DEF 14A of Chegg, Inc, Apr 17, 2025

DEF 14A of Chegg, Inc

Filed Apr 17, 2025 · FY20240001364954-25-000039

Open on EDGAR

  1. 2025 Director Nominee

    2025 Director Nominee We introduce our 2025 director nominee below.

  2. 2025 Director Nominee

    | | | | | Committee Memberships | | | | Name | Age | Director Since | Independent | Audit Committee | Compensation Committee | Governance and Sustainability Committee | | Marcela Martin | 53 | 2021 | YES | ■ | | | | ■ - Member | | | | | | |

  3. Election of Directors

    Election of Directors Our Board of Directors currently consists of 9 directors and is divided into three classes, with each class serving for three years and with the terms of office of the respective classes expiring in successive years. Directors in Class III will stand for election at this meeting. The terms of office of directors in Class I and Class II do not expire until the Annual Meetings of Stockholders to be held in 2026 and 2027, respectively. At the recommendation of our Governance and Sustainability Committee, our Board of Directors proposes that the Class III nominee named below be elected as a Class III director for a three-year term expiring at the Annual Meeting of Stockholders to be held in 2028 and until such director’s successor is duly elected and qualified, or until such director’s earlier resignation or removal. Shares of our common stock represented by proxies will be voted “FOR” the election of the nominee named below, unless the proxy is marked to abstain. If the nominee for any reason is unable to serve or for good cause will not serve, the proxies may be voted for such substitute nominee as the proxy holder may determine. The nominee has consented to being named in this proxy statement and to serve if elected. Proxies may not be voted for more than one director. Stockholders may not cumulate votes in the election of director.

  4. Nominee to the Board of Directors

    Nominee to the Board of Directors The nominee, and her age, occupation, and length of service on our Board of Directors are provided in the table below. Additional biographical description of the nominee is set forth in the text below the table. This description includes the primary individual experience, qualifications, qualities and skills of the nominee that led to the conclusion that the nominee should serve as a member of our Board of Directors at this time. There are three directors in the class whose term of office expires in 2025, one of whom, Marcela Martin, has been nominated for re-election to the Board. Unless otherwise instructed, the persons (the “proxyholders”) named in the form of proxy card attached to this Proxy Statement, as filed with the SEC, intend to vote the proxies held by them for the election of Marcela Martin. The proxies cannot be voted for more than one candidate for director. The Board knows of no reason why this nominee would be unable or unwilling to serve, but if that would be the case, proxies received will be voted for the election of such other persons, if any, as the Board may designate. Directors elected at the Annual Meeting will hold office until the 2028 Annual Meeting of Stockholders and until their successors are duly elected and qualified.

  5. Nominee to the Board of Directors

    | Name of Director/Nominee | Age(2) | Principal Occupation | Joined Our Board | | Marcela Martin(1) | 53 | Chief Financial Officer, Contentsquare | September 2021 |

  6. Nominee to the Board of Directors

    | (1) Member of the Audit Committee. | | (2) Age as of the Record Date of the 2025 Annual Meeting. |

  7. Nominee to the Board of Directors

    | Chegg, Inc. | 21 | Proxy Statement for the 2025 Annual Meeting of Stockholders |

  8. Nominee to the Board of Directors

    | | | Marcela Martin Marcela Martin brings extensive experience in the finance, tech, and media industries and has served on our board of directors since September 2021. Ms. Martin currently serves as Chief Financial Officer at Contentsquare as of November 2024. Previously, Ms. Martin served as Advisor, and earlier, as Chief Financial Officer at Ouro from January 2024 to November 2024 and Ms. Martin also served as the President of Buzzfeed, Inc. from August 2022 to January 2024. Ms. Martin was Chief Financial Officer at Squarespace from November 2020 to July 2022 and Senior Vice President and Chief Financial Officer from January 2019 to November 2020 at Booking.com. Ms. Martin was Executive Vice President and Chief Financial Officer of National Geographic Partners from January 2016 to December 2018. From 2003 to 2007, Ms. Martin was Vice President and Deputy Chief Financial Officer for Fox International Channels and Executive Vice President and Chief Financial Officer from 2007 to 2016. Ms. Martin currently serves on the Board of Directors of Cvent. Ms. Martin holds a B.S. in Accounting from the University of Moron, Argentina, and an M.B.A. from the University of Liverpool, United Kingdom. | | | Member of Audit Committee. DIRECTOR SINCE: 2021 | | | | | We believe that Ms. Martin should continue to serve on our Board of Directors due to her extensive financial experience through her service as a Chief Financial Officer of public and private entities. |

  9. Nominee to the Board of Directors

    | Chegg, Inc. | 22 | Proxy Statement for the 2025 Annual Meeting of Stockholders |

  10. Continuing Directors

    Continuing Directors The directors who are serving for terms that end in 2026 and 2027, and their ages, principal occupations and length of service on our Board of Directors are provided in the table below. Additional biographical descriptions of each continuing director are set forth in the text below the table. These descriptions include the primary individual experience, qualifications, qualities and skills of each continuing director that led to the conclusion that each director should continue to serve as a member of our Board of Directors at this time.

  11. Continuing Directors

    | Name of Director | Age(7) | Principal Occupation | Joined Our Board | | CLASS I DIRECTORS - TERMS EXPIRING 2026: | | | | | Renee Budig(1)(2) | 64 | Former Executive Vice President and Chief Financial Officer, Paramount Streaming, a division of Paramount Global, Inc. | November 2015 | | Dan Rosensweig(3) | 63 | Executive Chairman and Co-Chairperson, Chegg, Inc. | March 2010 | | Ted Schlein(4)(5) | 61 | General Partner, Kleiner Perkins | December 2008 | | Nathan Schultz | 47 | President and Chief Executive Officer, Chegg, Inc. | June 2024 | | CLASS II DIRECTORS - TERMS EXPIRING 2027: | | | | | Marne Levine(2)(6) | 54 | Former Chief Business Officer, Meta Platforms, Inc. | May 2013 | | Richard Sarnoff(3)(5) | 66 | Chairman of Media, KKR Americas Private Equity | August 2012 |

  12. Continuing Directors

    | (1) Chair of the Audit Committee. | | (2) Member of the Compensation Committee | | (3) Co-Chairperson of the of Board of Directors. | | (4) Member of the Governance and Sustainability Committee. | | (5) Member of the Audit Committee. | | (6) Chair of the Governance and Sustainability Committee. | | (7) Age as of the Record Date of the 2025 Annual Meeting. |

  13. Continuing Directors

    | Learn with Chegg Chegg is a student’s ride-or-die, 24/7, always-answers-when-you-call partner. | |

  14. Continuing Directors

    | Chegg, Inc. | 23 | Proxy Statement for the 2025 Annual Meeting of Stockholders |

  15. Class I Directors

    Class I Directors

  16. Class I Directors

    | | | Renee Budig Renee Budig has served on our Board of Directors since November 2015. From September 2012 to January 2021, Ms. Budig served as the Executive Vice President and Chief Financial Officer of Paramount Streaming, a division of Paramount Global Inc. (formerly CBS Interactive, a division of CBS Inc.), an online content network for information and entertainment. From 2010 to September 2012, Ms. Budig served as Chief Financial Officer of Hightail, Inc. (formerly branded YouSendIt and acquired by OpenText), a cloud service that allowed users to send, receive, digitally sign and synchronize files. From 2006 to 2010, Ms. Budig was the Vice President of Finance at Netflix, Inc., a multinational provider of on-demand Internet streaming media. Ms. Budig served on the board of directors of iRhythm Technologies from April 2020 to May 2023. Ms. Budig holds a B.S. in Business Administration from the University of California, Berkeley. | | | Chair of Audit Committee and Member of Compensation Committee DIRECTOR SINCE: 2015 | | | | | We believe that Ms. Budig should continue to serve on our Board of Directors due to her extensive background in consumer technology companies and her financial expertise through her service as a Chief Financial Officer. |

  17. Class I Directors

    | | | Dan Rosensweig Dan Rosensweig currently serves as Chegg’s Executive Chairman since June 2024 and as Co-Chairperson of our Board of Directors since July 2018. Mr. Rosensweig served as our President and Chief Executive Officer from February 2010 to June 2024. Mr. Rosensweig also served as the Chairperson of our Board of Directors from March 2010 to July 2018. From 2009 to 2010, Mr. Rosensweig served as President and Chief Executive Officer of RedOctane, a business unit of Activision Publishing, Inc. and developer, publisher, and distributor of Guitar Hero. From 2007 to 2009, Mr. Rosensweig was an Operating Principal at the Quadrangle Group, a private investment firm. From 2002 to 2009, Mr. Rosensweig served as Chief Operating Officer of Yahoo! Inc., an internet content and service provider. Prior to serving at Yahoo!, Mr. Rosensweig served as the President of CNET Networks and prior to that as Chief Executive Officer and President of ZDNet, until it was acquired by CNET Networks. Mr. Rosensweig currently serves on the board of directors of Adobe Systems Incorporated. Mr. Rosensweig holds a B.A. in Political Science from Hobart and William Smith Colleges. | | | Executive Chairman and Co-Chairperson of the Board of Directors DIRECTOR SINCE: 2010 | | | | | We believe that Mr. Rosensweig should continue to serve on our Board of Directors due to the perspective and experience he brings as our Executive Chairman and his extensive experience with consumer internet and media companies. |

