CHGG

SEC source: 0001364954-21-000025 · wf-form4_161482509674677.xml · nonDerivative · entry 3

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 185,062

F3 · kind: The reported shares were withheld to cover the Reporting Person's tax liability in connection with the vesting of RSUs.

SEC source: 0001364954-21-000025 · wf-form4_161482509674677.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 195,930

F2 · shares: Represents the number of shares of Common Stock subject to performance-based restricted stock units ("PSUs") granted to the Reporting Person in 2020 (the "2020 PSUs") that shall now be subject totime-based vesting following the Compensation Committee's determination of the achievement of certain performance measurements on February 27, 2021. The shares subject to the 2020 PSUs allocated to eachperformance metric shall vest as follows: 1/3 shall vest on March 1, 2021, and then the remaining 2/3rds shall vest in equal quarterly installments over the next 24 months, subject to the Reporting Person'scontinued service through each vesting date.

SEC source: 0001364954-21-000025 · wf-form4_161482509674677.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 152,024

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 1/3vesting on March 1, 2022 and then the remaining shares vesting in equal quarterly installments thereafter for 24 months.

SEC source: 0001364954-21-000024 · wf-form4_161482490866587.xml · derivative · entry 6

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 46,678

Underlying: Common Stock · 46,678 shares

Expires 2025-03-01

F6 · kind: The PSU represents the contingent right to receive, following vesting, between 0% and 150% of one share of common stock based upon the achievement of pre-established total shareholder return of the Issuer's Common Stock calculated beginning from the closing price of the Issuer's Common Stock on the date of grant and using the average of the daily closing prices of the Issuer's Common Stock for any 60 consecutive trading days with the final trading day during the performance period ending on February 29, 2024 (the "TSR Performance Metric") and certification of such performance by the Compensation Committee following the conclusion of the performance period.

F7 · derivative.exercise_date: The PSUs shall be earned and become vested based upon both (i) attainment of the TSR Performance Metric and (ii) continued service of the Reporting Person through each vesting date, with 50% of the PSUs to vest on March 8, 2024 and 50% to vest on March 1, 2025.

F8 · derivative.underlying_shares: Shares represent 150% of the PSUs awarded, the maximum rate of undetermined achievement.

SEC source: 0001364954-21-000024 · wf-form4_161482490866587.xml · nonDerivative · entry 4

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 183,704

F4 · kind: The reported shares were withheld to cover the Reporting Person's tax liability in connection with the vesting of PSUs.

SEC source: 0001364954-21-000024 · wf-form4_161482490866587.xml · nonDerivative · entry 3

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 201,897

F3 · kind: The reported shares were withheld to cover the Reporting Person's tax liability in connection with the vesting of RSUs.

SEC source: 0001364954-21-000024 · wf-form4_161482490866587.xml · nonDerivative · entry 2

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 214,641

F2 · shares: Represents the number of shares of Common Stock subject to performance-based restricted stock units ("PSUs") granted to the Reporting Person in 2020 (the "2020 PSUs") that shall now be subject totime-based vesting following the Compensation Committee's determination of the achievement of certain performance measurements on February 27, 2021. The shares subject to the 2020 PSUs allocated to eachperformance metric shall vest as follows: 1/3 shall vest on March 1, 2021, and then the remaining 2/3rds shall vest in equal quarterly installments over the next 24 months, subject to the Reporting Person'scontinued service through each vesting date.

SEC source: 0001364954-21-000024 · wf-form4_161482490866587.xml · nonDerivative · entry 1

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 168,735

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 1, 2022 and then the remaining shares vesting in equal quarterly installments thereafter for 24 months.

SEC source: 0001364954-21-000021 · wf-form4_161482461266158.xml · derivative · entry 5

Schultz Nathan J. · CIK 0001586632 · PRESIDENT OF LEARNING SERVICES

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 72,935

Underlying: Common Stock · 72,935 shares

Expires 2025-03-01

F5 · kind: The PSU represents the contingent right to receive, following vesting, between 0% and 150% of one share of common stock based upon the achievement of pre-established total shareholder return of the Issuer's Common Stock calculated beginning from the closing price of the Issuer's Common Stock on the date of grant and using the average of the daily closing prices of the Issuer's Common Stock for any 60 consecutive trading days with the final trading day during the performance period ending on February 29, 2024 (the "TSR Performance Metric") and certification of such performance by the Compensation Committee following the conclusion of the performance period.

