8-K - CHGG - Equibles

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

WASHINGTON, D.C. 20549

FORM 8-K

CURRENT REPORT

PURSUANT TO SECTION 13 OR 15(d)

OF THE SECURITIES EXCHANGE ACT OF 1934

Date of report (Date of earliest event reported): October 21, 2025

Chegg, Inc.

(Exact name of registrant as specified in its charter)

Delaware	001-36180	20-3237489
(State or other jurisdiction of incorporation)	(Commission File Number)	(IRS Employer Identification No.)
3990 Freedom Circle
---	---	---
Santa Clara,	California	95054
(Address of principal executive offices)		(Zip Code)

(408) 855-5700

(Registrant’s telephone number, including area code)

Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions:

☐ Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)

☐ Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)

☐ Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))

☐ Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

Securities registered pursuant to Section 12(b) of the Act:

Title of each class	Trading Symbol(s)	Name of each exchange on which registered
Common stock, $0.001 par value per share	CHGG	The New York Stock Exchange

Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 of the Securities Act of 1933 (§230.405 of this chapter) or Rule 12b-2 of the Securities Exchange Act of 1934 (§240.12b-2 of this chapter).

Emerging growth company ☐

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐

Item 2.02 Results of Operations and Financial Condition.

On October 27, 2025, Chegg, Inc. (“we,” “us,” “our,” “Company” or “Chegg”) issued a press release announcing the workforce reduction, management changes and conclusion of the previously announced strategic review process to explore

alternatives, each as described in Items 2.05, 5.02 and 7.01 below, and its reaffirmation of previously announced guidance for the quarter ended September 30, 2025. A copy of the press release is attached as Exhibit 99.1 to this Current Report on Form 8-K and is incorporated herein by reference. The Company is scheduled to release its earnings results for the third quarter of 2025, which ended on September 30, 2025, on Monday, November 10, 2025.

The information contained in this Item 2.02, including the press release attached as Exhibit 99.1 to this Current Report on Form 8-K, shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended, or otherwise subject to the liabilities of that section or Sections 11 and 12(a)(2) of the Securities Act of 1933, as amended. The information contained in this Item 2.02 and in the accompanying Exhibit 99.1 shall not be incorporated by reference into any registration statement or other document filed by Chegg with the Securities and Exchange Commission (“SEC”), whether made before or after the date of this Current Report on Form 8-K, regardless of any general incorporation language in such filing, except as shall be expressly set forth by specific reference in such filing.

Item 2.05 Costs Associated with Exit or Disposal Activities.

On October 27, 2025, we announced a restructuring plan that includes a reduction of our global workforce, which is expected to impact approximately 388 employees, or about 45% of our current workforce, as well as other actions to streamline our operations. We are undertaking these actions to better align our cost structure with our newly announced strategic focus relating to our operations on a stand-alone basis.

We estimate that we will incur charges of approximately $15 million to $19 million in connection with these actions, primarily consisting of expenditures for employee transition and severance payments, employee benefits and other related costs. We expect that substantially all of these charges will be incurred by the first quarter of 2026, with approximately $12 million to $16 million by the fourth quarter of 2026. The estimated charges and the timing of such charges are based on certain assumptions, including local law requirements in various jurisdictions, and actual amounts may differ materially from such estimates. We may incur other charges or cash expenditures not currently contemplated due to unanticipated events that may occur as a result of or in connection with the implementation of the planned workforce reduction.

Item 5.02 Departure of Directors or Principal Officers; Election of Directors; Appointment of Principal Officers; Compensatory Arrangements of Certain Officers.

Chief Executive Officer Transition

On October 27, 2025, we announced that our Board of Directors (the “Board”) and Nathan Schultz have mutually agreed that Mr. Schultz will step down as President, Chief Executive Officer and a member of the Board, effective immediately. Mr. Schultz will assist with the transition of his responsibilities and has agreed to serve as Executive Advisor and an employee until December 31, 2025 (the “Separation Date”). The Board has appointed Dan Rosensweig, our Executive Chair and Chairperson of the Board, to resume his role as President and Chief Executive Officer, effective immediately.

Mr. Rosensweig, age 64, has served as Chegg’s Executive Chairman since June 2024 and as Co-Chairperson of the Board 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 the Board 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.

In connection with Mr. Schultz’s transition, on October 27, 2025, the Company and Mr. Schultz entered into a transition and separation agreement (the “Schultz Agreement”), pursuant to which, until the Separation Date, Mr. Schultz will continue to receive his base salary and previously granted outstanding equity awards will continue to vest. In addition, Mr. Schultz will be eligible for separation payments and benefits pursuant to the termination “other than for Cause” provisions of the previously disclosed Chegg, Inc. Severance Plan, adopted effective October 17, 2024 (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). In addition, Performance Subject Awards held by Mr. Schultz with respect to which the performance period ends on December 31, 2025 will remain outstanding and eligible to vest in connection with the performance certification scheduled to occur in February 2026. The Schultz Agreement includes a general release of claims from Mr. Schultz in favor of the Company, and provides that Mr. Schultz must continue to comply

with applicable post-employment restrictive covenants under his employee confidential information and inventions assignment agreement.

A copy of the Schultz Agreement is attached as Exhibit 10.1 to this Current Report on Form 8-K.

In connection with Mr. Rosensweig’s appointment as President and Chief Executive Officer, on October 27, 2025, he entered into a letter agreement (the “Offer Letter”) with the Company. Pursuant to the Offer Letter, Mr. Rosensweig will serve as the Company’s President and Chief Executive Officer, will continue to serve as a member of the Company’s Board and as Chairman, and will continue to be employed on an “at-will” basis.

Under the Offer Letter, Mr. Rosensweig will continue to receive an annual base salary of $850,000 and, subject to approval by the Board or its Compensation Committee, will receive an award of (i) restricted stock units covering 1,650,000 shares, one-third of which vests on the first anniversary of the vesting commencement date and the remainder of which vests on a quarterly basis over the following two years, subject to continuous service through each vesting date; and (ii) performance-based restricted stock units covering up to 3,850,000 shares that vest based on certification of achievement of certain stock-price hurdles within the 36 month period following the date of grant, with certification events occurring after 18 months and 36 months.

The Offer Letter provides that Mr. Rosensweig will participate in the Severance Plan at the Chief Executive Officer level, as described under Item 5.02 of the Company’s Current Report on Form 8-K filed with the SEC on October 21, 2024, subject to the terms of the Severance Plan and a related participation agreement entered into between the Company and Mr. Rosensweig.

The Offer Letter also provides that Mr. Rosensweig is not currently eligible for an annual cash bonus and that he will not receive additional cash or equity compensation for his service on the Board.

Mr. Rosensweig will continue to be eligible to participate in the Company’s employee benefits on the same terms as other senior executives and will remain subject to his previously executed Confidentiality Agreement and the Company’s confidentiality, proprietary information and inventions assignment, insider trading, code of conduct and other applicable policies. Mr. Rosensweig will also continue to be covered under the Company’s director and officer liability insurance and eligible for indemnification in accordance with the Company’s bylaws and his previously executed indemnification agreement.

A copy of the Offer Letter is attached as Exhibit 10.2 to this Current Report on Form 8-K.

There is no arrangement or understanding between Mr. Rosensweig and any other persons pursuant to which Mr. Rosensweig was appointed as the Company’s President and Chief Executive Officer. There are no family relationships between Mr. Rosensweig and any director or executive officer of the Company, and he has no direct or indirect material interest in any transaction required to be disclosed pursuant to Item 404(a) of Regulation S-K.

Resignation of Director

On October 21, 2025, Richard Sarnoff, a member of our Board, notified the Company of his decision to resign from the Board, effective immediately. Mr. Sarnoff’s resignation is not the result of any dispute or disagreement with management or any matter relating to the Company’s operations, policies, or practices.

Item 7.01 Regulation FD Disclosure.

On October 27, 2025, we issued a press release announcing that the Board unanimously approved the conclusion of its review of strategic alternatives that was announced in February 2025, and, concurrently therewith, announced strategic updates related to our operations on a stand-alone basis. A copy of the press release is attached as Exhibit 99.1 to this Current Report on Form 8-K and is incorporated herein by reference.

