Schultz Nathan J.

SEC source: 0001586632-25-000004 · wk-form4_1757979007.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · CEO & PRESIDENT

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,464,391

F2 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001586632-25-000004 · wk-form4_1757979007.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · CEO & PRESIDENT

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,482,884

F1 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the performance stock units ("PSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-25-000074 · wk-form4_1750113390.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · CEO & PRESIDENT

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,485,090

F2 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-25-000074 · wk-form4_1750113390.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · CEO & PRESIDENT

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,540,480

F1 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the performance stock units ("PSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-25-000057 · wk-form4_1748365275.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,555,497

F1 · shares: On May 22, 2025, the reporting person transferred 144,448 shares of common stock to the Nathan Schultz and Debbie Schultz Co-TTEE Schultz Family Trust.

F2 · balance_after: Includes 8000 shares acquired under the 2013 Amended and Restated Chegg, Inc. Employee Stock Purchase Plan (ESPP) on May 15, 2025.

SEC source: 0001364954-25-000062 · wk-form4a_1749250283.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · CEO & PRESIDENT

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,555,497

F1 · shares: On May 22, 2025, the reporting person transferred 144,448 shares of common stock to the Nathan Schultz and Debbie Schultz Co-TTEE Schultz Family Trust.

F2 · balance_after: Includes 8000 shares acquired under the 2013 Amended and Restated Chegg, Inc. Employee Stock Purchase Plan (ESPP) on May 15, 2025.

SEC source: 0001364954-25-000024 · wk-form4_1741989901.xml · nonDerivative · entry 3

Schultz Nathan J. · CIK 0001586632 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,691,945

F3 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the performance stock units ("PSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-25-000024 · wk-form4_1741989901.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,695,056

F2 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-25-000024 · wk-form4_1741989901.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,703,539

F1 · shares: Represents the number of shares of Common Stock subject to performance-based restricted stock units ("PSUs") granted to the Reporting Person in 2024 (the "2024 PSUs") that shall now be subject to time-based vesting following the Compensation Committee's determination of the achievement of certain performance measurements on March 3, 2025. The shares subject to the 2024 PSUs allocated to each "2024 performance metric" shall vest 100% on June 12, 2025, subject to the Reporting Person's continued service through each vesting date.

SEC source: 0001364954-25-000005 · wk-form4_1737070735.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,667,734

F1 · shares: Represents an award of Restricted Stock Units (" RSU"). Each RSU represents a contingent right to receive one share of common stock of the Issuer upon vesting. The RSU award will vest over a 2-year period with 50% vesting on January 12, 2026, and the remaining shares vesting in 4 equal quarterly installments thereafter, subject to the recipient's continued service up to and through the Vesting Date.

SEC source: 0001364954-24-000094 · wk-form4_1734385554.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 667,734

F2 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the performance stock units ("PSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-24-000094 · wk-form4_1734385554.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 672,140

F1 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-24-000074 · wk-form4_1726523672.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 684,154

F2 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the performance stock units ("PSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-24-000074 · wk-form4_1726523672.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 688,180

F1 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-24-000060 · wk-form4_1718401572.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 698,405

F2 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the performance stock units ("PSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-24-000060 · wk-form4_1718401572.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 701,506

F1 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-24-000044 · wk-form4_1717540123.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · Director · CEO and President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 709,964

F1 · shares: Represents an award of restricted stock units ("RSU"). Each RSU represents a contingent right to receive one share of common stock of the Issuer upon vesting. The RSU will vest over a 3-year period with 1/3 vesting on June 12, 2025 and then the remaining shares vesting in 8 equal quarterly installments thereafter, subject to recipient's continued service up to and through each vesting date.

F2 · balance_after: Includes 2,413 shares acquired under the Amended and Restated 2013 Chegg, Inc. Employee Stock Purchase Plan (ESPP) on May 15, 2024.

SEC source: 0001364954-24-000021 · wk-form4_1710455873.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 221,105

F2 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the performance stock units ("PSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-24-000021 · wk-form4_1710455873.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 230,802

F1 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-25-000045 · wk-form4a_1744927110.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 331,731

F1 · shares: Includes 24,648 shares of Common Stock acquired upon the satisfaction of certain performance-based vesting criteria and vesting of a portion of the earned shares underlying performance-based restricted stock unit awards granted to the Reporting Person in 2023, and 49,298 earned shares underlying such award, vesting in equal quarterly installments for the 24 months commencing on March 12, 2024, subject to the Reporting Person's continued service up to and through the applicable vesting dates.

F2 · balance_after: The amount of securities beneficially owned following the reported transaction and the share withholding transactions previously reported on the original Form 4 filed on March 12, 2024 is 295,051 shares.

SEC source: 0001364954-24-000019 · wk-form4_1709682394.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 257,785

F2 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the performance stock units ("PSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-24-000019 · wk-form4_1709682394.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 258,515

F1 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-24-000011 · wk-form4_1708727848.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 259,378

F1 · shares: On February 21, 2024, the reporting person transferred 161,647 shares of common stock to the Nathan Schultz and Debbie Schultz Co-TTEE Schultz Family Trust.