F6 · derivative.exercise_date: The PSUs shall be earned and become vested based upon both (i) attainment of the TSR Performance Metric and (ii) continued service of the Reporting Person through each vesting date, with 50% of the PSUsto vest on March 8, 2024 and 50% to vest on March 1, 2025.

F7 · derivative.underlying_shares: Shares represent 150% of the PSUs awarded, the maximum rate of undetermined achievement.

SEC source: 0001364954-21-000021 · wf-form4_161482461266158.xml · nonDerivative · entry 4

Schultz Nathan J. · CIK 0001586632 · PRESIDENT OF LEARNING SERVICES

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 276,154

F4 · kind: The reported shares were withheld to cover the Reporting Person's tax liability in connection with the vesting of PSUs.

SEC source: 0001364954-21-000021 · wf-form4_161482461266158.xml · nonDerivative · entry 3

Schultz Nathan J. · CIK 0001586632 · PRESIDENT OF LEARNING SERVICES

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 300,758

F3 · kind: The reported shares were withheld to cover the Reporting Person's tax liability in connection with the vesting of RSUs.

SEC source: 0001364954-21-000021 · wf-form4_161482461266158.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · PRESIDENT OF LEARNING SERVICES

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 318,477

F2 · shares: Represents the number of shares of Common Stock subject to performance-based restricted stock units ("PSUs") granted to the Reporting Person in 2020 (the "2020 PSUs") that shall now be subject totime-based vesting following the Compensation Committee's determination of the achievement of certain performance measurements on February 27, 2021. The shares subject to the 2020 PSUs allocated to eachperformance metric shall vest as follows: 1/3 shall vest on March 1, 2021, and then the remaining 2/3rds shall vest in equal quarterly installments over the next 24 months, subject to the Reporting Person'scontinued service through each vesting date.

SEC source: 0001364954-21-000021 · wf-form4_161482461266158.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · PRESIDENT OF LEARNING SERVICES

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 251,530

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 1, 2022 and then the remaining shares vesting in equal quarterly installments thereafter for 24 months.

SEC source: 0001364954-21-000027 · wf-form4a_161499469251452.xml · derivative · entry 4

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 58,348

Underlying: Common Stock · 58,348 shares

Expires 2021-03-01

F5 · kind: The PSU represents the contingent right to receive, following vesting, between 0% and 150% of one share of common stock based upon the achievement of pre-established total shareholder return of the Issuer's Common Stock calculated beginning from the closing price of the Issuer's Common Stock on the date of grant and using the average of the daily closing prices of the Issuer's Common Stock for any 60 consecutive trading days with the final trading day during the performance period ending on February 29, 2024 (the "TSR Performance Metric") and certification of such performance by the Compensation Committee following the conclusion of the performance period.

F2 · shares: This amendment to Form 4 filed on March 3, 2021 is filed to correct (a) the number of securities beneficially owned following the transactions reported in column 5 of Table I, and (b) the number of PSUs reflected in Column 5 of Table II, which was inadvertently reported as 0.

F6 · derivative.exercise_date: The PSUs shall be earned and become vested based upon both (i) attainment of the TSR Performance Metric and (ii) continued service of the Reporting Person through each vesting date, with 50% of the PSUsto vest on March 8, 2024 and 50% to vest on March 1, 2025.

F7 · derivative.underlying_shares: Shares represent 150% of the PSUs awarded, the maximum rate of undetermined achievement.

SEC source: 0001364954-21-000027 · wf-form4a_161499469251452.xml · nonDerivative · entry 3

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 169,937

F4 · kind: The reported shares were withheld to cover the Reporting Person's tax liability in connection with the vesting of performance stock units.

F2 · balance_after: This amendment to Form 4 filed on March 3, 2021 is filed to correct (a) the number of securities beneficially owned following the transactions reported in column 5 of Table I, and (b) the number of PSUs reflected in Column 5 of Table II, which was inadvertently reported as 0.

SEC source: 0001364954-21-000027 · wf-form4a_161499469251452.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 187,062

F3 · kind: The reported shares were withheld to cover the Reporting Person's tax liability in connection with the vesting of restricted stock units.