  18. Class I Directors

    | Chegg, Inc. | 24 | Proxy Statement for the 2025 Annual Meeting of Stockholders |

  19. Class I Directors

    | | | Ted Schlein Ted Schlein has served on our Board of Directors since December 2008. Mr. Schlein has served as a General Partner of Kleiner Perkins, a venture capital firm, since November 1996. Mr. Schlein is also Chairman and a General Partner of Ballistic Ventures. From 1986 to 1996, Mr. Schlein served in various executive positions at Symantec Corporation, a provider of internet security technology and business management technology solutions, including as Vice President of Enterprise Products. Mr. Schlein currently serves on the boards of directors of a number of privately held companies. Mr. Schlein holds a B.A. in Economics from the University of Pennsylvania. | | | Member of Audit Committee and Governance and Sustainability Committee DIRECTOR SINCE: 2008 | | | | | We believe that Mr. Schlein should continue to serve on our Board of Directors due to his extensive experience working with and investing in technology companies. |

  20. Class I Directors

    | | | Nathan Schultz Nathan Schultz has served as our President, Chief Executive Officer and Member of our Board of Directors since June 1, 2024. From October 2022 to June 2024, Mr. Schultz served as our Chief Operating Officer and previously served as our President of Learning Services from December 2018 to October 2022, our Chief Learning Officer from June 2014 until December 2018, our Chief Content Officer from May 2012 until June 2014, our Vice President of Content Management from 2010 to May 2012 and our Director of Textbook Strategy from 2008 to 2010. Prior to joining us, Mr. Schultz served in various management positions at R.R. Bowker LLC, a provider of bibliographic information and management solutions; Monument Information Resource, a marketing intelligence resource acquired by R.R. Bowker; Pearson Education, an education publishing and assessment service; and Jones & Bartlett Learning LLC, a division of Ascend Learning Company and provider of education solutions. Mr. Schultz holds a B.A. in History from Elon University. | | | President and Chief Executive Officer DIRECTOR SINCE: 2024 | | | | | We believe that Mr. Schultz should continue to serve on our Board of Directors due to the perspective and experience he brings as our Chief Executive Officer and his extensive experience with education. |

  21. Class I Directors

    | Chegg, Inc. | 25 | Proxy Statement for the 2025 Annual Meeting of Stockholders |

  22. Class II Directors

    Class II Directors

  23. Class II Directors

    | | | Marne Levine Marne Levine brings extensive experience in the policy, communication, and technology fields, and has served on our Board of Directors since May 2013. From September 2021 to February 2023, Ms. Levine served as the Chief Business Officer at Meta Platforms, Inc. (doing business as Meta and formerly known as Facebook, Inc.), a social media company, and served as its Vice President of Global Partnerships, Business and Corporate Development from February 2019 to June 2021. Previously, Ms. Levine served as Chief Operating Officer of Instagram from December 2014 to February 2019 where she was responsible for helping to scale the company’s business and operations globally and turn Instagram from a beloved app into a thriving business. She joined Meta in 2010 as Meta’s first Vice President of Global Policy, a position she held for four years. Prior to Meta, Ms. Levine served in the Obama Administration as Chief of Staff of the National Economic Council (NEC) at the White House and Special Assistant to the President for Economic Policy. From 2006 to 2008, Ms. Levine was Head of Product Management for Revolution Money, an early-stage start-up working on person-to-person online money transfers, which was ultimately sold to American Express. Prior to this, she served as Chief of Staff to Larry Summers, then President of Harvard University. Ms. Levine began her career in 1993 at the United States Department of Treasury under President Bill Clinton where she held several leadership positions. She holds a B.A. in Political Science and Communications from Miami University and an M.B.A. from Harvard Business School. | | | Member of Compensation Committee and Chair of Governance and Sustainability Committee DIRECTOR SINCE: 2013 | | | | | We believe that Ms. Levine should continue to serve on our Board of Directors due to her extensive experience scaling brands globally and serving in executive positions at global technology companies. |

  24. Class II Directors

    | Chegg, Inc. | 26 | Proxy Statement for the 2025 Annual Meeting of Stockholders |

  25. Class II Directors

    | | | Richard Sarnoff Richard Sarnoff has served on our Board of Directors since August 2012 and as a Co-Chairperson of our Board of Directors since July 2018. He was named Chairman of Media for KKR’s Private Equity platform in the Americas in 2022. From 2014 through 2021, he served first as Managing Director and then as Partner and Head of the Media and Communications industry group, leading investments in the Media, Telecom, Information Services, Digital Media and Education sectors in the US. From 2011 to 2014, Mr. Sarnoff was a Senior Adviser to KKR. Mr. Sarnoff currently serves on the Board of Directors of Simon & Schuster, OverDrive, Teaching Strategies, AST SpaceMobile and Lightcast, as well as numerous not-for-profit organizations. Until 2011, Mr. Sarnoff was a longstanding senior executive at Bertelsmann AG, Europe’s largest media company, where he served in the early 2000’s as EVP and Chief Financial Officer of Bertelsmann’s book publishing division, Random House, during which time he also Chaired the Association of American Publishers (AAP.) In 2006, Mr. Sarnoff established Bertelsmann's digital media arm, BDMI, and as President oversaw the corporation’s global investment activities in digital media. In 2008, Mr. Sarnoff was named Co-Chairman of Bertelsmann’s US holding company, Bertelsmann Inc., and served on the Supervisory Board of Bertelsmann AG for six years. Mr. Sarnoff holds a BA from Princeton University in Art History and an MBA from Harvard University. | | | Member of Audit Committee and Co-Chairperson of the Board of Directors DIRECTOR SINCE: 2012 | | | | | We believe that Mr. Sarnoff should continue to serve on our Board of Directors due to his extensive experience serving in senior leadership roles in media and digital technology companies and investing in education companies. |

  26. Class II Directors

    There are no familial relationships among our directors and officers.

  27. Class II Directors

    | Chegg, Inc. | 27 | Proxy Statement for the 2025 Annual Meeting of Stockholders |

  28. Director Compensation

    Director Compensation We compensate our non-employee directors with a combination of cash and equity. The form and amount of compensation paid to our non-employee directors for serving on our Board of Directors and its committees is designed to be competitive in light of industry practices and the obligations imposed by such service. In order to align the long-term interests of our directors with those of our stockholders, the majority of director compensation is provided in equity-based compensation. The Compensation Committee, after considering the information, analysis and recommendations provided by Aon Consulting, Inc., its independent compensation consultant, including data regarding compensation paid to non-employee directors by companies in our “peer group” (as described in the “Executive Compensation—Compensation Discussion and Analysis” section of this proxy statement), evaluates the appropriate level and form of compensation for non-employee directors and recommends compensation changes to the Board when appropriate.

  29. 2024 Director Compensation Table

    2024 Director Compensation Table

  30. 2024 Director Compensation Table

    | Name | Fees Earned or Paid in Cash ($)(6) | RSU Awards ($)(7) | Total ($)(8) | | Sarah Bond(1) | 49,674 | 199,997 | 249,671 | | Renee Budig(2) | 66,813 | 199,997 | 266,810 | | Paul LeBlanc(3) | 42,935 | 199,997 | 242,932 | | Marne Levine(4) | 55,761 | 199,997 | 255,758 | | Marcela Martin | 50,000 | 199,997 | 249,997 | | Richard Sarnoff | 70,052 | 199,997 | 270,049 | | Ted Schlein | 60,000 | 199,997 | 259,997 | | Melanie Whelan | 60,000 | 199,997 | 259,997 | | John (Jed) York(5) | 54,306 | 199,997 | 254,303 |

  31. 2024 Director Compensation Table

    | (1) Ms. Bond resigned from the Board of Directors and as a member of the Compensation Committee effective September 18, 2024. | | (2) Committee fees for Ms. Budig are prorated to reflect her transition as a member to the Compensation Committee effective April 3, 2024. | | (3) Mr. LeBlanc resigned from the Board of Directors and as chair the Governance and Sustainability Committee effective September 18, 2024. | | (4) Committee fees for Ms. Levine are pro-rated to reflect her transition from the Governance and Sustainability Committee Chair effective September 18, 2024. | | (5) Committee fees for Mr. York are prorated to reflect his resignation as a member of the Compensation Committee effective June 5, 2024. | | (6) All director fees were paid at the end of the quarter for which services were provided. | | (7) Amounts shown in this column do not reflect dollar amounts actually received by non-employee directors. Instead these amounts reflect the aggregate grant date fair value calculated in accordance with Financial Accounting Standards Board, Accounting Standards Codification Topic 718, Compensation-Stock Compensation, (formerly SFAS 123R) (“ASC 718”), for awards granted during 2024. During 2024, each non-employee member of the Board of Directors, who was a director as of the close of our 2024 Annual Meeting of Stockholders on June 5, 2024, was granted an RSU award covering 54,347 shares of our common stock with an aggregate grant date fair value of $199,997. The grant date fair value for RSUs was determined using the closing share price of our common stock on the date of grant. For information on other valuation assumptions with respect to stock awards, refer to notes 2 and 13 of the notes to consolidated financial statements contained in our Annual Report on Form 10-K for the fiscal year ended December 31, 2024. There can be no assurance that this grant date fair value will ever be realized by the non-employee director. | | (8) Non-employee directors receive no other form of remuneration, perquisites or benefits for their service as members of our Board of Directors, but they are reimbursed for their reasonable travel expenses incurred in attending Board of Directors and committee meetings and certain Chegg events and approved continuing education programs. |

  32. 2024 Director Compensation Table

    | Chegg, Inc. | 29 | Proxy Statement for the 2025 Annual Meeting of Stockholders |

  33. 2024 Director Compensation Table

    Our non-employee directors held the following number of stock options and unvested RSU awards as of December 31, 2024.