The information contained in this Item 7.01, including the press release attached as Exhibit 99.1 to this Current Report on Form 8-K, shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended, or otherwise subject to the liabilities of that section or Sections 11 and 12(a)(2) of the Securities Act of 1933, as amended. The information contained in this Item 7.01 and in the accompanying Exhibit 99.1 shall not be incorporated by reference into any registration statement or other document filed by Chegg with the SEC, whether made before or after the date of this Current Report on Form 8-K, regardless of any general incorporation language in such filing, except as shall be expressly set forth by specific reference in such filing.

Forward-Looking Statements

This Current Report on Form 8-K contains forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995. All statements contained in this Current Report, including statements regarding our expectations regarding and the impact of our leadership transition and the conclusion of our process to explore strategic alternatives, Chegg's restructuring plan, reduction in force, the number of employees impacted, the amount of the charges in connection with the actions, the timing that such charges will be incurred, the impact of the actions on our non-GAAP financial measures, the amount of the cost savings and the timing of those savings, implementation of our new strategic focus to position Chegg for a return to sustainable growth and profitability over time, our reiteration of revenue and adjusted EBITDA guidance for Q3 2025, the impact of AI technology on our business and all statements about our financial outlook generally, are forward-looking statements. The words “will,” “plan,” “expect,” “intend,” “anticipate” and similar expressions are intended to identify these forward-looking statements. These forward-looking statements are subject to a number of risks, uncertainties and assumptions outside of our control. Important factors that could cause actual results to differ materially from those expressed or implied by these forward-looking statements include the following: our ability to successfully implement our new strategic focus and priorities; the effects of AI technology on our business and the economy generally; our ability to attract new learners to, and retain existing learners on, our learning platform in light of declining revenue and user traffic; the impact and effectiveness of our internal restructuring activities; our ability to effectively control operating costs; our ability to innovate and offer new products and services in response to competitive technology and market developments, including generative AI; competition in all aspects of our business, including with respect to AI and our expectation that such competition will increase; the outcome of our litigation against Google; our ability to maintain our services and systems without interruption, including as a result of technical issues, cybersecurity threats, or cyber-attacks; third-party payment processing risks; the outcome of any current litigation and investigations; the possibility that the NYSE may delist our common stock; and general economic, political and industry conditions, including escalating international trade tensions, tariffs and trade restrictions, fluctuating inflation, recession and war. These and other important risk factors are described more fully in documents filed with the SEC, including our Annual Report on Form 10-K for the year ended December 31, 2024 filed with the SEC on February 24, 2025, as supplemented by the Company’s subsequent Quarterly Reports on Form 10-Q filed with the SEC, and could cause actual results to differ materially from expectations. In addition, new risks may emerge from time to time, and it is not possible for us to predict all risks, nor can we assess the impact of all factors on our business or the extent to which any factor, or combination of factors, may cause actual results to differ materially from those contained in any forward-looking statements made. In light of these risks, uncertainties and assumptions, the future events discussed in this Current Report on Form 8-K may not occur and actual future results may be materially different from those anticipated or implied in the forward-looking statements.

Item 9.01 Financial Statements and Exhibits.

(d) Exhibits

Exhibit No.	Description
10.1	Transition and Separation Agreement, dated October 27, 2025, between the Company and Mr. Schultz
10.2	Offer Letter, dated October 27, 2025, between the Company and Mr. Rosensweig
99.01	Press release issued by Chegg, Inc., dated October 27, 2025 (Chegg to Remain a Standalone Public Company to Maximize Shareholder Value)
104	Cover Page Interactive Data File (embedded within the Inline XBRL document)

SIGNATURES

Pursuant to the requirements of the Securities Exchange Act of 1934, the Registrant has duly caused this report to be signed on its behalf by the undersigned thereunto duly authorized.

CHEGG, INC.
By: /S/ DAVID LONGO
David Longo
Chief Financial Officer

Date: October 27, 2025

ex101

October 24, 2025 Nathan Schultz Via email Dear Nathan: This letter sets forth the terms of the transition and separation agreement (the “Agreement”) that CHEGG, INC. (the “Company”) is offering to you to aid in your employment transition. 1. SEPARATION. If you timely sign this Agreement within five (5) business days after you receive it, your employment with the Company will continue through December 31, 2025, which will become your employment termination date (the “Separation Date”), unless your employment terminates sooner pursuant to Section 2(c) below. If termination occurs earlier or later than December 31, 2025, the actual date of termination shall become the “Separation Date” for purposes of this Agreement. The date of your timely execution of this Agreement shall be the “Effective Date.” 2. TRANSITION PERIOD. (a) Duties & Schedule. Upon the Effective Date, you will cease to serve as Chief Executive Officer, and/or as an officer of the Company and/or any subsidiary or affiliate of the Company, and will cease to serve in any role or position in which you are acting as a representative or agent of the Company (except as set forth herein), and will cease to serve in your role as a director of the board of directors of the Company (the “Board”) and any role as a director of the board of directors of any subsidiary or affiliate of the Company. You agree to submit such documentation as the Board may require to confirm your departure from the Board as of the Effective Date. Upon the Effective Date and through the Separation Date (the “Transition Period”), your title will be Executive Advisor, and you will assist the Company with the orderly transition of your work, including making yourself available for reasonable requests from the Board or authorized committee thereof related to your transition. Additionally, during the Transition Period, you will be expected to continue to advise on certain ongoing projects, as designated by the Board and/or the Company’s new CEO. You agree to perform such services during the Transition Period in good faith and to the best of your abilities. You agree to continue to comply with all of the Company’s policies and procedures and with all of your statutory and contractual obligations to the Company, including, without limitation, your obligations under your Confidentiality Agreement (as defined below), which you acknowledge and agree are contractual commitments that remain binding upon you during the Transition Period. (b) Compensation/Benefits. During the Transition Period, you will be paid at the same base salary rate, an annualized rate of $1,000,000 per year, less payroll deductions and

Page 2 withholdings. In addition, your outstanding Company equity awards will continue to vest under the existing terms and conditions set forth in the governing plan documents and award agreement. You will continue to be eligible for the Company’s standard benefits, subject to the terms and conditions applicable to such plans and programs. For clarity, you shall not be eligible for payment of any bonuses for 2025 (except as set forth in Section 4 herein). (c) Messaging. All public or internal statements concerning your departure shall be consistent with the Chegg Project Civic Assets communications plan. Nothing in this Agreement shall prevent the Company from making any disclosures that it determines, in consultation with counsel, are required by applicable law, regulation, or stock-exchange rule. (d) Termination. Nothing in this Agreement alters your employment at will status. Accordingly, during the Transition Period you are entitled to resign your employment for any reason with or without advance notice, and the Company may terminate your employment with or without Cause (as defined in the Severance Plan, defined below) or advance notice. If prior to December 31, 2025 the Company terminates your employment without Cause, then you will remain eligible for the Severance Benefits (as defined and described below), provided that you have satisfied the Severance Preconditions (as set forth below). If prior to December 31, 2025, you resign your employment for any reason or the Company terminates your employment with Cause, then you will no longer be eligible for participation in any Company benefit plans, and you will not be entitled to the Severance Benefits. 3. FINAL PAY. On the Separation Date, the Company will pay you all accrued salary earned through the Separation Date, subject to standard payroll deductions and withholdings. You are entitled to this payment regardless of whether or not you sign this Agreement. Since the Company has a nonaccrual vacation policy, you do not have any accrued vacation or other paid time off and thus will not be paid out for any accrued vacation or other paid time off. 4. SEVERANCE BENEFITS. If you: (i) timely sign this Agreement; (ii) comply with your obligations under it; (iii) have not resigned your employment and your employment has not been terminated by the Company for Cause; and (iv) timely sign, return, and allow to become effective the Separation Date Release attached as Exhibit A hereto ((i)-(iv) collectively, the “Severance Preconditions”), then your employment termination will be deemed a termination “other than for Cause” “on or before the second anniversary of the Effective Date and other than during the Change in Control Determination Period,” pursuant to that certain Participation Agreement entered into pursuant to the Company’s Severance Plan, signed by you on December 3, 2024 (such Participation Agreement and plan being referred to collectively herein as the “Severance Plan”), a copy of which is attached as Exhibit B hereto, and accordingly, pursuant to Section 4.3 of the Severance Plan the Company will provide you with the following severance benefits (the “Severance Benefits”). Capitalized terms not defined in this Agreement shall have the meaning set forth in the Severance Plan. (a) Severance Pay. The Company will pay you, as severance, the equivalent of 125% of your annual base salary in effect as of the Separation Date, in the total amount of $1,250,000) (calculated as 1.25 x $1,000,000), subject to applicable payroll deductions and