F2 · balance_after: This amendment to Form 4 filed on March 3, 2021 is filed to correct (a) the number of securities beneficially owned following the transactions reported in column 5 of Table I, and (b) the number of PSUs reflected in Column 5 of Table II, which was inadvertently reported as 0.

SEC source: 0001364954-21-000027 · wf-form4a_161499469251452.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 197,930

F1 · shares: Represents the number of shares of Common Stock subject to performance-based restricted stock units ("PSUs") granted to the Reporting Person in 2020 (the "2020 PSUs") that shall now be subject to time-based vesting following the Compensation Committee's determination of the achievement of certain performance measurements on February 27, 2021. The shares subject to the 2020 PSUs allocated to each performance metric shall vest as follows: 1/3 shall vest on March 1, 2021, 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.

F2 · balance_after: This amendment to Form 4 filed on March 3, 2021 is filed to correct (a) the number of securities beneficially owned following the transactions reported in column 5 of Table I, and (b) the number of PSUs reflected in Column 5 of Table II, which was inadvertently reported as 0.

SEC source: 0001364954-21-000029 · wf-form4a_161603008050115.xml · derivative · entry 1

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 46,678

Underlying: Common Stock · 46,678 shares

Expires 2025-03-01

F1 · derivative.exercise_price: The PSU represents the contingent right to receive, following vesting, between 0% and 150% of one share of common stock based upon the achievement of pre-established total shareholder return of the Issuer's Common Stock calculated beginning from the closing price of the Issuer's Common Stock on the date of grant and using the average of the daily closing prices of the Issuer's Common Stock for any 60 consecutive trading days with the final trading day during the performance period ending on February 29, 2024 (the "TSR Performance Metric") and certification of such performance by the Compensation Committee following the conclusion of the performance period.

F2 · shares: The amendment on Form 4 is to correct the number of PSUs reflected in column 5 inadvertently reflected as 0 in the Form 4 filed on March 3, 2021 and should have reflected 46,678 PSUs.

F3 · shares: Represents the maximum amount that the Reporting Person will receive assuming the Maximum Performance Level of the TSR Performance Metric.

F4 · derivative.exercise_date: The PSUs shall be earned and become vested based upon both (i) attainment of the TSR Performance Metric and (ii) continued service of the Reporting Person through each vesting date, with 50% of the PSUs to vest on March 8, 2024 and 50% to vest on March 1, 2025.

F3 · derivative.underlying_shares: Represents the maximum amount that the Reporting Person will receive assuming the Maximum Performance Level of the TSR Performance Metric.

F3 · balance_after: Represents the maximum amount that the Reporting Person will receive assuming the Maximum Performance Level of the TSR Performance Metric.

SEC source: 0001364954-21-000040 · wf-form4a_161956610159030.xml · derivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 145,871

Underlying: Common Stock · 145,871 shares

Expires 2025-03-01

F1 · derivative.exercise_price: Each Performance Stock Unit ("PSU") represents the contingent right to receive, following vesting, between 0% and 150% of one share of Common Stock based upon the achievement of a pre-established total shareholder return of the Issuer's Common Stock calculated beginning from the closing price of the Issuer's Common Stock on the date of grant and using the average of the daily closing prices of the Issuer's Common Stock for any 60 consecutive trading days with the final trading day during the performance period ending on February 29, 2024 (the "TSR Performance Metric") and certification of such performance by the Compensation Committee following the conclusion of the performance period.

F2 · shares: This amendment to Form 4 filed on March 3, 2021 is filed to correct the number of PSUs reflected in Column 5 of Table II, which was inadvertently reported as 0 and should have reflected 145,871 PSUs.

F3 · shares: Represents the maximum number of PSUs that the Reporting Person will receive assuming the Maximum Performance Level (150%) of the TSR Performance Metric.

F4 · derivative.exercise_date: The PSUs shall be earned and become vested based upon both (i) attainment of the TSR Performance Metric and (ii) continued service of the Reporting Person through each vesting date, with 50% of the PSUs to vest on March 8, 2024 and 50% to vest on March 1, 2025.

F3 · derivative.underlying_shares: Represents the maximum number of PSUs that the Reporting Person will receive assuming the Maximum Performance Level (150%) of the TSR Performance Metric.