  34. 2024 Director Compensation Table

    | Name | Option Awards | RSU Awards | | Sarah Bond(1) | — | — | | Renee Budig | 43,445 | 54,347 | | Paul LeBlanc(2) | — | — | | Marne Levine | 58,175 | 54,347 | | Marcela Martin | — | 54,347 | | Richard Sarnoff | — | 54,347 | | Ted Schlein | — | 54,347 | | Melanie Whelan | — | 54,347 | | John (Jed) York | 80,456 | 54,347 |

  35. 2024 Director Compensation Table

    | (1) Ms. Bond resigned from the Board of Directors and as a member of the Compensation Committee effective September 18, 2024. Ms. Bond's RSU award was forfeited on September 18, 2024. | | (2) Mr. LeBlanc resigned from the Board of Directors and as chair the Governance and Sustainability Committee effective September 18, 2024. Mr. LeBlanc's RSU award was forfeited on September 18, 2024. |

  36. 2024 Director Compensation Table

    | | Our Board of Directors recommends a vote “FOR” the Class III director nominee. |

  37. 2024 Director Compensation Table

    | Chegg Helping students thrive. | |

  38. 2024 Director Compensation Table

    | Chegg, Inc. | 30 | Proxy Statement for the 2025 Annual Meeting of Stockholders |

  39. 2024 Director Compensation Table

    | | | Proposal No. 2 |

  40. 2024 Compensation Highlights

    2024 Compensation Highlights Our executive compensation programs reflect our commitment to pay for performance and our prioritization of stockholder alignment while being designed to attract and retain leadership in our next phase of growth. Our Compensation Committee determined that Chegg’s compensation philosophy and objectives would be best served and fulfilled with a mix of base salary and equity grants. In 2024, the Compensation Committee determined a new base salary and granted equity awards for Mr. Schultz, Mr. Rosensweig, and Mr. Longo in connection with their new roles as our new Chief Executive Officer, Executive Chairman, and Chief Financial Officer, respectively, and in each case based on the responsibilities associated with their new positions. For each of Mr. Schultz, Mr. Rosenzweig, and Mr. Longo, the salary and size and composition of the equity grant was determined based on the Committee’s review, together with its independent compensation consultant, of benchmarking data. The data referenced base salaries and grants received by employees in similarly leveled positions of comparator companies. The Compensation Committee sought, in particular, to structure the equity grant in order to provide a competitive compensation package that would promote long-term retention with our Company and provide an immediate alignment with our stockholders. No salary adjustment or equity grants were made to either Mr. Brown or Ms. Lem prior to their retirements.

  41. CEO Realizable Compensation

    CEO Realizable Compensation In addition, by delivering the majority of our NEOs' compensation in the form of equity, the value ultimately realized by our executives continues to be closely linked to our stock price performance. As of December 31, 2024, our CEO’s “realizable value” of compensation (see below chart) is only 42% of target, further demonstrating alignment between pay and performance. Target total direct compensation reflects salary paid through 2024 and the grant date fair value of the 2024 equity awards, including RSUs and PSUs. Realizable value reflects salary paid during 2024 and value of the 2024 equity awards based on Chegg’s closing stock price of $1.61 on December 31, 2024, with the 2024 PSUs earned at 17.4% of target.

  42. Compensation Practices

    | What We Do | •Pay-for-Performance •Prioritize stockholder alignment with a majority of pay mix allocated to equity compensation, half of which is performance-conditioned for our executive officers •Use a representative and relevant peer group for assessing compensation •Consider stockholder dilution, burn rate, and stock-based compensation expense in our equity compensation decisions •Include caps on individual payouts in incentive plans •Maintain a recoupment policy on cash or equity incentive awards in the event of a financial restatement •Maintain stock ownership guidelines for our executive officers and non-employee directors •Maintain a Compensation Committee comprised solely of independent directors •Retain an independent compensation consultant •Conduct ongoing stockholder outreach •Conduct an annual Say-On-Pay vote | | What We Don't Do | •Provide guaranteed annual salary increases or bonuses •Provide excise tax gross-ups •Provide defined benefit or contribution retirement plans or arrangements, other than our Section 401(k) plan which is generally available to all employees •Provide excessive benefits and/or perquisites to our executive officers •Include “single-trigger” vesting change of control provisions in equity awards •Allow hedging or monetization transactions, such as zero cost collars and forward sale transactions |

  43. Compensation Philosophy and Objectives

    Compensation Philosophy and Objectives Our executive compensation program is designed to: •Attract, motivate and retain highly qualified executive officers in a competitive market; •Reward the achievement of challenging business objectives; and •Align our executive officers’ interests with those of our stockholders by providing a majority of total compensation in the form of equity awards. We operate in a fast-paced, innovative education software and services industry, which is an emerging category with very few public company peers in the United States. Our executive team possesses a unique mix of education software industry experience and the ability to scale for high growth and profitability. Our leaders are difficult to replace, and we compete for talent in the highly competitive San Francisco Bay Area market. To retain key talent and remain competitive in our labor market, we provide compensation to our employees that recognizes and incentivizes high performance. Our total direct compensation to our executive officers consists of two components: base salary and equity incentive compensation. Our base salaries provide a stable source of income and keep our compensation competitive. Our time and performance-based equity compensation provides an incentive for our executive officers to achieve both short-term and long-term corporate goals. We generally do not grant cash bonuses to our executives. We recognize that short-term cash incentives are a standard component of executive compensation. However, we have opted to break from this common practice because we feel that linking a significant portion of executive compensation to equity provides for sustainable growth and aligns our executives’ goals with our stockholders’ interests. We believe that allocating a meaningful percentage of compensation to equity-based opportunities motivates our executive officers to create long-term stockholder value. To that end, our equity compensation is comprised of time-based RSUs and PSUs, with vesting of the PSUs based on three equally weighted metrics. Our total direct compensation is generally targeted at market competitive ranges, and while competitive market data informs the pay decisions of our Compensation Committee, it is not the determinative factor in setting our executives’ compensation. In setting compensation levels, our Compensation Committee further takes into account our financial and market performance on an absolute basis and relative to our peer group, as well as individual factors, including, but not limited to, job responsibilities and complexity of the role, contributions to Chegg, market competition for talent, experience and tenure.

  44. Role of Our Compensation Committee, Management and Independent Compensation Consultant

    Role of Our Compensation Committee, Management and Independent Compensation Consultant

  45. Role of Our Independent Compensation Consultant

    Role of Our Independent Compensation Consultant For fiscal year 2023, the Compensation Committee retained Frederic W. Cook & Co., Inc. ("FW Cook") as its independent compensation consultant, and for fiscal year 2024 the Compensation Committee has retained Aon as its independent compensation consultant. The Compensation Committee determined that each of FW Cook and Aon is an independent compensation advisor including for purposes of the Dodd-Frank Act and other applicable SEC and NYSE regulations. FW Cook and did not perform services any services for us in 2023, other than executive and general compensation survey consulting services. The Committee has assessed the independence of Aon’s services for us in 2024 pursuant to SEC and NYSE regulations. In doing so, the Committee considered each of the factors set forth by the SEC and the NYSE with respect to a compensation consultant’s independence. The Committee also considered the nature and amount of work performed for the Committee and the fees paid for those services in relation to the firm’s total revenues. Based on its consideration of the foregoing and other relevant factors, the Committee concluded that there are no conflicts of interest, and that Aon is independent. During fiscal year 2023, FW Cook was retained to, among other activities, develop our compensation peer group for 2024. During 2024, Aon was retained to, among other activities, review our compensation philosophy and objectives, develop an updated compensation peer group, gather and analyze compensation data for our compensation peer group, evaluate compensation practices and pay levels for our executives and non-employee directors, and review and recommend certain compensation arrangements with our executives. In the course of fulfilling these responsibilities, representatives of Aon attended Compensation Committee meetings and met with management from time to time to gather relevant information.

  46. 2024 Compensation Peer Group

    2024 Compensation Peer Group Our Compensation Committee considered market data compiled by its independent compensation consultant to better inform its determination of the key components of our executive compensation program and to develop a program that it believes will enable us to compete effectively for new executives and retain existing executives. In general, this market data consists of compensation information from both broad-based third-party compensation surveys and a compensation “peer group”. Our peer group for purposes of making determinations with respect to 2024 compensation consists of software companies that are similar to us in revenue, market capitalization, market capitalization to revenue ratio, growth, and relevant geographic locations where we compete for executive talent (generally San Francisco Bay Area, Los Angeles, and New York). While Chegg is classified by MSCI and S&P under the Global Industry Classification Standard ("GICS") in the “Education Services” sub-industry, our peer group and competitive market consists primarily of other software, SaaS, and internet companies. Therefore, the industries considered for our peer group extend beyond Education Services and also include companies in the following GICS industries: “Application Software,” “Interactive Media and Services,” “Internet & Direct Retail Marketing” and “Systems Software.”

