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Dear Shareholders: We are very honored to report back to you on our first fiscal year as a public company. For Chegg, 2013 was an exciting and productive year, as we completed our initial public offering in November, and experienced strong growth in revenue, customers and engagement, while effectively managing against increased competition in our print business. Though we started in the textbook rental business, we are now addressing a much larger opportunity in higher education, a $1 trillion industry that for the first time is being significantly disrupted by technology and innovation. The existing higher education system is one that has evolved bureaucratically to conform to the needs of institutions, faculty, publishers and funders, and fails to serve its primary customer—the student. At the same time, the global economy is far more competitive, demanding that students update their skills more often, manage career-change more frequently, and take charge of their own education. The growing gap between the demands on the student and the capabilities of the existing higher education system is reflected in the fact that as college tuition and fees have significantly outpaced inflation, employers complain that students are graduating without the necessary skills to compete. Realizing this, students are questioning the value of the degree that has left over 70% of them carrying approximately $30,000 in student debt while facing a job market yielding a 44% underemployment rate for recent graduates. At Chegg, we are focused on leveraging technology to bridge this gap, putting students directly in control of their education and career. We are building the leading student-first connected learning platform. With nearly 7 million active members already, Chegg now reaches 30% of all US college students and 40% of high school seniors intending to go to college. On our platform, students can research and get matched to the right colleges and scholarships, review courses and professors, order required materials more cheaply, get valuable help through our Chegg Study and Q&A network, and get matched with internships in their intended field. One of the inherent strengths of our model is that the more students engage our platform, the more powerfully it works for them. Increased engagement helps inform the overall student-graph, enabling us to deliver more personalized products and services, thereby improving the experience and engagement further. An example of our ability to extend the Chegg platform and deliver more relevant and engaging services to students is our partnership with Internships.com. Since launching at scale in December with more than 70,000 opportunities from 40,000 different companies, our students have been spending an average of 11 minutes per visit, browsing over five internship postings each, on average. This is a powerful indicator not just of the interest students have in services beyond the classroom, but also of our ability to deliver those services on our platform via the knowledge we accumulate in the student graph. In 2013, we saw evidence that our student-first strategy is working: • Total revenue grew 20% with digital revenue up 86% • Revenue from our digital businesses expanded to 21% of total, up 8 percentage points from 2012. • Textbook revenue grew 10% on unit growth of 17% • New customers increased 22% and active members 31% • Chegg Study customers grew 45% to more than 460,000. • And engagement was strong in key areas, including course review where the number of student course reviews on Chegg reached 1.1 million, an increase of 644,000 over 2012. In our textbook rental business, unit growth of 17% indicates that we continued to grab market share in an increasingly competitive market. Though we saw the average rental price of textbooks decline—impacting gross margins in the fourth quarter—it helped drive stronger customer growth and the improved mix of our higher margin digital revenue. In 2014, we plan to expand the Chegg platform further, but will be cognizant of both cash and expense. Following our IPO, we finished fiscal 2013 with $138 million in cash and marketable securities, zero debt, and expect to manage the overall business to be approximately free-cash-flow breakeven in 2014. We also plan to continue to leverage the inherent viral nature of our platform where strong word-of-mouth leads to lower customer acquisition costs and lower operating expense as a percentage of revenue. In 2013, roughly half of our customers came from word of mouth, helping us drive down customer acquisition costs by 40%. I’d like to thank our shareholders for joining Chegg. We are very excited about the student-first platform we are building, and look forward to demonstrating our continued progress throughout the year. Sincerely, Dan Rosensweig President & CEO Chegg, Inc. 2014 Proxy Statement [THIS PAGE INTENTIONALLY LEFT BLANK] April 11, 2014 To Our Stockholders, You are cordially invited to attend the 2014 Annual Meeting of Stockholders of Chegg, Inc. The meeting will be held at 3990 Freedom Circle, Santa Clara, California on Thursday, May 22, 2014 at 9:00 a.m. Pacific Time. Under the Securities and Exchange Commission rules that allow companies to furnish proxy materials to stockholders over the Internet, we have elected to deliver our proxy materials to our stockholders over the Internet. 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 11, 2014, 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 2014 Annual Meeting of Stockholders and 2014 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 [THIS PAGE INTENTIONALLY LEFT BLANK] CHEGG, INC. 3990 Freedom Circle Santa Clara, CA 95054 NOTICE OF ANNUAL MEETING OF STOCKHOLDERS To Our Stockholders: NOTICE IS HEREBY GIVEN that the 2014 Annual Meeting of Stockholders of Chegg, Inc. will be held on Thursday, May 22, 2014, 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 three Class I directors of Chegg, Inc. each to serve until the third annual meeting of stockholders following this meeting and until his successor has been elected and qualified or until his 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, 2014. 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 March 28, 2014 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 11, 2014 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 enclosed Notice of Internet Availability of Proxy Materials. CHEGG, INC. PROXY STATEMENT FOR 2014 ANNUAL MEETING OF STOCKHOLDERS GENERAL PROXY INFORMATION Information About Solicitation and Voting 5 Internet Availability of Proxy Materials 5 General Information About the Meeting 5 CORPORATE GOVERNANCE STANDARDS AND DIRECTOR INDEPENDENCE 9 Corporate Governance Guidelines 9 Board Leadership Structure 9 Our Board of Directors’ Role in Risk Oversight 9 Independence of Directors 10 Committees of Our Board of Directors 10 Compensation Committee Interlocks and Insider Participation 12 Board and Committee Meetings and Attendance 12 Board Attendance at Annual Stockholders’ Meeting 13 Presiding Director of Non-Employee Director Meetings 13 Communication with Directors 13 Code of Business Conduct and Ethics 13 NOMINATIONS PROCESS AND DIRECTOR QUALIFICATIONS 14 Nomination to the Board of Directors 14 Director Qualifications 14 PROPOSAL NO. 1 ELECTION OF DIRECTORS 15 Nominees to the Board of Directors 15 Continuing Directors 16 Director Compensation 17 PROPOSAL NO.