CHEGG, INC 10-K

ITEM 7A. QUANTITATIVE AND QUALITATIVE DISCLOSURES ABOUT MARKET RISK We are exposed to market risk, including changes to foreign currency exchange rates and interest rates. Foreign Currency Exchange Risk Our results of operations and cash flows are subject to fluctuations due to changes in foreign currency exchange rates, particularly changes in the Indian Rupee, Euro, and British Pound Sterling, and changes in the relative value of the U.S. dollar to these currencies may have an impact. We have experienced and will continue to experience fluctuations in net income (loss) as a result of transaction gains or losses related to remeasuring certain amounts that are denominated in foreign currencies. We accept foreign currencies from our international customers and our international revenues have grown to 15% and 11% of total net revenues during the years ended December 31, 2022 and 2021, respectively. Additionally, a portion of our operating expenses are incurred outside of the United States and are denominated in foreign currencies. Unfavorable fluctuations in foreign currency exchange rates may have an adverse impact on our total net revenues or total operating expenses, however, we do not believe a hypothetical 10% strengthening or weakening of the U.S. dollar against foreign currencies would have a material impact on our results of operations. To date, we have not entered into derivatives or hedging strategies to mitigate risk related to changes in foreign currency exchange rates and continually monitor our foreign currency exchange exposure. Interest Rate Sensitivity We had cash and cash equivalents totaling $473.7 million and $854.1 million as of December 31, 2022 and 2021, respectively, and investments of $800.2 million and $1.4 billion as of December 31, 2022 and 2021, respectively. Our cash and cash equivalents consist of cash and money market funds and investments consist of commercial paper, corporate debt securities, U.S. treasury securities and agency bonds. Changes in U.S. interest rates, such as those that have occurred in 2022, affect the interest earned on our cash and cash equivalents and investments and the market value of those securities. A hypothetical 100 basis point increase or decrease in interest rates would result in a $6.0 million increase or decline in the fair value of our investments as of December 31, 2022. Any realized gains or losses resulting from interest rate changes would only occur if we sold the investments prior to maturity. We were not exposed to material risks due to changes in market interest rates given the liquidity of the cash, cash equivalents, and investments in which we invested our cash. We carry our notes at face value less unamortized debt issuance costs on our consolidated balance sheets. Because the 2026 notes and 2025 notes have a fixed annual interest rate of 0.0% and 0.125%, respectively, we do not have any economic interest rate exposure or financial statement risk associated with changes in interest rates. The fair value of the notes, however, 49 Table of Contents may fluctuate when interest rates and the market price of our stock changes. See Note 11, “Convertible Senior Notes,” of the Notes to Consolidated Financial Statements of Part II, Item 8 of this Annual Report on Form 10-K for additional information. 50 Table of Contents ITEM 8. CONSOLIDATED FINANCIAL STATEMENTS AND SUPPLEMENTARY DATA Index to Consolidated Financial Statements Page Report of Independent Registered Public Accounting Firm (PCAOB ID No. 34 ) 52 Consolidated Balance Sheets 55 Consolidated Statements of Operations 56 Consolidated Statements of Comprehensive Income (Loss) 57 Consolidated Statements of Stockholders’ Equity 58 Consolidated Statements of Cash Flows 59 Notes to Consolidated Financial Statements 60 51 Table of Contents REPORT OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM To the Stockholders and the Board of Directors of Chegg, Inc. Opinion on the Financial Statements We have audited the accompanying consolidated balance sheets of Chegg, Inc. and subsidiaries (the "Company") as of December 31, 2022 and 2021, the related consolidated statements of operations, comprehensive income (loss), stockholders' equity, and cash flows, for each of the three years in the period ended December 31, 2022, and the related notes and the schedule listed in the Index at Item 15.2 (collectively referred to as the "financial statements"). In our opinion, the financial statements present fairly, in all material respects, the financial position of the Company as of December 31, 2022 and 2021, and the results of its operations and its cash flows for each of the three years in the period ended December 31, 2022, in conformity with accounting principles generally accepted in the United States of America. We have also audited, in accordance with the standards of the Public Company Accounting Oversight Board (United States) (PCAOB), the Company's internal control over financial reporting as of December 31, 2022, based on criteria established in Internal Control — Integrated Framework (2013) issued by the Committee of Sponsoring Organizations of the Treadway Commission and our report dated February 21, 2023, expressed an unqualified opinion on the Company's internal control over financial reporting. Basis for Opinion These financial statements are the responsibility of the Company's management. Our responsibility is to express an opinion on the Company's financial statements based on our audits. We are a public accounting firm registered with the PCAOB and are required to be independent with respect to the Company in accordance with the U.S. federal securities laws and the applicable rules and regulations of the Securities and Exchange Commission and the PCAOB. We conducted our audits in accordance with the standards of the PCAOB. Those standards require that we plan and perform the audit to obtain reasonable assurance about whether the financial statements are free of material misstatement, whether due to error or fraud. Our audits included performing procedures to assess the risks of material misstatement of the financial statements, whether due to error or fraud, and performing procedures that respond to those risks. Such procedures included examining, on a test basis, evidence regarding the amounts and disclosures in the financial statements. Our audits also included evaluating the accounting principles used and significant estimates made by management, as well as evaluating the overall presentation of the financial statements. We believe that our audits provide a reasonable basis for our opinion. Critical Audit Matters The critical audit matters communicated below are matters arising from the current-period audit of the financial statements that were communicated or required to be communicated to the audit committee and that (1) relate to accounts or disclosures that are material to the financial statements and (2) involved our especially challenging, subjective, or complex judgments. The communication of critical audit matters does not alter in any way our opinion on the financial statements, taken as a whole, and we are not, by communicating the critical audit matters below, providing separate opinions on the critical audit matters or on the accounts or disclosures to which they relate. Accounting for income taxes - Deferred Tax Assets — Refer to Notes 2 and 17 to the financial statements Critical Audit Matter Description The Company accounts for income taxes under the asset and liability method, which requires the recognition of deferred tax assets and liabilities for the expected future tax consequences of events that have been included in the Company’s consolidated financial statements or tax returns. In assessing the realization of deferred tax assets, the Company considers whether it is more likely than not that all or some portion of deferred tax assets will not be realized. The realization of the deferred tax assets is dependent upon the generation of future taxable income during the periods in which those temporary differences become deductible. During the year ended December 31, 2022, the Company recorded a benefit from income taxes primarily due to partial release of the valuation allowance resulting in a net deferred tax asset of $165.7 million as of December 31, 2022. The valuation allowance decreased by $202.2 million in the year end December 31, 2022. The release of the valuation allowance is the result of the Company’s expectation that their domestic operations will continue to be profitable and is based on a detailed evaluation of all available evidence. 52 Table of Contents We identified management’s determination that it is more likely than not that sufficient taxable income will be generated in the future to realize deferred tax assets as a critical audit matter because of the judgments and estimates management makes related to taxable income. This required a high degree of auditor judgment and an increased extent of effort, including the need to involve our income tax specialists, when performing audit procedures to evaluate the reasonableness of management’s estimates of taxable income and assumptions related to the partial release of the valuation allowance. How the Critical Audit Matter Was Addressed in the Audit Our audit procedures related to deferred tax assets included the following, among others: • We tested the effectiveness of controls over deferred tax assets, including management’s controls over the estimates of taxable income and the determination of whether it is more likely than not that the deferred tax assets will be realized. • We utilized income tax specialists to assist in: ◦ Evaluating the reasonableness of the methods, assumptions, and judgments used by management to determine the deferred tax assets and valuation allowance was necessary. ◦ Testing the projected future reversal of temporary differences by jurisdiction, including underlying management assumptions. ◦ Evaluating the timing of the valuation release and whether the taxable income in prior carryback years was of the appropriate character and available under the tax law. • We evaluated whether the estimates of future taxable income were consistent with evidence obtained in other areas of the audit and evaluated the reasonableness of management’s ability to accurately estimate future taxable income by comparing to historical results, internal budgets, and other publicly available information. Convertible Senior Notes - Refer to Notes 2 and 11 to the financial statements Critical Audit Matter Description During the year ended December 31, 2022, the Company extinguished $500 million principal amount of the convertible senior notes due in 2026 (“2026 Notes”) which had a carrying value of $494.7 million for total consideration of $401.2 million (including $1.3 million in fees). The Company elected to reacquire and not cancel the extinguished 2026 notes and left the associated capped call transactions outstanding. This resulted in a gain on extinguishment of $93.5 million. Auditing the following elements involved a higher degree of auditor judgment and an increased extent of effort due to the nature and extent of specialized skill and knowledge required of the Company’s accounting assessment of the settlement including the conclusion that the settlement should be accounted for as an extinguishment. How the Critical Audit Matter Was Addressed in the Audit Our audit procedures related to evaluating the extinguishment of the 2026 Notes included the following, among others: • We tested the operating effectiveness of the controls over the Company’s accounting for the extinguishment of the 2026 Notes. • Our testing included reading the underlying agreements and evaluating the Company’s accounting analysis underlying the accounting of the 2026 Notes, including the determination of the balance sheet classification of each transaction, identification of any derivatives included in the arrangements, and determination that the 2026 Notes was a debt extinguishment. • We utilized the assistance of professionals within our firm having experience in accounting for convertible debt instruments, and we evaluated management’s assessment of the accounting for the extinguishment. /S/ DELOITTE & TOUCHE LLP San Jose, California February 21, 2023 We have served as the Company’s auditor since 2018. 53 Table of Contents REPORT OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM To the stockholders and the Board of Directors of Chegg, Inc. Opinion on Internal Control over Financial Reporting We have audited the internal control over financial reporting of Chegg, Inc. and subsidiaries (the “Company”) as of December 31, 2022, based on criteria established in Internal Control — Integrated Framework (2013) issued by the Committee of Sponsoring Organizations of the Treadway Commission (COSO). In our opinion, the Company maintained, in all material respects, effective internal control over financial reporting as of December 31, 2022, based on criteria established in Internal Control — Integrated Framework (2013) issued by COSO . We have also audited, in accordance with the standards of the Public Company Accounting Oversight Board (United States) (PCAOB), the consolidated financial statements as of and for the year ended December 31, 2022, of the Company and our report dated February 21, 2023, expressed an unqualified opinion on those financial statements. As described in Management’s Annual Report on Internal Control Over Financial Reporting, management excluded from its assessment the internal control over financial reporting at Busuu Online S.L., which was acquired on January 13, 2022, and whose financial statements constitute less than 1% of total assets and 5% of total net revenues of the consolidated financial statement amounts as of and for the year ended December 31, 2022. Accordingly, our audit did not include the internal control over financial reporting at Busuu Online S.L. Basis for Opinion The Company’s management is responsible for maintaining effective internal control over financial reporting and for its assessment of the effectiveness of internal control over financial reporting, included in the accompanying Management’s Annual Report on Internal Control Over Financial Reporting. Our responsibility is to express an opinion on the Company’s internal control over financial reporting based on our audit. We are a public accounting firm registered with the PCAOB and are required to be independent with respect to the Company in accordance with the U.S. federal securities laws and the applicable rules and regulations of the Securities and Exchange Commission and the PCAOB. We conducted our audit in accordance with the standards of the PCAOB. Those standards require that we plan and perform the audit to obtain reasonable assurance about whether effective internal control over financial reporting was maintained in all material respects. Our audit included obtaining an understanding of internal control over financial reporting, assessing the risk that a material weakness exists, testing and evaluating the design and operating effectiveness of internal control based on the assessed risk, and performing such other procedures as we considered necessary in the circumstances. We believe that our audit provides a reasonable basis for our opinion. Definition and Limitations of Internal Control over Financial Reporting A company’s internal control over financial reporting is a process designed to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles. A company’s internal control over financial reporting includes those policies and procedures that (1) pertain to the maintenance of records that, in reasonable detail, accurately and fairly reflect the transactions and dispositions of the assets of the company; (2) provide reasonable assurance that transactions are recorded as necessary to permit preparation of financial statements in accordance with generally accepted accounting principles, and that receipts and expenditures of the company are being made only in accordance with authorizations of management and directors of the company; and (3) provide reasonable assurance regarding prevention or timely detection of unauthorized acquisition, use, or disposition of the company’s assets that could have a material effect on the financial statements. Because of its inherent limitations, internal control over financial reporting may not prevent or detect misstatements. Also, projections of any evaluation of effectiveness to future periods are subject to the risk that controls may become inadequate because of changes in conditions, or that the degree of compliance with the policies or procedures may deteriorate. /S/ DELOITTE & TOUCHE LLP San Jose, California February 21, 2023 54 Table of Contents CHEGG, INC. CONSOLIDATED BALANCE SHEETS (in thousands, except for number of shares and par value) December 31, 2022 2021 Assets Current assets Cash and cash equivalents $ 473,677 $ 854,078 Short-term investments 583,973 691,781 Accounts receivable, net of allowance of $ 394 and $ 153 at December 31, 2022 and December 31, 2021, respectively 23,515 17,850 Prepaid expenses 28,481 35,093 Other current assets 34,754 23,846 Total current assets 1,144,400 1,622,648 Long-term investments 216,233 745,993 Textbook library, net — 11,241 Property and equipment, net 204,383 169,938 Goodwill 615,093 289,763 Intangible assets, net 78,333 40,566 Right of use assets 18,838 18,062 Deferred tax assets 167,524 1,365 Other assets 20,612 19,670 Total assets $ 2,465,416 $ 2,919,246 Liabilities and stockholders’ equity Current liabilities Accounts payable $ 12,367 $ 11,992 Deferred revenue 56,273 35,143 Accrued liabilities 70,234 67,209 Total current liabilities 138,874 114,344 Long-term liabilities Convertible senior notes, net 1,188,593 1,678,155 Long-term operating lease liabilities 13,375 12,447 Other long-term liabilities 7,985 7,383 Total long-term liabilities 1,209,953 1,697,985 Total liabilities 1,348,827 1,812,329 Commitments and contingencies Stockholders’ equity: Preferred stock, $ 0.001 par value – 10,000,000 shares authorized, no shares issued and outstanding at December 31, 2022 and December 31, 2021 — — Common stock, $ 0.001 par value – 400,000,000 shares authorized; 126,473,827 and 136,951,956 shares issued and outstanding at December 31, 2022 and December 31, 2021, respectively 126 137 Additional paid-in capital 1,244,504 1,449,305 Accumulated other comprehensive loss ( 57,488 ) ( 5,334 ) Accumulated deficit ( 70,553 ) ( 337,191 ) Total stockholders’ equity 1,116,589 1,106,917 Total liabilities and stockholders’ equity $ 2,465,416 $ 2,919,246 See Notes to Consolidated Financial Statements. 