4: We are also expanding our skills offering into Europe, combining language learning with broader workforce capabilities.

Speaker #3: Underlying all of this has been the restructuring of our workforce to becoming AI-first. AI allows us to personalize learning and prove outcomes and scale more efficiently and affordably, giving us a much leaner operating model which allows us to return to being a growth business with high margins.

Dan Rosensweig: AI allows us to personalize learning, improve outcomes, and scale more efficiently and affordably, giving us a much leaner operating model, which allows us to return to being a growth business with high margins. I look at the arc of what we have built and where we are headed, I feel genuinely confident. AI created real headwinds for this company, we responded by strengthening our balance sheet, rebuilding an AI-first cost structure, and expanding our vision towards a much larger opportunity. We are becoming an employability business, one that helps students develop skills, find internships, lands jobs, and grows throughout their careers. That is a more durable market, we are uniquely positioned to own it. The financial foundation David will walk you through is what makes that all possible, and we look forward to updating you on our progress next quarter.

Speaker #3: When I look at the arc of what we have built and where we are headed, I feel genuinely confident. AI created real headwinds for this company, and we responded by strengthening our balance sheet, rebuilding an AI-first cost structure, and expanding our vision towards a much larger opportunity.

Speaker #3: We are becoming an employability business, one that helps students develop skills, find internships, land jobs, and grow throughout their careers. That is a more durable market, and we are uniquely positioned to own it.

Speaker #3: The financial foundation David will walk you through is what makes that all possible. And we look forward to updating you on our progress next quarter.

Speaker #3: With that, I'll turn it over to David.

Dan Rosensweig: With that, I'll turn it over to David.

Speaker #4: Thank you, Dan, and good morning. Today, I will be reviewing our financial performance for the second quarter of 2026, along with the company's outlook for the third quarter.

David Longo: Thank you, Dan, and good morning. Today, I will be reviewing our financial performance for Q2 2026, along with the company's outlook for Q3. Our Q2 results exceeded our expectations, reflecting continued execution against our priorities. We are excited to take Chegg into its next chapter by expanding our focus on employability, addressing students' evolving needs while helping employers build a more skilled workforce, creating what we believe is a significant opportunity for long-term profitable growth. As we execute on our strategy, AI is improving operational efficiency across the company and driving meaningful gains in profitability and cash generation. We also repurchased shares during the quarter, reflecting our confidence in the company's long-term value while maintaining a disciplined approach to capital allocation. In the quarter, total revenue was $51.8 million, exceeding our expectations.

Speaker #4: Our second quarter results exceeded our expectations reflecting continued execution against our priorities. We are excited to take CHEGG into its next chapter by expanding our focus on employability addressing students evolving needs while helping employers build a more skilled workforce creating what we believe is a significant opportunity for long-term profitable growth.

Speaker #4: As we execute on our strategy, AI is improving operational efficiency across the company and driving meaningful gains in profitability and cash generation. We also repurchased shares during the quarter, reflecting our confidence in the company's long-term value while maintaining a disciplined approach to capital allocation.

Speaker #4: In the quarter, total revenue was $51.8 million, exceeding our expectations. We expanded our distribution partnerships, which we expect to contribute more meaningfully later this year, while remaining focused on efficiently managing our academic services products to maximize cash generation.

David Longo: We expanded our distribution partnerships, which we expect to contribute more meaningfully later this year, while remaining focused on efficiently managing our academic services products to maximize cash generation. Chegg Study monthly retention continued to be very strong, reinforcing its long-term cash generation potential. Turning to expenses, Q2 non-GAAP operating expenses were $32.3 million, nearly cutting our expenses in half compared to Q2 of last year. This significant reduction reflects our disciplined approach to expense management and enhanced use of AI to improve productivity and drive efficiencies across the company. We continue to identify opportunities to further optimize our cost structure. Adjusted EBITDA for the quarter was $9.1 million, representing a margin of 17%. Q2 CapEx was $3.7 million, down by 49% year over year. For full year 2026, we are targeting a 60% reduction in CapEx.

Speaker #4: CHEGG study monthly retention continued to be very strong, reinforcing its long-term cash generation potential. Turning to expenses, Q2 non-GAAP operating expenses were $32.3 million, nearly cutting our expenses in half compared to the second quarter of last year.