F3 · balance_after: Represents the maximum number of PSUs that the Reporting Person will receive assuming the Maximum Performance Level (150%) of the TSR Performance Metric.

SEC source: 0001364954-21-000039 · wf-form4a_161956598092351.xml · derivative · entry 1

TOMASELLO ROBIN · CIK 0001608511 · VP, CORPORATE CONTROLLER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 14,587

Underlying: Common Stock · 14,587 shares

Expires 2025-03-01

F1 · derivative.exercise_price: Each Performance Stock Unit ("PSU") represents the contingent right to receive, following vesting, between 0% and 150% of one share of Common Stock based upon the achievement of a pre-established total shareholder return of the Issuer's Common Stock calculated beginning from the closing price of the Issuer's Common Stock on the date of grant and using the average of the daily closing prices of the Issuer's Common Stock for any 60 consecutive trading days with the final trading day during the performance period ending on February 29, 2024 (the "TSR Performance Metric") and certification of such performance by the Compensation Committee following the conclusion of the performance period.

F2 · shares: This amendment to Form 4 filed on March 3, 2021 is filed to correct the number of PSUs reflected in Column 5 of Table II, which was inadvertently reported as 0 and should have reflected 14,587 PSUs.

F3 · shares: Represents the maximum number of PSUs that the Reporting Person will receive assuming the Maximum Performance Level (150%) of the TSR Performance Metric.

F4 · derivative.exercise_date: The PSUs shall be earned and become vested based upon both (i) attainment of the TSR Performance Metric and (ii) continued service of the Reporting Person through each vesting date, with 50% of the PSUs to vest on March 8, 2024 and 50% to vest on March 1, 2025.

F3 · derivative.underlying_shares: Represents the maximum number of PSUs that the Reporting Person will receive assuming the Maximum Performance Level (150%) of the TSR Performance Metric.

F3 · balance_after: Represents the maximum number of PSUs that the Reporting Person will receive assuming the Maximum Performance Level (150%) of the TSR Performance Metric.

SEC source: 0001364954-21-000037 · wf-form4a_161956385372136.xml · derivative · entry 1

Schultz Nathan J. · CIK 0001586632 · PRESIDENT OF LEARNING SERVICES

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 72,935

Underlying: Common Stock · 72,935 shares

Expires 2025-03-01

F1 · derivative.exercise_price: Each Performance Stock Unit ("PSU") represents the contingent right to receive, following vesting, between 0% and 150% of one share of Common Stock based upon the achievement of a pre-established total shareholder return of the Issuer's Common Stock calculated beginning from the closing price of the Issuer's Common Stock on the date of grant and using the average of the daily closing prices of the Issuer's Common Stock for any 60 consecutive trading days with the final trading day during the performance period ending on February 29, 2024 (the "TSR Performance Metric") and certification of such performance by the Compensation Committee following the conclusion of the performance period.

F2 · shares: This amendment to Form 4 filed on March 3, 2021 is filed to correct the number of PSUs reflected in Column 5 of Table II, which was inadvertently reported as 0 and should have reflected 72,935 PSUs.

F3 · shares: Represents the maximum number of PSUs that the Reporting Person will receive assuming the Maximum Performance Level (150%) of the TSR Performance Metric.

F4 · derivative.exercise_date: The PSUs shall be earned and become vested based upon both (i) attainment of the TSR Performance Metric and (ii) continued service of the Reporting Person through each vesting date, with 50% of the PSUs to vest on March 8, 2024 and 50% to vest on March 1, 2025.

F3 · derivative.underlying_shares: Represents the maximum number of PSUs that the Reporting Person will receive assuming the Maximum Performance Level (150%) of the TSR Performance Metric.

F3 · balance_after: Represents the maximum number of PSUs that the Reporting Person will receive assuming the Maximum Performance Level (150%) of the TSR Performance Metric.

SEC source: 0001364954-21-000016 · wf-form4_161412150906892.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,607,090

F1 · kind: The shares were sold in a public offering of the Issuer's common stock to the underwriters who were given an option to purchase additional shares from Mr. Rosensweig.

F2 · price: Represents the net price per share. The gross price per share was $102.00.

SEC source: 0001364954-21-000002 · wf-form4_161014521272628.xml · nonDerivative · entry 3

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,907,090

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on February 21, 2020.