  47. 2024 Compensation Peer Group

    | Chegg, Inc. | 52 | Proxy Statement for the 2025 Annual Meeting of Stockholders |

  48. 2024 Compensation Peer Group

    Each year, the Compensation Committee, with the assistance of its independent compensation consultant, conducts an annual review of the compensation levels and practices of our peer companies. As part of the review, the Compensation Committee assesses our compensation peer group to ensure the constituents continue to generally meet the selection criteria listed above. For the 2024 compensation peer group, the Compensation Committee, in October 2023, approved changes to the peer group taking into account Chegg’s market capitalization as it existed at that time and for the prior fiscal year, resulting in the removal of nine total companies, four of which were acquired (Coupa Software, Inc., Momentive Global Inc., New Relic, Inc. and Sumo Logic, Inc.) and five of which were more than four times Chegg's then-market capitalization previously included in the peer group reviewed by the Compensation Committee (Dropbox, Inc., Guidewire Software, Inc., Nutanix, Inc., Okta, Inc., and Smartsheet, Inc.). Ten new companies were added to the 2024 compensation peer group as a result of the 2023 assessment: Cerence, Inc., Coursera, Inc., Digital Turbine, Inc., Everbridge, Inc., Model N, Inc., Powerschool Holdings, Inc., Stride, Inc., Udemy, Inc., Yext, Inc., and ZipRecruiter, Inc. Chegg was in the 37th percentile of the peer group’s market capitalization and the 61st percentile of the peer group's revenue for the trailing four quarters. For our 2024 compensation decisions, our compensation peer group consisted of the 19 companies set forth below:

  49. 2024 Compensation Peer Group

    | 2U, Inc. | Coursera, Inc. | PowerSchool Holdings, Inc. | Udemy, Inc. | | Alteryx, Inc. | Digital Turbine, Inc. | Progress Software Corporation | Yelp, Inc. | | Blackbaud, Inc. | Everbridge, Inc. | Qualys, Inc. | Yext, Inc. | | Box, Inc. | LivePerson, Inc. | RingCentral, Inc. | ZipRecruiter, Inc. | | Cerence Inc. | Model N, Inc. | Stride, Inc. | |

  50. 2024 Compensation Peer Group

    The peer group information serves as a data point in determining the appropriate pay mix and overall compensation, but the Compensation Committee does not seek to align its compensation against any specific company member of our compensation peer group.

  51. Nathan Schultz Transition – New President and Chief Executive Officer

    Nathan Schultz Transition – New President and Chief Executive Officer Effective June 1, 2024, Nathan Schultz was appointed as our President and Chief Executive Officer and as a Class I director of the Board. Prior to his appointment as Chief Executive Officer, Mr. Schultz served as the Company’s Chief Operating Officer since October 2022, and he has been with the Company since 2008. In connection with his new appointment, Mr. Schultz’s received (i) a base salary of $1,000,000, (ii) RSUs with an approximate grant date value of $1,579,875, and (iii) PSUs with an approximate grant date value of $1,579,875, which will only vest upon achievement of specified goals. The RSUs vest over three years, with one-third vesting in March 2025 and the remainder vesting in eight equal quarterly installments for 24 months thereafter, subject to Mr. Schultz’s continued service on the applicable vesting dates. The PSUs are allocated between multiple tranches, become earned and eligible to vest upon the achievement of certain performance goals, as determined by the Compensation Committee, and are subject to a total three-year time-based vesting period (to the extent earned) subject to Mr. Schultz’s continued service on the applicable vesting dates.

  52. Dan Rosensweig Transition – New Executive Chair

    Dan Rosensweig Transition – New Executive Chair Effective as of the same date of June 1, 2024, Dan Rosensweig resigned from his positions as President and CEO and was appointed as our Executive Chair. Mr. Rosensweig is continuing to serve as a Co-Chairperson of the Board. In connection with his appointment as Executive Chair, Mr. Rosensweig received (i) a base salary of $850,000, (ii) RSUs with an approximate grant date value of $1,077,188, and (iii) PSUs with an approximate grant value of $359,063, which will only vest upon achievement of specified goals. The RSUs vest over three years, with 50% vesting on the first anniversary of the vesting commencement date and the remainder vesting in eight equal quarterly installments for 24 months thereafter, subject to Mr. Rosensweig’s continued service on the applicable vesting dates. The PSUs are allocated to a single tranche, become earned and eligible to vest upon the achievement of certain performance goals, as determined by the Compensation Committee, and are subject to a total three-year time-based vesting period (to the extent earned), subject to Mr. Rosensweig’s continued service on the applicable vesting dates.

  53. David Longo Transition – New Chief Financial Officer Upon Andrew Brown’s Retirement

    David Longo Transition – New Chief Financial Officer Upon Andrew Brown’s Retirement Effective February 21, 2024, David Longo was appointed as our Chief Financial Officer, Principal Financial Officer, Principal Accounting Officer, and Treasurer. Mr. Longo replaced Andrew Brown, who resigned effective February 21, 2024 and, as part of a planned transition, remained an employee of the Company until his retirement on June 7, 2024. Prior to his appointment as Chief Financial Officer, Mr. Longo served as the Company’s Vice President, Chief Accounting Officer, Corporate Controller, Assistant Treasurer, and Principal Accounting Officer since December 2021. In connection with his new appointment, Mr. Longo received (i) a base salary of $680,000 and (ii) RSUs with an approximate grant date value of $1,900,000 million. The RSUs vested in full in March 2025, with such vesting subject to Mr. Longo’s continued service through the vesting date.

  54. Elements of Fiscal Year 2024 Compensation

    Elements of Fiscal Year 2024 Compensation 2024 CEO Pay Mix. Consistent with our compensation philosophy and objectives, we provide compensation to our Chief Executive Officer and our executive officers in the form of base salaries, RSUs and PSUs. We generally do not provide annual cash incentive opportunities, which are typically provided by our peer companies, as our equity incentive compensation is intended to tie the majority of our executive officers’ pay to the delivery of stockholder value. Equity compensation in fiscal year 2024 constitutes 76% of the total pay mix for our Chief Executive Officer, Nathan Schultz.

  55. 2024 CEO Target Pay Mix(1)

    | Performance-Based RSUs |

  56. 2024 CEO Target Pay Mix(1)

    | Represents 50% of the target incentive value of our annual equity awards. Designed to motivate and reward the CEO to drive critical annual performance goals. Performance is measured based on three equally weighted financial metrics in 2024, consisting of (1) total net revenues, (2) adjusted EBITDA and (3) free cash flow. |

  57. 2024 CEO Target Pay Mix(1)

    | Time-Based RSUs |

  58. 2024 CEO Target Pay Mix(1)

    | Represents 50% of the target incentive value of our annual equity awards. Intended to provide retention value and align the interests of the CEO and stockholders. |

  59. 2024 CEO Target Pay Mix(1)

    | (1) Target pay mix represents annual base salary rates as of the fiscal year end, RSUs at grant date fair value, and PSUs at grant date fair value, assuming the target performance level is achieved. |

  60. Equity Incentive Compensation

    Equity Incentive Compensation The Compensation Committee believes that equity compensation should represent a significant amount of our executive officers’ total compensation so that the interests of our executive officers are aligned with those of our stockholders. The Compensation Committee determines the amount of equity compensation appropriate for each NEO based on a variety of factors, including our compensation objectives; corporate operational and financial performance and relative stockholder return; each executive’s responsibilities; the compensation peer group and third-party survey market analysis provided by its independent compensation consultant; historical equity grants and equity holdings; and internal parity, overall share usage and equity pool availability and, for executive officers other than the Chief Executive Officer, recommendations from the Chief Executive Officer.

  61. Equity Incentive Compensation

    | Chegg, Inc. | 56 | Proxy Statement for the 2025 Annual Meeting of Stockholders |

  62. Equity Incentive Compensation

    Executive officers are initially granted an equity award, generally in the form of RSUs, when they join us, based on their position and their relevant prior experience. Thereafter, equity awards are generally granted annually to eligible executive officers. The Compensation Committee has the discretion to grant equity awards in addition to these annual grants based on, among other factors, changes in job responsibilities, performance and experience, or material changes in market compensation. In October 2022, the Compensation Committee determined to increase Mr. Schultz’s 2023 annual target equity award value to $6.6 million in connection with his promotion to Chief Operating Officer. Rather than granting Mr. Schultz an off-cycle grant in connection with his promotion, Mr. Schultz was granted this annual equity award on March 27, 2023, and it was split into 50% RSUs and 50% PSUs. In 2024, the Compensation Committee determined to grant equity awards in connection with executive leadership transitions for our Chief Executive Officer, Chief Financial Officer, and Executive Chair. Our Chief Executive Officer Mr. Schultz and our Executive Chair Mr. Rosensweig each received a mix of RSUs and PSUs in June 2024, while our Chief Financial Officer Mr. Longo received only RSUs in April 2024. Mr. Schultz’s target equity award mix consisted of 50% RSUs and 50% PSUs, while Mr. Rosensweig’s target equity award mix consisted of 75% RSUs and 25% PSUs. Mr. Brown and Mr. Lem, both of whom left the Company did not receive any equity awards in 2024. The Compensation Committee routinely evaluates and considers the type of awards granted under our equity incentive program and may, in the future, decide that other types of awards or a different mix of awards are appropriate to provide incentives to our executive officers. The Company does not grant stock options, stock appreciation rights, or similar instruments with option-like features and has no policies or practices to disclose pursuant to Item 402(x)(1) of Regulation S-K.