Speaker #4: This significant reduction reflects our disciplined approach to expense management and enhanced use of AI to improve productivity and drive efficiencies across the company. We continue to identify opportunities to further optimize our cost structure.

Speaker #4: Adjusted EBITDA for the quarter was $9.1 million, representing a margin of 17%. Second quarter capex was $3.7 million, down by 49% year over year, for a full year 2026.

Speaker #4: We are targeting a 60% reduction in capex. Free cash flow in the quarter was $6.4 million, which includes approximately $1.5 million of severance payments related to prior restructuring actions.

David Longo: Free cash flow in the quarter was $6.4 million, which includes approximately $1.5 million of severance payments related to prior restructuring actions. In H1 of the year, we generated $9.5 million in free cash flow despite $14.4 million in severance payments. We expect to continue to generate meaningful free cash flow in H2 of the year. Looking at the balance sheet, we ended the quarter with $72.3 million in cash and investments and a net cash position of $38.5 million, providing us flexibility as we execute on our priorities.

Speaker #4: In the first half of the year, we generated $9.5 million in free cash flow despite $14.4 million in severance payments. We expect to continue to generate meaningful free cash flow in the second half of the year.

Speaker #4: Looking at the balance sheet, we ended the quarter with $72.3 million in cash and investments, and a net cash position of $38.5 million. Providing us flexibility as we execute on our priorities.

Speaker #4: We've built a strong foundation for the future and are encouraged by the continued durability of our academic services products driven by strong monthly retention, the progress we are making leveraging AI to meaningfully improve our cost structure, the early traction we are seeing with new skilling distribution partnerships, and the significant opportunity we see to expand through employability.

David Longo: We've built a strong foundation for the future and are encouraged by the continued durability of our academic services products, driven by strong monthly retention, the progress we are making leveraging AI to meaningfully improve our cost structure, the early traction we are seeing with new skilling distribution partnerships, and the significant opportunity we see to expand through employability. Together, these reinforce our confidence in generating meaningful cash flow and creating long-term value. During Q2, we repurchased $1.7 million of our common stock and have $120.7 million remaining on our securities repurchase authorization. We believe our shares represent an attractive use of capital. Our strong balance sheet and continued ability to generate meaningful cash flow provide us with flexibility to allocate capital where we believe will create the longest long-term value for shareholders. That includes investing behind our strategic priorities while also evaluating further share repurchases.

Speaker #4: Together, these reinforce our confidence in generating meaningful cash flow and creating long-term value. During the second quarter, we repurchased $1.7 million of our common stock and have $120.7 million remaining on our securities repurchase authorization.

Speaker #4: We believe our shares represent an attractive use of capital. Our strong balance sheet and continued ability to generate meaningful cash flow provide us with flexibility to allocate capital where we believe will create the longest long-term value for shareholders.

Speaker #4: That includes investing behind our strategic priorities while also evaluating further share repurchases. In addition, we expect to fully repay the convertible debt in the third quarter, further strengthening our balance sheet, increasing our financial flexibility.

David Longo: We expect to fully repay the convertible debt in Q3, further strengthening our balance sheet, increasing our financial flexibility. Moving to guidance. As we execute on our expanded opportunity focused on building an employability platform, our academic services and Chegg Skills businesses are becoming increasingly integrated. We believe total revenue and adjusted EBITDA are the most meaningful ways to measure progress. Beginning this quarter, we are providing guidance for total revenue rather than separate revenue guidance. Looking ahead to Q3 guidance, we expect total revenue between $43 million and $44 million, gross margin in the range of 48% to 49%, and adjusted EBITDA between $1 million and $2 million. In closing, we have strengthened the business for long-term success. The company is leaner, more efficient, and well-positioned to generate meaningful free cash flow in 2026.

Speaker #4: Moving to guidance, as we execute on our expanded opportunity focused on building an employability platform, our academic services and CHEGG skilling businesses are becoming increasingly integrated, and we believe total revenue and adjusted EBITDA are the most meaningful ways to measure progress.