55 Table of Contents CHEGG, INC. CONSOLIDATED STATEMENTS OF OPERATIONS (in thousands, except per share amounts) Years Ended December 31, 2022 2021 2020 Net revenues $ 766,897 $ 776,265 $ 644,338 Cost of revenues 197,396 254,904 205,417 Gross profit 569,501 521,361 438,921 Operating expenses: Research and development 196,637 178,821 170,905 Sales and marketing 147,660 105,414 81,914 General and administrative 216,247 159,019 129,349 Total operating expenses 560,544 443,254 382,168 Income from operations 8,957 78,107 56,753 Interest expense, net and other income, net: Interest expense, net ( 6,040 ) ( 6,896 ) ( 66,297 ) Other income (expense), net 101,029 ( 65,472 ) 8,683 Total interest expense, net and other income (expense), net 94,989 ( 72,368 ) ( 57,614 ) Income (loss) before benefit from (provision for) income taxes 103,946 5,739 ( 861 ) Benefit from (provision for) income taxes 162,692 ( 7,197 ) ( 5,360 ) Net income (loss) $ 266,638 $ ( 1,458 ) $ ( 6,221 ) Net income (loss) per share Basic $ 2.09 $ ( 0.01 ) $ ( 0.05 ) Diluted $ 1.34 $ ( 0.01 ) $ ( 0.05 ) Weighted average shares used to compute net income (loss) per share Basic 127,557 141,262 125,367 Diluted 149,859 141,262 125,367 See Notes to Consolidated Financial Statements. 56 Table of Contents CHEGG, INC. CONSOLIDATED STATEMENTS OF COMPREHENSIVE INCOME (LOSS) (in thousands) Years Ended December 31, 2022 2021 2020 Net income (loss) $ 266,638 $ ( 1,458 ) $ ( 6,221 ) Other comprehensive (loss) income Change in net unrealized (loss) gain on investments, net of tax ( 1,348 ) ( 5,729 ) 1,037 Change in foreign currency translation adjustments, net of tax ( 50,806 ) ( 1,135 ) 1,589 Other comprehensive (loss) income ( 52,154 ) ( 6,864 ) 2,626 Total comprehensive income (loss) $ 214,484 $ ( 8,322 ) $ ( 3,595 ) See Notes to Consolidated Financial Statements. 57 Table of Contents CHEGG, INC. CONSOLIDATED STATEMENTS OF STOCKHOLDERS' EQUITY (in thousands) Common Stock Shares Par Value Additional Paid-In Capital Accumulated Other Comprehensive Loss Accumulated Deficit Total Stockholders’ Equity Balances at December 31, 2019 121,584 $ 122 $ 916,095 $ ( 1,096 ) $ ( 416,292 ) $ 498,829 Cumulative-effect adjustment to accumulated deficit related to adoption of ASU 2016-13 — — — — ( 88 ) ( 88 ) Equity component of 2026 convertible senior notes, net of issuance costs — — 237,462 — — 237,462 Purchase of 2026 convertible senior notes capped call — — ( 103,400 ) — — ( 103,400 ) Equity component related to conversions of 2023 convertible senior notes — — ( 442,667 ) — — ( 442,667 ) Issuance of common stock upon conversion of 2023 convertible senior notes 4,182 4 327,137 — — 327,141 Proceeds from capped call related to conversions of 2023 convertible senior notes — — 77,095 — — 77,095 Issuance of common stock upon exercise of stock options and ESPP 1,154 1 15,480 — — 15,481 Net share settlement of equity awards 2,424 2 ( 80,680 ) — — ( 80,678 ) Share-based compensation expense — — 84,055 — — 84,055 Other comprehensive income — — — 2,626 — 2,626 Net loss — — — — ( 6,221 ) ( 6,221 ) Balances at December 31, 2020 129,344 129 1,030,577 1,530 ( 422,601 ) 609,635 Cumulative-effect adjustment related to adoption of ASU 2020-06 — — ( 465,006 ) — 86,868 ( 378,138 ) Issuance of common stock in connection with equity offering, net of offering costs 10,975 11 1,091,455 — — 1,091,466 Equity component on conversions of 2023 notes and 2025 notes — — ( 236,921 ) — — ( 236,921 ) Issuance of common stock upon conversion of 2023 notes 2,983 3 235,518 — — 235,521 Net proceeds from capped call related to conversions and extinguishments of 2023 notes and 2025 notes — — 67,770 — — 67,770 Issuance of common stock upon exercise of stock options and ESPP 413 — 8,885 — — 8,885 Net share settlement of equity awards 1,640 2 ( 94,423 ) — — ( 94,421 ) Repurchase of common stock ( 8,403 ) ( 8 ) ( 299,992 ) — — ( 300,000 ) Share-based compensation expense — — 111,442 — — 111,442 Other comprehensive loss — — — ( 6,864 ) — ( 6,864 ) Net loss — — — — ( 1,458 ) ( 1,458 ) Balances at December 31, 2021 136,952 137 1,449,305 ( 5,334 ) ( 337,191 ) 1,106,917 Repurchases of common stock ( 12,709 ) ( 13 ) ( 323,515 ) — — ( 323,528 ) Issuance of common stock upon exercise of stock options and ESPP 437 — 6,475 — — 6,475 Net share settlement of equity awards 1,794 2 ( 26,549 ) — — ( 26,547 ) Share-based compensation expense — — 138,788 — — 138,788 Other comprehensive loss — — — ( 52,154 ) — ( 52,154 ) Net income — — — — 266,638 266,638 Balances at December 31, 2022 126,474 $ 126 $ 1,244,504 $ ( 57,488 ) $ ( 70,553 ) $ 1,116,589 See Notes to Consolidated Financial Statements. 58 Table of Contents CHEGG, INC. CONSOLIDATED STATEMENTS OF CASH FLOWS (in thousands) Years Ended December 31, 2022 2021 2020 Cash flows from operating activities Net income (loss) $ 266,638 $ ( 1,458 ) $ ( 6,221 ) Adjustments to reconcile net income (loss) to net cash provided by operating activities: Print textbook depreciation expense 1,610 10,859 15,397 Other depreciation and amortization expense 89,997 63,274 47,018 Share-based compensation expense 133,456 108,846 84,055 Amortization of debt discount and issuance costs 5,166 5,922 64,573 (Gain)/loss on early extinguishments of debt ( 93,519 ) 78,152 4,286 Loss on change in fair value of derivative instruments, net — 7,148 — Repayment of convertible senior notes attributable to debt discount — — ( 20,433 ) Gain on foreign currency remeasurement of purchase consideration ( 4,628 ) — — Deferred tax assets ( 168,679 ) ( 1,104 ) ( 109 ) Loss from write-offs of property and equipment 3,549 2,115 1,211 (Gain)/loss on textbook library, net ( 4,976 ) 10,956 ( 1,453 ) Operating lease expense, net of accretion 6,327 5,994 4,901 Realized loss/(gain) on sale of investments 9,675 178 ( 308 ) Impairment on lease related assets 5,225 — — Gain on sale of strategic equity investments — ( 12,496 ) — Loss from impairment of strategic equity investment — — 10,000 Other non-cash items 378 ( 47 ) 190 Change in assets and liabilities, net of effect of acquisition of businesses: Accounts receivable ( 3,752 ) ( 5,004 ) ( 400 ) Prepaid expenses and other current assets 17,191 ( 21,854 ) 5,419 Other assets 14,563 16,387 ( 4,214 ) Accounts payable ( 4,144 ) 3,241 1,119 Deferred revenue 7,538 2,523 12,918 Accrued liabilities ( 20,111 ) 5,199 22,444 Other liabilities ( 5,768 ) ( 5,607 ) ( 3,951 ) Net cash provided by operating activities 255,736 273,224 236,442 Cash flows from investing activities Purchases of property and equipment ( 103,092 ) ( 94,180 ) ( 81,317 ) Purchases of textbooks ( 3,815 ) ( 10,931 ) ( 58,567 ) Proceeds from disposition of textbooks 6,003 8,714 7,569 Purchases of investments ( 730,509 ) ( 1,688,384 ) ( 1,045,564 ) Proceeds from sale of investments 458,489 206,041 — Maturities of investments 884,940 1,204,787 539,889 Proceeds from sale of strategic equity investments — 16,076 — Acquisition of businesses, net of cash acquired ( 401,125 ) ( 7,891 ) ( 92,796 ) Purchase of strategic equity investment ( 6,000 ) — ( 2,000 ) Net cash provided by (used in) investing activities 104,891 ( 365,768 ) ( 732,786 ) Cash flows from financing activities Proceeds from common stock issued under stock plans, net 6,477 8,887 15,483 Payment of taxes related to the net share settlement of equity awards ( 26,549 ) ( 94,423 ) ( 80,680 ) Proceeds from equity offering, net of offering costs — 1,091,466 — Repayment of convertible senior notes ( 401,203 ) ( 300,762 ) ( 303,967 ) Proceeds from exercise of convertible senior notes capped call — 69,005 77,095 Payment of escrow related to acquisition — ( 7,451 ) — Repurchase of common stock ( 323,528 ) ( 300,000 ) — Proceeds from issuance of convertible senior notes, net of issuance costs — — 984,096 Purchase of convertible senior notes capped call — — ( 103,400 ) Net cash (used in) provided by financing activities ( 744,803 ) 466,722 588,627 Effect of exchange rate changes 4,137 — — Net (decrease) increase in cash, cash equivalents and restricted cash ( 380,039 ) 374,178 92,283 Cash, cash equivalents and restricted cash, beginning of period 855,893 481,715 389,432 Cash, cash equivalents and restricted cash, end of period $ 475,854 $ 855,893 $ 481,715 See Notes to Consolidated Financial Statements. Years Ended December 31, 2022 2021 2020 Supplemental cash flow data: Cash paid during the period for: Interest $ 875 $ 1,053 $ 1,766 Income taxes, net of refunds $ 6,841 $ 7,388 $ 3,436 Cash paid for amounts included in the measurement of lease liabilities: Operating cash flows from operating leases $ 8,863 $ 7,772 $ 6,790 Right of use assets obtained in exchange for lease obligations: Operating leases $ 10,232 $ — $ 13,688 Non-cash investing and financing activities: Accrued purchases of long-lived assets $ 4,927 $ 2,982 $ 1,588 Accrued escrow related to acquisition $ — $ — $ 7,451 Issuance of common stock related to repayment of convertible senior notes $ — $ 235,521 $ 327,141 December 31, 2022 2021 2020 Reconciliation of cash, cash equivalents and restricted cash: Cash and cash equivalents $ 473,677 $ 854,078 $ 479,853 Restricted cash included in other current assets 63 — 122 Restricted cash included in other assets 2,114 1,815 1,740 Total cash, cash equivalents and restricted cash $ 475,854 $ 855,893 $ 481,715 See Notes to Consolidated Financial Statements. 59 Table of Contents CHEGG, INC. NOTES TO CONSOLIDATED FINANCIAL STATEMENTS Note 1. Background and Basis of Presentation Company and Background Chegg, Inc. (“we,” “us,” “our,” “Company” or “Chegg”), headquartered in Santa Clara, California, was incorporated as a Delaware corporation in July 2005. Millions of people all around the world Learn with Chegg. Our mission is to improve learning and learning outcomes by putting students first. We support life-long learners all over the world, starting with their academic journey and extending through their careers. The Chegg platform provides products and services to support learners with their academic course materials, as well as their career and personal skills developments. Basis of Presentation Our fiscal year ends on December 31 and in this report we refer to the year ended December 31, 2022, December 31, 2021, and December 31, 2020 as 2022, 2021, and 2020, respectively. Reclassification of Prior Period Presentation In order to conform with current period presentation, $ 1.4 million of deferred tax assets have been reclassified from other assets on our consolidated balance sheet as of December 31, 2021. Additionally $ 1.1 million and $ 0.1 million of deferred tax assets during the years ended December 31, 2021 and 2020, respectively, and $ 0.2 million and $ 0.3 million realized loss/(gain) on sale of investments during the years ended December 31, 2021 and 2020, respectively, have been reclassified from other non-cash items on our consolidated statements of cash flows. These changes in presentation do not affect previously reported results. Note 2. Significant Accounting Policies Use of Estimates The preparation of financial statements in conformity with generally accepted accounting principles in the United States requires management to make estimates, judgments, and assumptions that affect the reported amounts of assets and liabilities; the disclosure of contingent liabilities at the date of the financial statements; and the reported amounts of revenues and expenses during the reporting periods. Significant estimates, assumptions, and judgments are used for, but not limited to: revenue recognition, share-based compensation expense including grant-date fair value of PSUs with a market-based condition and estimated forfeitures, accounting for income taxes, useful lives assigned to long-lived assets for depreciation and amortization, impairment of goodwill and long-lived assets, the valuation of acquired intangible assets, and internal-use software and website development costs. We base our estimates on historical experience, knowledge of current business conditions, and various other factors we believe to be reasonable under the circumstances. These estimates are based on management’s knowledge about current events and expectations about actions we may undertake in the future. Actual results could differ from these estimates, and such differences could be material to our financial position and results of operations. Principles of Consolidation The consolidated financial statements include the accounts of Chegg and our wholly owned subsidiaries. All intercompany accounts and transactions have been eliminated in consolidation. The consolidated financial statements have been prepared in accordance with U.S. GAAP. Cash and Cash Equivalents and Restricted Cash We consider all highly liquid investments with an original maturity date of three months or less from the date of purchase to be cash equivalents. Our cash and cash equivalents consist of cash and money market funds at financial institutions, and are stated at cost, which approximates fair value. We classify certain restricted cash balances within other current assets and other assets on the accompanying consolidated balance sheets based upon the term of the remaining restrictions. 