Page 3 withholdings (the “Severance Pay”). The Severance Pay will be paid in a lump sum within thirty (30) days of the Release Effective Date (as defined in the Separation Date Release). (b) Pro Rated Annual Bonus Severance. The Company will pay you an additional cash lump sum payment equal to the sum of (i) your pro rata target annual bonus that you could have earned, but did not and will not earn, for 2025, in the total amount of $225,000 (calculated as ($1,000,000 x 30%) * 365/365), less the $75,000 bonus previously paid with respect to the first half of 2025, and (ii) $375,000 (calculated as 1.25 * $300,000) subject to applicable payroll deductions and withholdings (the “Annual Bonus Severance”). The Annual Bonus Severance will be paid at the same time as the Severance Pay. (c) COBRA Severance. To the extent provided by the federal COBRA law or, if applicable, state insurance laws, and by the Company’s current group health insurance policies, you will be eligible to continue your group health insurance benefits at your own expense following the Separation Date. As an additional severance benefit under this Agreement, provided that you timely elect continued coverage under COBRA, then the Company shall pay the premiums on your behalf for your continued coverage under the Company’s group health plans, including coverage for your eligible dependents, for fifteen (15) months or, in any such case, until such earlier date on which you become eligible for health coverage from another employer or cease to be eligible for COBRA coverage for any reason (the “COBRA Payment Period”). Upon the conclusion of such period of insurance premium payments made by the Company, you will be responsible for the entire payment of premiums (or payment for the cost of coverage) required under COBRA for the duration of your eligible COBRA coverage period. Notwithstanding the foregoing, if you timely elect continued group health plan continuation coverage under COBRA and at any time thereafter the Company determines, in its sole discretion, that it cannot provide the COBRA premium benefits without potentially incurring financial costs or penalties under applicable law, then in lieu of paying the employer portion of the COBRA premiums on your behalf, the Company will instead pay you, on the last day of each remaining month of the applicable COBRA Payment Period a fully taxable cash payment equal to the COBRA premium for that month, subject to applicable tax withholding, which such payments shall end upon expiration of the applicable COBRA Payment Period. (d) Equity Vesting. You were granted certain equity awards (the “Equity Awards”), pursuant to applicable award agreement(s), grant notice(s) and applicable plan documents (the “Equity Award Documents”). Under the terms of the Equity Award Documents, vesting of your Equity Awards will cease as of the Separation Date, except as set forth below. As an additional Severance Benefit, each of the outstanding, unvested Time-Vesting Awards held by you shall accelerate and become vested and exercisable or settled with respect to the number of unvested shares of the Equity Awards that would have vested had you remained employed by the Company for an additional twelve (12) months after the Separation Date and as a supplemental Severance Benefit, each of the outstanding, unvested Time-Vesting Awards held by you shall accelerate and become vested and exercisable or settled with respect to the number of unvested shares of the Equity Awards that would have vested had you remained employed by the Company for an additional month beyond such twelve (12) month period (with such acceleration totaling in the aggregate 1,154,808 shares of your Time-Vesting Awards), assuming your

Page 4 employment ends on the anticipated employment separation date). None of your Equity Awards are Performance Satisfied Awards. Performance Subject Awards shall be forfeited in accordance with their terms, except as set forth in Section 5 below, and except with respect to Performance Subject Awards with respect to which the performance period ends on December 31, 2025 (the “Specified Performance Subject Awards”). Any Specified Performance Subject Awards shall remain outstanding and eligible to vest in connection with the performance certification scheduled to occur in February 2026. Any Specified Performance Subject Awards that do not vest in connection with such certification shall be forfeited. 5. Eligibility for CIC Severance Benefits. You will remain eligible for increased severance benefits (the “CIC Severance Benefits”) in the event that you remain employed through the Transition Period (or are terminated without Cause before the end of the Transition Period) and the Company experiences a Change in Control (as defined in the Severance Plan) within three (3) months after the Separation Date (the “Change in Control Period”). Specifically, subject to satisfaction of the Severance Preconditions, in the event that the Company experiences a Change in Control during the Change in Control Period, then pursuant to Section 4.1 of the Severance Plan: (a) you will receive an additional $250,000 as additional Severance Pay described in Section 4(a) herein, subject to applicable withholdings and deductions and payable within fifteen (15) business days after the effective date of the Change in Control; (b) you will receive an additional $75,000 in respect to the Annual Severance Bonus set forth in Section 4Error! Reference source not found. above subject to applicable withholdings and deductions and payable within fifteen (15) business days after the effective date of the Change in Control; (c) the COBRA Payment Period will be increased by an additional three (3) months, to eighteen (18) months; (d) each of your then-outstanding, unvested Time-Vesting Awards and Performance Satisfied Awards shall accelerate and become vested and exercisable or settled with respect to one hundred percent (100%) of the unvested shares subject thereto and each of your Performance Subject Awards shall be treated in accordance with the terms thereof (the “Vesting Acceleration”) as of the effective date of the Change in Control. The Equity Awards will otherwise remain subject to the terms and conditions of the applicable Equity Award Documents. For the avoidance of doubt, under no circumstances will you be eligible for the full severance benefits set forth in both Section 4 of this Agreement and the full CIC Severance Benefits set forth in the Participation Agreement. 6. OTHER COMPENSATION OR BENEFITS. You acknowledge that, except as expressly provided in this Agreement, you have not earned, will not earn, and will not receive from the Company any additional compensation (including base salary, bonus, incentive compensation, or equity), severance, or benefits before, on or after the Separation Date, with the exception of any vested right you may have under the express terms of a written ERISA-qualified benefit plan (e.g., 401(k) account) or any vested stock options. You acknowledge and agree that the benefits offered to you herein fulfill and exceed all of the Company’s obligations to pay you any severance benefits in connection with your employment termination, pursuant to the Severance Plan and any other agreement, plan or policy. 7. EXPENSE REIMBURSEMENTS. You agree that, within thirty (30) days after the Separation Date, you will submit your final documented expense reimbursement statement

Page 5 reflecting all business expenses you incurred through the Separation Date, if any, for which you seek reimbursement. The Company will reimburse you for these expenses pursuant to its regular business practice. The Company shall also directly pay or reimburse you for your reasonable legal fees incurred in negotiating and drafting this Agreement up to a maximum of four thousand dollars ($4,000) within ten (10) days of the Company’s receipt of an invoice for such services (which may be redacted to preserve privilege). 8. RELEASE OF CLAIMS. (a) General Release of Claims. In exchange for the consideration provided to you under this Agreement to which you would not otherwise be entitled, you hereby generally and completely release the Company, and its affiliated, related, parent and subsidiary entities, and its and their current and former directors, officers, employees, shareholders, partners, agents, attorneys, predecessors, successors, insurers, affiliates, and assigns from any and all claims, liabilities, demands, causes of action, and obligations, both known and unknown, arising from or in any way related to events, acts, conduct, or omissions occurring at any time prior to and including the date you sign this Agreement. (b) Scope of Release. This general release includes, but is not limited to: (i) all claims arising from or in any way related to your employment with the Company, the decision to terminate that employment, or the termination of that employment; (ii) all claims related to your compensation or benefits from the Company, including salary, bonuses, commissions, vacation pay, expense reimbursements, severance pay, fringe benefits, stock, stock options, or any other ownership, equity, or profits interests in the Company; (iii) all claims for breach of contract, wrongful termination, and breach of the implied covenant of good faith and fair dealing; (iv) all tort claims, including claims for fraud, defamation, emotional distress, and discharge in violation of public policy; and (v) all federal, state, and local statutory claims, including claims for discrimination, harassment, retaliation, attorneys’ fees, or other claims arising under the federal Civil Rights Act of 1964 (as amended), the California Labor Code (as amended), the California Family Rights Act, the California Fair Employment and Housing Act (as amended). You acknowledge that you have been advised, pursuant to California Government Code Section 12964.5(b)(4), that you have the right to consult an attorney regarding this Agreement and that you were given a reasonable time period of not less than five (5) business days in which to do so. You further acknowledge and agree that, in the event you sign this Agreement prior to the end of the reasonable time period provided by the Company, your decision to accept such shortening of time is knowing and voluntary and is not induced by the Company through fraud, misrepresentation, or a threat to withdraw or alter the offer prior to the expiration of the reasonable time period, or by providing different terms to employees who sign such an agreement prior to the expiration of the time period. You acknowledge and agree that the release of claims provided in this Section 7 is not provided in exchange for a raise, bonus, or as a condition of continued employment, but rather in exchange for your eligibility to receive the benefits under this Agreement to which you are not otherwise eligible to receive.