  63. Restricted Stock Units

    Restricted Stock Units We grant RSUs because they provide retentive value for our executive officers and are linked to creating stockholder value as the award value increases with our stock price appreciation. The Compensation Committee recommended, and the Board approved, a grant of RSUs to Mr. Longo in connection with his promotion to Chief Financial Officer in February 2024. Mr. Longo’s RSUs, which were granted in April 2024, vested in full on March 12, 2025. The vesting of Mr. Longo’s RSU award was conditioned on his service through the vesting date. The Compensation Committee recommended, and the Board approved, a grant of RSUs to each of Mr. Schultz and Mr. Rosensweig in connection with their respective appointments as Chief Executive Officer and Executive Chair effective as of June 1, 2024. Mr. Schultz’s RSU award vests as to one-third of the underlying shares of common stock on the one-year anniversary of the vesting commencement date (June 12, 2025), with the remaining amount vesting in eight equal quarterly installments over the next 24 months, conditioned on his service up to and through the applicable time-based vesting dates. Half of Mr. Rosensweig’s RSU award vests as to the underlying shares of common stock on the one-year anniversary of the vesting commencement date (June 12, 2025), with the remaining amount vesting in eight equal quarterly installments over the next 24 months, conditioned on his service up to and through the applicable time-based vesting dates.

  64. Restricted Stock Units

    | Chegg, Inc. | 57 | Proxy Statement for the 2025 Annual Meeting of Stockholders |

  65. Restricted Stock Units

    The following table displays the details of the RSU awards granted to our executives for 2024:

  66. Restricted Stock Units

    | Named Executive Officer | Number of Shares Granted | Target Value ($)(1) | Vesting Conditions | | Nathan Schultz | 412,500 | 1,579,875 | Vests over three years, with one-third vesting on the first anniversary of the vesting commencement date and the remainder in eight equal quarterly installments thereafter. | | Dan Rosensweig | 281,250 | 1,077,188 | Vests over three years, with half vesting on the first anniversary of the vesting commencement date and the remainder in eight equal quarterly installments thereafter. | | David Longo | 265,734 | 1,900,000 | Vests in full one year after the vesting commencement date. |

  67. Restricted Stock Units

    | (1) The target value represents the grant date fair value calculated in accordance with Financial Accounting Standards Board ("FASB") Accounting Standards Codification ("ASC") Topic 718 ("ASC 718") of the granted PSUs, denominated at target payout levels. |

  68. Performance-Based Restricted Stock Units

    Performance-Based Restricted Stock Units We grant PSUs because they are linked to stockholder value creation, like RSUs, but are also leveraged to our financial performance and allow us to set appropriate annual goals that we believe are critical to drive long-term success. The Compensation Committee recommended, and the Board approved, a grant of PSUs to our newly appointed Chief Executive Officer Mr. Schultz and our newly appointed Executive Chair Mr. Rosensweig, effective as of June 1, 2024. The PSUs are subject to the achievement of certain financial performance goals and are conditioned on Mr. Schultz’s and Mr. Rosensweig’s service up to and through the applicable time-based vesting dates. The Compensation Committee determined the achievement of these PSUs in March 2025 based on three equally weighted performance metrics: (1) fiscal year 2024 total net revenue, (2) fiscal year 2024 adjusted EBITDA, and (3) fiscal year 2024 free cash flow (each as defined below). The performance metrics related to total net revenue and adjusted EBITDA are the same metrics used for PSU awards granted during 2023. In 2024, the Compensation Committee included free cash flow as a third performance metric in response to stockholder feedback and because it is an indicator of, among other things, (i) the amount of cash that the business is generating, (ii) the leverage in our business model, (iii) our liquidity, and (iv) what drives stockholder value for Chegg. The Compensation Committee selected total net revenue, rather than Chegg Services revenue which it had used previously, to recognize the importance of the diversity of the Company’s revenue sources. Along with total net revenue, the Compensation Committee selected adjusted EBITDA, a non-GAAP measure of profitability, as both are the most important drivers of stockholder value for Chegg and are primary components of our overall revenue growth and profitability. We believe that each of these are appropriate performance measures for our executive officers, as their decisions can significantly impact these metrics, and the selection of these three measures as PSU metrics ensures our executive officers are incentivized in accordance with the long-term interests of our stockholders. The performance metrics are synchronized with the corporate strategic plan and associated metrics and targets approved by our Board of Directors. While in previous years we used a one-year performance period for our annual cycle PSUs, the 2024 PSUs granted to Mr. Schultz and Mr. Rosensweig have a total three-year vesting period, with partial vesting after the first year. Similar to our rationale for the use of annual cycle PSUs in prior years, we believe that the annual payouts allow us the flexibility to set appropriate annual goals to drive stockholder value given our growth expectations and the rapidly changing nature of the industry in which we operate. Upon the determination of the level of attainment of the performance metrics, a percentage of PSUs may be earned based on actual achievement. Any PSUs that are not earned are forfeited at the respective vesting dates.

  69. Performance-Based Restricted Stock Units

    | Chegg, Inc. | 58 | Proxy Statement for the 2025 Annual Meeting of Stockholders |

  70. Performance-Based Restricted Stock Units

    The following table displays the details of the PSU awards granted to our executives for 2024:

  71. Performance-Based Restricted Stock Units

    | Named Executive Officer | Number of Shares Granted | Target Value ($)(1) | Vesting Conditions | | Nathan Schultz | 412,500 | 1,579,875 | Allocated between two equal tranches, total three-year vesting period. The first tranche vests in full after the first anniversary of the vesting commencement date upon the determination of the attainment of the 2024 PSU Performance Metrics. The second tranche vests 50% on the second anniversary of the vesting commencement date and 50% on the third anniversary of the vesting commencement date based on attainment of the Performance Metrics. | | Dan Rosensweig | 93,750 | 359,063 | Allocated to a single tranche, total three-year vesting period. The PSUs vest one-third on each of the first, second, and third anniversaries of the vesting commencement date based on attainment of the 2024 PSU Performance Metrics. |

  72. Performance-Based Restricted Stock Units

    | (1) The target value represents the grant date fair value calculated in accordance with FASB ASC 718 of the granted PSUs, denominated at target payout levels. |

  73. Performance-Based Restricted Stock Units

    The number of PSUs that may be earned range from 0% to 150% of the total number of shares subject to the PSU award depending on the level of performance achieved for each goal. No payout will be made for performance below the threshold level. The metrics are equally weighted (each representing one-third of the target number of shares) and measured separately, and the resulting number of earned PSUs with respect to each metric are added together for the total number of earned PSUs that are eligible to vest over time. If actual performance falls between the threshold, target, or maximum levels, linear interpolation will be used to determine the number of PSUs earned, as set forth in the table below:

  74. Performance-Based Restricted Stock Units

    | Performance Level | Threshold | Target | Maximum | | Payout % of Award | 50% | 100% | 150% | | Total Net Revenues | $627,500,000 | $660,000,000 | $693,000,000 | | Adjusted EBITDA* | $149,000,000 | $165,000,000 | $182,000,000 | | Free Cash Flow* | $68,000,000 | $85,000,000 | $102,000,000 |

  75. Performance-Based Restricted Stock Units

    *Adjusted EBITDA and free cash flow are non-GAAP financial measures, as defined above. A reconciliation of net loss to EBITDA and to adjusted EBITDA and a reconciliation of net cash provided by operating activities to free cash flow, in each case prepared in accordance with GAAP, is included as Appendix A to this proxy statement. The Compensation Committee recognizes the importance of establishing rigorous but realistic performance targets with respect to our annual cycle PSUs in order to motivate executives to drive strong performance that translates to value creation for stockholders, and the 2024 performance targets were established in consideration of those factors and our business environment.

  76. Performance-Based Restricted Stock Units

    | Chegg, Inc. | 59 | Proxy Statement for the 2025 Annual Meeting of Stockholders |

  77. 2024 Equity Incentive Awards

    2024 Equity Incentive Awards The grant date fair value calculated in accordance with FASB ASC 718 of the annual cycle RSUs and PSUs, is set forth in the table below, denominated at target payout levels.