60 Table of Contents Fair Value Measurements We account for certain assets and liabilities at fair value. We have established a fair value hierarchy used to determine the fair value of our financial instruments as follows: Level 1—Inputs are unadjusted quoted prices in active markets for identical assets or liabilities. Level 2—Inputs are quoted prices for similar assets and liabilities in active markets or inputs that are observable for the assets or liabilities, either directly or indirectly through market corroboration, for substantially the full term of the financial instruments. Level 3—Inputs are unobservable inputs based on our own assumptions used to measure assets and liabilities at fair value; the inputs require significant management judgment or estimation. A financial instrument’s classification within the fair value hierarchy is based on the lowest level of any input that is significant to the fair value measurement. The methods described above may produce a fair value calculation that may not be indicative of net realizable value or reflective of future fair values. Furthermore, while we believe our valuation methods are appropriate and consistent with other market participants, the use of different methodologies or assumptions to determine the fair value of certain financial instruments could result in a different fair value measurement at the reporting date. Investments We hold investments in commercial paper, corporate debt securities, U.S. treasury securities and agency bonds. We classify our investments as available-for-sale that are either short or long-term based on the remaining contractual maturity of the investment. Our investments are carried at estimated fair value with any unrealized gains and losses, unrelated to credit loss factors, net of taxes, included in other comprehensive (loss) income on our consolidated statements of stockholders’ equity. Unrealized losses related to credit loss factors are recorded through an allowance for credit losses in other income (expense), net on our consolidated statements of operations, rather than as a reduction to other comprehensive (loss) income, when a decline in fair value has resulted from a credit loss. When evaluating whether an investment's unrealized losses are related to credit factors, we review factors such as the extent to which fair value is below its cost basis, any changes to the credit rating of the security, adverse conditions specifically related to the security, changes in market interest rates and our intent to sell, or whether it is more likely than not we will be required to sell, before recovery of cost basis. We invest in highly rated securities with a weighted average maturity of eighteen months or less. In addition, our investment policy limits the amount of our credit exposure to any one issuer or industry sector and requires investments to be investment grade, with the primary objective of preserving capital and maintaining liquidity. Fair values were determined for each individual security in the investment portfolio. We determine realized gains or losses on the sale of investments on a specific identification method, and record such gains or losses as other income (expense), net. The estimated fair value of our investments are based on quoted prices in active markets for identical assets (Level 1 inputs) or inputs other than quoted prices that are observable either directly or indirectly (Level 2 inputs) in determining fair value. Other than our money market funds and U.S. treasury securities, we classify our fixed income available-for-sale investments as having Level 2 inputs. The valuation techniques used to measure the fair value of our investments having Level 2 inputs were derived from non-binding market consensus prices that are corroborated by observable market data or quoted market prices for similar instruments. We do not hold any investments valued with a Level 3 input. Accounts Receivable, Net of Allowance Accounts receivable are recorded at the invoiced amount and are non-interest bearing. We generally grant uncollateralized credit terms to our customers, which include partners and advertising customers. We maintain an allowance to account for potentially uncollectible receivables. We assess the creditworthiness of our customers based on multiple sources of information, and analyze such factors as our historical bad debt experience, industry and geographic concentrations of credit risk, economic trends, and customer payment history. This assessment requires significant judgment. Because of this assessment, we maintain an allowance for estimated losses resulting from the inability of certain customers to make all of their required payments. In making this estimate, we analyze historical payment performance and current economic trends when evaluating the adequacy of the allowance for doubtful accounts. Accounts receivable are written off as a decrease to the allowance when all collection efforts have been exhausted and an account is deemed uncollectible. 61 Table of Contents Concentration of Credit Risk Financial instruments that potentially subject us to concentrations of credit risk consist primarily of cash and cash equivalents, restricted cash, and investments in highly liquid instruments in accordance with our investment policy. We place the majority of our cash and cash equivalents and restricted cash with financial institutions in the United States that we believe to be of high credit quality, and accordingly minimal credit risk exists with respect to these instruments. Certain of our cash balances held with a financial institution are in excess of Federal Deposit Insurance Corporation limits. Our investment portfolio consists of investments diversified among security types, industries and issuers. Our investments were held and managed by recognized financial institutions that followed our investment policy with the main objective of preserving capital, generating a competitive return, and maintaining liquidity. Concentrations of credit risk with respect to accounts receivables exist to the full extent of amounts presented in the financial statements. We had one customer that represented over 10 % of our net accounts receivable balance as of December 31, 2022 and no customers that represented over 10 % of our net accounts receivable balance as of December 31, 2021. No customers represented over 10 % of net revenues during the years ended December 31, 2022, 2021 or 2020. Property and Equipment Property and equipment are recorded at cost less accumulated depreciation and content amortization. Depreciation and content amortization are computed using the straight-line method over the following estimated useful lives of the assets: Classification Useful Life Content - Textbook Solutions and Questions and Answers Shorter of the licensed content term or 5 years Content - Other Shorter of the licensed content term or 2.5 years Leasehold improvements Shorter of the remaining lease term or 5 years Internal-use software and website development 3 years Furniture and fixtures 5 years Computers and equipment 3 years Depreciation and content amortization expense are generally classified within the corresponding cost of revenues and operating expenses categories on our consolidated statements of operations. The cost of maintenance and repairs is expensed as incurred. When assets are retired or otherwise disposed of, the cost and related accumulated depreciation and amortization are removed from their respective accounts, and any gain or loss on such sale or disposal is reflected in income from operations. Internal-Use Software and Website Development Costs We capitalize certain costs associated with software developed or obtained for internal use and website and application development. We capitalize costs when preliminary development efforts are successfully completed, management has authorized and committed project funding and it is probable that the project will be completed and the software will be used as intended. Such costs are amortized on a straight-line basis over a three year estimated useful life of the related asset. Costs incurred prior to meeting these criteria, together with costs incurred for training and maintenance, are expensed as incurred. Costs incurred for enhancements that are expected to result in additional material functionality are capitalized and amortized over the estimated useful life of the upgrades. Business Combinations We allocate the fair value of purchase consideration to the tangible assets acquired, liabilities assumed and intangible assets acquired through a business combination based on their estimated fair values. The excess of the fair value of purchase consideration over the fair values of these identifiable assets acquired and liabilities assumed is recorded as goodwill. Such valuations require management to make significant estimates and assumptions, especially with respect to intangible assets. Significant estimates in valuing certain intangible assets include, but are not limited to, future expected cash flows from acquired users, acquired technology, and trade names from a market participant perspective, useful lives and discount rates. Management’s estimates of fair value are based upon assumptions believed to be reasonable, but which are inherently uncertain and unpredictable and, as a result, actual results may differ from estimates. During the measurement period, which is not to exceed one year from the acquisition date, we may record adjustments to the assets acquired and liabilities assumed, with the 62 Table of Contents corresponding offset to goodwill. Upon the conclusion of the measurement period, any subsequent adjustments are recorded to earnings. Goodwill and Indefinite-Lived Intangible Asset Goodwill represents the excess of the fair value of purchase consideration paid over the estimated fair value of assets acquired and liabilities assumed in a business combination. Our indefinite-lived intangible asset represents the internships.com trade name. Goodwill and our indefinite-lived intangible asset are not amortized but rather tested for impairment at least annually, or more frequently if certain events or indicators of impairment occur between annual impairment tests. We first assess qualitative factors to determine whether it is necessary to perform the quantitative impairment test. In our qualitative assessment, we consider factors including economic conditions, industry and market conditions and developments, overall financial performance and other relevant entity-specific events in determining whether it is more likely than not that the fair value of our reporting unit is less than the carrying amount. We completed our annual impairment test in 2022 and 2021, each of which did not result in any impairment as our qualitative assessment did not indicate that it is more likely than not that the fair value of our reporting unit is less than the carrying amount. Acquired Intangible Assets and Other Long-Lived Assets Acquired intangible assets with finite useful lives, which include developed technology, content library, customer lists, trade names, domain names, and non-compete agreements, are amortized over their estimated useful lives. We assess the impairment of acquired intangible assets and other long-lived assets when events or changes in circumstances indicate that the carrying amount of such assets may not be recoverable. Leases We determine if an arrangement is a lease at inception. Operating leases are included in operating lease right of use (ROU) assets and operating lease liabilities within current liabilities and long-term liabilities on our consolidated balance sheets. Operating lease ROU assets and operating lease liabilities are recognized based on the present value of the future minimum lease payments over the lease term at commencement date. Our leases do not provide an implicit rate and therefore we use our incremental borrowing rate based on the information available at commencement date in determining the present value of future minimum lease payments. Our incremental borrowing rate is estimated based on the estimated rate incurred to borrow, on a collateralized basis over a similar term as our leases, an amount equal to the lease payments in a similar economic environment. Our lease terms may include options to extend or terminate the lease when it is reasonably certain that we will exercise such options. We do not record leases on our consolidated balance sheet with a term of one year or less. We do not separate lease and non-lease components but rather account for each separate component as a single lease component for all underlying classes of assets. Some of our leases include payments that are dependent on an index, such as the Consumer Price Index (CPI), and our minimum lease payments include payments based on the index at inception with any future changes in such indices recognized as an expense in the period of change. Where leases contain escalation clauses, rent abatement, or concessions, such as rent holidays and landlord or tenant incentives or allowances, we apply them in the determination of straight-line operating lease cost over the lease term. ROU assets are evaluated for impairment whenever events or changes in circumstances indicate that the carrying amount may not be recoverable. Strategic Investments We have entered into strategic investments that do not have readily determinable fair values and have elected to account for these investments at cost, minus impairment, if any, plus or minus changes resulting from observable price changes in orderly transactions for the identical or a similar investment of the same issuer, if any. Strategic investments are included in other assets on our consolidated balance sheets. We assess our strategic investments for impairment whenever events or changes in circumstances indicate that they may be impaired. The factors we consider in our evaluation include, but are not limited to, a significant deterioration in the earnings performance or business prospects of the investee or factors that raise significant concerns about the investee’s ability to continue as a going concern, such as negative cash flows from operations or working capital deficiencies. Convertible Senior Notes, net In August 2020, we issued $ 1.0 billion in aggregate principal amount of 0 % convertible senior notes due in 2026 (2026 notes). In March 2019, we issued $ 700 million in aggregate principal amount of 0.125 % convertible senior notes due in 2025 (2025 notes, together with the 2026 notes, the notes) and in April 2019, the initial purchasers fully exercised their option to purchase $ 100 million of additional 2025 notes for aggregate total gross proceeds of $ 800 million. The notes, including the 63 Table of Contents embedded conversion features, are accounted for under the traditional convertible debt accounting model entirely as a liability net of unamortized issuance costs. The carrying amount of the liability is classified as a current liability if we have committed to settle with current assets; otherwise, we classify it as a long-term liability as we retain the election to settle conversion requests in shares of our common stock. The embedded conversion features are not remeasured as long as they do not meet the separation requirement of a derivative; otherwise, they are classified as derivative instruments and recorded at fair value with changes in fair value recorded in other income (expense), net on our consolidated statements of operations. The fair value of any derivative instruments related to the notes are determined utilizing Level 2 inputs. Issuance costs are amortized on a straight-line basis, which approximates the effective interest rate method, to interest expense over the term of the notes. In accounting for conversions of the notes, the carrying amount of the converted notes is reduced by the total consideration paid or issued for the respective converted notes and the difference is recorded to additional paid-in capital on our consolidated balance sheets. In accounting for extinguishments of the notes, the reacquisition price of the extinguished notes is compared to the carrying amount of the respective extinguished notes and a gain or loss is recorded in other income (expense), net on our consolidated statements of operations. Revenue Recognition and Deferred Revenue We recognize revenues when the control of goods or services is transferred to our customers, in an amount that reflects the consideration we expect to be entitled to in exchange for those goods or services. We determine revenue recognition through the following steps: • Identification of the contract, or contracts, with a customer • Identification of the performance obligations in the contract • Determination of the transaction price • Allocation of the transaction price to the performance obligations in the contract • Recognition of revenue when, or as, we satisfy a performance obligation Revenues are presented net of sales tax collected from customers to be remitted to governmental authorities and net of allowances for estimated and actual refunds, which are based on historical data. Revenues from our Chegg Study Pack, Chegg Study, Chegg Writing, Chegg Math, and Busuu offerings are primarily recognized ratably over the monthly subscription period. Revenues from Skills are recognized either ratably over a six month course offering depending on the instruction type of the course, adjusted for an estimate of non-redemption. Revenues from advertising services are recognized upon fulfillment. Beginning in April 2022, revenues from print textbooks owned by GT are recognized immediately on a net basis based on our role in the transaction as an agent. Prior to April 2022, revenues from our print textbooks offering included operating lease income from print textbooks that we owned recognized as the total transaction amount, paid upon commencement of the lease, ratably over the lease term or rental term, generally a two - to five-month period. Students generally had the option to purchase the print textbook at the end of the term or on a just-in-time basis and we would charge them for the book and recognize the revenues immediately. Beginning in December 2022, revenues from eTextbooks fulfilled by GT are recognized immediately on a net basis based on our role in the transaction as an agent. Prior to December 2022, eTextbooks revenues were recognized ratably over the contractual period, generally a two - to five-month period. Revenues from print textbooks owned by a partner are recognized as a revenue share on the total transaction amount of a rental or sale transaction immediately when a print textbook ships to a student. Shipping and handling activities are expensed as incurred. Some of our customer arrangements include multiple performance obligations. We have determined these performance obligations qualify as distinct performance obligations, as the customer can benefit from the service on its own or together with other resources that are readily available to the customer, and our promise to transfer the service is separately identifiable from other promises in the contract. For these arrangements that contain multiple performance obligations, we allocate the transaction price based on the relative standalone selling price (SSP) method by comparing the SSP of each distinct performance obligation to the total value of the contract. We determine the SSP based on our historical pricing and discounting practices for the distinct performance obligation when sold separately. If the SSP is not directly observable, we estimate the SSP by considering information such as market conditions, and information about the customer. Additionally, we limit the amount of revenues recognized for delivered promises to the amount that is not contingent on future delivery of services or other future performance obligations. Some of our customer arrangements may include an amount of variable consideration in addition to a fixed revenue share that we earn. This variable consideration can either increase or decrease the total transaction price depending on the nature of the variable consideration. We estimate the amount of variable consideration that we will earn at the inception of the contract, adjusted during each period, and include an estimated amount each period. 