DEF 14A of Chegg, Inc, Apr 28, 2026

DEF 14A of Chegg, Inc

Filed Apr 28, 2026 · FY20250001364954-26-000040

Open on EDGAR
  1. 2026 Director Nominees

    2026 Director Nominees We introduce our 2026 director nominees below.

  2. 2026 Director Nominees

    | | | | | Committee Memberships | | | | Name | Age | Director Since | Independent | Audit Committee | Compensation Committee | Governance and Sustainability Committee | | Renee Budig (Class III) | 65 | 2015 | YES | ■ | ■ | | | Dan Rosensweig (Class I) | 64 | 2010 | NO | | | | | Ted Schlein (Class I) | 62 | 2008 | YES | ■ | | ■ | | ■ - Member | | | | | | |

  3. Election of Directors

    Election of Directors Our Board of Directors currently consists of five 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 I will stand for election at this meeting. In addition, due to the rebalance of the classes that the Board approved on March 25, 2026, as discussed in more detail below, Ms. Budig, a former Class I director was moved to Class III and will stand for election at this meeting. The terms of office of our other current directors in Class II and Class III do not expire until the Annual Meetings of Stockholders to be held in 2027 and 2028, respectively. At the recommendation of our Governance and Sustainability Committee, our Board of Directors proposes the individuals named below for election to the Board at the Annual Meeting. Dan Rosensweig and Ted Schlein have been nominated for election as Class I directors for a three-year term expiring at the Annual Meeting of Stockholders to be held in 2029, and until their respective successors have been duly elected and qualified or until their earlier resignation or removal. In addition, in order to achieve an as equal balance as reasonably possible for the composition of the classes of directors, on March 25, 2026, Ms. Budig was moved from Class I to Class III. As a result, to ensure that our stockholders have an opportunity to vote on Ms. Budig's election at least every three years, she has been nominated to stand for election at this meeting with a term expiring at the Annual Meeting of Stockholders to be held in 2028 with the other Class III director. The Board consists of two Class I directors, one Class II director, and two Class III directors. Unless otherwise instructed, shares of our common stock represented by proxies will be voted “FOR” the election of each nominee named below. The Board knows of no reason why any nominee would be unable or unwilling to serve as a director if elected. 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. Each nominee has consented to being named in this proxy statement and to serve if elected. Proxies only can be voted for the number of persons named as nominees in this proxy statement, which is three, and stockholders may not cumulate their votes.

  4. Election of Directors

    | Chegg, Inc. | 20 | Proxy Statement for the 2026 Annual Meeting of Stockholders |

  5. Nominees to the Board of Directors

    Nominees to the Board of Directors The nominees, and their ages, occupations, and length of service on our Board of Directors are provided in the table below. Additional biographical description of each nominee is set forth in the pages that follow. This description includes the primary experience, qualifications, qualities and skills of each nominee that led to the conclusion that such nominee should serve as a member of our Board of Directors at this time.

  6. Nominees to the Board of Directors

    | Name of Director/Nominee | Age(6) | Principal Occupation | Joined Our Board | | Renee Budig(1)(2)(3) | 65 | Former Executive Vice President and Chief Financial Officer, Paramount Streaming, a division of Paramount Global, Inc. | November 2015 | | Dan Rosensweig(4) | 64 | President and Chief Executive Officer, Executive Chairman of Chegg Inc. | March 2010 | | Ted Schlein(1)(4)(5) | 62 | General Partner of Kleiner Perkins | December 2008 |

  7. Nominees to the Board of Directors

    | (1) Member of the Audit Committee. | | (2) Member of the Compensation Committee. | | (3) As noted above, effective as of March 25, 2026, Ms. Budig was moved from Class I to Class III and as a result she is nominated to be re-elected to the Board as a Class III Member, with a term expiring at the 2028 annual meeting. | | (4) Class I Member. | | (5) Member of the Governance and Sustainability Committee. | | (6) Age as of the Record Date of the 2026 Annual Meeting. |

  8. Continuing Directors

    Continuing Directors Our other directors who are serving for terms that end in 2027 and 2028, 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 pages that follow. These descriptions include the primary 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.

  9. Continuing Directors

    | Name of Director | Age(4) | Principal Occupation | Joined Our Board | | CLASS II DIRECTOR - TERM EXPIRING 2027: | | | | | Marne Levine(1)(2) | 55 | Chief Operating Officer, Brain Co | May 2013 | | CLASS III DIRECTOR - TERM EXPIRING 2028: | | | | | Marcela Martin(2)(3) | 54 | Chief Financial Officer and Chief Operating Officer, Contentsquare | September 2021 |

  10. Continuing Directors

    | (1) Member of the Compensation Committee | | (2) Member of the Governance and Sustainability Committee. | | (3) Member of the Audit Committee. | | (4) Age as of the Record Date of the 2026 Annual Meeting. |

  11. Continuing Directors

    | Chegg, Inc. | 21 | Proxy Statement for the 2026 Annual Meeting of Stockholders |

  12. Directors for Election

    Directors for Election

  13. Directors for Election

    | | | 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 Compensation Committee and Member of Audit Committee DIRECTOR SINCE: 2015 (Class III) | | | | | 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. |

  14. Directors for Election

    | Chegg, Inc. | 22 | Proxy Statement for the 2026 Annual Meeting of Stockholders |

  15. Directors for Election

    | | | Dan Rosensweig Dan Rosensweig has served as Chegg’s President and Chief Executive Officer since October 27, 2025, as Executive Chairman since June 2024 and as Chairperson of our Board of Directors since October 2025. Mr. Rosensweig previously served as our President and Chief Executive Officer from February 2010 to June 2024, as Co-Chairperson of our Board of Directors from July 2018 to October 2025 and as 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 and Rent the Runway, Inc. Mr. Rosensweig holds a B.A. in Political Science from Hobart and William Smith Colleges. | | | President and Chief Executive Officer; Chairperson of the Board of Directors DIRECTOR SINCE: 2010 (Class I) | | | | | We believe that Mr. Rosensweig should continue to serve on our Board of Directors due to the perspective and experience he brings as our President and Chief Executive Officer and his extensive experience with consumer internet and media companies. |

  16. Directors for Election

    | | | 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 previously served on the board of directors of IronNet, Inc. from August 2021 to February 2024. 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 (Class I) | | | | | 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. |

  17. Directors for Election

    | Chegg, Inc. | 23 | Proxy Statement for the 2026 Annual Meeting of Stockholders |

  18. 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, including data regarding compensation paid to non-employee directors by companies in our “peer group” (as described in the “Executive Compensation” 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.