SEC source: 0001364954-23-000155 · wk-form4_1702591855.xml · nonDerivative · entry 3

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 421,025

F3 · kind: The sales reported in this Form 4 were effectuated pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on November 10, 2022.

SEC source: 0001364954-23-000155 · wk-form4_1702591855.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 422,375

F2 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreements governing the PSUs to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-23-000155 · wk-form4_1702591855.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 423,629

F1 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-23-000153 · wk-form4_1701801337.xml · nonDerivative · entry 3

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 426,802

F3 · kind: The sales reported in this Form 4 were pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on November 10, 2022.

F4 · price: The reported price in Column 4 is a weighted average sale price. These shares were sold in multiple transactions at prices ranging from $10.05 to $10.26 per share. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001364954-23-000153 · wk-form4_1701801337.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 427,432

F2 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreements governing the PSUs to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-23-000153 · wk-form4_1701801337.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 428,458

F1 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-23-000131 · wk-form4_1694734034.xml · nonDerivative · entry 3

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 429,501

F3 · kind: The sales reported in this Form 4 were pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on November 10, 2022.

SEC source: 0001364954-23-000131 · wk-form4_1694734034.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 431,048

F2 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreements governing the PSUs to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-23-000131 · wk-form4_1694734034.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 432,302

F1 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-23-000128 · wk-form4_1694032711.xml · nonDerivative · entry 3

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 434,816

F3 · kind: The sales reported in this Form 4 were pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on November 10, 2022.

SEC source: 0001364954-23-000128 · wk-form4_1694032711.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 435,634

F2 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreements governing the PSUs to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-23-000128 · wk-form4_1694032711.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 436,350

F1 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-23-000110 · wk-form4_1686785605.xml · nonDerivative · entry 3

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 437,078

F3 · kind: The sales reported in this Form 4 were pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on November 10, 2022.

SEC source: 0001364954-23-000110 · wk-form4_1686785605.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 438,829

F2 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreements governing the PSUs to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-23-000110 · wk-form4_1686785605.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 439,704

F1 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-23-000088 · wk-form4_1686003456.xml · nonDerivative · entry 3

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 441,917

F4 · kind: The sales reported in this Form 4 were pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on November 10, 2022.

SEC source: 0001364954-23-000088 · wk-form4_1686003456.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 442,735

F3 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreements governing the PSUs to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-23-000088 · wk-form4_1686003456.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 443,451

F1 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

F2 · balance_after: Includes 876 shares acquired under the 2013 Chegg, Inc. Employee Stock Purchase Plan (ESPP) on May 15, 2023.

SEC source: 0001364954-23-000045 · wf-form4_168013517883103.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 443,303

F1 · shares: Represents an award of restricted stock units ("RSU"). Each RSU represents a contingent right to receive one share of common stock of the Issuer upon vesting. The RSU will vest over a 3-year period with 1/3 vesting on March 12, 2024 and with the remaining shares vesting in equal quarterly installments thereafter for 24 months, subject to recipient's continued service up to and through the vesting dates.

SEC source: 0001364954-23-000038 · wf-form4_167908624589075.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 235,626

F1 · kind: The sales reported in this Form 4 were effectuated pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on November 10, 2022.

SEC source: 0001364954-23-000033 · wf-form4_167883834842518.xml · nonDerivative · entry 3

Schultz Nathan J. · CIK 0001586632 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 242,633

F3 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreements governing the PSUs to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-23-000033 · wf-form4_167883834842518.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 246,131

F2 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-23-000033 · wf-form4_167883834842518.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 254,981

F1 · shares: Represents the number of shares of Common Stock subject to performance-based restricted stock units ("PSUs") granted to the Reporting Person in 2022 (the "2022 PSUs") that shall now be subject to time-based vesting following the Compensation Committee's review of the achievement of certain performance measurements on February 8, 2023. The shares subject to the 2022 PSUs allocated to each performance metric shall vest as follows: 1/3 vested on March 12, 2023, and then the remaining 2/3rds shall vest in equal quarterly installments over the next 24 months, subject to the Reporting Person's continued service through each vesting date.

SEC source: 0001364954-23-000017 · wf-form4_167788583472752.xml · nonDerivative · entry 3

Schultz Nathan J. · CIK 0001586632 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 224,637

F3 · kind: The sales reported in this Form 4 were effectuated pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on November 10, 2022.

SEC source: 0001364954-23-000017 · wf-form4_167788583472752.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 228,678

F2 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the performance stock units ("PSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-23-000017 · wf-form4_167788583472752.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 231,345

F1 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-23-000006 · wf-form4_167546190812702.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 233,360

F1 · kind: The sales reported in this Form 4 were effectuated pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on November 10, 2022.

F2 · price: The reported price in Column 4 is a weighted average sale price. These shares were sold in multiple transactions at prices ranging from $20.53 to $20.96 per share. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.