Speaker #4: Beginning this quarter, we are providing guidance for total revenue rather than separate revenue guidance. Looking ahead to Q3 guidance, we expect total revenue between $43 million and $44 million gross margin in the range of $48 to $49%, and adjusted EBITDA between $1 million and $2 million.

Speaker #4: In closing, we have strengthened the business for long-term success. The company is leaner, more efficient, and well-positioned to generate meaningful free cash flow in 2026.

Speaker #4: We are executing our strategy with focus and discipline while leaning into a large, new opportunity positioning us to drive sustainable growth, improve profitability, and create long-term shareholder value.

David Longo: We are executing our strategy with focus and discipline while leaning into a large new opportunity, positioning us to drive sustainable growth, improve profitability, and create long-term shareholder value. We have a strong balance sheet, which provides additional financial flexibility as we continue executing our strategy. With that, I will turn the call over to the operator for your questions.

Speaker #4: We have a strong balance sheet which provides additional financial flexibility as we continue executing our strategy. With that, I will turn the call over to the operator for your questions.

Speaker #1: Thank you. At this time, we'll be conducting a question and answer session. If you'd like to ask a question, please press star one on your telephone keypad.

Operator 2: Thank you. At this time, we'll be conducting a question and answer session. If you'd like to ask a question, please press star one on your telephone keypad. A confirmation tone will indicate your line is in the question queue. You may press star two if you'd like to remove your question from the queue. One moment, please, while we poll for questions. Our first question comes from Ryan MacDonald with Needham & Company. Your line is now live.

Operator: Thank you. At this time, we'll be conducting a question and answer session. If you'd like to ask a question, please press star one on your telephone keypad. A confirmation tone will indicate your line is in the question queue. You may press star two if you'd like to remove your question from the queue. One moment, please, while we poll for questions. Our first question comes from Ryan MacDonald with Needham & Company. Your line is now live.

Speaker #1: A confirmation tone will indicate your line is in the question queue. You may press star two if you'd like to remove your question from the queue.

Speaker #1: One moment, please, while we poll for questions. Our first question comes from Ryan McDonald with Needham and Company. Your line is now live.

Speaker #5: Hi, thanks for taking my questions. Dan, it's great to hear about the new vision for Chegg and the priorities moving forward.

Ryan MacDonald: Thanks for taking my questions. Dan, great to hear about the sort of new vision for Chegg and sort of the priorities moving forward. Maybe starting with sort of the new experience around helping students connect and find new job opportunities and internship opportunities. Can you just talk about sort of what you were seeing in the market that sort of pushed you in this direction? Are there specific gaps that you were seeing in a LinkedIn or an Indeed or a Handshake that you felt like Chegg could sort of take advantage of here? As we think about growing this, how do you drive awareness amongst the student population? Will you leverage sort of career services relationships? Would love to hear more there. Thanks.

Speaker #5: Maybe starting with sort of the new experience around helping students connect and find new job opportunities and internship opportunities. Can you just talk about sort of what you were seeing in the market, that sort of pushed you in this direction?

Speaker #5: Are there specific gaps from that you were seeing in a LinkedIn or an Indeed or a Handshake that you felt like that CHEGG could sort of take advantage of here?

Speaker #5: And then as we think about growing this, how do you drive awareness amongst the student population? Will you leverage sort of career services relationships?

Speaker #5: We'd love to hear more there. Thanks.

Speaker #2: Yeah. Great question. And we've been working on this for quite some time. We just feel that now is the time to start talking about it.

Dan Rosensweig: Yeah, great question. We've been working on this for quite some time. We just feel that now is the time to start talking about it, because step one was make sure that the company could pay off its debt, which we'll be out of debt shortly. Second thing is to make sure our balance sheet, as David said, is really strong, which we're going to have substantial cash. You already see we have substantial cash net of debt, and that's only going to grow over the rest of this year and to next year. The value of the company, we think, is undervalued simply because of the amount of cash we're going to generate.

Speaker #2: Because step one was make sure that the company could pay off its debt, which will be out of debt shortly. Second thing is to make sure our balance sheet is data set is really strong, which we're going to have substantial cash.

Speaker #2: You already see we have substantial cash net of debt, and that's only going to grow. Over the rest of this year and to next year.