  19. 2025 Director Compensation Table

    2025 Director Compensation Table The following table provides information for the year ended December 31, 2025 regarding all compensation awarded to, earned by or paid to each person who served as a non-employee director for some portion or all of 2025. Mr. Schultz, our former President and Chief Executive Officer, did not receive any compensation for his service as a director during the year ended December 31, 2025. Mr. Rosensweig, our current President and Chief Executive Officer, received compensation as Executive Chair during 2025; all of Mr. Rosensweig's compensation is reported in the Summary Compensation Table, and not in the table below.

  20. 2025 Director Compensation Table

    | Name | Fees Earned or Paid in Cash ($)(6) | RSU Awards ($)(7) | Total ($)(8) | | Renee Budig(1) | 70,000 | 186,185 | 256,185 | | Marne Levine | 65,380 | 186,185 | 251,565 | | Marcela Martin(2) | 65,000 | 186,185 | 251,185 | | Richard Sarnoff(3) | 78,329 | 68,750 | 147,079 | | Ted Schlein | 60,000 | 186,185 | 246,185 | | Melanie Whelan(4) | 25,598 | — | 25,598 | | John (Jed) York(5) | 21,332 | — | 21,332 |

  21. 2025 Director Compensation Table

    | (1) Committee fees for Ms. Budig are prorated to reflect her transition from a member of the Compensation Committee to Chair of the Compensation Committee, effective June 4, 2025, and from Chair of the Audit Committee to a member of the Audit Committee, effective June 4, 2025. |

  22. 2025 Director Compensation Table

    | Chegg, Inc. | 27 | Proxy Statement for the 2026 Annual Meeting of Stockholders |

  23. 2025 Director Compensation Table

    | (2) Committee fees for Ms. Martin are prorated to reflect her transition from a member of the Audit Committee to Chair of the Audit Committee, effective June 4, 2025, and to a member of the Governance and Sustainability Committee, effective June 4, 2025. The cash fee paid to Ms. Martin in 2025 included an overpayment of $3,533 due to an administrative failure to prorate her fees paid related to the changes in her committee service in June 2025. The cash fee paid in the first quarter of 2026 was reduced by the amount of the overpayment in 2025. The amount reported in this table is the amount actually paid in 2025. | | (3) All director fees for Mr. Sarnoff are prorated to reflect his resignation from the Board of Directors, including as a member of the Audit Committee, member of the Compensation Committee and Co-Chairperson of the Board of Directors effective October 21, 2025. | | (4) All director fees for Ms. Whelan are prorated to account for her departure from the Board of Directors, including as Chair of the Compensation Committee, with her term ending effective June 4, 2025. | | (5) All director fees for Mr. York are prorated to account for his decision not to stand for reelection, with his term as a director, and as a member of the Governance and Sustainability Committee, ending at our 2025 Annual Meeting of Stockholders. | | (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 2025. During 2025, each non-employee member of the Board of Directors, who was a director as of the close of our 2025 Annual Meeting of Stockholders on June 4, 2025, was granted an RSU award covering 55,000 shares of our common stock with an aggregate grant date fair value of $68,750 (referred to in the narrative as the June Board Grant). Additionally, each non-employee member of the Board of Directors, who was a director on November 17, 2025, was granted a "true-up" RSU award covering 115,132 shares of our common stock with an aggregate grant fair value of $117,435 (referred to in the narrative as the November Board Grant). 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, 2025. 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. |

  24. 2025 Director Compensation Table

    Our non-employee directors held the following number of stock options and unvested RSU awards as of December 31, 2025.

  25. 2025 Director Compensation Table

    | Name | Option Awards ($) | RSU Awards ($) | | Renee Budig(1) | 58,175 | 170,132 | | Marne Levine | 58,175 | 170,132 | | Marcela Martin | — | 170,132 | | Ted Schlein | 58,175 | 170,132 |

  26. 2025 Director Compensation Table

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

  27. 2025 Director Compensation Table

    | Chegg, Inc. | 28 | Proxy Statement for the 2026 Annual Meeting of Stockholders |

  28. 2025 Director Compensation Table

    | | | Proposal No. 2 |

  29. General

    General After the Effective Time of the Reverse Stock Split, should the Board of Directors elect to implement it, each stockholder will own a reduced number of shares of common stock. However, the Reverse Stock Split would affect all of our stockholders uniformly and would not affect any stockholder’s percentage ownership interests in the Company, except to the extent that the Reverse Stock Split would result in any of our stockholders owning a fractional share as described above. Voting rights and other rights and preferences of the holders of our common stock would not be affected by the Reverse Stock Split (other than as a result of the rounding down to the next whole share in lieu of fractional shares). For example, a holder of 2% of the voting power of the outstanding shares of our common stock immediately prior to the Reverse Stock Split would continue to hold 2% (assuming there is no impact as a result of the rounding down of share amounts in lieu of issuing fractional shares) of the voting power of the outstanding shares of our common stock immediately after the Reverse Stock Split. The number of stockholders of record would not be affected by the Reverse Stock Split. The principal effects of the Reverse Stock Split would be that: •each 4 to 15 shares of our common stock owned by a stockholder (depending on the Reverse Stock Split ratio selected by our Board of Directors) would be combined into one new share of our common stock; •no fractional shares of common stock would be issued in connection with the Reverse Stock Split; instead, holders of common stock who would otherwise receive a fractional share of common stock pursuant to the Reverse Stock Split would receive a number of shares rounded down to the next whole share in lieu of the fractional share, as explained above; •by reducing the number of shares of common stock outstanding without reducing the number of shares of available but unissued common stock, the Reverse Stock Split will effectively increase the relative number of authorized but unissued shares, which the Board of Directors may use in connection with future financings or other issuances; •based upon the Reverse Stock Split ratio selected by our Board of Directors, proportionate adjustments would be made to the per share exercise price and the number of shares issuable upon the exercise or vesting of all then outstanding equity awards with respect to the number of shares of common stock subject to such award and the exercise price thereof, in each case to the extent applicable, subject to the terms of such awards; •the number of shares of common stock authorized under the 2023 Equity Incentive Plan, the Amended and Restated 2013 Employee Stock Purchase Plan, and the 2023 Equity Inducement Plan, will be proportionately adjusted for the Reverse Stock Split ratio selected by our Board of Directors; and •the number of stockholders owning “odd lots” of less than 100 shares of our common stock may potentially increase; odd lot shares may be more difficult to sell, and brokerage commissions and other costs of transactions in odd lots generally are proportionately higher than the costs of transactions in “round lots” of even multiples of 100 shares. However, we believe that the benefits of the Reverse Stock Split outweigh any potential negative effects.