Page 6 (c) Section 1542 Waiver. In giving the release herein, which includes claims which may be unknown to you at present, you acknowledge that you have read and understand Section 1542 of the California Civil Code, which reads as follows: “A general release does not extend to claims that the creditor or releasing party does not know or suspect to exist in his or her favor at the time of executing the release and that, if known by him or her, would have materially affected his or her settlement with the debtor or released party.” You hereby expressly waive and relinquish all rights and benefits under that section and any law of any other jurisdiction of similar effect with respect to your release of claims herein, including but not limited to your release of unknown claims. (d) Exceptions. Notwithstanding the foregoing, you are not releasing the Company hereby from: (i) any obligation to indemnify you pursuant to the Articles and Bylaws of the Company, any valid fully executed indemnification agreement with the Company, applicable law, or applicable directors and officers liability insurance; (ii) any claims that cannot be waived by law; or (iii) any claims for breach of this Agreement. 9. PROTECTED RIGHTS. You understand that nothing in this Agreement limits your ability to file a charge or complaint with the Equal Employment Opportunity Commission, the Department of Labor, the National Labor Relations Board, the Occupational Safety and Health Administration, the Department of Justice, the Securities and Exchange Commission or any other federal, state or local governmental agency or commission (“Government Agencies”). You further understand this Agreement does not limit your ability to communicate with any Government Agencies or otherwise participate in any investigation or proceeding that may be conducted by any Government Agency, including providing documents or other information, without notice to the Company. While this Agreement does not limit your right to receive a government-issued award for information provided to any Government Agency in connection with a government whistleblower program or protected whistleblower activity, you understand and agree that, to the maximum extent permitted by law, you are otherwise waiving any and all rights you may have to individual relief based on any claims that you have released and any rights you have waived by signing this Agreement. Nothing in this Agreement prevents you from discussing or disclosing information about unlawful acts in the workplace, such as harassment or discrimination or any other conduct that you have reason to believe is unlawful. Furthermore, nothing in this Agreement waives any rights you may have under Section 7 of the National Labor Relations Act (subject to the release of claims set forth herein). 10. RETURN OF COMPANY PROPERTY. You agree that by the Separation Date (or earlier if requested by the Company), you will return to the Company all Company documents (and all copies thereof) and other Company property in your possession or control, including, but not limited to, Company files, notes, drawings, records, plans, forecasts, reports, studies, analyses, proposals, agreements, drafts, financial and operational information, research and development information, Company device and account login and password information, sales and marketing information, customer lists, prospect information, pipeline reports, sales reports, personnel information, specifications, code, software, databases, computer-recorded information, tangible property and equipment (including, but not limited to, computing and electronic devices, mobile telephones, servers), credit cards, entry cards, identification badges and keys; and any materials

Page 7 of any kind which contain or embody any proprietary or confidential information of the Company (and all reproductions or embodiments thereof in whole or in part). You agree that you will make a diligent search to locate any such documents, property and information by the close of business on the Separation Date or as soon as possible thereafter. If you have used any personally owned computer or other electronic device, server, or e-mail system to receive, store, review, prepare or transmit any Company confidential or proprietary data, materials or information, by the Separation Date (or earlier if requested by the Company), you shall provide the Company with a computer-useable copy of such information and then permanently delete and expunge such Company confidential or proprietary information from those systems; and you agree to provide the Company access to your system as requested to verify that the necessary copying and/or deletion is completed. 11. CONFIDENTIAL INFORMATION OBLIGATIONS. You acknowledge and reaffirm your continuing obligations under your Employee Confidentiality and Inventions Agreement (the “Confidentiality Agreement”), a copy of which is attached hereto as Exhibit C and incorporated herein by reference. The Company acknowledges that each of the post-term obligations in Section 12(b) of the Confidentiality Agreement is void and that it shall take no steps to enforce those provisions. 12. MUTUAL NON-DISPARAGEMENT. Except to the extent permitted by the “Protected Rights” Section above, you agree not to disparage the Company, its officers, directors, employees, shareholders, parents, subsidiaries, affiliates, and agents, in any manner likely to be harmful to its or their business, business reputation, or personal reputation, and the Company agrees not to disparage you in any manner likely to be harmful to your business or personal reputation; however, the Company’s obligations under this provision extend only to its current directors, officers, and executives (at the Vice President-level and above), and only for so long as each remains a director, officer, or executive of the Company. Notwithstanding the foregoing, nothing herein shall prevent (a) any person or entity from responding accurately and fully to any question, inquiry or request for information when required by legal process or in connection with any government agency or commission investigation or proceeding, (b) the Company from making any disclosures reasonably required or advisable to fulfill any corporate reporting obligations or its fiduciary duties, and (c) any person from making any statements and disclosures specifically authorized in the “Protected Rights” Section above. You acknowledge and agree that the non-disparagement obligation provided in this Section is not provided in exchange for a raise, bonus, or as a condition of continued employment, but rather in exchange for your eligibility to receive the benefits under this Agreement to which you are not otherwise eligible to receive. 13. NO VOLUNTARY ADVERSE ACTION. You agree that you will not voluntarily (except in response to legal compulsion or as permitted under the section of this Agreement entitled “Protected Rights”) assist any person in bringing or pursuing any proposed or pending litigation, arbitration, administrative claim or other formal proceeding against the Company, its parent or subsidiary entities, affiliates, officers, directors, employees or agents.

Page 8 14. COOPERATION. You agree to cooperate fully with the Company in connection with its actual or contemplated defense, prosecution, or investigation of any claims or demands by or against third parties, or other matters arising from events, acts, or failures to act that occurred during the period of your employment by the Company. Such cooperation includes, without limitation, making yourself available to the Company upon reasonable notice, without subpoena, to provide complete, truthful and accurate information in witness interviews, depositions, and trial testimony. The Company will reimburse you for reasonable out-of-pocket expenses you incur in connection with any such cooperation (excluding foregone wages) and will make reasonable efforts to accommodate your scheduling needs. 15. NO ADMISSIONS. You understand and agree that the promises and payments in consideration of this Agreement shall not be construed to be an admission of any liability or obligation by the Company to you or to any other person, and that the Company makes no such admission. 16. REPRESENTATIONS. You hereby represent that you have: been paid all compensation owed and for all hours worked; received all leave and leave benefits and protections for which you are eligible pursuant to the Family and Medical Leave Act or otherwise; and not suffered any on-the-job injury for which you have not already filed a workers’ compensation claim. 17. MISCELLANEOUS. This Agreement, including its exhibits, constitutes the complete, final and exclusive embodiment of the entire agreement between you and the Company with regard to its subject matter. It is entered into without reliance on any promise or representation, written or oral, other than those expressly contained herein, and it supersedes any other such promises, warranties or representations. This Agreement may not be modified or amended except in a writing signed by both you and a duly authorized officer of the Company. This Agreement will bind the heirs, personal representatives, successors and assigns of both you and the Company, and inure to the benefit of both you and the Company, their heirs, successors and assigns. If any provision of this Agreement is determined to be invalid or unenforceable, in whole or in part, this determination will not affect any other provision of this Agreement and the provision in question will be modified by the court so as to be rendered enforceable to the fullest extent permitted by law, consistent with the intent of the parties. This Agreement will be deemed to have been entered into and will be construed and enforced in accordance with the laws of the state or commonwealth in which you primarily performed work for the Company, without regard to conflict of laws principles. Any ambiguity in this Agreement shall not be construed against either party as the drafter. Any waiver of a breach of this Agreement shall be in writing and shall not be deemed to be a waiver of any successive breach. This Agreement may be delivered and executed via facsimile, electronic mail (including PDF or any electronic signature complying with the U.S. federal ESIGN Act of 2000, Uniform Electronic Transactions Act, or other applicable law) or other transmission method and shall be deemed to have been duly and validly delivered and executed and be valid and effective for all purposes. [Signature page to follow]