64 Table of Contents For sales of third-party products, we evaluate whether we are acting as a principal or an agent. Where our role in a transaction is that of principal, revenues are recognized on a gross basis. This requires revenue to comprise the gross value of the transaction billed to the customer, after trade discounts, with any related expenditure charged as a cost of revenues. Where our role in a transaction is that of an agent, revenues are recognized on a net basis with revenues representing the margin earned. Our determination is based on our evaluation of whether we control the specified goods or services prior to transferring them to the customer. When deciding the most appropriate basis for presenting revenues or costs of revenues, both the legal form and substance of the agreement between us and our business partners are reviewed to determine each party’s respective role in the transaction. In relation to print textbooks owned by a partner, we recognize revenues on a net basis based on our role in the transaction as an agent as we have concluded that we do not control the use of the print textbooks, and therefore record only the net revenue share we earn. We have concluded that we control our Subscription Services, print textbooks that we own for rental or purchase until April 2022, and eTextbook service until December 2022 and therefore we recognize revenues and cost of revenues on a gross basis. Beginning in April 2022 for print textbooks and December 2022 for eTextbooks, we have concluded that GT controls the service and we recognize revenues on a net basis based on our role in the transaction as an agent. Contract assets are contained within other current assets and other assets on our consolidated balance sheets. Contract assets represent the goods or services that we have transferred to a customer before invoicing the customer and primarily consist of the income sharing payment arrangements we offer to students for our Skills service. Contract receivables are contained within accounts receivable, net on our consolidated balance sheets and represent unconditional consideration that will be received solely due to the passage of time. Contract liabilities are contained within deferred revenue on our consolidated balance sheets. Deferred revenue primarily consists of advanced payments from students related to subscription performance obligations that have not been satisfied and estimated variable consideration. Deferred revenue related to rental and subscription performance obligations is recognized as revenues ratably over the term for subscriptions or when the services are provided and all other revenue recognition criteria have been met. Deferred revenue related to variable consideration is recognized as revenues during each reporting period based on the estimated amount we believe we will earn over the life of the contract. We have elected a practical expedient to record incremental costs to obtain or fulfill a contract when the amortization period would have been one year or less as incurred. These incremental costs primarily relate to sales commissions costs and are recorded in sales and marketing expense on our consolidated statements of operations. Cost of Revenues Our cost of revenues consists primarily of expenses associated with the delivery and distribution of our products and services. Cost of revenues primarily consists of content amortization expense related to content that we develop, license from publishers, or acquire through acquisitions, web hosting fees, customer support fees, payment processing costs, amortization of acquired intangible assets, order fulfillment fees primarily related to outbound shipping and fulfillment as well as publisher content fees for eTextbooks, write-downs for print textbooks, the gain or loss on print textbooks liquidated, the net book value of print textbooks purchased by students at the end of the term or on a just-in-time basis, print textbook depreciation expense, personnel costs and other direct costs related to providing content or services. In addition, cost of revenues includes allocated information technology and facilities costs. As a result of our partnership with GT, we no longer incur costs associated with order fulfillment fees related to outbound shipping and fulfillment, write-downs for print textbooks, the gain or loss on print textbooks liquidated, the net book value of print textbooks purchased by students at the end of the term or on a just-in-time basis, and print textbook depreciation expense, Research and Development Costs Our research and development expenses consist of salaries, benefits, and share-based compensation expense for employees on our product, engineering, and technical teams who are responsible for maintaining our website, developing new products, and improving existing products. Research and development costs also include technology costs to support our research and development, and outside services. We expense substantially all of our research and development expenses as they are incurred. 65 Table of Contents Advertising Costs Advertising costs are expensed as incurred and consist primarily of online advertising and marketing promotional expenditures. During the years ended December 31, 2022, 2021, and 2020, advertising costs were approximately $ 62.0 million, $ 45.1 million and $ 35.3 million, respectively. Share-based Compensation Expense Share-based compensation expense for restricted stock units (RSUs), performance-based restricted stock units (PSUs) with either a market-based condition or financial and strategic performance targets, and the employee stock purchase plan (ESPP) is accounted for under the fair value method based on the grant-date fair value of the award. Share-based compensation expense for RSUs and PSUs with financial and strategic performance targets is measured based on the closing fair market value of our common stock, PSUs with a market-based condition are estimated using a Monte Carlo simulation model, and ESPP is estimated using the Black-Scholes-Merton option pricing model. We recognize share-based compensation expense on a straight-line basis for RSUs and ESPP and on a graded basis for PSUs. Vesting for all awards is subject to continued service over the requisite service period, which is generally the vesting period. Vesting of PSUs with a market-based condition is also subject to the achievement of certain per share price of our common stock targets and vesting of PSUs with financial and strategic performance targets is also subject to our achievement of specified financial and strategic performance targets. RSUs and PSUs are converted into shares of our common stock upon vesting on a one -for-one basis. RSUs typically vest over three or four years , while PSUs with a market-based condition typically vest over a four-year period and PSUs with financial and strategic performance targets typically vest over a three-year period. Share-based compensation expense for PSUs with a market-based condition is recognized regardless of whether the market condition is satisfied whereas share-based compensation expense for PSUs with financial performance targets is recognized upon estimated or actual achievement of such targets. We assess the achievement of financial and strategic performance targets on a quarterly basis and adjust our share-based compensation expense as appropriate. These amounts are reduced by estimated forfeitures, which are estimated at the time of the grant and revised, if necessary, in subsequent periods if actual forfeitures differ from those estimates. Income Taxes We account for income taxes under an asset and liability method whereby deferred tax asset and liability account balances are determined based on differences between the financial reporting and the tax basis of assets and liabilities and are measured using the enacted tax rates and laws that will be in effect when the differences are expected to reverse. Valuation allowances are established, when necessary, to reduce deferred tax assets to an amount that is more likely than not to be realized. We record uncertain tax positions on the basis of a two-step process in which (1) we determine whether it is more likely than not that the tax positions will be sustained on the basis of technical merits of the position and (2) for those tax positions that meet the more likely than not recognition threshold, we recognize the tax benefit as the largest amount that is cumulative more than 50% likely to be realized upon ultimate settlement with the related tax authority. Our policy is to include interest and penalties related to unrecognized tax benefits as a component of income tax expense. Net Income (Loss) Per Share Basic net income (loss) per share is computed by dividing net income (loss) by the weighted-average number of shares of common stock outstanding during the period. Diluted net income (loss) per share is computed by adjusting net income (loss) for all related interest expense and gains and losses recognized during the period, net of tax, and giving effect to all potential shares of common stock, including stock options, PSUs, RSUs, and shares related to convertible senior notes, to the extent dilutive. This assumes that all stock options and dilutive convertible shares were exercised or converted and is computed by applying the treasury stock method for outstanding stock options, PSUs, and RSUs, and the if-converted method for outstanding convertible senior notes. Under the treasury stock method, options, PSUs, and RSUs are assumed to be exercised or vested at the beginning of the period (or at the time of issuance, if later) and as if funds obtained thereby were used to purchase common stock at the average market price during the period. Under the if-converted method, outstanding convertible senior notes are assumed to be converted into common stock at the beginning of the period (or at the time of issuance, if later). 66 Table of Contents Foreign Currency Translation and Remeasurement The functional currency of our foreign subsidiaries is the local currency and our reporting currency is the U.S. Dollar. Adjustments resulting from the translation of foreign currencies into U.S. Dollars for balance sheet amounts are based on the exchange rates as of the consolidated balance sheet date. Revenues and expenses are translated at average exchange rates during the period. Foreign currency translation gains or losses are included in accumulated other comprehensive loss as a component of stockholders’ equity on the consolidated balance sheets. Gains or losses resulting from the remeasurement of foreign currency transactions, which are denominated in currencies other than the functional currency, are included in general and administrative expense on the consolidated statements of operations. During the year ended December 31, 2022, the net gains from remeasurement of foreign currency transactions were $ 3.7 million, largely driven by our acquisition of Busuu, and were not material during the years ended December 31, 2021 and 2020. Recent Accounting Pronouncements Recently Issued Accounting Pronouncements Not Yet Adopted There were no accounting pronouncements issued during the year ended December 31, 2022 that would have an impact on our financial statements. Recently Adopted Accounting Pronouncements In October 2021, the Financial Accounting Standards Board (FASB) issued Accounting Standards Update (ASU) 2021-08, Business Combinations-Accounting for Contract Assets and Contract Liabilities from Contracts with Customers (Topic 805). The new guidance requires contract assets and contract liabilities acquired in a business combination to be recognized in accordance with Accounting Standards Codification (ASC) Topic 606 as if the acquirer had originated the contracts. The standard is effective for fiscal years beginning after December 15, 2022, including interim periods within those fiscal years. We early adopted ASU 2021-08 on January 1, 2022 and applied it to our acquisition of Busuu. The most significant impacts were an increase in contract liabilities, contained within deferred revenue, and goodwill on our consolidated balance sheets. In May 2021, the FASB issued ASU 2021-04, Issuer’s Accounting for Certain Modifications or Exchanges of Freestanding Equity-Classified Written Call Options . ASU 2021-04 aims to clarify and reduce diversity in an issuer’s accounting for modifications or exchanges of freestanding equity-classified written call options that remain equity classified after modification or exchange based on the economic substance of the modification or exchange. Early adoption is permitted and the guidance must be applied prospectively to all modifications or exchanges that occur on or after the date of adoption. The guidance is effective for annual periods beginning after December 15, 2021. We adopted ASU 2021-04 on January 1, 2022 under the prospective method of adoption and there was no impact to our results of operations as we did not modify or exchange any freestanding equity-classified written call options. Note 3. Revenues Revenue Recognition Revenues are recognized when control of the promised goods or services is transferred to our customers, in an amount that reflects the consideration we expect to be entitled to in exchange for those goods or services. The majority of our revenues are recognized over time as services are performed, with certain revenues being recognized at a point in time. We have changed our revenue disaggregation to Subscription Services and Skills and Other to better reflect the nature and timing of revenue and cash flows. Subscription Services includes revenues from our Chegg Study Pack, Chegg Study, Chegg Writing, Chegg Math, and Busuu offerings. Skills and Other includes revenues from our Skills, advertising services, print textbooks and eTextbooks offerings. We no longer present our Required Materials product line separately as we no longer expect to have significant revenue from our print textbook and eTextbooks offerings due to recognizing a revenue share as a result of our partnership with GT. 67 Table of Contents The following table sets forth our total net revenues for the periods shown disaggregated for our Subscription Services and Skills and Other product lines (in thousands, except percentages): Years Ended December 31, Change in 2022 Change in 2021 2022 2021 2020 $ % $ % Subscription Services $ 671,968 $ 616,817 $ 460,612 $ 55,151 9 % $ 156,205 34 % Skills and Other 94,929 159,448 183,726 ( 64,519 ) ( 40 ) ( 24,278 ) ( 13 ) Total net revenues $ 766,897 $ 776,265 $ 644,338 $ ( 9,368 ) ( 1 ) $ 131,927 20 During the years ended December 31, 2022, 2021, and 2020, we recognized $ 33.9 million, $ 32.6 million and $ 18.3 million, respectively, of revenues that were included in our deferred revenue balance at the beginning of each respective fiscal year. During the years ended December 31, 2022 and 2020, we recognized an immaterial amount from performance obligations satisfied in previous periods. During the year ended December 31, 2021, we recognized a reduction of revenues of $ 4.9 million from performance obligations satisfied in previous periods, primarily related to our Skills offering. During the years ended December 31, 2022, 2021 and 2020, we recognized $ 5.1 million, $ 34.6 million and $ 50.8 million, respectively, of operating lease income from print textbook rentals that we own. The decreases in operating lease income are primarily due to the transition of our print textbook and eTextbook offerings. For further information, refer to Note 7, “Required Materials Transition.” Contract Balances The following table presents our accounts receivable, net, contract assets, and deferred revenue balances (in thousands, except percentages): December 31, Change 2022 2021 $ % Accounts receivable, net $ 23,515 $ 17,850 $ 5,665 32 % Contract assets 11,946 14,231 ( 2,285 ) ( 16 ) Deferred revenue 56,273 35,143 21,130 60 During the year ended December 31, 2022, our accounts receivable, net balance increased by $ 5.7 million, or 32 %, primarily due to timing of billings and seasonality of our business. During the year ended December 31, 2022, our contract assets balance decreased by $ 2.3 million or 16 %, primarily due to our Skills offering. During the year ended December 31, 2022, our deferred revenue balance increased by $ 21.1 million, or 60 %, primarily due to acquired deferred revenue in conjunction with our acquisition of Busuu, increased bookings and seasonality of our business. 