  30. Effect on Outstanding Equity Awards and Equity Plans

    Effect on Outstanding Equity Awards and Equity Plans If our stockholders approve the Reverse Stock Split and our Board of Directors decides to implement the Reverse Stock Split, as of the Effective Time and based on the Reverse Stock Split ratio selected by our Board of Directors, proportionate adjustments will be made to all then-outstanding equity awards with respect to the number of shares of common stock subject to such award and the exercise price thereof. In addition, the number of shares of common stock available for issuance under the 2023 Equity Incentive Plan, the Amended and Restated 2013 Employee Stock Purchase Plan, and the 2023 Equity Inducement Plan will be proportionately adjusted for the Reverse Stock Split ratio selected by our Board of Directors, such that fewer shares will be subject to such plans.

  31. 2025 Key Compensation Decisions

    2025 Key Compensation Decisions As the Compensation Committee continues its focus on aligning executives’ compensation with the Company’s overall business strategies, attracting and retaining highly qualified executives, and providing incentives that drive stockholder value, the Compensation Committee made the following key decisions with respect to executive compensation for 2025: •Established Compensation for Our Chief Executive Officer. In connection with his appointment as Chief Executive Officer, the Compensation Committee entered into an offer letter which established 2025 compensation for Mr. Rosensweig that is focused on retention and is predominantly performance‑oriented. •Adopted a New Annual Incentive Plan. At the start of 2025, the Compensation Committee adopted a new annual incentive plan for executive officers to better align pay outcomes with Chegg’s evolving strategic priorities and annual performance objectives.

  32. Compensation Practices

    | What We Do | •Pay-for-Performance •Prioritize stockholder alignment with a majority of pay mix allocated to an annual incentive program and equity compensation •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 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 |

  33. Role of Our Independent Compensation Consultant

    Role of Our Independent Compensation Consultant The Compensation Committee has retained Aon as its independent compensation consultant. The Compensation Committee has assessed the independence of Aon 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 for purposes of the Dodd-Frank Act and other applicable SEC and NYSE regulations. During 2024 and 2025, 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.

  34. 2025 Compensation Peer Group

    2025 Compensation Peer Group Our Compensation Committee considered market data compiled by Aon to help 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 2025 compensation consists of companies that are similar to us in revenue, and market capitalization, with a focus on maintaining year-over-year consistency when possible. 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 with the following GICS classifications: “Application Software,” “Interactive Media and Services,” “Human Resource and Employment Services” and “Systems Software.” 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 2025 compensation peer group, the Compensation Committee approved changes to the peer group in October 2024, taking into account Chegg’s market capitalization and revenue.

  35. 2025 Compensation Peer Group

    | Chegg, Inc. | 51 | Proxy Statement for the 2026 Annual Meeting of Stockholders |

  36. 2025 Compensation Peer Group

    Based on the peer group analysis performed in 2024, four companies were removed from the peer group as they no longer fit the selection criteria (Box, Inc., Qualys, Inc., RingCentral, Inc. and Yelp, Inc.), while nine companies were added as having characteristics that were more similar to Chegg (A10 Networks, Inc., Adtalem Global Education Inc., Laureate Education Inc., Perdoceo Education Corporation, SecureWorks Corp., Skillsoft Corp., Strategic Education, Inc., Vimeo, Inc. and Xperi, Inc.). Four companies that ceased to be publicly traded were removed from the 2025 peer group (Alteryx, Inc., Everbridge, Inc., Model N, Inc. and 2U, Inc.). Chegg was in the 59th percentile of the peer group’s revenues for the trailing four quarters and in the 13th percentile of the peer group’s market capitalization. For our 2025 compensation decisions, our peer group consisted of the 20 companies set forth below:

  37. 2025 Compensation Peer Group

    | A10 Networks, Inc. | Digital Turbine, Inc. | Progress Software Corporation | Udemy, Inc. | | Adtalem Global Education Inc. | Laureate Education Inc. | SecureWorks Corp. | Vimeo, Inc. | | Blackbaud, Inc. | LivePerson, Inc. | Skillsoft Corp. | Xperi Inc. | | Cerence Inc. | Perdoceo Education Corporation | Strategic Education, Inc. | Yext, Inc. | | Coursera, Inc. | PowerSchool Holdings, Inc. | Stride, Inc. | ZipRecruiter, Inc. |

  38. 2025 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 the median or any specific company member of our compensation peer group. The Compensation Committee believes that the compensation practices of our peer group provided us with appropriate compensation reference points for evaluating and determining the compensation of our NEOs during 2025. Consistent with best practices for corporate governance, the Compensation Committee will review our peer group annually. In addition to the peer group criteria above, the Compensation Committee also referenced general and specific industry surveys from other sources. The market data is used both as a reference point and to provide information on the range of competitive pay levels and current compensation practices in our industry.

  39. Dan Rosensweig Transition – President, Chief Executive Officer and Executive Chairman of the Board

    In addition, the Compensation Committee structured Mr. Rosensweig’s long-term incentive awards so that approximately 70% is granted in the form of performance-based restricted stock units (PSUs) that vest only upon achievement of rigorous multi‑year stock‑price goals, with the remaining 30% in multi‑year time‑based restricted stock units (RSUs). This design aligns his realizable pay with long‑term stockholder value creation and his continued service as Chief Executive Officer. The Committee awarded 1,650,000 RSUs with a grant date value of $1,683,000, and 3,850,000 PSUs with a grant date fair value of $2,387,000 (determined using a Monte Carlo simulation model), which will only vest upon achievement of specified goals. The Compensation Committee sought, in particular, to structure the equity grant in order to provide a competitive compensation package that would promote Mr. Rosensweig’s long-term retention with our Company and provide alignment with our stockholders. In addition, pursuant to the CEO Agreement we entered into with Mr. Rosensweig effective October 27, 2025, Mr. Rosensweig became eligible for the Chegg, Inc. Severance Plan (the "Severance Plan"). See "Severance Arrangements", below for more detail.