  78. 2024 Equity Incentive Awards

    | | Number of Shares Granted | | Grant Date Fair Value of Awards | | | Named Executive Officer | Time-Vesting RSUs (#) | PSUs (Target) (#) | Time-Vesting RSUs ($) | PSUs (Target) ($) | | Nathan Schultz | 412,500 | 412,500 | 1,579,875 | 1,579,875 | | Dan Rosensweig | 281,250 | 93,750 | 1,077,188 | 359,063 | | David Longo | 265,734 | — | 1,899,998 | 0 |

  79. Fiscal Year 2024 Performance-Based Restricted Stock Units Payout

    Fiscal Year 2024 Performance-Based Restricted Stock Units Payout In March 2025, the Compensation Committee certified our financial performance in 2024 with respect to the 2024 PSU metrics. We achieved the following results, resulting in a weighted average payout of 17.4% of Target:

  80. Fiscal Year 2024 Performance-Based Restricted Stock Units Payout

    | Performance Metric | Achievement | Percent of Award Earned | Component Weighting | Subtotal | | Total Net Revenues | $617,574,000 | —% | 1/3 | —% | | Adjusted EBITDA* | $149,667,000 | 52.1% | 1/3 | 17.4% | | Free Cash Flow* | $50,252,000 | —% | 1/3 | —% | | Total Performance (rounded) | | | | 17.4% |

  81. Fiscal Year 2024 Performance-Based Restricted Stock Units Payout

    The Compensation Committee did not use any discretionary authority to adjust the resulting corporate performance from the financial measures reflected in the table above. The 2024 PSUs awarded to Mr. Schultz vest over a three-year, time-based vesting schedule with two equally allocated tranches as follows: the earned portion of the first tranche, representing one-half of the total PSUs, will vest on June 12, 2025, and the earned portion of the second tranche will vest 50% on June 12, 2026, and the remaining 50% on June 12, 2027. The 2024 PSUs awarded to Mr. Rosensweig similarly vest over a three-year time-based vesting schedule as follows: one-third will vest on June 12, 2025, one-third will vest on June 12, 2026, and one-third will vest on June 12, 2027. Mr. Longo was not awarded PSUs in connection with his appointment as Chief Financial Officer.

  82. Total Stockholder Return PSUs

    Total Stockholder Return PSUs During 2021, to incentivize our executives' long-term engagement, drive the next phase of our growth and support retention, we granted special absolute total stockholder return PSUs (the “TSR PSUs”) to certain of our executive officers. The TSR PSUs were eligible to be earned based on share price growth over a three-year performance period from March 1, 2021 through February 29, 2024 (subject to a four-year time-vesting period from the grant date). The TSR PSU goal was measured by calculating the percentage of growth of our share price from $99.05 - the closing trading price of our common stock on the March 1, 2021 grant date. The TSR PSUs were eligible to vest if the Company achieved absolute TSR growth of between 25% and 75% during the three-year performance period. As previously disclosed, during this three-year performance period, none of the performance goals for the TSR PSUs were achieved; and therefore, no portion of this award was earned.

  83. Total Stockholder Return PSUs

    | Chegg, Inc. | 60 | Proxy Statement for the 2025 Annual Meeting of Stockholders |

  84. Severance and Change-of-Control Arrangements

    Severance and Change-of-Control Arrangements To enable us to attract talented executives, as well as ensure ongoing retention when considering potential corporate transactions that may create uncertainty as to future employment, we offer certain post-employment and change-of-control payments and benefits to certain NEOs. Given the nature and competitiveness of our industry, the Compensation Committee believes these severance and change-of-control protections are essential elements of our NEOs' compensation program and assist us in recruiting, retaining, and developing key management talent. Our change-of-control benefits are intended to allow key employees, including our NEOs, to focus their attention on the business operations of our Company in the face of the potentially disruptive impact of a rumored, or actual change-of-control transaction, to assess takeover bids objectively without regard to the potential impact on their own job security and to allow for a smooth transition in the event of a change-of-control. The Committee reviewed and adopted an updated Severance Plan in October 2024 following a review of market practices and Chegg’s specific needs. A detailed description of the terms of the Severance Plan can be found under the "Termination and Change of Control Arrangements" section of this proxy statement. We have entered into an employment agreement with Mr. Rosensweig and adopted a Severance Plan in which each of the NEOs, other than Mr. Rosensweig, participates. These arrangements provide, as applicable, cash severance benefits and equity award vesting acceleration in the event of certain terminations of employment both outside a change-of-control and in connection with a change-of-control (i.e., double-trigger severance protections). We do not provide “single trigger” protections or tax gross-ups if an executive is subject to excise taxes as a result of severance or change-of-control benefits. A detailed description of the terms of Mr. Rosensweig’s offer letter and the Severance Plan can be found under the “Termination and Change of Control Arrangements” section of this proxy statement.

  85. Summary Compensation

    | Name and Principal Position(1) | Year | Salary ($) | Stock Awards ($)(1) | All Other Compensation ($)(2) | Total ($) | | Nathan Schultz | 2024 | 958,333 | 3,159,750 | 13,800 | 4,131,883 | | President and Chief Executive Officer | 2023 | 900,000 | 6,599,975 | 13,200 | 7,513,175 | | | 2022 | 821,875 | 5,499,946 | 12,200 | 6,334,021 | | Dan Rosensweig | 2024 | 954,167 | 1,436,250 | 13,800 | 2,404,217 | | Executive Chair and Co-Chairperson of our Board of Directors, Former President and Chief Executive Officer | 2023 | 1,100,000 | 3,666,649 | 13,200 | 4,779,849 | | | 2022 | 1,075,000 | 10,999,964 | 12,200 | 12,087,164 | | David Longo | 2024 | 651,813 | 1,899,998 | 13,800 | 2,565,611 | | Chief Financial Officer | 2023 | — | — | — | — | | Andrew Brown | 2024 | 360,938 | — | 11,000 | 371,938 | | Former Chief Financial Officer | 2023 | 850,000 | 1,833,325 | 13,200 | 2,671,525 | | | 2022 | 806,250 | 5,499,946 | 12,200 | 6,318,396 | | Esther Lem | 2024 | 302,500 | — | 18,979 | 321,479 | | Former Chief Marketing Officer | 2023 | 605,000 | 1,173,318 | 2,017 | 1,780,334 | | | 2022 | 591,250 | 3,519,960 | 12,200 | 4,123,410 |

  86. Grants of Plan Based Awards

    Grants of Plan Based Awards The following table sets forth certain information regarding grants of plan-based awards to each of our NEOs during fiscal year 2024.

  87. Grants of Plan Based Awards

    | | Grant Date | Board Approval Date | Award Type | Estimated Possible Payout Under Equity Incentive Plan Awards(1) | | | All Other Stock Awards: Number of Shares of Stock or Units (#)(2) | Grant Date Fair Value of Stock and Option Awards(3) | | | | Name | | | | Threshold (#) | Target (#) | Maximum (#) | | Threshold ($) | Target ($) | Maximum ($) | | Nathan Schultz | 6/1/2024 | 4/24/2024 | PSU | 103,125 | 206,250 | 309,375 | — | 395,969 | 789,938 | 1,184,906 | | | 6/1/2024 | 4/24/2024 | PSU | 103,125 | 206,250 | 309,375 | — | 395,969 | 789,938 | 1,184,906 | | | 6/1/2024 | 4/24/2024 | RSU | — | — | — | 412,500 | 1,579,875 | 1,579,875 | 1,579,875 | | Dan Rosensweig | 6/1/2024 | 4/24/2024 | PSU | 46,875 | 93,750 | 140,625 | — | 179,531 | 359,063 | 538,594 | | | 6/1/2024 | 4/24/2024 | RSU | — | — | — | 281,250 | 1,077,188 | 1,077,188 | 1,077,188 | | David Longo | 4/12/2024 | 4/11/2024 | RSU | — | — | — | 265,734 | 1,899,998 | 1,899,998 | 1,899,998 | | Andrew Brown | N/A | N/A | N/A | — | — | — | — | — | — | — | | Esther Lem | N/A | N/A | N/A | — | — | — | — | — | — | — |

  88. Grants of Plan Based Awards

    | (1) Upon the achievement by December 31, 2024 of certain Company performance metric measurements approved by the Compensation Committee as described under the heading “Elements of Fiscal Year Compensation—Equity Incentive Compensation—Performance-Based Restricted Stock Units,” Mr. Schultz' award vests in two equal tranches of 206,250 PSUs. Mr. Schultz's first tranche of PSUs earned with respect to the performance metric shall vest 100% on June 12, 2025. Mr. Schultz's second tranche of PSUs earned with respect to the performance metric shall vest one-half on June 12, 2026 and June 12, 2027, subject in each case to Mr. Schultz' continued service up to and through the applicable vesting dates. Mr. Rosensweig's PSUs shall vest one-third on June 12, 2025, June 12, 2026 and June 12, 2027, subject in each case to Mr. Rosensweig's continued service up to and through the applicable vesting dates. | | (2) Mr. Schultz's shares will vest one-third on June 12, 2025, and 8.33% shall vest on each quarterly anniversary thereafter such that the RSUs shall be fully vested on June 12, 2027, subject in each case to Mr. Schultz's continued service to and through the applicable vesting dates. Mr. Rosensweig's shares will vest 50% on June 12, 2025, and 6.25% shall vest on each quarterly anniversary thereafter such that the RSUs shall be fully vested on June 12, 2027, subject in each case to Mr. Rosensweig's continued service up to and through the applicable vesting dates. 100% of Mr. Longo's shares vested on March 12, 2025. | | (3) Reflects the grant date fair value of each equity award at the target performance level computed in accordance with ASC 718 and described in footnote 1 to the Summary Compensation Table. The assumptions used in the valuation of these awards are set forth in notes 2 and 13 to our consolidated financial statements included in our Annual Report on Form 10-K for the year ended December 31, 2024. These amounts may not correspond to the actual value that may be realized by the NEOs. |

  89. Grants of Plan Based Awards

    | Chegg, Inc. | 65 | Proxy Statement for the 2025 Annual Meeting of Stockholders |

  90. Outstanding Equity Awards at December 31, 2024 Table

    Outstanding Equity Awards at December 31, 2024 Table The following table provides information with respect to outstanding equity awards as of December 31, 2024 with respect to our NEOs.