68 Table of Contents Note 4. Net Income (Loss) Per Share The following table sets forth the computation of basic and diluted net income (loss) per share (in thousands, except per share amounts): Years Ended December 31, 2022 2021 2020 Basic Numerator: Net income (loss) $ 266,638 $ ( 1,458 ) $ ( 6,221 ) Denominator: Weighted average shares used to compute net income (loss) per share, basic 127,557 141,262 125,367 Net income (loss) per share, basic $ 2.09 $ ( 0.01 ) $ ( 0.05 ) Diluted Numerator: Net income (loss) $ 266,638 $ ( 1,458 ) $ ( 6,221 ) Convertible senior notes activity, net of tax (1) ( 65,444 ) — — Net income (loss), diluted $ 201,194 $ ( 1,458 ) $ ( 6,221 ) Denominator: Weighted average shares used to compute net income (loss) per share, basic 127,557 141,262 125,367 Shares related to stock plan activity 968 — — Shares related to convertible senior notes 21,334 — — Weighted average shares used to compute net income (loss) per share, diluted 149,859 141,262 125,367 Net income (loss) per share, diluted $ 1.34 $ ( 0.01 ) $ ( 0.05 ) (1) Primarily includes the gain on early extinguishment on our 2026 notes, net of tax. For further information, see Note 11, “Convertible Senior Notes.” The following potential weighted-average shares of common stock outstanding were excluded from the computation of diluted net income (loss) per share because including them would have been anti-dilutive (in thousands): Years Ended December 31, 2022 2021 2020 Shares related to stock plan activity 3,556 2,545 4,470 Shares related to convertible senior notes — 23,300 4,942 Total common stock equivalents 3,556 25,845 9,412 69 Table of Contents Note 5. Cash and Cash Equivalents, and Investments and Fair Value Measurements The following tables show our cash and cash equivalents, and investments’ fair value level classification, adjusted cost, unrealized gain, unrealized loss and fair value as of December 31, 2022 and 2021 (in thousands): December 31, 2022 Fair Value Level Adjusted Cost Unrealized Gain Unrealized Loss Fair Value Cash and cash equivalents: Cash $ 33,532 $ — $ — $ 33,532 Money market funds Level 1 440,145 — — 440,145 Total cash and cash equivalents $ 473,677 $ — $ — $ 473,677 Short-term investments: Commercial paper Level 2 $ 11,744 $ — $ ( 29 ) $ 11,715 Corporate debt securities Level 2 491,459 — ( 4,130 ) 487,329 U.S. treasury securities Level 1 85,271 — ( 342 ) 84,929 Total short-term investments $ 588,474 $ — $ ( 4,501 ) $ 583,973 Long-term investments: Corporate debt securities Level 2 $ 125,735 $ 158 $ ( 909 ) $ 124,984 Agency bonds Level 2 60,635 — ( 141 ) 60,494 U.S. treasury securities Level 1 30,633 122 — 30,755 Total long-term investments $ 217,003 $ 280 $ ( 1,050 ) $ 216,233 December 31, 2021 Fair Value Level Adjusted Cost Unrealized Gain Unrealized Loss Fair Value Cash and cash equivalents: Cash $ 30,324 $ — $ — $ 30,324 Money market funds Level 1 823,754 — — 823,754 Total cash and cash equivalents $ 854,078 $ — $ — $ 854,078 Short-term investments: Commercial paper Level 2 $ 124,211 $ 2 $ ( 33 ) $ 124,180 Corporate debt securities Level 2 552,609 36 ( 546 ) 552,099 Agency bonds Level 2 15,500 2 — 15,502 Total short-term investments $ 692,320 $ 40 $ ( 579 ) $ 691,781 Long-term investments: Corporate debt securities Level 2 $ 724,517 $ — $ ( 3,277 ) $ 721,240 U.S. treasury securities Level 1 $ 24,860 $ — $ ( 107 ) $ 24,753 Total long-term investments $ 749,377 $ — $ ( 3,384 ) $ 745,993 As of December 31, 2022, we determined that the declines in the market value of our investment portfolio were not driven by credit related factors. During the years ended December 31, 2022, 2021 and 2020, we did not recognize any losses on our investments due to credit related factors. 70 Table of Contents The following table presents the gross realized gain and loss related to our investments (in thousands): Years Ended December 31, 2022 2021 2020 Realized gain $ 64 $ 84 $ 308 Realized loss ( 9,739 ) ( 262 ) — Realized (loss)/gain on sale of investments $ ( 9,675 ) $ ( 178 ) $ 308 The following table shows our cash equivalents and investments' adjusted cost and fair value by contractual maturity as of December 31, 2022 (in thousands): December 31, 2022 Cost Fair Value Due within one year $ 588,474 $ 583,973 Due after one year through three years 217,003 216,233 Investments not due at a single maturity date 440,145 440,145 Total $ 1,245,622 $ 1,240,351 Investments not due at a single maturity date in the preceding table consisted of money market funds. Strategic Investments In July 2022, we completed an investment of $ 6.0 million in Knack Technologies, Inc. (Knack), a privately held U.S. based peer-to-peer tutoring platform for higher education institutions. We do not have the ability to exercise significant influence over Knack's operating and financial policies and have elected to account for our investment at cost as it does not have a readily determinable fair value. We previously invested $ 2.0 million in TAPD, Inc., also known as Frank; a U.S.-based service that helps students access financial aid and $ 3.0 million in a foreign entity to explore expanding our reach internationally. In 2021, we sold our investments for total consideration of $ 17.5 million, resulting in a $ 12.5 million gain included within other income (expense), net on our consolidated statements of operations. We received cash payments of $ 16.1 million included within cash flows from investing activities on our consolidated statements of cash flows. We did not record any impairment charges on our strategic investments, other than a $ 10.0 million impairment charge previously recorded in 2020 on our strategic investment in WayUp, Inc. During the years ended December 31, 2022, 2021 and 2020, there were no significant identified events or changes in circumstances that would be considered an indicator for impairment. There were no observable price changes in orderly transactions for the identical or similar investments of the same issuers during the years ended December 31, 2022, 2021 and 2020. Financial Instruments Not Recorded at Fair Value on a Recurring Basis We report our financial instruments at fair value with the exception of the notes. The estimated fair value of the notes was determined based on the trading price of the notes as of the last day of trading for the period. We consider the fair value of the notes to be a Level 2 measurement due to the limited trading activity. The estimated fair value of the 2026 notes as of December 31, 2022 and 2021 was $ 385.0 million and $ 840.0 million, respectively. The estimated fair value of the 2025 notes as of December 31, 2022 and 2021 was $ 640.5 million and $ 682.2 million, respectively. For further information on the notes refer to Note 11, “Convertible Senior Notes.” 71 Table of Contents Note 6. Property and Equipment, Net Property and equipment, net consisted of the following (in thousands): December 31, 2022 2021 Content $ 339,879 $ 258,005 Internal-use software and website development 45,422 29,711 Leasehold improvements 10,860 19,913 Furniture and fixtures 4,952 4,352 Computer and equipment 3,321 3,370 Property and equipment 404,434 315,351 Less accumulated depreciation and amortization ( 200,051 ) ( 145,413 ) Property and equipment, net $ 204,383 $ 169,938 Depreciation and content amortization expense during the years ended December 31, 2022, 2021, and 2020 were approximately $ 64.1 million, $ 49.6 million, and $ 32.6 million, respectively. Note 7. Required Materials Transition In April 2022, we entered into definitive agreements regarding the sale of our print textbook library and partnership with GT Marketplace, LLC (GT) for our print textbook and eTextbook offerings, previously presented as our Required Materials product line. We will continue to offer these products services on our website and maintain relationships with the students, however, GT has purchased our existing print textbook library for $ 14 million, subject to payment terms and certain adjustments, and will continue to make print textbook investments and provide fulfillment logistics for print textbook transactions. Beginning December 2022, GT also began fulfilling eTextbook transactions. Upon board of directors approval of the transaction with GT in April 2022, our net textbook library and unrecognized deferred revenue related to print textbook transactions met the criteria to be classified as a held for sale asset group which had a carrying amount of $ 7.7 million. During the year ended December 31, 2022, we subsequently sold the held for sale asset group to GT at a gain of $ 4.4 million, subject to certain adjustments, included in cost of revenues on our consolidated statement of operations. As of December 31, 2022, we had no amounts related to textbook library, net recorded on our consolidated balance sheets. Beginning in April 2022, we no longer recognize operating lease income from print textbooks that we own ratable on a gross basis. Beginning in December 2022, we no longer recognize revenues from eTextbooks ratable over the customer's contractual period. In relation to print textbooks owned by GT and eTextbooks fulfilled by GT, we recognize revenues immediately on a net basis, representing the margin earned, based on our role in the transaction as an agent as we have concluded that we do not control the use of the print textbooks, and therefore record only the net revenue share we earn. During the years ended December 31, 2022, 2021, and 2020, print textbook depreciation expense was $ 1.6 million, $ 10.9 million and $ 15.4 million, respectively. During the years ended December 31, 2022 and 2020, net gain on textbook library was $ 5.0 million and $ 1.5 million, respectively, and during the year ended December 31, 2021, net loss on textbook library was $ 11.0 million. Note 8. Acquisition On January 13, 2022, we completed our acquisition of 100 % of the outstanding shares of Busuu Online S.L (Busuu) in cash, an online language learning company that offers a comprehensive solution through a combination of self-paced lessons, live classes with expert tutors and the ability to learn and practice with members of the Busuu language learning community. The acquisition helps to expand our existing offerings and global reach through language learning, allowing us to drive further into international markets. 72 Table of Contents The following table presents the allocation of purchase consideration recorded on our consolidated balance sheet as of the acquisition date (in thousands): Busuu Cash and cash equivalents $ 20,525 Accounts receivable 2,446 Right of use assets 2,715 Other acquired assets 3,710 Acquired intangible assets 71,600 Total identifiable assets acquired 100,996 Accounts payable ( 5,174 ) Accrued liabilities (1) ( 21,964 ) Deferred revenue ( 16,761 ) Long term operating lease liabilities ( 2,038 ) Other long-term liabilities (1) ( 1,646 ) Net identifiable assets acquired 53,413 Goodwill 368,237 Total fair value of purchase consideration $ 421,650 (1) During the year ended December 31, 2022, we recorded a $ 0.8 million decrease to accrued liabilities and a $ 1.7 million increase to other long-term liabilities as a result of measurement period adjustments to the fair value of the initial liabilities related to taxes. Goodwill is primarily attributable to the potential for expanding our offerings to include an online language learning platform and global reach allowing us to drive further into international markets. Substantially all of the amounts recorded for intangible assets and goodwill are deductible for tax purposes. The following table presents the details of the allocation of purchase consideration to the acquired intangible assets (in thousands, except weighted-average amortization period): Busuu Amount Weighted-Average Amortization Period (in months) Trade name $ 4,600 72 Customer lists 18,000 24 Developed technology 49,000 84 Total acquired intangible assets $ 71,600 68 During the years ended December 31, 2022 and 2021, we incurred acquisition-related expenses of $ 0.6 million and $ 5.3 million, respectively, associated with our acquisition of Busuu, which have been included in general and administrative expense on our consolidated statement of operations. The purchase consideration was paid in Euros, which is different from our functional currency of United States Dollars. We initially funded an equivalent of $ 417.0 million that was remeasured at $ 421.7 million at closing, which is included in our statement of cash flows as a cash outflow from investing activities net of cash acquired, resulting in a $ 4.6 million gain included in other income (expense), net on our consolidated statement of operations. The Busuu purchase agreement provides for additional payments of up to approximately $ 25.5 million, subject to the continued employment of certain key employees. These payments are not included in the fair value of the purchase consideration but rather are expensed ratably as acquisition-related compensation costs and classified based on the employees' job function, on our consolidated statement of operations. As of December 31, 2022, we have recorded approximately $ 7.3 million within accrued liabilities on our consolidated balance sheets for these payments. Since the acquisition date, we have recorded revenues and net loss from Busuu of $ 38.1 million and $ 38.9 million, respectively. These results should not be taken as representative of future results of operations of the combined company. The following unaudited supplemental pro forma revenues and earnings is for informational purposes only and presents our 73 Table of Contents combined results as if the acquisition of Busuu had occurred on January 1, 2021. During the years ended December 31, 2022 and 2021, our unaudited supplemental pro forma revenues would have been $ 767.6 million and $ 820.2 million, respectively. During the years ended December 31, 2022 and 2021, our unaudited supplemental pro forma earnings would have been a net income of $ 268.0 million, and net loss of $ 44.7 million, respectively. The unaudited supplemental pro forma earnings information includes the historical combined operating results adjusted for acquisition-related compensation costs, amortization of intangible assets, share-based compensation expense and acquisition-related expenses and does not necessarily reflect the actual results that would have been achieved, nor is it necessarily indicative of our future consolidated results. Note 9. Goodwill and Intangible Assets Goodwill consists of the following (in thousands): Years Ended December 31, 2022 2021 Beginning balance $ 289,763 $ 285,214 Additions due to acquisitions 367,376 5,782 Foreign currency translation adjustment ( 42,907 ) ( 707 ) Measurement period adjustments related to prior acquisitions (1) 861 ( 526 ) Ending balance $ 615,093 $ 289,763 (1) For further information, see Note 8, “Acquisition.” Intangible assets as of December 31, 2022 and December 31, 2021 consist of the following (in thousands, except weighted-average amortization period): December 31, 2022 Weighted-Average Amortization Period (in months) Gross Carrying Amount Accumulated Amortization Foreign Currency Translation Adjustment Net Carrying Amount Developed technologies 80 $ 106,703 $ ( 44,410 ) $ ( 5,751 ) $ 56,542 Content libraries 60 12,230 ( 9,279 ) — 2,951 Customer lists 35 34,190 ( 22,074 ) ( 1,318 ) 10,798 Trade and domain names 52 16,213 ( 11,225 ) ( 546 ) 4,442 Indefinite-lived trade name — 3,600 — — 3,600 Total intangible assets 67 $ 172,936 $ ( 86,988 ) $ ( 7,615 ) $ 78,333 December 31, 2021 Weighted-Average Amortization Period (in months) Gross Carrying Amount Accumulated Amortization Foreign Currency Translation Adjustment Net Carrying Amount Developed technologies 76 $ 57,521 $ ( 31,790 ) $ — $ 25,731 Content libraries 60 12,230 ( 6,836 ) — 5,394 Customer lists 47 16,190 ( 12,432 ) — 3,758 Trade and domain names 44 11,613 ( 9,530 ) — 2,083 Indefinite-lived trade name — 3,600 — — 3,600 Total intangible assets 65 $ 101,154 $ ( 60,588 ) $ — $ 40,566 During the years ended December 31, 2022, 2021 and 2020, amortization expense related to our intangible assets totaled approximately $ 25.9 million, $ 13.7 million and $ 14.3 million, respectively. 