  40. Letter Agreement with Mr. Longo, our Chief Financial Officer

    Letter Agreement with Mr. Longo, our Chief Financial Officer In November 2025, the Compensation Committee approved a letter agreement with our Chief Financial Officer, Mr. Longo, to support leadership continuity during a period of strategic transition. As Chegg is undergoing a critical transition, the Board viewed retaining an experienced Chief Financial Officer as essential to managing the Company’s restructuring, capital allocation, and overall financial risk. Given limitations on the use of equity resulting from Chegg’s stock price and available share reserve, the Compensation Committee approved a balanced mix of retention and performance-based incentives, in the form of both cash and equity, to help ensure continuity in this key role, while keeping Mr. Longo’s total compensation reasonable relative to market. Under the letter agreement, the Compensation Committee increased Mr. Longo’s annual base salary from $680,000 to $750,000, effective November 16, 2025. In addition, the Compensation Committee awarded Mr. Longo up to four quarterly cash retention bonuses of $250,000 each, which are payable if Mr. Longo remains employed through each of four specified retention dates in November 2025, February 2026, May 2026, and August 2026. See “Company-Wide Retention Program” for details regarding the additional retention bonus that Mr. Longo received in 2025 pursuant to a Company-wide retention plan for all employees. The letter agreement also provided for an additional equity award that consisted of RSUs and PSUs, with grant date values of $510,000 and $310,000, respectively. Finally, in addition to the severance benefits, Mr. Longo may become entitled to under the Severance Plan, if he becomes entitled to severance benefits due to an involuntary termination in connection with a change in control, he will receive a lump sum cash severance bonus of $500,000, payable within 30 business days following the closing of the applicable transaction, subject to the same conditions that apply to his severance benefits generally.

  41. Nathan Schultz Transition – Transition to Executive Advisor

    Nathan Schultz Transition – Transition to Executive Advisor Effective October 27, 2025, Mr. Schultz transitioned from his position as Chief Executive Officer and director to serve as Executive Advisor through December 31, 2025. During the transition period, he continued to receive his existing salary, benefits, and vesting under his outstanding equity awards. Upon termination, he received separation benefits consistent with the terms of the Severance Plan for a termination without cause, including fully vesting in his restricted stock units and being eligible to vest in the performance stock units with a performance period which ended December 31, 2025. He also received his retention bonus under the Company-wide retention plan for all employees.

  42. Elements of 2025 Compensation

    Elements of 2025 Compensation Consistent with our compensation philosophy and objectives, we provide compensation to our Chief Executive Officer and our other executive officers in the form of base salaries, annual bonuses, and RSUs and PSUs. Our equity incentive compensation is intended to tie the majority of our executive officers’ pay to the delivery of stockholder value. Additionally, in December 2024, the Compensation Committee approved a company-wide cash retention bonus program for all employees.

  43. Annual Incentive Program

    Annual Incentive Program In light of the evolving dynamics in our industry and Chegg’s ongoing strategic transition, the Compensation Committee established a new 2025 annual incentive program for Mr. Longo and Mr. Schultz in December 2024. Mr. Rosensweig was not eligible for the annual incentive program in 2025. The annual incentive program used two objective financial measures: total net revenues (25% weighting) and adjusted EBITDA (75% weighting)—with 50% of each executive’s target annual cash incentive tied to performance in the first half of the year (H1) and the remaining 50% tied to performance in the second half (H2). The Compensation Committee adopted this bifurcated structure for the year so that bonus goals would remain relevant and appropriately demanding in a business that can change quickly, rather than relying on a single set of full‑year goals that might become too easy or no longer realistic. Given the significant uncertainty facing the business and the difficulty of setting precise goals at the start of the year, the Compensation Committee adopted a straightforward structure with a threshold and a target performance level for each half of the year. Each half of the year is measured separately, and any bonus not earned for one period cannot be made up in the other, which was intended to promote steady performance throughout the year.

  44. Annual Incentive Program

    | Chegg, Inc. | 55 | Proxy Statement for the 2026 Annual Meeting of Stockholders |

  45. Annual Incentive Program

    Under the program, no bonus would be earned unless performance reached at least a threshold level, at which point 50% of the target opportunity is paid; payouts between threshold and target are determined on a straight‑line, interpolated basis. In addition, payouts for each metric are capped at 100% of target, regardless of actual attainment. The Compensation Committee believes this design enhances pay‑for‑performance alignment and serves as an important risk‑management tool, ensuring that incentive outcomes remain appropriately rigorous, responsive to Chegg’s changing business conditions, and aligned with stockholder interests.

  46. 2025 Annual Bonus Metric and Payout: H1- First Six Months

    2025 Annual Bonus Metric and Payout: H1- First Six Months

  47. 2025 Annual Bonus Metric and Payout: H1- First Six Months

    | Metric | Overall Weighting | Period | Threshold ($M) | Target ($M) | Actual | Attainment (%) | Payout (%) | | 2025 Total Net Revenues | 25% | H1- First Six Months | 207.1 | 218.0 | 226.5 | 103.9 | 100.0 | | 2025 Adjusted EBITDA | 75% | H1 – First Six Months | 22.5 | 25.0 | 42.4 | 165.2 | 100.0 | | Total | | | | | | | 100.0 |

  48. 2025 Annual Bonus Metric and Payout: H2 - Second Six Months

    2025 Annual Bonus Metric and Payout: H2 - Second Six Months

  49. 2025 Annual Bonus Metric and Payout: H2 - Second Six Months

    | Metric | Overall Weighting | Period | Threshold ($M) | Target ($M) | Actual | Attainment (%) | Payout (%) | | 2025 Total Net Revenues | 25% | H2 – Second Six Months | 181.0 | 191.0 | 150.4 | 0.0 | 0.0 | | 2025 Adjusted EBITDA | 75% | H2 – Second Six Months | 13.5 | 15.0 | 26.2 | 174.7 | 100.0 | | Total | | | | | | | 75.0% |

  50. Annual Incentive Achievement and Payout Levels

    Annual Incentive Achievement and Payout Levels The Compensation Committee set annual bonus targets at 15% of salary, which is a lower percentage of salary than typical market practice. The Committee adopted this structure, particularly in the early years of this design, to help maintain a balanced overall cash compensation opportunity while still providing a meaningful performance-based incentive. The following table shows the target opportunity achievement, and amount payable for each of Mr. Longo and Mr. Schultz.