Speaker #2: So the value of the company, we think, is undervalued simply because of the amount of cash we're going to generate. The skills business continues to grow.

Dan Rosensweig: The skills business continues to grow, the real opportunity that we have always believed in is that we ask the Jeff Bezos question, which is, rather than what's changing, what's never going to change? At the end of the day, college students go to college for one reason, which is to get a better job. The fear over employment, unemployment that relates to technology and AI is rampant. I'm sure you know that. The biggest question that students have been asking us to solve for them is Which classes do I take? What major do I take? If I take these classes, what skills am I actually going to have that will allow me to be employable? Then, Help me identify the companies, help me build my network. LinkedIn doesn't help you build a network. Nobody does, but we will.

Speaker #2: But the real opportunity that we have always believed in is that we asked the Jeff Bezos question, which is rather than what's changing what's never going to change.

Speaker #2: And at the end of the day, college students go to college for one reason, which is to get a better job. And the fear over employment, unemployment, that relates to technology and AI is rampant.

Speaker #2: I'm sure you know that. And the biggest question that students have been asking us to solve for them is how which classes do I take?

Speaker #2: What these classes, what skills am I actually going to have that will allow me to be employable? And then help me identify the companies, help me build my network.

Speaker #2: LinkedIn doesn't help you build a network. Nobody does. But we will. So help me build a network. Help me connect to these people. Help me write my resume.

Dan Rosensweig: Help me build a network, help me connect with these people, help me write my resume, help me write my cover letter, help me prepare for the interview. Nobody was putting all of this together in one place, nobody was focused exclusively on the student. Handshake existed, but as you know, Handshake evolved its business to now be in the data business. We have huge legacy customers that still use Chegg. You can see that in our numbers. You can see that in the amount of traffic that we're generating. We have the ability to reach students in the millions. Awareness won't be difficult for us because we still get massive traffic and we still have a substantial customer base. On top of that, over, I don't know, 12, 13 years ago, we bought the site internships.com.

Speaker #2: Help me write my cover letter. Help me prepare for the interview. Nobody was putting all of this together in one place, and nobody was focused exclusively on the student.

Speaker #2: Handshakes existed, but as you know, Handshakes evolved. It's business to now be in the data business. And so we have huge legacy customers that still use CHEGG.

Speaker #2: You can see that in our numbers. You can see that in the amount of profits that we're generating. And so we have the ability to reach students in the millions.

Speaker #2: So awareness won't be difficult for us because we still get massive traffic, and we still have substantial customer base. On top of that, over, I don't know, 12, 13 years ago, we bought the site internships.com.

Speaker #2: We haven't used it in a bunch of years because of the difficulties that we've been facing, but we took it out of mock balls.

Dan Rosensweig: We haven't used it in a bunch of years because of the difficulties that we've been facing, we took it out of mothballs. The organic traffic that goes to there is quite substantial. We have been testing Chegg as a front door, Internships as a front door. We very quickly got over 10,000 beta testers of the original product. We brought in a number of interns who have actually helped us design and build the product because it's for them. We're excited. Just anybody that has a student in college or going to college, the number one fear of the student and the parent is, Will my child get a job? Where will they work? How are they going to get the skills? We're the company that is going to solve many of those issues for them, and we couldn't be more excited.

Speaker #2: The organic traffic that goes to there is quite substantial. And so we have been testing CHEGG as a front door internships as a front door.

Speaker #2: We very quickly got over 10,000 beta testers of the original product. We brought in a number of interns who have actually helped us design and build the product because it's for them.

Speaker #2: And so we're excited. So just anybody that has a student in college or going to college, the number one fear of the student and the parents is, will my child get a job?

Speaker #2: Where will they work? How are they going to get the skills? And we're the company that is going to solve many of those issues for them.

Speaker #2: And it couldn't be more exciting. We think we have the assets to do it. We think we have the brand to do it.

Dan Rosensweig: We think we have the assets to do it. We think we have the brand to do it. We think we have the data to do it. A couple of years ago, we got punched in the face by AI, now we're using AI to punch back.

Speaker #2: We think we have the data to do it. And so a couple of years ago, we got punched in the face by AI. Now we're using AI to punch back.

