CHGG

SEC source: 0001364954-23-000086 · wk-form4_1686003230.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,895,761

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: 0001364954-23-000087 · wk-form4_1686003340.xml · nonDerivative · entry 2

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 301,263

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: 0001364954-23-000087 · wk-form4_1686003340.xml · nonDerivative · entry 1

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 301,979

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: 0001364954-23-000088 · 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: 0001364954-23-000076 · wf-form4_168428644521350.xml · derivative · entry 3

Levine Marne L. · CIK 0001586643 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 36,041 shares

Expires 2023-05-14

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_date: The stock option grant was fully vested on 5/15/2016.

SEC source: 0001364954-23-000076 · wf-form4_168428644521350.xml · nonDerivative · entry 2

Levine Marne L. · CIK 0001586643 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 46,713

F1 · kind: The proceeds from the disposition of the common stock were used to pay the exercise price for certain of the director stock options expiring on 5/14/2023.

SEC source: 0001364954-23-000076 · wf-form4_168428644521350.xml · nonDerivative · entry 1

Levine Marne L. · CIK 0001586643 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 57,910

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001364954-23-000047 · wf-form4_168151891668789.xml · nonDerivative · entry 1

Longo David · CIK 0001902785 · CHIEF ACCOUNTING OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 67,483

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: 0001364954-23-000046 · wf-form4_168013526727137.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,897,033

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 vests with respect to 100% of the shares subject to the RSU on March 12, 2024 (the "Vesting Date"), subject to recipient's continued service up to and through the Vesting Date.

SEC source: 0001364954-23-000044 · wf-form4_168013508179927.xml · nonDerivative · entry 1

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 301,831

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 vests with respect to 100% of the shares subject to the RSU on March 12, 2024 (the "Vesting Date"), subject to recipient's service up to and through the Vesting Date.

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: 0001364954-23-000043 · wf-form4_168013495100907.xml · nonDerivative · entry 1

Longo David · CIK 0001902785 · CHIEF ACCOUNTING OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 68,600

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 2-year period with 50% vesting on 3/12/2024 and with the remaining shares vesting in equal quarterly installments thereafter for 12 months, subject to the 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: 0001364954-23-000035 · wf-form4_167883850306049.xml · nonDerivative · entry 3

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,781,657

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: 0001364954-23-000035 · wf-form4_167883850306049.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,788,950

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: 0001364954-23-000035 · wf-form4_167883850306049.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,812,811

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: 0001364954-23-000036 · wf-form4_167883858482490.xml · nonDerivative · entry 3

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 244,143

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: 0001364954-23-000036 · wf-form4_167883858482490.xml · nonDerivative · entry 2

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 247,641

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: 0001364954-23-000036 · wf-form4_167883858482490.xml · nonDerivative · entry 1

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 256,491

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: 0001364954-23-000037 · wf-form4_167883867021926.xml · nonDerivative · entry 3

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 182,817

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: 0001364954-23-000037 · wf-form4_167883867021926.xml · nonDerivative · entry 2

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 185,056

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: 0001364954-23-000037 · wf-form4_167883867021926.xml · nonDerivative · entry 1

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 190,720

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: 0001364954-23-000033 · 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: 0001364954-23-000034 · wf-form4_167883841781124.xml · nonDerivative · entry 3

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 173,090

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: 0001364954-23-000034 · wf-form4_167883841781124.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 175,888

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: 0001364954-23-000034 · wf-form4_167883841781124.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 182,968

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: 0001364954-23-000027 · wf-form4_167831699800767.xml · nonDerivative · entry 1

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 171,300

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 December 9, 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 $16.62 to $17.09 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: 0001364954-23-000017 · 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: 0001364954-23-000021 · wf-form4_167788624991528.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,752,123

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: 0001364954-23-000021 · wf-form4_167788624991528.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,757,916

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: 0001364954-23-000019 · wf-form4_167788604807619.xml · nonDerivative · entry 2

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 226,147

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: 0001364954-23-000019 · wf-form4_167788604807619.xml · nonDerivative · entry 1

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 228,861

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: 0001364954-23-000023 · wf-form4_167788642521932.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 158,693

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: 0001364954-23-000023 · wf-form4_167788642521932.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 160,742

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: 0001364954-23-000025 · wf-form4_167788660337166.xml · nonDerivative · entry 2

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 177,000

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: 0001364954-23-000025 · wf-form4_167788660337166.xml · nonDerivative · entry 1

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 179,018

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: 0001364954-23-000017 · 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.

SEC source: 0001364954-23-000004 · wf-form4_167398895299299.xml · nonDerivative · entry 1

Longo David · CIK 0001902785 · Chief Accounting Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 47,623

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 767 shares acquired under the 2013 Chegg, Inc. Employee Stock Purchase Plan (ESPP) on November 15, 2022.

SEC source: 0001364954-23-000002 · wf-form4_167295688706207.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 237,500

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 $25.09 to $25.72 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: 0001364954-22-000122 · wf-form4_167027981087537.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,762,307

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: 0001364954-22-000122 · wf-form4_167027981087537.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO & CO-CHAIRMAN

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,770,523

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: 0001364954-22-000123 · wf-form4_167027983223489.xml · nonDerivative · entry 2

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 230,876

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 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: 0001364954-22-000123 · wf-form4_167027983223489.xml · nonDerivative · entry 1

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 234,670

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 1,334 shares acquired under the 2013 Chegg, Inc. Employee Stock Purchase Plan (ESPP) on November 15, 2022.

SEC source: 0001364954-22-000124 · wf-form4_167027985408074.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 262,500

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: 0001364954-22-000124 · wf-form4_167027985408074.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 266,294

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.