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2014 ANNUAL REPORT Dear Stockholder: 2014 was a year of progress and transformation. We continued to grow and expand our leading student‐first connected learning platform, the Student Hub, while accelerating our business model from print to digital with an aim to unlock greater shareholder value. We believe that Chegg’s Student Hub is more important and needed than ever. The U.S. high school and college demographic is approximately 34 million strong and this group is digitally empowered and self‐directed. They believe deeply that technology is enriching their lives by helping them to more easily and efficiently connect with the people, places and things that matter to them. We’ve seen the impact of this in major industries such as media (Netflix), transportation (Uber), and commerce (eBay). Yet when it comes to higher education ‐ arguably the most critical stage in their lives ‐ each step of the way remains stubbornly tethered to dated and antiquated processes that are not only slow and indirect but built to serve multitudes of other constituents ahead of the student. Chegg is disrupting this dated and antiquated higher education system by putting students first and building an ecosystem of tools and services to empower students to improve their own outcomes. Through the Student Hub, students can research schools and get matched to scholarships and colleges online; attain required course materials more cheaply and efficiently; access learning tools that help them master complex content faster; and map their careers while connecting with employers in their field of interest. In essence, our Student Hub is the digital platform empowering today’s self‐directed student throughout the higher education process. Throughout 2014, students continued to respond well to Chegg, as we finished the year reaching nearly 50% of all U.S. college students and 75% of college‐bound high school students in the U.S. In addition, we saw very strong subscriber growth with the number of subscribers to our digital learning services growing 54%, and passing one million. We also made excellent progress building and acquiring new digital services that meet more student needs. We launched Chegg Tutors, where students can now connect directly with high quality tutors anytime, anywhere and from any device, for as little as 50 cents a minute. Our platform has grown to over 10,000 active tutors. We also launched Chegg Career Center, powered by internships.com, with over 2 million registered users, and 90,000 internships from 60,000 companies nationally. This is good for both students and employers. Students can plan their careers while researching and connecting with desired internships nationally in their area of interest. Employers will be able to use the Chegg Career Center to efficiently recruit recent graduates nationally via a single point of access that can be filtered by school, major, coursework, completed internships, skills, geography and more. And finally, we partnered with the Ingram Content Group to transform our print textbook business model by transitioning all responsibilities for textbook procurement, warehousing and logistics to Ingram. This transformation will allow us to focus more on growing our higher margin digital services while continuing to offer our highly valued textbook rental business, and receive all the benefits from being the textbook rental provider of choice to students. We believe these changes position Chegg to become a pure digital revenue business by the end of 2016 with high growth, high margin and high cash flow. As we enter 2015, we believe we are better positioned than ever to drive increased customer and stockholder value and look forward to reporting our progress along the way. Thank you for your continued support. Sincerely, Dan Rosensweig, President & CEO Chegg, Inc. 2015 Proxy Statement April 24, 2015 To Our Stockholders, You are cordially invited to attend the 2015 Annual Meeting of Stockholders of Chegg, Inc. The meeting will be held at 3990 Freedom Circle, Santa Clara, California on Thursday, June 4, 2015 at 9:00 a.m. (Pacific Time). We have elected to deliver our proxy materials to our stockholders over the Internet in accordance with Securities and Exchange Commission rules. We believe that this delivery process reduces our environmental impact and lowers the costs of printing and distributing our proxy materials without impacting our stockholders’ timely access to this important information. On April 24, 2015, we sent a Notice of Internet Availability of Proxy Materials (the “Notice”) to our stockholders, which contains instructions on how to access our proxy statement for our 2015 Annual Meeting of Stockholders and annual report to stockholders. The Notice also provides instructions on how to vote by telephone or through the Internet and includes instructions on how to