Speaker #5: I like it. And then as you think about sort of this sort of all-in-one way to assist a student, from how to get the job or identify how to identify the skills they need to get the job, how is that sort of informing your content creation strategy with the skills business in terms of sort of the partners that you select and do at some point, do you start to maybe bring more of the content creation in-house yourself, or use AI to create some of this content for the student?

Ryan MacDonald: I like it. As you think about this sort of all-in-one way to assist a student, from how to get the job or how to identify the skills they need to get the job, how is that sort of informing your content creation strategy with the Chegg Skills business in terms of the partners that you select and do at some point, do you start to maybe bring more of the content creation in-house yourself or use AI to create some of this content for the student? Thanks.

Speaker #5: Thanks.

Speaker #2: Yeah. Well, so if you think about it, Chegg's legacy—Chegg was AI before there was AI. So, we have a pristine 100-and-something million pairs of Q&A that we built on our expert network.

Dan Rosensweig: Well, if you think about it, with Chegg's legacy, Chegg was AI before there was AI. We have a pristine 100 and something million pairs of Q&A that we built on our expert network. All the data businesses now are trying to build an expert network in order to train their models. We already have it. Our ability to answer any and all questions around any subject matter has always been available, and we focused on academics. We're going to focus on academics and job-related questions. That's an advantage that we have that others don't have. In terms of content creation, that'll be one of the areas, but our SEO strategy will expand dramatically based on the listings, based on the data that we have about students.

Speaker #2: And all the data businesses now are trying to build an expert network in order to train their models. So we already have it. So our ability to answer any and all questions around any subject matter has always been available.

Speaker #2: We focused on academics. Now we're going to focus on academics and job-related questions. So that's an advantage that we have that others don't have.

Speaker #2: But in terms of content creation, so that'll be one of the areas. But our SEO strategy will expand dramatically based on listings, based on the data that we have around students.

Speaker #2: Remember, we start with schools that students go to, the classes they take, the majors they have. We're able to identify people that took those classes and where they worked.

Dan Rosensweig: Remember, we start with schools that students go to, the classes they take, the majors they have. We're able to identify people that took those classes and where they work, and we're able to identify those alumni and try to build a relationship between the student and the alumni. You point to a very exciting area, which will come later on down the line, which is one of the things that we're talking about that I mentioned in the skilling part of our prepared remarks, is we're taking all the courses that we've developed, and we're basically going to turn them into 5,000 artifacts of content that will make them shorter, much more accessible, much more affordable, be able to assess the student on the skills that they think they have, and then be able to train them up on it at a very affordable rate.

Speaker #2: And we're able to identify those alumni and try to build a relationship between the students.

Speaker #5: And the alumni.

Speaker #2: So but you point to a very exciting area, which will come later on down the line, which is one of the things that we're talking about that I mentioned in the skilling part of our prepared marks.

Speaker #2: We're taking all the courses that we've developed, and we're basically going to turn them into 5,000 artifacts of content that will make them shorter, much more accessible, much more affordable, be able to assess the student on the skills that they think they have, and then be able to train them up on it at a very affordable rate.

Speaker #2: So that will come later. But it's not so much the partners we're picking. It's the content we're creating. And that content will constantly evolve same as the answers and the questions did for students on academics around the professional needs of students.

Dan Rosensweig: That will come later, but it's not so much the partners we're picking, it's the content we're creating. That content will constantly evolve, same as the answers and the questions did for students on academics, around the professional needs of students. It will be led by what companies are actually recommending the necessary skills that students will have. AI allows us to do all that quickly, affordably, personalize each experience. When we look at the opportunity, the academic opportunity, I think at our peak, 25% of all students in the country had subscribed to Chegg. Unfortunately, another 25% had stolen it. It built quite a large business. If you ask me which TAM is bigger in the college market, and even in the high school market that doesn't go to college. Remember, 50% of the high school market never attends higher education.

Speaker #2: And it will be led by what companies are actually recommending the necessary skills that students will have. And AI allows us to do all that quickly, affordably, personalize each experience.

Speaker #2: So when we look at the opportunity the academic opportunity I think at our peak 25% of all students in the country had subscribed to CHEGG.