74 Table of Contents As of December 31, 2022, the estimated future amortization expense related to our intangible assets is as follows (in thousands): 2023 $ 23,978 2024 13,286 2025 11,195 2026 10,848 2027 8,692 Thereafter 6,734 Total $ 74,733 Note 10. Balance Sheet Details Other Current Assets Other current assets consist of the following (in thousands): December 31, 2022 2021 Insurance recovery related to loss contingency $ — $ 7,800 Other 34,754 16,046 Other current assets $ 34,754 $ 23,846 Accrued Liabilities Accrued liabilities consist of the following (in thousands): December 31, 2022 2021 Taxes payable $ 15,132 $ 11,127 Current operating lease liabilities 7,487 6,663 Acquisition-related compensation 7,741 417 Accrued content related costs 4,736 6,448 Accrued purchases of long-lived assets 4,927 2,982 Payment processing fees 4,253 3,419 Order fulfillment fees 2,917 6,254 Refund reserve 1,499 1,392 Restructuring short term — 785 Loss contingency — 8,000 Other 21,542 19,722 Accrued liabilities $ 70,234 $ 67,209 Note 11. Convertible Senior Notes In August 2020, we issued $ 1.0 billion in aggregate principal amount of 0 % convertible senior notes due in 2026 (2026 notes). The aggregate principal amount of the 2026 notes includes $ 100 million from the initial purchasers fully exercising their option to purchase additional notes. In March 2019, we issued $ 700 million in aggregate principal amount of 0.125 % convertible senior notes due in 2025 (2025 notes, together with the 2026 notes, the notes) and in April 2019, the initial purchasers fully exercised their option to purchase $ 100 million of additional 2025 notes for aggregate total principal amount of $ 800 million. The notes were issued in private placements to qualified institutional buyers pursuant to Rule 144A of the Securities Act of 1933, as amended. 75 Table of Contents The total net proceeds from the notes are as follows (in thousands): 2026 Notes 2025 Notes Principal amount $ 1,000,000 $ 800,000 Less initial purchasers’ discount ( 15,000 ) ( 18,998 ) Less other issuance costs ( 904 ) ( 822 ) Net proceeds $ 984,096 $ 780,180 During the year ended December 31, 2022, in connection with our securities repurchase program, we extinguished $ 500.0 million aggregate principal amount of the 2026 notes in privately-negotiated transactions for $ 399.9 million, which was paid to the holders in cash. We also incurred approximately $ 1.3 million in fees resulting in total consideration of $ 401.2 million. The carrying amount of the extinguished 2026 notes was $ 494.7 million resulting in a $ 93.5 million gain on early extinguishment of debt. We elected to reacquire and not cancel the extinguished 2026 notes and left the associated capped call transactions outstanding. As of December 31, 2022, we had 9,297,800 shares remaining underlying the 2026 notes capped call transactions. During the year ended December 31, 2021, we settled $ 115.6 million of aggregate principal amount of the 0.25 % convertible senior notes due in 2023 (2023 notes), consisting of $ 24.7 million related to requests for conversions and $ 90.9 million pursuant to our election of our option to redeem the remaining outstanding 2023 notes, for a total aggregate consideration of $ 351.1 million, consisting of $ 115.6 million in cash and 2,983,011 shares of our common stock with an aggregate value of $ 235.5 million. The carrying amount of the 2023 notes was $ 114.2 million, resulting in a $ 236.9 million difference that was recorded in additional paid-in capital on our consolidated balance sheet. Additionally, we entered into 2023 notes capped call privately-negotiated transactions which terminated capped call transactions underlying 4,288,459 shares of our common stock and received aggregate cash proceeds of $ 45.2 million. As of December 31, 2021, no amounts of our 2023 notes remain outstanding and no shares remain underlying the 2023 notes capped call transactions. In March 2021, in connection with our securities repurchase program, we extinguished $ 100.0 million aggregate principal amount of the 2025 notes in privately-negotiated transactions for aggregate consideration of $ 184.9 million, which was paid in cash. Upon execution, we concluded that the 2025 notes embedded conversion features no longer met the derivative scope exception and, as a result, initially recorded a derivative liability of $ 176.5 million, related to the fair value of extinguished 2025 notes. We settled the derivative liability for aggregate consideration of $ 184.9 million resulting in a $ 8.4 million loss on change in fair value. The carrying amount of the 2025 notes subject to the extinguishment was $ 98.3 million resulting in a $ 78.2 million loss on early extinguishment of debt. Additionally, we entered into 2025 notes capped call privately-negotiated transactions which terminated capped call transactions underlying 1,939,560 shares of our common stock and received aggregate cash proceeds of $ 23.9 million. Upon execution, we concluded that the capped call transactions no longer met the derivative scope exception and, as a result recorded a derivative liability of $ 22.6 million related to the fair value of terminated 2025 notes capped call transactions. We settled the capped call transactions for aggregate consideration of $ 23.9 million resulting in a $ 1.3 million gain on change in fair value. During the year ended December 31, 2020, in connection with our securities repurchase program, we extinguished $ 57.4 million aggregate principal amount of the 2023 notes in privately-negotiated transactions for an aggregate consideration of $ 149.6 million, which was paid in cash. Of the $ 149.6 million consideration, we allocated $ 52.6 million and $ 97.0 million to the liability and equity components of the extinguished 2023 notes, respectively. The fair value of the liability component was calculated by measuring the fair value of similar debt instruments that do not have an associated convertible feature. The carrying amount of the liability component of the 2023 notes subject to the extinguishment was $ 51.6 million resulting in a $ 1.0 million loss on early extinguishment which was recorded in other income (expense), net on our consolidated statements of operations. Additionally, we terminated 2023 notes capped call transactions underlying 2,131,354 shares of our common stock and received cash proceeds of $ 19.7 million. During the year ended December 31, 2020, in connection with our issuance of the 2026 notes, we exchanged $ 172.0 million aggregate principal amount of the 2023 notes in privately-negotiated transactions for an aggregate consideration of $ 501.7 million, consisting of $ 174.6 million in cash and 4,182,320 shares of our common stock with a value of $ 327.1 million. Of the $ 501.7 million consideration, we allocated $ 156.1 million and $ 345.6 million to the liability and equity components of the exchanged 2023 notes, respectively. The fair value of the liability component was calculated by measuring the fair value of similar debt instruments that do not have an associated convertible feature. The carrying amount of the liability component of the 2023 notes subject to the exchange was $ 152.8 million resulting in a $ 3.3 million loss on early extinguishment of debt which was recorded in other income (expense), net on our consolidated statements of operations. 76 Table of Contents Additionally, we terminated 2023 notes capped call transactions underlying 6,380,815 shares of our common stock and received cash proceeds of $ 57.4 million. The notes are our senior, unsecured obligations and are governed by indenture agreements by and between us and Computershare Trust Company, National Association (as successor to Wells Fargo Bank, National Association), as Trustee (the indentures). The 2026 notes bear no interest and will mature on September 1, 2026, unless repurchased, redeemed or converted in accordance with their terms prior to such date. The 2025 notes bear interest of 0.125 % per year which is payable semi-annually in arrears on March 15 and September 15 of each year, beginning on September 15, 2019. The 2025 notes will mature on March 15, 2025, unless repurchased, redeemed or converted in accordance with their terms prior to such date. Each $1,000 principal amount of the 2026 notes will initially be convertible into 9.2978 shares of our common stock. This is equivalent to an initial conversion price of approximately $ 107.55 per share, which is subject to adjustment in certain circumstances. Each $1,000 principal amount of the 2025 notes will initially be convertible into 19.3956 shares of our common stock. This is equivalent to an initial conversion price of approximately $ 51.56 per share, which is subject to adjustment in certain circumstances. Prior to the close of business on the business day immediately preceding June 1, 2026 for the 2026 notes and December 15, 2024 for the 2025 notes, the notes are convertible at the option of holders only upon satisfaction of the following circumstances: • during any calendar quarter commencing after the calendar quarter ending on December 31, 2020 for the 2026 notes and June 30, 2019 for the 2025 notes, if the last reported sale price of our common stock for at least 20 trading days (whether or not consecutive) during a period of 30 consecutive trading days ending on, and including, the last trading day of the immediately preceding calendar quarter is greater than or equal to 130 % of the respective conversion price for the notes on each applicable trading day; • during the five -business day period after any 10 consecutive trading day period (the measurement period) in which the trading price per $1,000 principal amount of notes for each trading day of the measurement period was less than 98 % of the product of the last reported sale price of our common stock and the conversion rate on each such trading day; • if we call any or all of the notes for redemption, at any time prior to the close of business on the second scheduled trading day immediately preceding the redemption date; or • upon the occurrence of certain specified corporate events described in the indentures. On or after June 1, 2026 for the 2026 notes and December 15, 2024 for the 2025 notes until the close of business on the second scheduled trading day immediately preceding the respective maturity dates, holders may convert their notes at any time, regardless of the foregoing circumstances. Upon conversion, the notes may be settled in shares of our common stock, cash or a combination of cash and shares of our common stock, at our election. During the year ended December 31, 2022, the conditions allowing holders of the 2026 notes and 2025 notes to convert were not met and therefore the 2026 notes and 2025 notes are not convertible. If we undergo a fundamental change, as defined in the indentures, prior to the respective maturity dates, subject to certain conditions, holders of the notes may require us to repurchase for cash all or any portion of their notes at a repurchase price equal to 100 % of the principal amount of the notes to be repurchased, plus accrued and unpaid interest to, but excluding, the fundamental change repurchase date. In addition, if specific corporate events, described in the indentures, occur prior to the respective maturity dates, we will also increase the conversion rate for a holder who elects to convert their notes in connection with such specified corporate events. The net carrying amount of the notes is as follows (in thousands): December 31, 2022 December 31, 2021 2026 Notes 2025 Notes 2026 Notes 2025 Notes Principal amount $ 500,000 $ 699,979 $ 1,000,000 $ 699,982 Unamortized issuance costs ( 4,837 ) ( 6,549 ) ( 12,309 ) ( 9,518 ) Net carrying amount $ 495,163 $ 693,430 $ 987,691 $ 690,464 77 Table of Contents The following table sets forth the total interest expense recognized related to the notes (in thousands): Years Ended December 31, 2022 2021 2020 2026 notes: Amortization of debt discount $ — $ — $ 14,568 Amortization of issuance costs 2,196 2,635 728 Total 2026 notes interest expense $ 2,196 $ 2,635 $ 15,296 2025 notes: Contractual interest expense $ 874 $ 896 $ 1,001 Amortization of debt discount — — 35,561 Amortization of issuance costs 2,970 3,045 2,443 Total 2025 notes interest expense $ 3,844 $ 3,941 $ 39,005 2023 notes: Contractual interest expense $ — $ 78 $ 691 Amortization of debt discount — — 10,073 Amortization of issuance costs — 242 1,200 Total 2023 notes interest expense $ — $ 320 $ 11,964 Capped Call Transactions Concurrently with the offering of the 2026 notes and 2025 notes, we used $ 103.4 million and $ 97.2 million, respectively, of the net proceeds to enter into privately negotiated capped call transactions which are expected to reduce or offset potential dilution to holders of our common stock upon conversion of the notes or offset the potential cash payments we would be required to make in excess of the principal amount of any converted notes. The capped call transactions automatically exercise upon conversion of the notes and as of December 31, 2022, cover 9,297,800 and 13,576,513 shares of our common stock for the 2026 notes and 2025 notes, respectively. These are intended to effectively increase the overall conversion price from $ 107.55 to $ 156.44 per share for the 2026 notes and $ 51.56 to $ 79.32 per share for the 2025 notes. The effective increase in conversion price as a result of the capped call transactions serves to reduce potential dilution to holders of our common stock and/or offset the cash payments we are required to make in excess of the principal amount of any converted notes. As these transactions meet certain accounting criteria, they are recorded in stockholders’ equity as a reduction of additional paid-in capital on our consolidated balance sheets and are not accounted for as derivatives. The fair value of the capped call instrument is not remeasured each reporting period. The cost of the capped call is not expected to be deductible for tax purposes. Note 12. Leases Our primary operating lease commitments at December 31, 2022 are related to our corporate headquarters and offices in the United States and internationally. As of December 31, 2022 and 2021, we had operating lease ROU assets of $ 18.8 million and $ 18.1 million, respectively, and operating lease liabilities of $ 20.9 million and $ 19.1 million, respectively. As of December 31, 2022 and 2021, our weighted average remaining lease term was 4.0 years and our weighted average discount rate was 5.2 % and 4.8 %, respectively. During the year ended December 31, 2022, we obtained $ 10.2 million of ROU assets in exchange for lease liabilities related to office spaces in Oregon and internationally in India, Israel, and the United Kingdom. During the year ended December 31, 2020, we obtained $ 13.7 million of ROU assets in exchange for lease liabilities related to office spaces in New York and internationally in India. During the years ended December 31, 2022, 2021 and 2020, operating lease expense, net of immaterial sublease income, was approximately $ 7.3 million, $ 7.1 million and $ 5.6 million, respectively. During the years ended December 31, 2022, 2021 and 2020, variable lease cost and short term lease cost were immaterial. During the year ended December 31, 2022, we consolidated our Santa Clara headquarters into one building and announced the closure of our San Francisco office. Upon both events, we determined that the carrying amount of the ROU asset was not recoverable. As a result, we recorded an impairment charge of $ 5.2 million, consisting of a $ 2.6 million impairment of a ROU asset and $ 2.6 million write-off of leasehold improvements, included in general and administrative expense on our 78 Table of Contents consolidated statement of operations. Our intent and ability to sublease the office as well as the local market conditions were factored in when measuring the amount of impairment. The aggregate future minimum lease payments and reconciliation to operating lease liabilities as of December 31, 2022, are as follows (in thousands): December 31, 2022 2023 $ 7,733 2024 4,862 2025 3,400 2026 3,256 2027 2,866 Thereafter 425 Total future minimum lease payments 22,542 Less imputed interest ( 1,680 ) Total operating lease liabilities $ 20,862 In February 2023, we entered into an amendment to extend the term of the lease for our corporate headquarters in Santa Clara, California through