SEC source: 0001364954-21-000002 · wf-form4_161014521272628.xml · nonDerivative · entry 2

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,907,190

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on February 21, 2020.

F3 · price: This transaction was executed in multiple trades at prices ranging from $90.88 to $91.80; the price reported above reflects the weighted average sale price. The reporting person will provide to the Commission, the issuer and any stockholder, upon request, full information regarding the number of shares and prices at which the transactions were effected.

SEC source: 0001364954-21-000002 · wf-form4_161014521272628.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,930,667

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on February 21, 2020.

F2 · price: This transaction was executed in multiple trades at prices ranging from $89.78 to $90.37; the price reported above reflects the weighted average sale price. The reporting person will provide to the Commission, the issuer and any stockholder, upon request, full information regarding the number of shares and prices at which the transactions were effected.

SEC source: 0001364954-20-000242 · wf-form4_160867368653544.xml · derivative · entry 3

Schultz Nathan J. · CIK 0001586632 · PRESIDENT OF LEARNING SERVICES

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 82,458 shares

Expires 2023-11-11

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.

F1 · kind: The exercise of options and sale of the resultant shares reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on December 12, 2019.

F3 · derivative.exercise_date: The stock option grant is fully vested.

SEC source: 0001364954-20-000242 · wf-form4_160867368653544.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · PRESIDENT OF LEARNING SERVICES

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 226,290

F1 · kind: The exercise of options and sale of the resultant shares reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on December 12, 2019.

F2 · price: This transaction was executed in multiple trades at prices ranging from $90.00 to $90.89; the price reported above reflects the weighted average sale price. The reporting person will provide to the Commission, the issuer and any stockholder, upon request, full information regarding the number of shares and prices at which the transactions were effected.

SEC source: 0001364954-20-000242 · wf-form4_160867368653544.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · PRESIDENT OF LEARNING SERVICES

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 308,748

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.

F1 · kind: The exercise of options and sale of the resultant shares reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on December 12, 2019.

SEC source: 0001364954-20-000240 · wf-form4_160798463576091.xml · nonDerivative · entry 1

Bond Sarah · CIK 0001816807 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,440

F1 · shares: Represents an award of restricted stock units ("RSU", and each a "RSU"). Each RSU represents a contingent right to receive one share of common stock of the Issuer upon vesting.

SEC source: 0001364954-20-000238 · wf-form4_160798439197393.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,935,090

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on February 21, 2020.

F2 · price: This transaction was executed in multiple trades at prices ranging from $80.37 to $82.69; the price reported above reflects the weighted average sale price. The reporting person will provide to the Commission, the issuer and any stockholder, upon request, full information regarding the number of shares and prices at which the transactions were effected.

SEC source: 0001364954-20-000230 · wf-form4_160704308141584.xml · nonDerivative · entry 3

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 131,832

F3 · kind: The sale reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 13,2020.

SEC source: 0001364954-20-000227 · wf-form4_160704302492433.xml · nonDerivative · entry 3

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 152,582

F3 · kind: The sale reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 12,2020.

F4 · price: This transaction was executed in multiple trades at prices ranging from $75.55 to $78.05; the price reported above reflects the weighted average sale price. The reporting person will provide to the Commission, the issuer and any stockholder, upon request, full information regarding the number of shares and prices at which the transactions were effected.

SEC source: 0001364954-20-000231 · wf-form4_160704309809940.xml · nonDerivative · entry 2

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,963,090

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 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: 0001364954-20-000231 · wf-form4_160704309809940.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,966,412

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 2019 PSUs to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the 2019 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: 0001364954-20-000229 · wf-form4_160704306294139.xml · nonDerivative · entry 2

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 136,287

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 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.

F3 · balance_after: The reporting person contributed 3,773 shares of CHGG common stock to the Andy and Pam Brown Family Trust on December 1, 2020, in a transaction that resulted in a change in form of beneficial ownership from direct to indirect.