  51. Annual Incentive Achievement and Payout Levels

    | Named Executive Officer | Period | Target Opportunity ($) | Bonus Target (as % of Earnings) | Metric Achievement (%) | Payable Amount ($) | | David Longo | H1- First Six Months | 340,000 | 15 | 100 | 51,000 | | | H2- Second Six Months | 348,750 | 15 | 75 | 39,234 | | Nathan Schultz | H1- First Six Months | 500,000 | 15 | 100 | 75,000 | | | H2- Second Six Months | 500,000 | 15 | 75 | 56,250(1) |

  52. Annual Incentive Achievement and Payout Levels

    (1) This amount was paid as part of Mr. Schultz's severance payment.

  53. Annual Incentive Achievement and Payout Levels

    | Chegg, Inc. | 56 | Proxy Statement for the 2026 Annual Meeting of Stockholders |

  54. 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. 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 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. In January 2025, Mr. Schultz and Mr. Longo each received a regular annual equity award. Both Mr. Rosensweig and Mr. Longo received off-cycle equity awards later in the year in connection with their respective letter agreements.

  55. 2025 Restricted Stock Units (RSUs)

    2025 Restricted Stock Units (RSUs) 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. As part of the annual grant cycle, the Compensation Committee recommended, and the Board subsequently approved, a grant of 1,000,000 time-based RSUs to each of Mr. Schultz and Mr. Longo, with a grant date value of $1.5 million, which was granted on January 14, 2025. The restricted stock awards were designed to promote retention over a two-year period, with 50% of the RSUs vesting on January 12, 2026, and the remaining 50% vesting in four equal quarterly installments over the following 12 months. The vesting of the RSU awards was subject to the officer's continued service through each vesting date. Mr. Schultz’s RSUs were fully vested in accordance with his Transition and Separation Agreement. Mr. Longo also received a retention equity grant of 500,000 RSUs on November 17, 2025, and Mr. Rosensweig received a grant of 1,650,000 RSUs on November 17, 2025, in connection with his transition from Executive Chair to Chief Executive Officer. These RSUs vest over three years, with one‑third of the award vesting after one-year, and the remaining two‑thirds vesting in equal quarterly installments thereafter, subject to continued employment with the Company.

  56. 2025 Performance-Based Restricted Stock Units (PSUs)

    2025 Performance-Based Restricted Stock Units (PSUs) PSUs awarded in 2025 to Mr. Rosensweig and Mr. Longo were divided into four tranches that can be earned only if Chegg’s stock price achieves and sustains increasingly higher stock‑price hurdles during a three‑year performance period beginning October 2025. Any earned PSUs vest in two installments, with tranches earned during the first 18 months vesting in April 2027 and any remaining earned tranches vesting in October 2028, subject to continued employment and Compensation Committee certification. Performance is measured at two points: the first at 18 months after grant and the second at 36 months after grant. Any PSUs not achieved by the second measurement date are automatically forfeited.

  57. 2025 Performance-Based Restricted Stock Units (PSUs)

    | Chegg, Inc. | 57 | Proxy Statement for the 2026 Annual Meeting of Stockholders |

  58. 2025 Performance-Based Restricted Stock Units (PSUs)

    | Tranche | Performance Goal (1) | Vesting Date | | 1st Tranche | 50% increase in stock price over October 28, 2025 closing price | April 2027 (if goal achieved within the first 18 months) | | 2nd Tranche | 75% increase in stock price over October 28, 2025 closing price | | | 3rd Tranche | 100% increase in stock price over October 28, 2025 closing price | October 2028 (if goal achieved within the last 18 months) | | 4th Tranche | 125% increase in stock price over October 28, 2025 closing price | |

  59. 2025 Performance-Based Restricted Stock Units (PSUs)

    | (1) PSUs will be earned only if the volume-weighted average stock price equals or exceeds the performance goal over a sixty-trading-day period. |

  60. 2024 PSUs - Fiscal Year 2025 Performance-Based Restricted Stock Units Payout for Mr. Schultz

    2024 PSUs - Fiscal Year 2025 Performance-Based Restricted Stock Units Payout for Mr. Schultz In June 2024, Mr. Schultz was granted PSUs that were subject to the achievement of specified performance goals. These 2024 PSUs were allocated into two equal tranches. Each tranche is measured over a separate performance period, with the first tranche based on 2024 performance and the second tranche based on 2025 performance. As described in detail in the Compensation Discussion and Analysis of our 2025 Proxy Statement, for the first tranche the Committee selected 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. And as detailed in our 2025 Proxy Statement, we achieved a weighted-average payout of 17.4% of target for the first tranche of the 2024 PSUs, and the corresponding award was distributed in June 2025. In 2025, the Compensation Committee set the fiscal 2025 performance metrics for the second tranche of Mr. Schultz’s 2024 PSUs. For the second tranche of the 2024 PSU awards, the Compensation Committee decided to use the same fiscal 2025 metrics of revenue and adjusted EBITDA, and the same threshold and target measures as the Committee adopted for the annual incentive plan. Mr. Schultz’s Transition and Separation Agreement provided for continued vesting of the 2024 PSU on the regular vesting dates, with half vesting in June 2026, and the remaining half vesting in June 2027. Payouts of the PSUs are determined on a linear basis between the threshold and target, and target and maximum level for each of H1 and H2, as shown in the tables below:

  61. 2025 Performance-Based Restricted Stock Units Payout - Tranche 2

    2025 Performance-Based Restricted Stock Units Payout - Tranche 2

  62. 2025 Performance-Based Restricted Stock Units Payout - Tranche 2

    | Target Number of Shares Eligible to Vest for Mr. Schultz | H1 Weighted Achievement (%) | H2 Weighted Achievement (%) | H1 + H2 Blended Achievement (%) | Resulting Number of Shares Eligible to Vest (#) | | 206,250 | 147.3 | 112.5 | 129.9 | 267,919 |

  63. 2025 Performance-Based Restricted Stock Units Payout - Tranche 2

    Mr. Schultz’s Transition and Separation Agreement provided for continued vesting of the above-described 2024 PSU on the regular vesting dates, with half vesting in June 2026, and the remaining half vesting in June 2027.

  64. Severance and Change in Control Benefits

    Severance and Change in Control Benefits Effective October 17, 2024, we adopted a Severance Plan in which each NEO participates (the "Covered Employees"). Messrs. Longo and Schultz have been eligible for the Severance Plan since its adoption and Mr. Rosensweig became eligible upon the effectiveness of his October 27, 2025 offer letter. 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.