Page 9 If this Agreement is acceptable to you, please sign below and return the original to me. You have five (5) business days to decide whether to accept this Agreement, and the Company’s offer contained herein will automatically expire if you do not sign and return it within that timeframe. We wish you the best in your future endeavors. Sincerely, By: /S/ DEBRA THOMPSON Debra Thompson Chief People Officer I HAVE READ, UNDERSTAND, AND AGREE FULLY TO THE FOREGOING AGREEMENT: /S/ NATHAN SCHULTZ Nathan Schultz 10/27/25 Date

EXHIBIT A SEPARATION DATE RELEASE (to be signed and returned to the Company on or within twenty-one (21) calendar days after the Separation Date) In exchange for benefits to be provided to me by the Company pursuant to my transition and separation agreement with the Company to which this Exhibit A is attached (the “Agreement”), I hereby provide the following Separation Date Release (the “Release”). Capitalized terms used but not defined herein shall have the meanings ascribed to them in the Agreement. I hereby represent that I have been paid all compensation owed and for all hours worked through the date I sign this Release, have received all the leave and leave benefits and protections for which I am eligible pursuant to the Family and Medical Leave Act or otherwise, and have not suffered any on-the-job injury for which I have not already filed a workers’ compensation claim. I acknowledge that, other than the benefits to be provided to me pursuant to the Agreement upon my execution of this Release, I have not earned and will not receive from the Company any additional compensation (including base salary, bonus, incentive compensation, or equity), severance, or benefits, with the exception of any vested right I may have under the express terms of a written ERISA-qualified benefit plan (e.g., 401(k) account) or any vested options. I hereby generally and completely release the Company, and its affiliated, related, parent and subsidiary entities, and its and their current and former directors, officers, employees, shareholders, partners, agents, attorneys, predecessors, successors, insurers, affiliates, and assigns from any and all claims, liabilities, demands, causes of action, and obligations, both known and unknown, that arise out of or are in any way related to events, acts, conduct, or omissions occurring at any time prior to and including the date I sign this Release. This general release includes, but is not limited to: (a) all claims arising out of or in any way related to my employment with the Company or the termination of that employment; (b) all claims related to my compensation or benefits from the Company, including salary, bonuses, commissions, vacation pay, expense reimbursements, severance pay, fringe benefits, stock, stock options, or any other ownership, equity, or profits interests in the Company; (c) all claims for breach of contract, wrongful termination, and breach of the implied covenant of good faith and fair dealing; (d) all tort claims, including claims for fraud, defamation, emotional distress, and discharge in violation of public policy; and (e) all federal, state, and local statutory claims, including claims for discrimination, harassment, retaliation, attorneys’ fees, or other claims arising under the federal Civil Rights Act of 1964 (as amended), the federal Americans with Disabilities Act of 1990, the Age Discrimination in Employment Act (“ADEA”), the California Labor Code (as amended), the California Family Rights Act, the California Fair Employment and Housing Act (as amended). Notwithstanding the foregoing, I am not releasing the Company hereby from any obligation to indemnify me pursuant to the Articles and Bylaws of the Company, any valid fully executed indemnification agreement with the Company, applicable

Page 2 law, or applicable directors and officers liability insurance. Also, excluded from this Release are any claims that cannot be waived by law. I acknowledge that I am knowingly and voluntarily waiving and releasing any rights I have under the ADEA, and that the consideration given for the waiver and releases I have given in this Agreement is in addition to anything of value to which I was already entitled. I further acknowledge that I have been advised, as required by the ADEA, that: (i) my waiver and release does not apply to any rights or claims arising after the date I sign this Agreement; (ii) I should consult with an attorney prior to signing this Agreement (although I may choose voluntarily not to do so); (iii) I have twenty-one (21) days to consider this Agreement (although I may choose voluntarily to sign it sooner); (iv) I have seven (7) days following the date I sign this Agreement to revoke this Agreement (in a written revocation sent to the Company); and (v) this Agreement will not be effective until the date upon which the revocation period has expired, which will be the eighth day after I sign this Agreement provided that I do not revoke it. I acknowledge that I am knowingly and voluntarily waiving and releasing any rights I have under the ADEA, and that the consideration given for the waiver and releases I have given in this Release is in addition to anything of value to which I was already entitled. I further acknowledge that I have been advised, as required by the ADEA, that: (a) my waiver and release does not apply to any rights or claims arising after the date I sign this Release; (b) I should consult with an attorney prior to signing this Release (although I may choose voluntarily not to do so); (c) I have twenty-one (21) days to consider this Release (although I may choose voluntarily to sign it sooner); (d) I have seven (7) days following the date I sign this Release to revoke this Release (in a written revocation sent to the Company); and (e) this Release will not be effective until the date upon which the revocation period has expired, which will be the eighth day after I sign this Release provided that I do not revoke it (the “Release Effective Date”). In giving the release herein, which includes claims which may be unknown to me at present, I acknowledge that I have read and understand Section 1542 of the California Civil Code, which reads as follows: “A general release does not extend to claims that the creditor or releasing party does not know or suspect to exist in his or her favor at the time of executing the release and that, if known by him or her, would have materially affected his or her settlement with the debtor or released party.” I hereby expressly waive and relinquish all rights and benefits under that section and any law of any other jurisdiction of similar effect with respect to my release of claims herein, including but not limited to my release of unknown claims. I understand that nothing in this Release limits my ability to file a charge or complaint with the Government Agencies. I further understand this Release does not limit my ability to communicate with any Government Agencies or otherwise participate in any investigation or proceeding that may be conducted by any Government Agency, including providing documents or other information, without notice to the Company. While this Release does not limit my right to receive a government-issued award for information provided to any Government Agency in connection with a government whistleblower program or protected whistleblower activity, I understand and

Page 3 agree that, to maximum extent permitted by law, I am otherwise waiving any and all rights I may have to individual relief based on any claims that I have released and any rights I have waived by signing this Release. Nothing in this Release waives any rights I may have under Section 7 of the National Labor Relations Act (subject to the release of claims set forth herein). This Separation Date Release, together with the Agreement (and its exhibits), constitutes the entire agreement between me, and the Company with respect to the subject matter hereof. I am not relying on any representation not contained herein or in the Agreement. UNDERSTOOD, ACCEPTED AND AGREED: _____________________________________ ______________________ Nathan Schultz Date

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Page 21 EXHIBIT C EMPLOYEE CONFIDENTIALITY AND INVENTIONS AGREEMENT

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ex102

325722163 v9 Chegg, Inc. Employment Agreement October 27, 2025 Daniel Rosensweig Sent via email Dear Dan: On behalf of Chegg, Inc. (the “Company”), this Employment Agreement (this “Agreement”) sets forth the terms and conditions of your continued employment with the Company. This Agreement replaces and supersedes in its entirety the April 24, 2024 Executive Chair Agreement between you and the Company. 1. Position. Effective as of October 27, 2025 (the “Effective Date”) you will be appointed as Chief Executive Officer (“CEO”) of the Company and will hold the title of CEO, President and Executive Chairman. You will continue to serve as a member of the Company’s Board of Directors (the “Board”), and in your capacity as CEO and President will report to the Board. You will have all of the duties, responsibilities and authority commensurate with the position of CEO and President. You will be expected to devote your full working time and attention to the business of the Company, and you will not render services to any other business without the prior approval of the Board. Notwithstanding the foregoing, you may manage personal investments, participate in civic, charitable, professional and academic activities (including serving on boards and committees), provided that such activities do not at the time the activity or activities commence or thereafter create an actual or potential business or fiduciary conflict of interest. 2. Term. Subject to the terms of this Agreement, this Agreement will remain in effect from the Effective Date and until terminated by you or the Company. 3. Base Salary. The Company will continue to pay you a base salary (the “Base Salary”) at the annualized rate of eight hundred and fifty thousand dollars ($850,000) per year, subject to annual review. Payment of your salary shall be less applicable withholding taxes and payable in accordance with the Company’s standard payroll schedule. At this time, you are not eligible for an annual bonus. 4. Benefits. You will continue to be eligible to participate in all employee retirement, welfare, insurance, benefit and vacation programs of the Company as are in effect from time to time and in which other senior executives of the Company are eligible to participate, on the same terms as such other senior executives. 5. Equity Awards. (a) RSUs. Subject to the approval of the Board or the Compensation Committee of the Board (the “Compensation Committee”), you will be granted an award of restricted stock units (“RSUs”) representing the right to acquire 1,650,000 shares of the Company’s common stock (“Common Stock”). As more fully described in the form of RSU award agreement that will be provided by the Company (the