November 2028 with additional future minimum lease payments of $ 7.6 million. As of December 31, 2022, this extended term had not yet commenced and therefore the additional future minimum lease payments are not included in the table above. Note 13. Commitments and Contingencies We may from time to time be subject to certain legal proceedings and claims in the ordinary course of business, including claims of alleged infringement of trademarks, patents, copyrights, and other intellectual property rights; employment claims; and general contract or other claims. We may also, from time to time, be subject to various legal or government claims, demands, disputes, investigations, or requests for information. Such matters may include, but not be limited to, claims, disputes, or investigations related to warranty, refund, breach of contract, employment, intellectual property, government regulation, or compliance or other matters. On February 14, 2023, Plaintiff Brian Stansell, individually and on behalf of other similarly situated stockholders of Chegg, filed a putative class action complaint in the Court of Chancery of the State of Delaware (Case No. 2023-0180) on behalf of all Chegg stockholders who were eligible to vote at Chegg's 2022 Annual Stockholders' Meeting, asserting breach of fiduciary duty claims against the members of Chegg's Board. The Company disputes these claims and intends to vigorously defend itself in this matter. On December 27, 2022, Plaintiff Sheri Moyer, individually and on behalf of all others similarly situated, filed a putative consumer class action in the United States District Court for the Northern District of California (Case No. 22-cv-09123) on behalf of all purchasers of a Chegg product or service as part of an automatic renewal plan or continuous service offer within the past four years. The Company disputes these claims and intends to vigorously defend itself in this matter. On November 09, 2022, Plaintiff Joshua Keller, individually and on behalf of all others similarly situated, filed a putative class action in the United States District Court for the Northern District of California (Case No. 22-cv-06986) on behalf of individuals whose data was allegedly impacted by past data breaches. The Company disputes these claims and intends to vigorously defend itself in this matter. On March 30, 2022, Joseph Robinson, derivatively on behalf of Chegg, filed a shareholder derivative complaint against Chegg and certain of its current and former directors and officers in the United States District Court for the Northern District of California, alleging violations of securities laws and breaches of fiduciary duties. This matter has been consolidated with Choi, below, and both matters are stayed. The Company disputes these claims and intends to vigorously defend itself in this matter. On January 12, 2022, Rak Joon Choi, derivatively on behalf of Chegg, filed a shareholder derivative complaint against Chegg and certain of its current and former directors and officers in the United States District Court for the Northern District of California, alleging violations of securities laws, breaches of fiduciary duties, unjust enrichment, abuse of control, gross 79 Table of Contents mismanagement, and waste of corporate assets. This matter has been consolidated with Robinson, above, and both matters are stayed. The Company disputes these claims and intends to vigorously defend itself in this matter. On December 22, 2021, Steven Leventhal, individually and on behalf of all others similarly situated, filed a purported securities fraud class action on behalf of all purchasers of Chegg common stock between May 5, 2020 and November 1, 2021, inclusive, against Chegg and certain of its current and former officers in the United States District Court for the Northern District of California (Case No. 5:21-cv-09953), alleging that Chegg and several of its officers made materially false and misleading statements in violation of Sections 10(b) and 20(a) of the Securities Exchange Act of 1934. On September 7, 2022, KBC Asset Management and The Pompano Beach Police & Firefighters Retirement System were appointed as lead plaintiff in the case. On December 8, 2022, Plaintiff filed his Amended Complaint and seeks unspecified compensatory damages, costs, and expenses, including counsel and expert fees. The Company disputes these claims and intends to vigorously defend itself in this matter. On September 13, 2021, Pearson Education, Inc. (Pearson) filed a complaint captioned Pearson Education, Inc. v. Chegg, Inc. (Pearson Complaint) in the United States District Court for the District of New Jersey against the Company (Case 2:21-cv-16866), alleging infringement of Pearson’s registered copyrights and exclusive rights under copyright in violation of the United States Copyright Act. Pearson is seeking injunctive relief, monetary damages, costs, and attorneys’ fees. The Company filed its answer to the Pearson Complaint on November 19, 2021. The Company disputes these claims and intends to vigorously defend itself in this matter. On June 18, 2020, we received a Civil Investigative Demand (CID) from the Federal Trade Commission (FTC) regarding certain alleged deceptive or unfair acts or practices related to consumer privacy and/or data security. On October 31, 2022, the FTC published the parties’ agreed-upon consent order regarding Chegg’s privacy and data security practices. On January 27, 2023, the FTC finalized its order (Final Order) requiring Chegg to implement a comprehensive information security program, limit the data the Company can collect and retain, offer users multifactor authentication to secure their accounts, and allow users to request access to and delete their data. No monetary penalties or fines were included in the Final Order. Between April 2020 and August 2020, over 16,000 individual arbitration demands were filed against us with each individual claimant claiming to have suffered damages as a result of the unauthorized access of certain items of their user data in April 2018 (the 2018 Data Incident). Related cases were also filed by the same counsel in Maryland and California. The company disputed and defended these claims. On August 22, 2021, Chegg and the claimants' legal counsel, on behalf of its clients, entered into a settlement agreement for these matters. As of December 2022, all but a de minimis number of these matters have been fully resolved. We have not recorded any contingent liabilities related to the above matters as we do not believe that a loss is probable and reasonably estimable in these matters. We are not aware of any other pending legal matters or claims, individually or in the aggregate, that are expected to have a material adverse impact on our consolidated financial position, results of operations, or cash flows. However, our analysis of whether a claim will proceed to litigation cannot be predicted with certainty, nor can the results of litigation be predicted with certainty. Nevertheless, defending any of these actions, regardless of the outcome, may be costly, time consuming, distract management personnel and have a negative effect on our business. An adverse outcome in any of these actions, including a judgment or settlement, may cause a material adverse effect on our future business, operating results or financial condition. Note 14. Guarantees and Indemnifications We have agreed to indemnify our directors and officers for certain events or occurrences, subject to certain limits, while such persons are or were serving at our request in such capacity. We may terminate the indemnification agreements with these persons upon termination of employment, but termination will not affect claims for indemnification related to events occurring prior to the effective date of termination. We have a directors’ and officers’ insurance policy that covers our potential exposure up to the limits of our insurance coverage. In addition, we also have other indemnification agreements with various vendors against certain claims, liabilities, losses, and damages. The maximum amount of potential future indemnification is unlimited. We believe the fair value of these indemnification agreements is immaterial. We have not recorded any liabilities for these agreements as of December 31, 2022. 80 Table of Contents Note 15. Common Stock We are authorized to issue 400 million shares of our common stock, with a par value per share of $ 0.001 . As of December 31, 2022, we have reserved the following shares of our common stock for future issuance: December 31, 2022 Outstanding stock options 326,258 Outstanding RSUs and PSUs 9,155,680 Shares available for grant under the 2013 Plan 34,699,188 Shares available for issuance under the 2013 ESPP 10,801,299 Total common shares reserved for future issuance 54,982,425 Stock Plans 2013 Equity Incentive Plan On June 6, 2013, the Board of Directors adopted our 2013 Equity Incentive Plan (the 2013 Plan), which was subsequently approved by our stockholders on August 29, 2013. The 2013 Plan became effective on November 11, 2013 and replaced the 2005 Plan. On the effective date of the 2013 Plan, 12,000,000 shares of our common stock were reserved for issuance, plus an additional 3,838,985 shares reserved but not issued or subject to outstanding awards under our 2005 Plan on the effective date of the 2013 Plan, plus, on and after the effective date of the 2013 Plan, (i) shares that are subject to outstanding awards under the 2005 Plan which cease to be subject to such awards, (ii) shares issued under the 2005 Plan that are forfeited or repurchased at their original issue price and (iii) shares subject to awards under the 2005 Plan that are used to pay the exercise price of an option or withheld to satisfy the tax withholding obligations related to any award. As of December 31, 2022, there were 34,699,188 shares available for grant under the 2013 Plan. The 2013 Plan permits the granting of incentive stock options, non-qualified stock options, RSUs, stock appreciation rights, restricted shares of common stock and performance share awards. The exercise price of stock options may not be less than the 100 % of the fair market value of the common stock on the date of grant. Options granted pursuant to the 2013 Plan generally expire no later than 10 years from the date of grant. The 2013 Plan terminates on June 6, 2023. 2013 Employee Stock Purchase Plan On June 6, 2013, our Board of Directors adopted our 2013 Employee Stock Purchase Plan (the 2013 ESPP) and our stockholders subsequently approved the 2013 ESPP Plan on August 29, 2013. The 2013 ESPP permits eligible employees to acquire shares of our common stock by accumulating funds through periodic payroll deductions of up to 15 % of base salary. Our 2013 ESPP is intended to qualify as an ESPP under Section 423 of the Code and employees will receive a 15 % discount to the lesser of the fair market value of our common stock on (i) the first trading day of the applicable offering period or (ii) the last day of each purchase period in the applicable offering period. Each offering period may run for no more than six months . We have reserved 4,000,000 shares of our common stock under our 2013 ESPP. The aggregate number of shares issued over the term of our 2013 ESPP will not exceed 20,000,000 shares of our common stock. As of December 31, 2022, there were 10,801,299 shares of common stock available for future issuance under the 2013 ESPP. Note 16. Stockholders' Equity Securities Repurchase Program 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. During the years ended December 31, 2022, 2021, and 2020, we entered into accelerated share repurchase (ASR) agreements with financial institutions to repurchase 19,965,836 for $ 600.0 million, repurchased 1,146,803 shares of our common stock in open market transactions for $ 23.1 million, and repurchased $ 500.0 million principal amount of the 2026 notes, $ 100.0 million principal amount of the 2025 notes and $ 57.4 million principal amount of the 2023 notes in privately-negotiated transactions for aggregate consideration of $ 734.4 million. As of December 31, 2022, we had $ 642.6 million remaining under the repurchase program, 81 Table of Contents which has no expiration date and will continue until otherwise suspended, terminated or modified at any time for any reason by our board of directors. Accelerated Share Repurchases On February 22, 2022 and December 3, 2021, we entered into accelerated share repurchase (ASR) agreements with financial institutions. Upon execution, we paid a fixed amount of $ 300.0 million for each ASR and received an initial delivery of shares of our common stock that represented 80 percent of the fixed amount for each ASR. We accounted for each ASR as two separate transactions, a repurchase of our common stock and an equity-linked contract indexed to our common stock that met certain accounting criteria for classification in stockholders' equity. During the years ended December 31, 2022 and 2021, we received a total of 11,562,475 and 8,403,361 shares of our common stock, respectively, which were retired immediately. Each ASR was recorded as a reduction to additional paid in capital on our consolidated statements of stockholders’ equity. We were not required to make any additional cash payments or delivery of common stock to the financial institutions upon settlement. Equity Offering In February 2021, we entered into an underwriting agreement pursuant to which we agreed to issue and sell 10,974,600 shares of our common stock at a public offering price of $ 102.00 per share generating aggregate net proceeds of $ 1,091.5 million, after deducting underwriting discounts and commissions of $ 26.9 million and offering expenses of $ 1.1 million. Share-based Compensation Expense Total share-based compensation expense recorded for employees and non-employees, is as follows (in thousands): Years Ended December 31, 2022 2021 2020 Cost of revenues $ 2,484 $ 1,621 $ 950 Research and development 41,335 37,131 31,588 Sales and marketing 13,857 13,887 9,606 General and administrative 75,780 56,207 41,911 Total share-based compensation expense $ 133,456 $ 108,846 $ 84,055 During the years ended December 31, 2022 and 2021, we capitalized share-based compensation expense of $ 5.3 million and $ 2.6 million, respectively. As of December 31, 2022, we had a total of approximately $ 220.1 million of unrecognized share-based compensation expense, related to unvested RSUs and PSUs, that is expected to be recognized over the remaining weighted average period of 2.4 years. PSU Grants with Financial and Strategic Performance Targets In March 2022, 2021, and 2020, we granted PSUs under the 2013 Plan to certain of our key executives. The PSUs entitle the executives to receive a certain number of shares of our common stock based on our satisfaction of certain financial and strategic performance targets during years ended December 31, 2022, 2021, and 2020, respectively. Based on the achievement of the performance conditions for the March 2022 and 2021 grants, the final settlement partially met the target threshold, and for the March 2020 grant, the final settlement met the target threshold, based on a specified objective formula approved by the Compensation Committee of the Board of Directors. These PSUs vest over a three-year period, with the initial vesting occurring one year after the grant date. During the years ended December 31, 2022, 2021, and 2020, the number of shares underlying the March 2022, March 2021, and March 2020 PSU grants totaled 614,177 , 278,644 , and 460,976 , respectively, and had a grant date fair value per share of $ 35.82 , $ 99.05 , and $ 39.21 , respectively. 