  65. Severance and Change in Control Benefits

    | Chegg, Inc. | 59 | Proxy Statement for the 2026 Annual Meeting of Stockholders |

  66. Severance and Change in Control Benefits

    Upon the termination of a Covered Employee’s employment for any reason, the Covered Employee will be entitled to receive (a) any earned but unpaid base salary, and (b) any vested employee benefits in accordance with the terms of the applicable employee benefit plan or program. In the event of a “qualifying termination", which is an involuntary termination by the Company without “cause” (as defined in the Severance Plan) or a resignation by the NEO for “good reason” (as defined in the Severance Plan), or a qualifying termination in connection with a change in control, Covered Employees under the Severance Plan will receive the benefits described below. However, an NEO’s change-in-control payments will be automatically reduced to the highest amount that avoids the 20% golden parachute excise tax, but only if this reduction results in a higher net after-tax benefit compared to receiving the full payment and paying the tax. The Severance Plan defines a “change in control” as “corporate transaction” in the 2023 Equity Incentive Plan, which includes: (i) the acquisition of 50% or more of the Company’s voting securities, (ii) the sale or other disposition of all or substantially all of the Company’s assets, (iii) certain mergers or consolidations with another company, (iv) a transaction which qualifies as a “corporate transaction” under Section 424(a) of the Code, or (v) a change in the effective control of the Company that occurs when a majority of members of the Board is replaced during any twelve (12) month period by members of the Board whose appointment or election is not endorsed by as majority of the members of the Board prior to the date of the appointment or election. All severance payments and benefits under the Severance Plan are subject to the Covered Employee executing a release of claims.

  67. Base Salary Severance

    Base Salary Severance The Covered Employee will receive a cash lump sum payment equal to the product of (i) such Covered Employee’s annual base salary rate as in effect on the date of the qualifying termination (disregarding for this purpose any decrease in annual base salary constituting Good Reason) and (ii) the relevant severance factor set forth in the table below. In addition, Mr. Longo's November 14, 2025 letter agreement provides for an additional transaction bonus payment of $500,000, if he is terminated in connection with a change in control.

  68. Bonus Plan Severance

    Bonus Plan Severance If the Covered Employee is eligible for an annual bonus under the Company’s annual incentive plan during such Covered Employee’s employment termination year, then the Covered Employee will receive an additional cash lump sum payment equal to: (i) the Covered Employee’s pro rata target annual bonus for the year of termination, calculated by multiplying the Covered Employee’s target annual bonus as of the date of termination by a fraction, the numerator of which is the number of days worked in the performance year and the denominator of which is 365; plus (ii) such Covered Employee’s target annual bonus for the year of termination multiplied by the relevant severance factor set forth in the table below, minus any earned bonuses paid during the Covered Employee's employment.

  69. Bonus Plan Severance

    | Chegg, Inc. | 60 | Proxy Statement for the 2026 Annual Meeting of Stockholders |

  70. Continued COBRA Coverage

    | | Base Salary Factor | | Bonus Plan Factor | | Continued COBRA Coverage | | | Termination Type and Timing | CEO | NEO | CEO | NEO | CEO | NEO | | Qualifying Termination in Connection with a Change in Control on or before October 17, 2026 | 1.5x | 1.25x | 1.5x | 1.25x | 18 months | 15 months | | Qualifying Termination in Connection with a Change in Control after October 17, 2026 | 1.5x | 1.0x | 1.5x | 1.0x | 18 months | 12 months | | Qualifying Termination Not in Connection with a Change in Control on or before October 17, 2026 | 1.25x | 1.25x | 1.25x | 1.25x | 15 months | 15 months | | Qualifying Termination Not in Connection with a Change in Control after October 17, 2026 | 1.0x | 1.0x | 0 | 0 | 12 months | 12 months |

  71. Involuntary Termination in Connection with a Change in Control

    Involuntary Termination in Connection with a Change in Control In the event of a qualifying termination in connection with a change in control, each of the Covered Employee’s then-outstanding, unvested time-vesting awards and performance awards for which the level of achievement has been determined will accelerate and become vested and exercisable or settled with respect to one hundred percent (100%) of the unvested shares subject thereto. Performance awards for which the performance level has not yet been determined will accelerate and become vested and exercisable or settled (if at all) as set forth in the terms of the applicable award agreement; provided, however, that any such awards whose measurement periods have not been completed as of the change in control, do not specify the calculation of performance upon a change in control, the performance will be deemed achieved at either the target level of performance described in the applicable award agreement or at the actual level of performance achieved under the terms of the applicable award agreement, if such performance is determinable as of immediately prior to the change in control, and the resulting number of achieved PSUs will accelerate and become vested in full.

  72. Qualifying Termination Not in Connection with a Change in Control

    Qualifying Termination Not in Connection with a Change in Control In the event of a qualifying termination not in connection with a change in control, each of the then-outstanding, unvested time-vesting awards and performance awards for which the level of achievement has been determined held by the Covered Employee will accelerate and become vested and exercisable or settled with respect to the number of unvested shares subject thereto that would have vested had the Covered Employee continued in employment with the Company following the Covered Employee’s qualifying termination for twelve (12) months.

  73. Qualifying Termination Not in Connection with a Change in Control

    | Chegg, Inc. | 61 | Proxy Statement for the 2026 Annual Meeting of Stockholders |

  74. Summary Compensation Table

    Summary Compensation Table The following table provides information regarding all compensation awarded to, earned by or paid to our NEOs for all services rendered in all capacities to us during fiscal years 2025 and 2024.

  75. Summary Compensation Table

    | Name and Principal Position | Year | Salary ($) | Bonus ($)(1) | Stock Awards ($)(2) | Non-Equity Incentive Plan Compensation ($) | All Other Compensation ($)(3) | Total ($) | | Dan Rosensweig | 2025 | 850,000 | — | 4,070,000 | — | 14,000 | 4,934,000 | | President, Chief Executive Officer and Executive Chairman | 2024 | 954,167 | — | 1,436,250 | — | 13,800 | 2,404,217 | | David Longo | 2025 | 688,750 | 353,313 | 2,320,000 | 90,234 | 14,000 | 3,466,297 | | Chief Financial Officer | 2024 | 651,813 | — | 1,899,998 | — | 13,800 | 2,565,611 | | Nathan Schultz | 2025 | 1,000,000 | 150,000 | 1,500,000 | 75,000 | 1,944,769 | 4,669,769 | | Former President and Chief Executive Officer | 2024 | 958,333 | — | 3,159,750 | — | 13,800 | 4,131,883 |