SEC source: 0001364954-20-000229 · wf-form4_160704306294139.xml · nonDerivative · entry 1

BROWN ANDREW J · CIK 0001226866 · CHIEF FINANCIAL OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 141,594

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 2019 PSUs to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the 2019 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: 0001364954-20-000230 · wf-form4_160704308141584.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 133,153

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 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: 0001364954-20-000230 · wf-form4_160704308141584.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 134,227

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 2019 PSUs to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the 2019 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: 0001364954-20-000228 · wf-form4_160704304630052.xml · nonDerivative · entry 1

TOMASELLO ROBIN · CIK 0001608511 · VP, CORPORATE CONTROLLER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 54,944

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 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: 0001364954-20-000227 · wf-form4_160704302492433.xml · nonDerivative · entry 2

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 154,845

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 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: 0001364954-20-000227 · wf-form4_160704302492433.xml · nonDerivative · entry 1

Lem Esther · CIK 0001587559 · CHIEF MARKETING OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 155,765

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 2019 PSUs to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the 2019 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: 0001364954-20-000226 · wf-form4_160704300374229.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · PRESIDENT OF LEARNING SERVICES

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 226,290

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 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: 0001364954-20-000226 · wf-form4_160704300374229.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · PRESIDENT OF LEARNING SERVICES

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 227,824

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 2019 PSUs to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the 2019 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.

F2 · balance_after: Includes 113 shares acquired under the Issuer's 2013 Employee Stock Purchase Plan on November 15, 2020.

SEC source: 0001364954-20-000216 · wf-form4_160617864375465.xml · nonDerivative · entry 1

TOMASELLO ROBIN · CIK 0001608511 · VP, CORPORATE CONTROLLER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 55,532

F1 · price: This transaction was executed in multiple trades at prices ranging from $71.043 to $72.050; the price reported above reflects the weighted average sale price. The reporting person will provide to the Commission, the issuer and any stockholder, upon request, full information regarding the number of shares and prices at which the transactions were effected.

F2 · balance_after: Includes 154 shares acquired under the Issuer's 2013 Employee Stock Purchase Plan on November 15, 2020.

SEC source: 0001364954-20-000214 · wf-form4_160591662933356.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,971,134

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on February 21, 2020.

F2 · price: This transaction was executed in multiple trades at prices ranging from $69.59 to $71.19; the price reported above reflects the weighted average sale price. The reporting person will provide to the Commission, the issuer and any stockholder, upon request, full information regarding the number of shares and prices at which the transactions were effected.

SEC source: 0001364954-20-000214 · wf-form4_160591662933356.xml · nonDerivative · entry 2

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

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 24,000

F3 · kind: On November 9, 2020, the Rosensweig Family Revocable Trust U/A/D 03-12-07 transferred 24,842 shares to The Rosensweig 2012 Irrevocable Children's Trust U/A/D 11-06-12. The Reporting Person is a Co-Trustee.

F4 · ownership.nature: Held by Daniel L and Linda Rosensweig, Co-Trustees of the Rosensweig Family Revocable Trust U/A/D 03-12-07. The Reporting Person is a Co-Trustee.

SEC source: 0001364954-20-000205 · wf-form4_160271226105489.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,999,134

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on February 21, 2020.

F2 · price: This transaction was executed in multiple trades at prices ranging from $81.295 to $82.87; the price reported above reflects the weighted average sale price. The reporting person will provide to the Commission, the issuer and any stockholder, upon request, full information regarding the number of shares and prices at which the transactions were effected.

SEC source: 0001364954-20-000199 · wf-form4_160167520926328.xml · derivative · entry 3

York John E. · CIK 0001586638 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 30,781

Underlying: Common Stock · 10,000 shares

Expires 2025-06-03

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.

F1 · kind: The exercise of options and sale of the resultant shares reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on December 6, 2019.

F3 · derivative.exercise_date: The stock option grant is fully vested.

SEC source: 0001364954-20-000199 · wf-form4_160167520926328.xml · nonDerivative · entry 2

York John E. · CIK 0001586638 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 16,792

F1 · kind: The exercise of options and sale of the resultant shares reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on December 6, 2019.

F2 · price: This transaction was executed in multiple trades at prices ranging from $72.06 to $74.69; the price reported above reflects the weighted average sale price. The reporting person will provide to the Commission, the issuer and any stockholder, upon request, full information regarding the number of shares and prices at which the transactions were effected.

SEC source: 0001364954-20-000199 · wf-form4_160167520926328.xml · nonDerivative · entry 1

York John E. · CIK 0001586638 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 26,792

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.

F1 · kind: The exercise of options and sale of the resultant shares reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on December 6, 2019.