82 Table of Contents 2021 PSU Grants with Market-Based Conditions In March 2021, we granted PSUs under the 2013 Equity Incentive Plan (the 2013 Plan) with market-based conditions to certain of our key employees. The number of shares of our common stock that may be issued to settle these PSUs range from 50 % at the threshold level to 150 % at the maximum level of the 100 % target level of the award depending on achieving a maximum average market value of the per share price of our common stock, for a period of 60 consecutive trading days, over a three-year performance period ending on the third anniversary of the date of grant. No payout will be made for performance below the 50 % threshold level. The market value of the per share price of our common stock must reach $ 123.81 , $ 148.58 , or $ 173.34 at the threshold, target, or maximum levels, respectively, for achievement of the award, which could result in issuance of 244,086 , 488,173 , or 732,260 shares of our common stock at each respective payout level. These PSUs will vest over a four-year period, with the initial vesting of 50 % of the award occurring in March 2024. The number of PSUs granted totaled 732,260 shares, which represents the maximum number of shares, and had a grant date fair value of $ 68.55 per share, determined under the Monte Carlo simulation approach described further below. As of December 31, 2022, the market-based conditions have not been met. Fair Value of PSUs with Market-Based Conditions We estimate the fair value of the PSUs using a Monte Carlo simulation approach, which utilizes the fair value of our common stock based on an active market and requires input on the following subjective assumptions: Expected Term . The expected term for the awards is the performance period of three years . Expected Volatility . The expected volatility is based on the historical average volatility of our stock price over the expected term. Expected Dividends . The dividend assumption is based on our historical experience. To date we have not paid any dividends on our common stock. Risk-Free Interest Rate . The risk-free interest rate used in the valuation method is the implied yield on the U.S. treasury zero-coupon issues, with a remaining term equal to the expected term. The following table summarizes the key assumptions used to determine the fair value of the awards: Expected term (years) 3.00 Expected volatility 49.04 % Expected dividends — % Risk-free interest rate 0.27 % RSUs and PSUs Activity RSUs and PSUs Outstanding Number of RSUs and PSUs Outstanding Weighted Average Grant Date Fair Value Balance at December 31, 2021 8,171,462 $ 46.36 Granted 5,551,727 27.68 Released ( 2,784,268 ) 48.10 Forfeited ( 1,783,241 ) 38.63 Balance at December 31, 2022 9,155,680 $ 36.03 The weighted-average grant-date fair value of RSUs and PSUs granted during the years ended December 31, 2022, 2021, and 2020 was $ 27.68 , $ 47.95 , and $ 45.37 , respectively. The total fair value of RSUs and PSUs vested as of the vesting dates during the years ended December 31, 2022, 2021, and 2020 was $ 74.2 million, $ 232.0 million, and $ 200.1 million, respectively. 83 Table of Contents Fair Value of 2013 ESPP Under the 2013 ESPP, rights to purchase shares are granted during the second and fourth quarter of each year. We estimate the fair value of each right to purchase shares under our 2013 ESPP using the Black-Scholes-Merton option-pricing model, which utilizes the fair value of our common stock based on active market and requires input on the following subjective assumptions: Expected Term. The expected term for rights to purchase shares under the 2013 ESPP is six months . Expected Volatility. The expected volatility is based on the average volatility of our stock price over the expected term. Expected Dividends. The dividend assumption is based on our historical experience. To date we have not paid any dividends on our common stock. Risk-Free Interest Rate. The risk-free interest rate used in the valuation method is the implied yield on the United States treasury zero-coupon issues, with a remaining term equal to the expected term. The following table summarizes the key assumptions used to determine the fair value of rights granted under the 2013 ESPP: Years Ended December 31, 2022 2021 2020 Expected term (years) 0.50 0.50 0.50 Expected volatility 70.37 %- 78.74 % 47.02 %- 99.96 % 52.06 %- 68.09 % Dividend yield — % — % — % Risk-free interest rate 1.54 %- 4.54 % 0.04 %- 0.07 % 0.12 %- 0.15 % Weighted-average grant-date fair value per share $ 8.71 $ 14.70 $ 20.52 2013 ESPP Activity There were 382,392 , 167,890 and 173,992 shares purchased under the 2013 ESPP during the years ended December 31, 2022, 2021 and 2020, respectively, at an average price per share of $ 15.61 , $ 40.35 and $ 38.85 , respectively, with cash proceeds from the issuance of shares of $ 6.0 million, $ 6.8 million and $ 6.8 million, respectively. Share-based compensation expense related to the 2013 ESPP was $ 3.1 million, $ 3.2 million, and $ 2.6 million during the years ended December 31, 2022, 2021 and 2020, respectively. Stock Option Activity Options Outstanding Number of Options Outstanding Weighted-Average Exercise Price per Share Weighted-Average Remaining Contractual Term in Years Aggregate Intrinsic Value Balance at December 31, 2021 381,756 $ 7.28 2.80 $ 8,942,541 Exercised ( 55,498 ) 8.78 Balance at December 31, 2022 326,258 $ 7.02 2.15 $ 5,954,714 We did no t grant any stock option awards during the years ended December 31, 2022, 2021, and 2020. The total intrinsic value of options exercised during the years ended December 31, 2022, 2021 and 2020, was approximately $ 1.3 million, $ 10.7 million and $ 53.5 million, respectively. Note 17. Income Taxes We recorded a benefit from income taxes of $ 162.7 million during the year ended December 31, 2022 and a provision for income taxes of $ 7.2 million and $ 5.4 million during the years ended December 31, 2021 and 2020, respectively. The benefit from income taxes during the year ended December 31, 2022 was primarily due to the release of the valuation allowance on certain U.S. and state deferred tax assets. The provision for income taxes during the year ended December 31, 2021 was 84 Table of Contents primarily due to state and foreign income tax expenses and the withholding taxes related to the sale of our strategic equity investment. The provision for income taxes during the year ended December 31, 2020 was primarily due to state and foreign income tax expense. Our benefit from (provision for) income taxes consisted of the following (in thousands): Years Ended December 31, 2022 2021 2020 Current income taxes: Federal $ ( 113 ) $ — $ — State ( 2,172 ) ( 852 ) ( 459 ) Foreign ( 3,702 ) ( 7,449 ) ( 5,010 ) Total current provision for income taxes ( 5,987 ) ( 8,301 ) ( 5,469 ) Deferred income taxes: Federal 147,236 ( 250 ) ( 187 ) State 19,995 ( 218 ) ( 255 ) Foreign 1,448 1,572 551 Total deferred benefit from income taxes 168,679 1,104 109 Total benefit from (provision for) income taxes $ 162,692 $ ( 7,197 ) $ ( 5,360 ) Income (loss) before benefit from (provision for) income taxes consisted of the following (in thousands): Years Ended December 31, 2022 2021 2020 United States $ 123,269 $ ( 6,256 ) $ ( 10,369 ) Foreign ( 19,323 ) 11,995 9,508 Total income (loss) before benefit from (provision for) income taxes $ 103,946 $ 5,739 $ ( 861 ) The differences between our benefit from (provision for) income taxes as presented in the accompanying consolidated statements of operations and the income tax expense computed at the federal statutory rate consists of the items shown in the following table as a percentage of income (loss) before benefit from (provision for) income taxes (in percentages): Years Ended December 31, 2022 2021 2020 Income tax at U.S. statutory rate 21.0 % 21.0 % 21.0 % State, net of federal benefit 1.6 ( 232.0 ) ( 169.5 ) Foreign rate differential ( 1.1 ) 35.5 ( 285.9 ) Share-based compensation 15.3 ( 209.0 ) 2,901.5 Non-deductible expenses 1.6 1.5 ( 50.3 ) Tax credits ( 0.7 ) ( 28.3 ) 351.6 Acquisition related — 17.2 — Convertible senior notes 15.0 ( 2,435.3 ) ( 5,854.8 ) Other 1.3 0.5 1.2 Change in valuation allowance ( 210.5 ) 2,954.3 2,462.7 Total ( 156.5 ) % 125.4 % ( 622.5 ) % 85 Table of Contents A summary of our deferred tax assets is as follows (in thousands): As of December 31, 2022 2021 Deferred tax assets: Accrued expenses and reserves $ 7,990 $ 6,402 Share-based compensation 10,078 8,979 Net operating loss and credits carryforwards 147,465 188,329 Property and equipment, textbooks and intangibles assets — 1,849 Convertible senior notes 16,648 32,254 Research and experimental expenditures capitalization 37,719 — Other items 6,777 7,221 Gross deferred tax assets 226,677 245,034 Valuation allowance ( 36,122 ) ( 238,317 ) Total deferred tax assets $ 190,555 $ 6,717 Deferred tax liabilities: Property and equipment, textbooks and intangibles assets $ ( 14,766 ) $ — Other ( 10,070 ) ( 7,878 ) Total deferred tax liabilities $ ( 24,836 ) $ ( 7,878 ) Net deferred tax asset (liability) $ 165,719 $ ( 1,161 ) As of December 31, 2022 and 2021, the deferred tax assets are primarily created by U.S. net operating loss and credits and the deferred tax liability was primarily created by the tax amortization of acquired indefinite lived intangible assets. As of December 31, 2022, we intend to permanently reinvest all 2018 and later earnings from our foreign subsidiaries. As such, we have not provided for any remaining tax effect, if any, of the outside basis difference of our foreign subsidiaries based upon plans of future reinvestment. The determination of the future tax consequences of the remittance of these earnings is not practicable. Realization of the deferred tax assets is dependent upon future taxable income, the amount and timing of which are uncertain. The valuation allowance decreased by approximately $ 202.2 million during the year ended December 31, 2022 and increased by approximately $ 86.5 million during the year ended December 31, 2021. Previously, we maintained a valuation allowance against our deferred tax assets until we expected that it would be more-likely-than not that they would be realized. The release of the valuation allowance is the result of our expectation that our domestic operations will continue to be profitable and is based on a detailed evaluation of all available evidence. The principal indicator leading to the release is the recent cumulative earnings of U.S. and certain state jurisdictions and the forecasted earnings in these jurisdictions. We continue to maintain a valuation allowance against our California deferred tax assets and our anticipated capital loss temporary differences. We will continue to quarterly assess the need for such valuation allowance. As of December 31, 2022, we had net operating loss carryforwards for federal and state income tax purposes of approximately $ 389 million and $ 344 million, respectively, which will begin to expire in years beginning 2028 and 2023, respectively. We also had net operating loss carryforwards for United Kingdom income tax purposes of approximately $ 88.6 million, which do not expire. As of December 31, 2022, we had tax credit carryforwards for federal and state income tax purposes of approximately $ 20.9 million and $ 16.1 million, respectively. The federal credits expire in various years beginning in 2030. The state credits do not expire. Utilization of our net operating losses and tax credit carryforwards may be subject to substantial annual limitations due to ownership change limitations provided by the Internal Revenue Code of 1986, as amended (IRC), and similar state provisions. Such annual limitations could result in the expiration of the net operating losses and tax credit carryforwards before utilization. 86 Table of Contents We recognize interest and penalties related to uncertain tax positions as a component of income tax expense. During the years ended December 31, 2022, 2021 and 2020, we recognized an increase of $ 26 thousand, $ 0.1 million and $ 0.1 million of interest and penalties, respectively. Accrued interest and penalties as of December 31, 2022 and 2021 were approximately $ 0.3 million . We file tax returns in U.S. federal, state, and certain foreign jurisdictions with varying statutes of limitations. Due to net operating loss and credit carryforwards, all of the tax years since inception through tax year 2022 remain subject to examination by the U.S. federal and some state authorities. Foreign jurisdictions remain subject to examination up to approximately seven years from the filing date, depending on the jurisdiction. United Kingdom income tax remains subject to examination by the HM Revenue & Custom for certain tax years due to net operating loss and credits carryforwards. A reconciliation of the beginning and ending balances of the total amount of unrecognized tax benefits, excluding accrued interest and penalties, is as follows (in thousands): Years Ended December 31, 2022 2021 2020 Beginning balance $ 16,805 $ 14,654 $ 10,993 Increase in tax positions for prior years 333 305 479 Decrease in tax positions for prior years ( 876 ) ( 952 ) ( 535 ) Decrease in tax positions for prior year settlement ( 386 ) ( 22 ) ( 208 ) Decrease in tax positions for prior years due to statutes lapsing — ( 426 ) ( 26 ) Increase in tax positions for current year 1,520 3,309 3,999 Change due to translation of foreign currencies ( 443 ) ( 63 ) ( 48 ) Ending balance $ 16,953 $ 16,805 $ 14,654 The amount of unrecognized tax benefits, if recognized, that would affect the effective tax rate is $ 11.6 million for the year ended December 31, 2022. One or more of these unrecognized tax benefits could be subject to a valuation allowance if, and when recognized in a future period, which could impact the timing of any related effective tax rate benefit. The actual amount of any taxes due could vary significantly depending on the ultimate timing and nature of any settlement. We believe that the amount by which the unrecognized tax benefits may increase or decrease within the next 12 months is not estimable. Note 18. Restructuring Charges In September 2021, we changed our go-to-market strategy for our Skills product offering which we believe will have the most growth potential to serve learners. This resulted in a management approved restructuring plan that impacted approximately 60 full-time employees and 100 part-time employees in the United States. During the year ended December 31, 2021, we recorded restructuring charges of $ 1.9 million related to one-time employee termination benefits classified on our consolidated statements of operations based on the employees' job function. During the years ended December 31, 2022 and 2021, we made cash payments of $ 0.8 million and $ 1.1 million, respectively, and have no amounts recorded related to this restructuring plan as of December 31, 2022. The following table summarizes the activity related to the restructuring liability (in thousands): Years Ended December 31, 2022 2021 Beginning balance $ 785 $ — Restructuring charges — 1,922 Cash payments ( 785 ) ( 1,137 ) Ending balance $ — $ 785 87 Table of Contents Note 19. Consolidated Statements of Operations Details Other income (expense), net consists of the following (in thousands): Years Ended December 31, 2022 2021 2020 Gain/(loss) on early extinguishment of debt (1) $ 93,519 $ ( 78,152 ) $ ( 4,286 ) Interest income 12,431 6,700 12,783 Realized (loss)/gain on sale of investments (2) ( 9,675 ) ( 178 ) 308 Foreign currency impact on purchase consideration (3) 4,628 — — Loss on change in fair value of derivative instruments, net (1) — ( 7,148 ) — Gain on sale of strategic equity investments (2) — 12,496 — Other 126 810 ( 122 ) Total other income (expense), net $ 101,029 $ ( 65,472 ) $ 8,683 (1) For further information, see Note 11, “Convertible Senior Notes.” (2) For further information, see Note 5, “Cash and Cash Equivalents, and Investments and Fair Value Measurements.” (3) For further information, see Note 8, “Acquisition.” Note 20. Employee Benefit Plan We sponsor a 401(k) savings plan for eligible employees and their beneficiaries. Contributions by us are discretionary and participants may contribute, on a pretax basis, a percentage of their annual compensation, not to exceed a maximum contribution amount pursuant to Section 401(k) of the IRC. During the years ended December 31, 2022, 2021, and 2020, matching contributions totaled approximately $ 4.4 million, $ 2.6 million and $ 2.2 million, respectively. Note 21. Segment Information Our chief operating decision-maker is our Chief Executive Officer who makes resource allocation decisions and reviews financial information presented on a consolidated basis. Accordingly, we have determined that we have a single operating and reportable segment and operating unit structure. Product Information We derive our revenues from our Subscription Services and Skills and Other product lines. Our Subscription Services include Chegg Study Pack, Chegg Study, Chegg Writing, Chegg Math, and Busuu. Our Skills and Other product line includes revenues from Skills, advertising services, print textbooks and eTextbooks. The following table sets forth our total net revenues for the periods shown for our Subscription Services and Skills and Other product lines (in thousands): Years Ended December 31, 2022 2021 2020 Subscription Services $ 671,968 $ 616,817 $ 460,612 Skills and Other 94,929 159,448 183,726 Total net revenues $ 766,897 $ 776,265 $ 644,338 The following table sets forth our total net revenues for the periods shown by geographic area (in thousands): Years Ended December 31, 2022 2021 United States $ 651,469 $ 690,013 International 115,428 86,252 Total net revenues $ 766,897 $ 776,265 During the year ended December 31, 2020, substantially all of our revenue was from the United States. As of December 31, 2022 and 2021, substantially all of our long-lived assets are located in the United States. 88 Table of Contents ITEM 9. CHANGES IN AND DISAGREEMENTS WITH ACCOUNTANTS ON ACCOUNTING AND FINANCIAL DISCLOSURE None.