receive a paper copy of the proxy materials by mail. The matters to be acted upon are described in the accompanying notice of annual meeting and proxy statement. Please use this opportunity to take part in our company’s affairs by voting on the business to come before the meeting. Whether or not you plan to attend the meeting, please vote by telephone or through the Internet or request, sign and return a proxy card to ensure your representation at the meeting. Your vote is important. Sincerely, Dan Rosensweig President and Chief Executive Officer CHEGG, INC. 3990 Freedom Circle Santa Clara, CA 95054 NOTICE OF ANNUAL MEETING OF STOCKHOLDERS To Our Stockholders: NOTICE IS HEREBY GIVEN that the 2015 Annual Meeting of Stockholders of Chegg, Inc. will be held on Thursday, June 4, 2015, at 9:00 a.m. (Pacific Time) at our offices located at 3990 Freedom Circle, Santa Clara, California. We are holding the meeting for the following purposes, which are more fully described in the accompanying proxy statement: 1. To elect two Class II directors of Chegg, Inc. each to serve until the third annual meeting of stockholders following this meeting and until his or her successor has been elected and qualified or until his or her earlier resignation or removal. 2. To ratify the appointment of Ernst & Young LLP as our independent registered public accounting firm for the fiscal year ending December 31, 2015. In addition, stockholders may be asked to consider and vote upon such other business as may properly come before the meeting or any adjournment or postponement thereof. Only stockholders of record of our common stock at the close of business on April 10, 2015 are entitled to notice of, and to vote at, the meeting and any adjournments or postponements thereof. For ten days prior to the meeting, a complete list of the stockholders entitled to vote at the meeting will be available during ordinary business hours at our headquarters for examination by any stockholder for any purpose relating to the meeting. Your vote as a Chegg, Inc. stockholder is very important. Each share of stock that you own represents one vote. For questions regarding your stock ownership, if you are a registered holder, you can contact our transfer agent, American Stock Transfer & Trust Company, through their website at www.amstock.com or by phone at (800) 937-5449. By Order of the Board of Directors, Robert Chesnut Senior Vice President, General Counsel and Secretary Santa Clara, California April 24, 2015 Whether or not you expect to attend the meeting, we encourage you to read the proxy statement and vote by telephone or through the Internet or request, sign and return your proxy card as soon as possible, so that your shares may be represented at the meeting. For specific instructions on how to vote your shares, please refer to the section entitled “General Information About the Meeting” beginning on page 1 of the proxy statement and the instructions on the Notice of Internet Availability of Proxy Materials that was mailed to you. CHEGG, INC. PROXY STATEMENT FOR 2015 ANNUAL MEETING OF STOCKHOLDERS GENERAL PROXY INFORMATION . 5 Information About Solicitation and Voting . 5 Internet Availability of Proxy Materials. 5 General Information About the Meeting . 5 CORPORATE GOVERNANCE STANDARDS AND DIRECTOR INDEPENDENCE . 8 Corporate Governance Guidelines . 8 Board Leadership Structure . 8 Our Board of Directors’ Role in Risk Oversight . 8 Independence of Directors . 8 Committees of Our Board of Directors . 9 Compensation Committee Interlocks and Insider Participation. 11 Board and Committee Meetings and Attendance. 11 Board Attendance at Annual Stockholders’ Meeting . 11 Presiding Director of Non-Employee Director Meetings . 11 Communication with Directors . 11 Code of Business Conduct and Ethics . 11 NOMINATIONS PROCESS AND DIRECTOR QUALIFICATIONS . 12 Nomination to the Board of Directors . 12 Director Qualifications. 12 PROPOSAL NO. 1 ELECTION OF DIRECTORS . 13 Nominees to the Board of Directors. 14 Continuing Directors . 14 Director Compensation . 16 PROPOSAL NO. 2 RATIFICATION OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM . 18 Principal Accountant Fees and Services. 18 Policy on Audit Committee Pre-Approval of Audit and Permissible Non-Audit Services of Independent Registered Public Accounting Firm . 18 SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT . 19 OUR MANAGEMENT . 22 EXECUTIVE COMPENSATION . 24 Executive Compensation Tables . 24 Termination and Change of Control Arrangements . 26 EQUITY COMPENSATION PLAN INFORMATION . 29 TRANSACTIONS WITH RELATED PARTIES, FOUNDERS AND CONTROL PERSONS. 30 Review, Approval or Ratification of Transactions with Related Parties . 30 REPORT OF THE AUDIT COMMITTEE. 31 ADDITIONAL INFORMATION . 32 Stockholder Proposals to be Presented at Next Annual Meeting . 32 Section 16(a) Beneficial.

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