325722163 v9 “RSU Agreement”), the RSUs will vest over three (3) years, with 1/3 vesting on the one-year anniversary of the first regularly occurring quarterly vesting date that occurs on or following the Transition Date and the remainder vesting in eight (8) equal quarterly installments thereafter, subject to your continued service on such vesting dates. (b) PSUs. Subject to the approval of the Board or the Compensation Committee, you will be granted an award of performance-based restricted stock units (“PSUs”) representing the right to acquire a maximum of 3,850,000 shares of Company Common Stock. As more fully described in the form of PSU award agreement that will be provided by the Company (the “PSU Agreement”), the PSUs will vest based upon the Compensation Committee’s certification of achievement of certain stock price thresholds (as set forth on Exhibit A hereto), as measured at 18 months and 36 months following the date of grant of the PSUs, subject to your continued service on such vesting dates, and subject to potential earlier vesting upon a Change in Control (as defined in the Chegg, Inc. Severance Plan, as it may be amended from time to time (the “Severance Plan”)) if the per-share price with respect to such Change in Control meets or exceeds one or more previously-uncertified stock price thresholds. The RSUs and the PSUs will be subject to the terms and conditions of the Company’s 2023 Equity Incentive Plan (as amended from time to time, the “2023 Plan”) and the RSU Agreement and PSU Agreement, respectively, and vested RSUs and PSUs will be settled as provided thereunder. Except as set forth in the award agreements and the Severance Plan, in the event that you cease service for any reason, you will immediately forfeit any then-unvested RSUs and PSUs without any further action by the Company. (c) Other Outstanding Company Equity Awards. Your other outstanding Company Equity Awards will continue to vest according to the existing vesting schedules applicable to such awards as of the Transition Date, subject to your continued service to the Company on each applicable vesting date, and shall be governed by the applicable Company Equity Plan and the written award agreements governing their grant. 6. Expenses and Reimbursement under Company Policies. The Company will continue to, in accordance with applicable Company policies and guidelines, reimburse you for all reasonable and necessary expenses incurred by you in connection with your performance of services on behalf of the Company. 7. No Other Board Compensation. You acknowledge that for so long as you are employed as CEO (or in any other employment position), you shall not receive any cash or equity compensation for your service on the Board. 8. Severance Plan Eligibility. You will be eligible to participate in the Chegg, Inc. Severance Plan, as it may be amended from time to time (the “Severance Plan”), pursuant to the terms and conditions of the Severance Plan and your Participation Agreement under the Severance Plan, provided that you and the Company have timely executed such Participation Agreement. 9. Section 280G. In the event that the severance and other benefits provided for in this Agreement or otherwise payable to you (a) constitute “parachute payments” within the meaning of Section 280G of the Internal Revenue Code of 1986, as amended (the “Code”), and (b) but for this Section, would be subject to the excise tax imposed by Section 4999 of the Code, then, your severance and other benefits under this Agreement shall be payable either (i) in full, or (ii) as to such lesser amount which would result in no portion of such severance and other benefits being subject to the excise tax under Section 4999 of the Code, whichever of the foregoing amounts, taking into account the applicable federal, state and local income taxes and the excise tax imposed by Section 4999, results in the receipt by you on an after-tax basis,

325722163 v9 of the greatest amount of severance benefits under this Agreement, notwithstanding that all or some portion of such severance benefits may be taxable under Section 4999 of the Code. 10. Section 409A. To the extent (a) any payments to which you become entitled under this Agreement, or any agreement or plan referenced herein, in connection with your termination of employment with the Company constitute deferred compensation subject to Section 409A of the Code and (b) you are deemed at the time of such termination of employment to be a “specified” employee under Section 409A of the Code, then such payment or payments shall not be made or commence until the earlier of (i) the expiration of the six (6)-month period measured from the date of your “separation from service” (as such term is at the time defined in regulations under Section 409A of the Code) with the Company; or (ii) the date of your death following such separation from service; provided, however, that such deferral shall only be effected to the extent required to avoid adverse tax treatment to you, including (without limitation) the additional twenty percent (20%) tax for which you would otherwise be liable under Section 409A(a)(1)(B) of the Code in the absence of such deferral. Upon the expiration of the applicable deferral period, any payments which would have otherwise been made during that period (whether in a single sum or in installments) in the absence of this paragraph shall be paid to you or your beneficiary in one lump sum (without interest). Except as otherwise expressly provided herein, to the extent any expense reimbursement or the provision of any in-kind benefit under this Agreement (or otherwise referenced herein) is determined to be subject to (and not exempt from) Section 409A of the Code, the amount of any such expenses eligible for reimbursement, or the provision of any in-kind benefit, in one calendar year shall not affect the expenses eligible for reimbursement or in kind benefits to be provided in any other calendar year, in no event shall any expenses be reimbursed after the last day of the calendar year following the calendar year in which you incurred such expenses, and in no event shall any right to reimbursement or the provision of any in-kind benefit be subject to liquidation or exchange for another benefit. To the extent that any provision of this Agreement is ambiguous as to its exemption or compliance with Section 409A, the provision will be read in such a manner so that all payments hereunder are exempt from Section 409A to the maximum permissible extent, and for any payments where such construction is not tenable, that those payments comply with Section 409A to the maximum permissible extent. To the extent any payment under this Agreement may be classified as a “short-term deferral” within the meaning of Section 409A, such payment shall be deemed a short-term deferral, even if it may also qualify for an exemption from Section 409A under another provision of Section 409A. Payments pursuant to this Agreement (or referenced in this Agreement), and each installment thereof, are intended to constitute separate payments for purposes of Section 1.409A-2(b)(2) of the regulations under Section 409A of the Code. Notwithstanding anything to the contrary in this Agreement, any reference herein to a termination of your employment is intended to constitute a “separation from service” within the meaning of Section 409A of the Code, and Section 1.409A-1(h) of the regulations promulgated thereunder, and shall be so construed. If the period during which you may sign the Release begins in one calendar year and ends in the following calendar year, then no severance payments or benefits that that would constitute deferred compensation within the meaning of Section 409A will be paid or provided until the later calendar year. 11. At Will Employment. Your service with the Company is for no specific period of time. Your employment with the Company continues to be “at will,” meaning that either you or the Company may terminate your service at any time and for any reason, with or without cause, subject to your rights under the Severance Plan. Any contrary representations that may have been made to you are superseded by this Agreement. This is the full and complete agreement between you and the Company on this term. Although your compensation and benefits, as well as the Company’s personnel policies and procedures, may change from time to time, the “at will” nature of your service may only be changed in an express written agreement signed by you and a member of the Board (other than you).