  76. Summary Compensation Table

    | (1) The amounts reported in this column represent a $250,000 retention bonus paid to Mr. Longo pursuant to his letter agreement, and $103,313 paid to Mr. Longo and $150,000 paid to Mr. Schultz pursuant to the Company-wide cash retention program. | | (2) The amounts reported in this column represent the aggregate grant date fair value of RSU and PSU awards granted under our 2023 Equity Incentive Plan, as computed in accordance with ASC 718. For fiscal year 2025, the amounts include PSUs granted to Mr. Rosensweig and Mr. Longo that will become vested only if our stock price reaches sustained stock price hurdles of 50%, 75%, 100%, and 125% above our October 28, 2025 stock price. A tranche of the total number of PSUs will become vested only as of a measurement date that is 18 months or 36 months following the grant date, subject to Mr. Rosensweig's or Mr. Longo's service until that date, and only if the volume weighted average closing price per share of stock equals or exceeds the target stock price over a sixty day trading period. If any PSUs have not vested by the end of the term of the award, they will be forfeited and Mr. Rosensweig and Mr. Longo will not realize the value of such PSUs. The PSUs are valued on the probable outcome of the market-condition goals, determined using a Monte Carlo simulation model. For information regarding assumptions, factors and methodologies used in our computations pursuant to Topic 718, see Note 2 to our consolidated financial statements in our Annual Report on Form 10-K for the year ended December 31, 2025. The value of the PSU awards at the grant date assuming that the highest level of performance conditions will be achieved was $3,927,000 for Mr. Rosensweig and $510,000 for Mr. Longo. | | (3) The amounts in the column represent our contributions to the account under our 401(k) plan for each NEO. For fiscal year 2025, for Mr. Schultz, the amounts further include (1) $1,700,000 paid under his Transition and Separation Agreement under which Mr. Schultz was eligible for separation payments and benefits pursuant to the termination “other than for Cause” provisions of the Chegg, Inc. Severance Plan (the "Severance Plan") that apply when the qualifying termination occurs within two years following adoption of the Severance Plan and is not in connection with a “Change in Control” (all terms as defined in the Severance Plan) and (2) $230,769 paid as a lump sum in connection with the termination of the Chegg, Inc. sabbatical program, under which all employees with more than 10 years of service who had not yet taken a sabbatical received a cash payment equal to the salary they would have earned during their sabbatical period. |

  77. Summary Compensation Table

    | Chegg, Inc. | 62 | Proxy Statement for the 2026 Annual Meeting of Stockholders |

  78. Outstanding Equity Awards at December 31, 2025

    Outstanding Equity Awards at December 31, 2025 The following table provides information with respect to outstanding equity awards as of December 31, 2025 with respect to our NEOs. Please see “Proposal No. 4 Approval of an Amendment to our Restated Certificate of Incorporation to effect a Reverse Stock Split” for disclosure on the proportionate adjustments that would be made to outstanding equity awards if the Reverse Stock Split (as defined in this proxy statement) is approved by our stockholders at the 2026 Annual Meeting and our Board of Directors decides to implement the Reverse Stock Split.

  79. Outstanding Equity Awards at December 31, 2025

    | | | Stock Awards | | | | | | Grant Date | Number of Shares that Have Not Vested (#) | Market Value of Shares that Have Not Vested ($)(1) | Equity Incentive Plan Awards: Number of Unearned Shares that Have Not Vested (#) | Equity Incentive Plan Awards: Market Value of Unearned Shares that Have Not Vested ($)(1) | | Name | | | | | | | Dan Rosensweig | 06/01/2024 (2) | 10,850 | 10,091 | — | — | | | 06/01/2024 (3) | 105,469 | 98,086 | — | — | | | 11/17/2025 (4) | 1,650,000 | 1,534,500 | — | — | | | 11/17/2025 (5) | — | — | 3,850,000 | 3,580,500 | | David Longo | 1/12/2022 (6) | 3,230 | 3,004 | — | — | | | 1/14/2025 (7) | 1,000,000 | 930,000 | — | — | | | 11/17/2025 (4) | 500,000 | 465,000 | — | — | | | 11/17/2025 (5) | — | — | 500,000 | 465,000 | | Nathan Schultz | 6/01/2024 (8) | 267,919 | 249,165 | — | — |

  80. Outstanding Equity Awards at December 31, 2025

    | (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, 2025 of $0.93. | | (2) The shares subject to the PSU award were earned 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 was achieved, therefore a weighted average of 17.36% of the shares subject to the PSU award were earned. One-third of the achieved shares vested on June 12, 2025, and the remaining tranches shown in the table above vest on June 12, 2026 and June 12, 2027, subject to Mr. Rosensweig's continued service up to and through each vesting date. | | (3) One-half of the originally granted RSUs vested on June 12, 2025 and 6.25% vest on each quarterly anniversary thereafter. The vesting is subject to Mr. Rosensweig’s continued service up to and through each vesting date. | | (4) One-third of the RSUs will vest on November 11, 2026, and 8.33% shall vest each quarterly anniversary thereafter. The vesting is subject to the NEO's continued service up to and through each vesting date. | | (5) The shares subject to the PSU award shall be earned only if our stock price reaches sustained stock price hurdles of 50%, 75%, 100%, and 125% above our October 28, 2025 stock price. A tranche of the total number of PSUs will become vested only as of a measurement date that is 18 months or 36 months following the grant date, subject to the NEO’s continued service until that date, and only if the volume weighted average closing price per share of stock equals or exceeds the target stock price over a sixty day trading period. | | (6) The shares vested on January 12, 2026. | | (7) One half of the shares vested on January 12, 2026, and 12.5% shall vest in quarterly installments thereafter. The vesting is subject to Mr. Longo's continued service up to and through each vesting date. | | (8) The shares subject to the PSU award were earned upon achievement by December 31, 2025 of Company performance metrics consisting of Chegg Total Net Revenue and adjusted EBITDA, as approved by the Compensation Committee. The Committee determined that the weighted average payout of 129.9% of target was achieved. One-half of the achieved shares shall vest on each of June 12, 2026 and June 12, 2027. |

  81. Outstanding Equity Awards at December 31, 2025

    | Chegg, Inc. | 63 | Proxy Statement for the 2026 Annual Meeting of Stockholders |

  82. Outstanding Equity Awards at December 31, 2025

    | | | Pay Versus Performance Disclosure |

  83. Outstanding Equity Awards at December 31, 2025

    Provided below is our “pay versus performance” disclosure as required pursuant to Item 402(v) of Regulation S-K promulgated under the Exchange Act. We are reporting as a “smaller reporting company” as defined under the U.S. federal securities laws. As such, and as required by Item 402(v), we have included: •A table that compares the total compensation of our NEOs as presented in the Summary Compensation Table (“SCT”) for each of the last three fiscal years to their pay calculated in accordance with Item 402(v) (referred to as “Compensation actually paid”, or “CAP”) and that compares their CAP to specified performance measures; and •Graphs that describe the relationships between CAP and our cumulative total stockholder return (“TSR”) and GAAP Net (Loss) Income. This disclosure has been prepared in accordance with Item 402(v) and does not necessarily reflect value actually realized by the NEOs, but rather is a value calculated under applicable SEC rules. Please refer to our narrative describing our "Executive Compensation" for a discussion of our executive compensation program objectives and the ways in which we align executive compensation with performance.

