CHEGG, INC 10-Q

ITEM 2. UNREGISTERED SALES OF EQUITY SECURITIES AND USE OF PROCEEDS Unregistered Sales of Securities We had no unregistered sales of our securities during the three months ended September 30, 2022. Purchases of Securities by the Registrant and Affiliated Purchasers The following table summarizes the securities repurchase activity during the three months ended September 30, 2022 (in thousands, except average price paid per security and total number of securities repurchased): Period Total Number of Securities Repurchased (2) Average Price Paid Per Security Total Number of Securities Purchased Pursuant to Publicly-Announced Plan Total Dollar Amount Purchased Pursuant to Publicly-Announced Plan Maximum Dollar Amount Remaining Available for Repurchase Pursuant to Publicly-Announced Plan July 1 - July 31 — — 1,065,491 August 1 - August 31 — — — — 1,065,491 September 1 - September 30 (1) 1,146,803 20.1032 1,146,803 23,054 642,564 (1) During the three months ended September 30, 2022, in addition to the $23.1 million repurchase of shares of our common stock, we also repurchased $399.9 million of the 2026 notes in privately-negotiated transactions resulting in total securities repurchases of $422.9 million. See Note 8, “Convertible Senior Notes” and Note 11, “Stockholders' Equity,” of our accompanying Notes to Condensed Consolidated Financial Statements included in Part I, Item 1, “Financial Statements (Unaudited)” of this Quarterly Report on Form 10-Q for additional information on the securities repurchase program and the repurchase of the 2026 notes. (2) In June 2022, our board of directors approved a $1.0 billion increase to our existing securities repurchase program authorizing the repurchase of up to $2.0 billion of our common stock and/or convertible notes, through open market purchases, block trades, and/or privately negotiated transactions or pursuant to Rule 10b5-1 plans, in compliance with applicable securities laws and other legal requirements. The timing, volume, and nature of the repurchases will be determined by management based on the capital needs of the business, market conditions, applicable legal requirements, and other factors. The repurchase program has no expiration date and will continue until otherwise suspended, terminated or modified at any time for any reason by our board of directors. 35 Table of Contents ITEM 6. EXHIBITS Incorporated by Reference Exhibit No. Exhibit Form File No Filing Date Exhibit No. Filed Herewith 31.01 Certification of Dan Rosensweig, Chief Executive Officer and Co-Chairperson, pursuant to Rule 13a-14(a)/15d-14(a), as adopted pursuant to Section 302 of the Sarbanes-Oxley Act of 2002 X 31.02 Certification of Andrew Brown, Chief Financial Officer, pursuant to Rule 13a-14(a)/15d-14(a), as adopted pursuant to Section 302 of the Sarbanes-Oxley Act of 2002 X 32.01** Certification pursuant to 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002 X 101.INS Inline XBRL Instance Document X 101.SCH Inline XBRL Taxonomy Extension Schema X 101.CAL Inline XBRL Taxonomy Extension Calculation X 101.LAB Inline XBRL Taxonomy Extension Labels X 101.PRE Inline XBRL Taxonomy Extension Presentation X 101.DEF Inline XBRL Taxonomy Extension Definition X 104 Cover Page Interactive Data File (formatted as Inline XBRL and contained in Exhibit 101). X ** This certification is deemed not filed for purposes of section 18 of the Securities Exchange Act of 1934, as amended (Exchange Act), or otherwise subject to the liability of that section, nor shall it be deemed incorporated by reference into any filing under the Securities Act of 1933, as amended, or the Exchange Act. 36 Table of Contents SIGNATURES Pursuant to the requirements of Section 13 or 15(d) 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. November 1, 2022 By: /S/ ANDREW BROWN Andrew Brown Chief Financial Officer (Duly Authorized Officer and Principal Financial Officer) 37