325722163 v9 12. Confidential Information and Other Company Policies. You will continue to be bound by and comply fully with your agreement regarding proprietary information, invention assignment and confidentiality with the Company (the “Confidentiality Agreement”), insider trading policy, code of conduct, and any other policies and programs adopted by the Company regulating the behavior of its employees, as such policies and programs may be amended from time to time to the extent the same are not inconsistent with this Agreement, unless you consent to the same at the time of such amendment. 13. Indemnification. You will continue to be named as an insured on the director and officer liability insurance policy currently maintained by the Company, or as may be maintained by the Company from time to time, and will continue to be subject to indemnification as required by the Company’s Bylaws and the Indemnification Agreement previously entered into between you and the Company. 14. Arbitration. To aid the rapid and economical resolution of disputes that may arise in connection with your employment with the Company, and in exchange for the mutual promises contained in this offer letter, you and the Company agree that any and all disputes, claims, or causes of action, in law or equity, including but not limited to statutory claims arising from or relating to the enforcement, breach, performance, or interpretation of this letter agreement, your employment with the Company, or the termination of your employment, shall be resolved, to the fullest extent permitted by law, by final, binding and confidential arbitration conducted by JAMS, Inc. (“JAMS”) or its successor, under JAMS’ then applicable rules and procedures appropriate to the relief being sought (available upon request and also currently available at the following web address: (i) https://www.jamsadr.com/rules-employment- arbitration/ and (ii) https://www.jamsadr.com/rules-comprehensive-arbitration/) in Santa Clara County, California. Notwithstanding the foregoing, if JAMS is unavailable due to location or otherwise, or if the parties mutually agree, then the arbitration shall be conducted by the American Arbitration Association (“AAA”) or its successor, under AAA’s then applicable rules and procedures appropriate to the relief being sought (available upon request and also currently available at the following web address: https://www.adr.org/sites/default/files/EmploymentRules-Web.pdf), at a location closest to where you last worked for the Company or another mutually agreeable location. Any demand for arbitration must be made within the statute of limitations applicable to the claim asserted as if such claim were asserted in court. Failure to demand arbitration (or, where applicable, file a counterclaim, crossclaim, or third-party claim) within such time limitation shall serve as a waiver and release with respect to all such claims. You acknowledge that by agreeing to this arbitration procedure, both you and the Company waive the right to resolve any such dispute through a trial by jury or judge. The Federal Arbitration Act, 9 U.S.C. § 1 et seq., will, to the fullest extent permitted by law, govern the interpretation and enforcement of this arbitration agreement and any arbitration proceedings. This provision shall not be mandatory for any claim or cause of action to the extent applicable law prohibits subjecting such claim or cause of action to mandatory arbitration and such applicable law is not preempted by the Federal Arbitration Act or otherwise invalid (collectively, the “Excluded Claims”), such as non-individual claims that cannot be waived under applicable law, claims or causes of action alleging sexual harassment or a nonconsensual sexual act or sexual contact, or unemployment or workers’ compensation claims brought before the applicable state governmental agency. In the event you or the Company intend to bring multiple claims, including one of the Excluded Claims listed above, the Excluded Claims may be filed with a court, while any other claims will remain subject to mandatory arbitration. You acknowledge and agree that proceedings of any non- individual claim(s) under the California Private Attorneys General Act (“PAGA”) that may be brought in court shall be stayed for the duration and pending a final resolution of the arbitration of any individual or individual PAGA claim. Nothing herein prevents you from filing and pursuing proceedings before a federal or state governmental agency, although if you choose to pursue a claim following the exhaustion of any applicable administrative remedies, that claim would be subject to this provision. In addition, with the exception of Excluded Claims arising out of 9 U.S.C. § 401 et seq., all claims, disputes, or causes of action under this section, whether by you or the Company, must be brought in an individual capacity, and shall not be brought as a plaintiff (or claimant) or class member in any purported class, representative, or

325722163 v9 collective proceeding, nor joined or consolidated with the claims of any other person or entity. You acknowledge that by agreeing to this arbitration procedure, both you and the Company waive all rights to have any dispute be brought, heard, administered, resolved, or arbitrated on a class, representative, or collective action basis. The arbitrator may not consolidate the claims of more than one person or entity, and may not preside over any form of representative or class proceeding. If a court finds, by means of a final decision, not subject to any further appeal or recourse, that the preceding sentences regarding class, representative, or collective claims or proceedings violate applicable law or are otherwise found unenforceable as to a particular claim or request for relief, the parties agree that any such claim(s) or request(s) for relief be severed from the arbitration and may proceed in a court of law rather than by arbitration. All other claims or requests for relief shall be arbitrated. You will have the right to be represented by legal counsel at any arbitration proceeding. Questions of whether a claim is subject to arbitration and procedural questions which grow out of the dispute and bear on the final disposition are matters for the arbitrator to decide, provided however, that if required by applicable law, a court and not the arbitrator may determine the enforceability of this paragraph with respect to Excluded Claims. The arbitrator shall: (a) have the authority to compel adequate discovery for the resolution of the dispute and to award such relief as would otherwise be permitted by law; and (b) issue a written statement signed by the arbitrator regarding the disposition of each claim and the relief, if any, awarded as to each claim, the reasons for the award, and the arbitrator’s essential findings and conclusions on which the award is based. The arbitrator shall be authorized to award all relief that you or the Company would be entitled to seek in a court of law. The Company shall pay all arbitration administrative fees in excess of the administrative fees that you would be required to pay if the dispute were decided in a court of law. Each party is responsible for its own attorneys’ fees, except as may be expressly set forth in your Employee Confidential Information and Inventions Assignment Agreement or as otherwise provided under applicable law. Nothing in this letter agreement is intended to prevent either you or the Company from obtaining injunctive relief in court to prevent irreparable harm pending the conclusion of any such arbitration. Any awards or orders in such arbitrations may be entered and enforced as judgments in the federal and state courts of any competent jurisdiction. 15. Compensation Recoupment. All amounts payable to you hereunder shall be subject to recoupment pursuant to the Company’s current compensation recoupment and forfeiture policy and any additional compensation recoupment policy or amendments to the then-current policy adopted by the Board or any committee thereof as required by law during the term of your service with the Company that is applicable generally to executive officers of the Company. 16. Miscellaneous. (a) Successors. The Company will require any successor (whether direct or indirect and whether by purchase, merger, consolidation, liquidation or otherwise) to all or substantially all of the Company’s business and/or assets to assume this Agreement and to agree expressly to perform this Agreement in the same manner and to the same extent as the Company would be required to perform it in the absence of a succession. For all purposes under this Agreement, the term “Company” will include any successor to the Company’s business and/or assets, or which becomes bound by this Agreement by operation of law. This Agreement and all of your rights hereunder will inure to the benefit of, and be enforceable by, your personal or legal representatives, executors, administrators, successors, heirs, distributes, devisees and legatees. (b) Notices. Notices under this Agreement must be in writing and will be deemed to have been given when personally delivered or two days after mailed by U.S. registered or certified mail, return receipt requested and postage prepaid or deposited with an overnight courier, with shipping charges prepaid. Mailed notices to you will be addressed to you at the home address which you have most recently

325722163 v9 communicated to the Company in writing. Notices to the Company will be addressed to the Board at the Company’s corporate headquarters. (c) Waiver. No provision of this Agreement will be modified or waived except in writing signed by you and a member of the Board (other than you). No waiver by either party of any breach of this Agreement by the other party will be considered a waiver of any other breach of this Agreement. (d) Severability. In the event that any provision hereof becomes or is declared by a court of competent jurisdiction to be illegal, unenforceable or void, this Agreement shall continue in full force and effect without said provision. (e) Withholding. All sums payable to you hereunder shall be reduced by all federal, state, local and other withholding and similar taxes and payments required by applicable law. (f) Entire Agreement. This Agreement, the Confidentiality Agreement, the Company Equity Plans and the equity award agreements representing your Company Equity Awards represent the entire agreement between the parties concerning the subject matter herein (and expressly supersede any prior agreements that you may have entered into regarding your employment with the Company, including but not limited to, the Executive Chair Agreement). This Agreement may be amended, or any of its provisions waived, only by a written document executed by you and a member of the Board (other than you) in the case of an amendment, or by the party against whom the waiver is asserted. (g) Governing Law. This Agreement will be governed by the laws of the State of California (other than its choice-of-law provisions). (h) Survival. The provisions of this Agreement shall survive the termination of your service for any reason to the extent necessary to enable the parties to enforce their respective rights under this Agreement.

325722163 v9 Please sign and date this Agreement and return it to me if you wish to accept service as Chief Executive Officer at the Company under the terms described above. Best regards, Chegg, Inc. /S/ RENEE BUDIG Renee Budig Chair of the Compensation Committee, Board of Directors I, the undersigned, hereby accept and agree to the terms and conditions of my service as Chief Executive Officer with the Company as set forth in this Agreement. /S/ DAN ROSENSWEIG Daniel Rosensweig 10/27/25 Date [Signature Page to Employment Agreement]