  91. Outstanding Equity Awards at December 31, 2024 Table

    | | | | Stock Awards | | | | | | Grant Date | | Number of Shares that Have Not Vested (#) | Market Value of Shares that Have Not Vested ($)(1) | Number of Unearned Shares that Have Not Vested (#) | Market Value of Unearned Shares that Have Not Vested ($)(1) | | Name | | Award Type | | | | | | Nathan Schultz | 3/1/2021(2) | TSR PSU | 36,468 | 58,713 | — | — | | | 3/28/2022(3) | PSU | 6,398 | 10,301 | — | — | | | 3/27/2023(4) | PSU | 86,533 | 139,318 | — | — | | | 6/1/2024(5) | PSU | 206,250 | 332,063 | — | — | | | 6/1/2024(6) | PSU | — | — | 206,250 | 332,063 | | | 3/28/2022(7) | RSU | 6,398 | 10,301 | — | — | | | 3/27/2023(8) | RSU | 86,534 | 139,320 | — | — | | | 6/1/2024(9) | RSU | 412,500 | 664,125 | — | — | | Dan Rosensweig | 3/1/2021(2) | TSR PSU | 72,936 | 117,427 | — | — | | | 3/28/2022(3) | PSU | 12,796 | 20,602 | — | — | | | 6/1/2024(10) | PSU | 93,750 | 150,938 | — | — | | | 3/28/2022(7) | RSU | 12,796 | 20,602 | — | — | | | 6/1/2024(11) | RSU | 281,250 | 452,813 | — | — | | David Longo | 1/12/2022(12) | RSU | 16,148 | 25,998 | — | — | | | 3/27/2023(13) | RSU | 2,623 | 4,223 | — | — | | | 4/12/2024(14) | RSU | 265,734 | 427,832 | — | — | | Andrew Brown | N/A | N/A | — | — | — | — | | Esther Lem | N/A | N/A | — | — | — | — |

  92. Outstanding Equity Awards at December 31, 2024 Table

    | (1) The market price for our common stock is based on the closing price per share of our common stock as listed on the New York Stock Exchange on December 31, 2024 of $1.61. | | (2) The shares subject to the TSR PSU award will be earned only upon achievement by February 29, 2024 of the Company performance metrics consisting of TSR as approved by the Compensation Committee. One-half of the achieved shares were to vest on March 1, 2024 and the remaining unvested portion of this TSR PSU were to vest on March 1, 2025, subject to the officers continued service up to and through each vesting date and the acceleration as described in "Termination and Change of Control Arrangements" below. None of the performance goals for the TSR PSUs were achieved; and therefore, no portion of this award was earned. | | (3) The shares subject to the PSU award were earned only upon achievement by December 31, 2022 of Company performance metrics consisting of Chegg Services Revenue and adjusted EBITDA as approved by the Compensation Committee. The Compensation Committee determined that the weighted average percentage of 39.5% of the measurements had been achieved, therefore a weighted average of 39.5% of the shares subject to the PSU award were earned. One-third of the achieved shares vested on March 12, 2023 and the remaining unvested portion of this PSU is scheduled to vest as to 8.33% on each quarterly anniversary thereafter such that the PSUs shall be fully vested on March 12, 2025, subject to the officer's continued service up to and through each vesting date and the acceleration as described in “Termination and Change of Control Arrangements” below. |

  93. Outstanding Equity Awards at December 31, 2024 Table

    | Chegg, Inc. | 66 | Proxy Statement for the 2025 Annual Meeting of Stockholders |

  94. Outstanding Equity Awards at December 31, 2024 Table

    | (4) The shares subject to the PSU award were earned only upon achievement by December 31, 2023 of Company performance metrics consisting of Chegg Services Revenue, adjusted EBITDA, and free cash flow as approved by the Compensation Committee. The Compensation Committee determined that the weighted average percentage of 35.6% of the measurements had been achieved, therefore a weighted average of 35.6% of the shares subject to the PSU award were earned. One-third of the achieved shares vested on March 12, 2024 and the remaining unvested portion of this PSU is scheduled to vest as to 8.33% on each quarterly anniversary thereafter such that the PSUs shall be fully vested on March 12, 2026, subject to the officer's continued service up to and through each vesting date and the acceleration as described in “Termination and Change of Control Arrangements” below. | | (5) The shares subject to the PSU award were earned only upon achievement by December 31, 2024 of Company performance metrics consisting of Chegg Services Revenue, adjusted EBITDA, and free cash flow as approved by the Compensation Committee. The Compensation Committee determined that the weighted average percentage of 17.36% of the measurements had been achieved, therefore a weighted average of 17.36% of the shares subject to the PSU award were earned. 100% of the PSUs shall vest on June 12, 2025, subject to the officer's continued service up to and through each vesting date and the acceleration as described in “Termination and Change of Control Arrangements” below. | | (6) The shares subject to the PSU award shall be earned only upon achievement by December 31, 2025 of Company performance metrics consisting of Chegg Services Revenue, adjusted EBITDA, and free cash flow as approved by the Compensation Committee. One-half of the achieved shares shall vest on June 12, 2026 and June 12, 2027, subject to the officer's continued service up to and through each vesting date and the acceleration as described in “Termination and Change of Control Arrangements” below. | | (7) One-third of the shares vested on March 12, 2023 and 8.33% shall vest on each quarterly anniversary thereafter such that the RSUs were to fully vest on March 12, 2025. The vesting is subject to the officer's continued service up to and through each vesting date and the acceleration as described in “Termination and Change of Control Arrangements” below. | | (8) One-third of the shares vested on March 12, 2024 and 8.33% shall vest on each quarterly anniversary thereafter such that the RSUs shall be fully vested on March 12, 2026. The vesting is subject to the officer's continued service up to and through each vesting date and the acceleration as described in “Termination and Change of Control Arrangements” below. | | (9) One-third of the shares shall vest on June 12, 2026 and 8.33% shall vest on each quarterly anniversary thereafter such that the RSUs shall be fully vested on June 12, 2026. The vesting is subject to the officer's continued service up to and through each vesting date and the acceleration as described in “Termination and Change of Control Arrangements” below. | | (10) The shares subject to the PSU award were earned only upon achievement by December 31, 2024 of Company performance metrics consisting of Chegg Services Revenue, adjusted EBITDA, and free cash flow as approved by the Compensation Committee. The Compensation Committee determined that the weighted average percentage of 17.36% of the measurements had been achieved, therefore a weighted average of 17.36% of the shares subject to the PSU award were earned. One-third of the achieved shares shall vest on June 12, 2025, June 12, 2026 and June 12, 2027, subject to the officer's continued service up to and through each vesting date and the acceleration as described in “Termination and Change of Control Arrangements” below. | | (11) One-half of the shares shall vest on June 12, 2025 and 6.25% shall vest on each quarterly anniversary thereafter such that the RSUs shall be fully vested on June 12, 2027. The vesting is subject to the officer's continued service up to and through each vesting date and the acceleration as described in “Termination and Change of Control Arrangements” below. | | (12) One-fourth of the shares vested on April 12, 2022 and 6.25% shall vest on each quarterly anniversary thereafter such that the RSUs were fully vested on April 12, 2025. The vesting was subject to the officer's continued service up to and through each vesting date and the acceleration as described in “Termination and Change of Control Arrangements” below. | | (13) One-half of the shares vested on March 12, 2024 and 12.5% shall vest on each quarterly anniversary thereafter such that the RSUs were fully vested on March 12, 2025. The vesting is subject to the officer's continued service up to and through each vesting date and the acceleration as described in “Termination and Change of Control Arrangements” below. | | (14) 100% of the shares vested on March 12, 2025. The vesting was subject to the officer's continued service up to and through each vesting date and the acceleration as described in “Termination and Change of Control Arrangements” below. |

  95. Outstanding Equity Awards at December 31, 2024 Table

    | Chegg, Inc. | 67 | Proxy Statement for the 2025 Annual Meeting of Stockholders |

  96. Option Exercises and Stock Vested Table

    Option Exercises and Stock Vested Table The following table presents information concerning the aggregate number of shares of our common stock for which options were exercised during fiscal year 2024 for each of the NEOs. In addition, the table presents information on shares of our common stock that were acquired upon the vesting of stock awards during 2024 for each of the NEOs on an aggregated basis.