  84. Pay Versus Performance Table

    Pay Versus Performance Table In accordance with Item 402(v), we provide the following disclosures for the Company's current and former Chief Executive Officers (our Principal Executive Officers or “PEOs”) and the average of our NEOs other than the PEO (“non-PEO NEOs”) for 2025, 2024, and 2023.

  85. Pay Versus Performance Table

    | 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(4) ($) | Net (Loss) Income (in millions) ($) | | 2025 | 4,934,000 | 4,620,667 | 4,669,769 | 3,748,474 | 3,466,297 | 2,637,018 | 3.68 | (103) | | 2024 | 2,404,217 | 196,478 | 4,131,883 | (693,309) | 1,086,343 | 234,181 | 6.37 | (837) | | 2023 | 4,779,849 | (688,671) | — | — | 3,104,169 | 196,528 | 44.95 | 18 |

  86. Pay Versus Performance Table

    | (1) Dan Rosensweig served as PEO during 2023 until May 31, 2024. Nathan Schultz served as PEO from June 1, 2024, until October 27, 2025. Dan Rosensweig reassumed the PEO role effective October 27, 2025. The non-PEO for 2025 was David Longo. The non-PEO NEOs for 2024 were David Longo, Andrew Brown and Esther Lem. The non-PEO NEOs for 2023 were Andrew Brown, Nathan Schultz, John Fillmore and Esther Lem. |

  87. Pay Versus Performance Table

    | Chegg, Inc. | 64 | Proxy Statement for the 2026 Annual Meeting of Stockholders |

  88. Pay Versus Performance Table

    | (2) To calculate CAP to the PEOs the following adjustments were made to SCT Total Compensation: |

  89. Pay Versus Performance Table

    | PEO | Summary Compensation Table Total for PEO ($) | Deductions from Summary Compensation Table Total(a) ($) | Total Adjustments ($) | Compensation Actually Paid to PEO ($) | | Dan Rosensweig | 4,934,000 | (4,070,000) | 3,756,667 | 4,620,667 | | Nathan Schultz | 4,669,769 | (1,500,000) | 578,705 | 3,748,474 |

  90. 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 2025. |

  91. Pay Versus Performance Table

    | SEC rules require certain adjustments be made to the SCT totals to determine CAP as reported in the Pay Versus Performance Table. A reconciliation of the SCT totals to CAP to our PEOs calculated in accordance with the SEC methodology for determining compensation actually paid under Item 402(v) of Regulation S-K is shown below. The valuation assumptions used to calculate fair values did not materially differ from those disclosed at the time of grant. The adjustments to determine CAP are as follows: |

  92. Pay Versus Performance Table

    | PEO | Year End Fair Value of Equity Awards Granted in Covered Year and Outstanding at End of Year ($) | Change in Fair Value of Awards Granted in Prior Year from the End of the Prior Fiscal Years to the End of the Covered Year ($) | Fair Value as of Vesting Date of Equity Awards Granted and Vested in the Covered Year ($) | Change in Fair Value from the End of the Prior Fiscal Year to the Vesting Date for Equity Awards Granted in Prior Fiscal Years ($) | Fair Value at the End of the Prior Year of Equity Awards that Failed to Meet Vesting Conditions in the Year ($) | Total Equity Adjustment ($) | | Dan Rosensweig | 3,883,000 | (79,098) | — | (47,235) | — | 3,756,667 | | Nathan Schultz | — | (82,898) | 930,000 | (147,788) | (120,609) | 578,705 |

  93. Pay Versus Performance Table

    | (3) To calculate CAP to the non-PEO NEOs (as an average) the following adjustments were made to the applicable SCT Total compensation: |

  94. Pay Versus Performance Table

    | Summary Compensation Table Total for non-PEO NEOs ($) | Deductions from Summary Compensation Table Total(a) ($) | Total Adjustments ($) | Compensation Actually Paid to non-PEO NEOs ($) | | 3,466,297 | (2,320,000) | 1,490,721 | 2,637,018 |

  95. 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 2025. |

  96. Pay Versus Performance Table

    SEC rules require certain adjustments be made to the SCT totals to determine CAP as reported in the Pay Versus Performance Table. A reconciliation of the SCT totals to CAP to our non-PEO NEOs calculated in accordance with the SEC methodology for determining compensation actually paid under Item 402(v) of Regulation S-K is shown below. The valuation assumptions used to calculate fair values did not materially differ from those disclosed at the time of grant. The adjustments to determine CAP are as follows:

  97. Pay Versus Performance Table

    | Year End Fair Value of Equity Awards Granted in Covered Year and Outstanding at End of Year ($) | Change in Fair Value of Awards Granted in Prior Year from the End of the Prior Fiscal Year to the End of the Covered Year ($) | Fair Value as of Vesting Date of Equity Awards Granted and Vested in the Covered Year ($) | Change in Fair Value from the End if the Prior Fiscal Year to the Vesting Date for Equity Awards Granted in Prior Fiscal Years ($) | Fair Value at the End of the Prior Year of Equity Awards that Failed to Meet Vesting Conditions in the Year ($) | Equity Value Included in Compensation Actually Paid ($) | | 1,700,000 | (2,196) | — | (207,083) | — | 1,490,721 |

  98. Pay Versus Performance Table

    | (4) Total stockholder return is calculated based on a fixed investment in the common stock of Chegg, Inc. of one hundred dollars measured from the market close on December 31, 2022 through and including the end of each fiscal year reported in the table. |

  99. Pay Versus Performance Table

    | Chegg, Inc. | 65 | Proxy Statement for the 2026 Annual Meeting of Stockholders |