325722163 v9 EXHIBIT A – PSU VESTING TERMS - SUMMARY The vesting terms of the PSUs will be set forth in the related award agreement. The following is a summary of such terms, and it is subject in all respects to the terms of the 2023 Plan and the related award agreement. The PSUs will become eligible to vest upon certification by the Compensation Committee that between the date of grant of the PSUs and the relevant Measurement Date (as defined below), the volume weighted average closing price per share of the Common Stock over a consecutive sixty (60) trading day period has equaled or exceeded a target stock price as set forth in the table below (each, a “Performance Goal”). “Measurement Date” shall mean either or both of (a) the date that is eighteen (18) months following the date of grant (the “First Measurement Date”); and (b) the date that is thirty-six (36) months following the date of grant (the “Second Measurement Date”). The period between the date of grant of the PSUs and the Second Measurement Date is the “Performance Period.” If an adjustment to the number of shares covered by the PSUs occurs pursuant to Section 2.4 of the 2023 Plan, the Performance Goals will be subject to a related adjustment by the Board or Compensation Committee in order to preserve the economics and intention of the PSUs. If the Compensation Committee certifies that achievement of a Performance Goal has occurred on or prior to the First Measurement Date, the related portion of the PSUs will vest on the First Measurement Date (or if later, the date of such certification). If the Compensation Committee certifies that achievement of a Performance Goal has occurred subsequent to the First Measurement Date and on or prior to the Second Measurement Date, the related portion of the PSUs will vest on the Second Measurement Date (or if later, the date of such certification). Any shares of Common Stock subject to the PSUs that have not vested based on performance during the Performance Period will be forfeited automatically upon certification of performance with respect to the Second Measurement Date. The Compensation Committee shall certify performance as soon as practicable after each Measurement Date. If, during the Performance Period, a Change in Control (as defined in the Severance Plan) occurs, then the Performance Period will be shortened such that the Performance Period will end as of the Change in Control and, to the extent that any previously-uncertified Performance Goals are achieved based on the value of the per-share consideration received by the Company’s stockholders in connection with the Change in Control (the “Per-Share Consideration”), the relevant Performance Goals will be deemed achieved under the PSU, as determined by the Compensation Committee in its sole discretion, and the applicable portion of the PSU will vest upon the Change in Control. Any shares of Common Stock subject to the PSU that have not vested prior to or upon the Change in Control will be forfeited automatically. Number of Shares Performance Goal 962,500 Stock price equal to 50% stock price appreciation over the closing stock price on October 28, 2025 962,500 Stock price equal to 75% stock price appreciation over the closing stock price on October 28, 2025

325722163 v9 962,500 Stock price equal to 100% stock price appreciation over the closing stock price on October 28, 2025 962,500 Stock price equal to 125% stock price appreciation over the closing stock price on October 28, 2025

Document

EXHIBIT 99.01

Chegg to Remain a Standalone Public Company to Maximize Shareholder Value

Chegg Announces Restructuring to Increase Cash Flow and Build Momentum in the $40+ Billion Skilling Market

Dan Rosensweig to Return as CEO of Chegg

SANTA CLARA, Calif., October 27, 2025 -- Chegg, Inc. (NYSE:CHGG), a leading learning platform, today announced it will remain a standalone public company and undertake a restructuring. Executive Chairman Dan Rosensweig will reassume the role of President and Chief Executive Officer, effective October 27, 2025. Current President and Chief Executive Officer Nathan Schultz will become an Executive Advisor to the CEO and Board of Directors.

“Leading Chegg has been a privilege. Over my 18 years at the company, we have helped millions of students learn and had a meaningful impact on their lives,” said Schultz. “I am proud of what we have accomplished and excited to see Chegg enter its next era of growth."

“Nathan’s impact on Chegg, education and me personally has been immeasurable. The Board and I are deeply grateful for his dedication and contributions. Nathan has helped Chegg transform from a textbook rental business into a global learning platform driven by AI,” said Rosensweig. “As I return to the CEO role, I’m confident Chegg has a bright future, and I look forward to exploring all paths to drive growth and enhance shareholder value.”

Chegg to Remain a Standalone Public Company

Over the past year, Chegg, together with its advisor Goldman Sachs, conducted a comprehensive strategic review evaluating a range of potential outcomes, including being acquired, a go-private transaction, and remaining a public standalone company. After thoughtful consideration of multiple proposals, the Board unanimously determined that remaining an independent public company offers the best opportunity to maximize long-term shareholder value.

Chegg to Restructure to Strengthen Cash Flow and Drive Growth in the $40+ Billion Skilling Market

The new realities of AI and reduced traffic from Google to content publishers have led to a significant decline in Chegg’s traffic and revenue. As a result, and reflecting the company’s continued investment in AI, Chegg is restructuring the way it operates its academic learning products. Chegg will deliver the services with a substantially lower cost structure, generating increased cash flow to invest in Chegg’s highest growth opportunity: the $40+ billion skilling market.

Chegg has evolved its learning platform into a skilling-focused business-to-business organization, building on its existing businesses in professional language learning, workplace readiness and AI-related skills courses. These businesses are expected to generate approximately $70 million of revenue in 2025 and achieve double-digit growth in 2026. This new strategic focus positions Chegg for a return to sustainable revenue and Adjusted EBITDA growth over time.

The restructuring will result in a reduction of 388 roles globally, or approximately 45% of the workforce. These actions will materially reduce 2026 non-GAAP expenses by approximately $100-110 million and result in expected charges of approximately $15-19 million, representing mostly cash severance payments.

Chegg is reiterating revenue and adjusted EBITDA guidance for Q3 2025, as the company continues to execute on the goals outlined during the Q2 2025 earnings call in August. Additional details about the restructuring will be shared in Chegg’s Q3 2025 earnings call on November 10, 2025.

“We are deeply grateful to everyone who has contributed to Chegg, and to those who remain committed to our mission and the opportunities that lie ahead,” added Rosensweig.

About Chegg

Chegg is a learning platform helping students and lifelong learners gain the skills and confidence to succeed. Building on over two decades of learning insights, Chegg combines personalized, AI-powered academic support with innovative tools for language learning and workplace readiness and professional upskilling. Chegg’s core product, Chegg Study, is moving to an AI-powered model that answers all new questions automatically, while students retain access to nearly 120 million archived expert answers. Chegg is strategically focused on Busuu, part of the $3.2 billion global language learning market, and Skills, serving the more than $40 billion educational benefit and strategic upskilling market, providing learners and employers with the tools they need to thrive in the evolving workplace. Chegg remains committed to its mission of improving learning outcomes and career opportunities for millions around the world. Chegg is a publicly held company based in Santa Clara, California, and trades on the NYSE under the symbol CHGG. For more information, visit www.chegg.com.

Forward-Looking Statements

This press release contains forward-looking statements made pursuant to the safe harbor provisions of the Private Securities Litigation Reform Act of 1995, which include, without limitation, statements regarding the impact of our leadership transition and the conclusion of our process to explore strategic alternatives; our newly announced restructuring plan, including the number of employees impacted by the reduction in force, the amount and timing of the charges we will incur in connection with these actions, the amount and timing of cost savings; our expectations regarding future revenue generation and growth; our ability to successfully implement our new strategic focus and positions Chegg for a return to sustainable revenue and Adjusted EBITDA growth over time; our revenue and adjusted EBITDA guidance for Q3 2025; our ability to weather current and future business challenges and to stabilize the business; the impact of generative AI on our business and all statements about our outlook. The words “anticipate,” “believe,” “estimate,” “expect,” “intend,” “project,” “endeavor,” “will,” “should,” “future,” “transition,” “outlook” and similar expressions, as they relate to Chegg, are intended to identify forward-looking statements. These statements are not guarantees of future performance, and are based on management’s expectations as of the date of this press release and assumptions that are inherently subject to uncertainties, risks and changes in circumstances that are difficult to predict. Forward-looking statements involve known and unknown risks, uncertainties and other factors that may cause actual results, performance or achievements to differ materially from any future results, performance or achievements. Important factors that could cause actual results to differ materially from those expressed or implied by these forward-looking statements include the following: the effects of AI technology on our business and the economy generally; our ability to stabilize the business by attracting new learners to, and retaining existing learners on, our learning platform in light of declining revenue and user traffic; the impact and effectiveness of our internal restructuring activities; our ability to effectively control operating costs; our ability to innovate and offer new products and services in response to competitive technology and market developments, including generative AI; competition in all aspects of our business, including with respect to AI and our expectation that such competition will increase; the outcome of our litigation against Google; our ability to maintain our services and systems without interruption, including as a result of technical issues, cybersecurity threats, or cyber-attacks; third-party payment processing risks; the outcome of any current litigation and investigations; the possibility that the NYSE may delist our common stock; and general economic, political and industry conditions, including escalating international trade tensions, including tariffs and trade restrictions, fluctuating inflation, recession and war. All information provided in this release and in the conference call is as of the date hereof, and Chegg undertakes no duty to update this information except as required by law. These and other important risk factors are described more fully in documents filed with the Securities and Exchange Commission, including our Annual Report on Form 10-K for the year ended December 31, 2024 filed with the Securities and Exchange Commission (the “Commission”) on February 24, 2025, as supplemented by the Company’s subsequent Quarterly Reports on Form 10-Q, and could cause actual results to differ materially from expectations.