  97. Option Exercises and Stock Vested Table

    | | Option Awards | | Stock Awards | | | | Number of Shares Acquired on Exercise | Value Realized on Exercise ($) | Number of Shares Acquired on Vesting(1) (#) | Value Realized on Vesting ($)(2) | | Name | | | | | | Nathan Schultz | — | — | 204,150 | 1,105,744 | | Dan Rosensweig | — | — | 236,207 | 1,607,621 | | David Longo | — | — | 31,271 | 177,363 | | Andrew Brown | — | — | — | — | | Esther Lem | — | — | — | — |

  98. Option Exercises and Stock Vested Table

    | (1) Amounts reflect the vesting of RSUs and PSUs. | | (2) The value realized on the shares acquired is the fair market value of the shares on the date of vesting, which was the closing price of our common stock on such date as traded on the NYSE. |

  99. Option Exercises and Stock Vested Table

    | Invested • Chegg We are unwavering supporters of students and a reliable, readily-available resource. | |

  100. Option Exercises and Stock Vested Table

    | Chegg, Inc. | 68 | Proxy Statement for the 2025 Annual Meeting of Stockholders |

  101. Chief Executive Officer Pay Ratio

    Chief Executive Officer Pay Ratio Pursuant to Section 953(b) of the Dodd-Frank Wall Street Reform and Consumer Protection Act and Item 402(u) of Regulation S-K (“Item 402(u)”), we are required to disclose the ratio of our principal executive officer’s annual total compensation to the annual total compensation of our median employee. For purposes of determining the Chief Executive Officer pay ratio, because we had multiple Chief Executive Officers for the year, we have used Nathan Schultz' compensation in 2024 plus Dan Rosensweig's compensation for the period he served as Chief Executive Officer in 2024. As disclosed in the Summary Compensation Table, the 2024 annual total compensation for our current Chief Executive Officer, Nathan Schultz was $4,131,883 and the 2024 annual total compensation for our Former President and Chief Executive Officer until May 31, 2024, Dan Rosensweig, was $2,404,217, resulting in an aggregate Chief Executive Officer total compensation of $6,536,100. The 2024 annual total compensation of our median employee was $78,674. Accordingly, the ratio of the 2024 annual total compensation of our Chief Executive Officer, Nathan Schultz, to the 2024 annual total compensation of our median employee is 53 to 1 and the ratio to our Former Chief Executive Officer, Dan Rosensweig, was 31 to 1, resulting in a aggregate Chief Executive Officer pay ratio of 83 to 1. We believe these ratios, which were calculated in a manner consistent with Item 402(u), to be a reasonable estimate, based upon the assumptions and adjustments described below.

  102. Compensation Measures and Calculation Methodology

    | | | Pay Versus Performance Disclosure |

  103. Pay Versus Performance Table

    Pay Versus Performance Table In accordance with Item 402(v), we provide below the tabular disclosure for the Company's President, Chief Executive Officer and Co-Chairperson (our Principal Executive Officer or “PEO”) and the average of our NEOs other than the PEO (“non-PEO NEOs”) for 2024, 2023, 2022 and 2021 and 2020.

  104. Pay Versus Performance Table

    | | | | | | | | Value of Initial Fixed S100 Investment Based On: | | | | | Fiscal Year | Summary Compensation Table Total for PEO Dan Rosensweig(1) ($) | Compensation Actually Paid to PEO Dan Rosensweig(2) ($) | Summary Compensation Table Total for PEO Nathan Schultz (1) ($) | Compensation Actually Paid to PEO Nathan Schultz(2) ($) | Average Summary Compensation Table Total for non-PEO NEOs(1) ($) | Average Compensation Actually Paid to non-PEO NEOS(3) ($) | Total Stockholder Return ($) | NASDAQ Composite Total Stockholder Return(4) ($) | Net (Loss) Income (in thousands) ($) | Adjusted EBITDA (in thousands)(5) ($) | | (a) | (b) | (c) | | | (d) | (e) | (f) | (g) | (h) | (i) | | 2024 | 2,404,217 | 196,478 | 4,131,883 | (693,309) | 1,086,343 | 234,181 | 4.25 | 215.22 | (837,068) | 149,667 | | 2023 | 4,779,849 | (688,671) | — | — | 3,104,169 | 196,528 | 29.97 | 167.30 | 18,180 | 222,400 | | 2022 | 12,087,164 | (4,776,037) | — | — | 5,471,691 | 2,348,120 | 67.34 | 116.65 | 266,638 | 254,525 | | 2021 | 21,005,605 | (2,978,784) | — | — | 9,280,385 | (826,037) | 80.98 | 174.36 | (1,458) | 265,859 | | 2020 | 10,381,080 | 36,270,875 | — | — | 4,285,861 | 13,669,798 | 238.27 | 143.64 | (6,221) | 207,058 |

  105. Pay Versus Performance Table

    | (1) Dan Rosensweig is the PEO for each year shown. Nathan Schultz, who became PEO in 2024, is shown as the second PEO for 2024.The non-PEO NEOs for 2020-2023 were Andrew Brown, Nathan Schultz, John Fillmore and Esther Lem. The Non-PEO NEOs for 2024 were David Longo, Andrew Brown and Esther Lem.. | | (2) To calculate CAP to the PEO in column (c) the following amounts were deducted from and added to the applicable SCT Total Compensation: |

  106. Pay Versus Performance Table

    | Fiscal Year | Summary Compensation Table Total for PEO ($) | Deductions from Summary Compensation Table Total(a) ($) | Inclusion of Equity Values Total l(b) ($) | Compensation Actually Paid to PEO ($) | | 2024 for PEO Dan Rosensweig | 2,404,217 | (1,436,250) | (771,489) | 196,478 | | 2024 for PEO Nathan Schultz | 4,131,883 | (3,159,750) | (1,665,442) | (693,309) |

  107. Pay Versus Performance Table

    | (a) Represents the grant date fair value of equity awards reported in the “Stock Awards” column in the Summary Compensation Table for 2024. |

  108. Pay Versus Performance Table

    | Chegg, Inc. | 75 | Proxy Statement for the 2025 Annual Meeting of Stockholders |

  109. Pay Versus Performance Table

    | (b) Reflects the value of equity calculated in accordance with the SEC methodology for determining compensation actually paid under Item 402(v) of Regulation S-K. The valuation assumptions used to calculate fair values did not materially differ from those disclosed at the time of grant. The amounts deducted or added in calculating the equity values included in CAP are as follows: |

  110. Pay Versus Performance Table

    | Year | Year End Fair Value of Equity Awards Granted in the Year ($) | Year Over Year Change in Fair Value of Outstanding and Unvested Equity Awards ($) | Fair Value as of Vesting Date of Equity Awards Granted and Vested in the Year ($) | Year over Year Change in Fair Value of Equity Awards Granted in Prior Years that Vested in the Year ($) | Fair Value at the End of the Prior Year of Equity Awards that Failed to Meet Vesting Conditions in the Year ($) | Value of Dividends or Other Earnings Paid on Stock or Option Awards not Otherwise Reflected in Fair Value or Total Compensation ($) | Equity Value Included in Compensation Actually Paid ($) | | | (a) | (b) | (c) | (d) | (e) | (f) | (g) = (a) + (b) + (c) + (d) - (e) + (f) | | 2024 for PEO Dan Rosensweig | 479,015 | (174,254) | — | (1,076,250) | — | — | (771,489) | | 2024 for PEO Nathan Schultz | 779,417 | (1,231,189) | — | (1,213,670) | — | — | (1,665,442) |

  111. Pay Versus Performance Table

    | (3) To calculate CAP to the non-PEO NEOs in the column (e) the following amounts were deducted from and added to the applicable SCT Total compensation: |

  112. Pay Versus Performance Table

    | Fiscal Year | Summary Compensation Table Total for non-PEO NEOs ($) | Deductions from Summary Compensation Table Total(a) ($) | Additions to Summary Compensation Table Total(b) ($) | Compensation Actually Paid to non-PEO NEOs ($) | | 2024 | 1,086,343 | (633,333) | (218,829) | 234,181 |

  113. Pay Versus Performance Table

    | (a) Represents the grant date fair value of equity awards reported in the “Stock Awards" column in the Summary Compensation Table for 2024. | | (b) Reflects the value of equity calculated in accordance with the SEC methodology for determining compensation actually paid under Item 402(v) of Regulation S-K. The valuation assumptions used to calculate fair values did not materially differ from those disclosed at the time of grant. The amounts deducted or added in calculating the equity values included in CAP are as follows: |

  114. Pay Versus Performance Table

    | Year | Year End Fair Value of Equity Awards Granted in the Year ($) | Year Over Year Change in Fair Value of Outstanding and Unvested Equity Awards ($) | Fair Value as of Vesting Date of Equity Awards Granted and Vested in the Year ($) | Year over Year Change in Fair Value of Equity Awards Granted in Prior Years that Vested in the Year ($) | Fair Value at the End of the Prior Year of Equity Awards that Failed to Meet Vesting Conditions in the Year ($) | Value of Dividends or Other Earnings Paid on Stock or Option Awards not Otherwise Reflected in Fair Value or Total Compensation ($) | Equity Value Included in Compensation Actually Paid ($) | | | (a) | (b) | (c) | (d) | (e) | (f) | (g) = (a) + (b) + (c) + (d) - (e) + (f) | | 2024 | 142,611 | (61,006) | — | (138,561) | (161,873) | — | (218,829) |

  115. Pay Versus Performance Table

    | (4) Reflects TSR indexed to $100 for the Nasdaq Composite Index, which is an industry line peer group reported in the performance graph included in the Company's 2024 Annual Report on Form 10-K. The amounts assume that $100 was invested at the market close on December 31, 2019, in the common stock of Chegg, Inc. and the NASDAQ Composite, and the NASDAQ Composite assumes reinvestment of dividends. | | (5) Please see page 49 for a definition of Adjusted EBITDA. |

  116. Pay Versus Performance Table

    | Chegg, Inc. | 76 | Proxy Statement for the 2025 Annual Meeting of Stockholders |