Speaker #2: Unfortunately, another 25% had stolen it. But it built quite a large business. But if you ask me which TAM is bigger in the college market, and even in the high school market that doesn't go to college...

Speaker #2: Remember, 50% of the high school market never attends higher education. So we think it's a bigger PAM, and we think the content creation will be around what do you need to know to be employable.

Dan Rosensweig: We think it's a bigger TAM, we think the content creation will be around what do you need to know to be employable? Also, what do you need to know about how to interview? What do you need to know about how to get over the first AI interview, if that's what's happening. You'll be able to rehearse in real time with our coach about what questions you're likely to get. We'll store all that content based on the experiences that we're able to monitor that students have with different employers. It's a multi-year effort to do it, but we thought because we're rolling out the first early version of it later on this quarter, that now is the time to talk about it. We couldn't be more excited.

Speaker #2: But also, what do you need to know about how to interview? What do you need to know about how to get over the first AI interview, if that's what's happening?

Speaker #5: You'll be able to rehearse in real time with our coach about what questions you're likely to get. And we'll store all that content based on the experiences that we're able to monitor that students have with different employers.

Speaker #5: So it's a multi-year effort to do it. But we thought, because we're rolling out the first early version of it later on in this quarter, that now is the time to finally talk about it.

Speaker #5: But we couldn't be more excited. Appreciate that. Maybe one for David. Can you talk about just maybe put a little more color around sort of expectations for free cash flow generation?

Ryan MacDonald: Appreciate that. Maybe one for David. Can you talk about, just maybe put a little more color around sort of expectations for free cash flow generation? It sounded like in the quarter that, obviously some good cash generation, but there were some severance payments, obviously, outgoing. How much more incremental severance payments are sort of there, and when should we start to see that sort of material ramp in the cash generation here?

Speaker #5: It sounded like in the quarter that obviously some good cash generation, but there were some severance payments obviously outgoing. How much more incremental severance payments are sort of there?

Speaker #5: And when should we start to see that sort of material ramp in the cash generation here?

Speaker #3: Yeah, sure. So the severance payments are for the almost all behind us at this point. And yeah, it was about 14, 15 million dollars in the first half of the year.

David Longo: Yeah, sure. The severance payments are almost all behind us at this point. It was about $14 million, $15 million in the H1 of the year. Q3 is a traditionally slower period for us, Q4 has always been our strongest cash generation period. I haven't really guided for either the quarter or the full year, just as some timing on payments and some annual contracts. We have payments in Q3, which is one of the lower quarters of revenue for coming in. We know we'll be free cash flow positive for the H2 of the year, and even believe within the quarterization, but just some timing there. If you take out those severance payments, which I know we can't, but if you kind of pro forma those out, just look at the cash generation in the H1.

Speaker #3: Q3 is traditionally a slower period for us, and then Q4 has always been our strongest cash generation period. So I haven't really guided for either the quarter or the full year, just the timing on payments and some annual contracts, where we have payments in Q3—which is one of the lower quarters of revenue—for coming in.

Speaker #3: We still believe we'll be we know we'll be free cash flow positive for the back half of the year. And even believe within the quarterization.

Speaker #3: But just some timing there. But if you take out the those severance payments, which I know we can't, but if you kind of pro forma those out, just look at the cash generation in the first half, we're pleased with that.

David Longo: We're pleased with that, we believe we can continue to do so through this year and next.

Speaker #3: And we believe we can continue to do so through this year and next.

Speaker #5: Awesome. Thanks for taking my questions. All right. Thanks, Mike.

Ryan MacDonald: Awesome. Thanks for taking my questions.

Dan Rosensweig: All right. Thanks, Ryan.

Speaker #1: Okay. We have reached the end of the question and answer session. And this concludes today's conference. You may disconnect your line at this time.

Operator 2: Okay, we have reached the end of the question and answer session. This concludes today's conference. You may disconnect your line at this time. We thank you for your participation.

Operator: Okay, we have reached the end of the question and answer session. This concludes today's conference. You may disconnect your line at this time. We thank you for your participation.

Q2 2026 Chegg Inc Earnings Call

Request DemoDemo

Chegg

Earnings