FILLMORE JOHN PAUL

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: 0001364954-23-000023 · 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: 0001364954-22-000121 · wf-form4_167027978533675.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 162,194

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: 0001364954-22-000121 · wf-form4_167027978533675.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 164,913

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: 0001364954-22-000094 · wf-form4_166250400693743.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 167,013

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: 0001364954-22-000094 · wf-form4_166250400693743.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 169,716

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: 0001364954-22-000072 · wf-form4_165429514640504.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 171,563

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: 0001364954-22-000072 · wf-form4_165429514640504.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 173,460

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

SEC source: 0001364954-22-000031 · wf-form4_164867475538497.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 174,082

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, 2023 and then the remaining shares vesting in equal quarterly installments thereafter for 24 months.

SEC source: 0001364954-22-000021 · wf-form4_164635643051023.xml · nonDerivative · entry 3

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 112,664

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: 0001364954-22-000021 · wf-form4_164635643051023.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 117,342

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: 0001364954-22-000021 · wf-form4_164635643051023.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 121,365

F1 · shares: Represents the number of shares of Common Stock subject to performance-based restricted stock units ("PSUs") granted to the Reporting Person in 2021 (the "2021 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 28, 2022. The shares subject to the 2021 PSUs allocated to each performance metric shall vest as follows: 1/3 shall vest on March 1, 2022, 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: 0001364954-21-000139 · wf-form4_163858084452002.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 101,512

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: 0001364954-21-000139 · wf-form4_163858084452002.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 104,937

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: 0001364954-21-000089 · wf-form4_163070664964404.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 107,276

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: 0001364954-21-000089 · wf-form4_163070664964404.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 110,699

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: 0001364954-21-000058 · wf-form4_162277082858476.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 113,038

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: 0001364954-21-000058 · wf-form4_162277082858476.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 116,461

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 368 shares acquired under the 2013 Chegg, Inc. Employee Stock Purchase Plan ("ESPP") on May 14, 2021.

SEC source: 0001364954-21-000036 · wf-form4_161860536858201.xml · derivative · entry 4

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 19,714 shares

Expires 2023-08-05

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.

F4 · derivative.exercise_date: The stock option was fully vested and exercisable as of June 10, 2017.

SEC source: 0001364954-21-000036 · wf-form4_161860536858201.xml · nonDerivative · entry 3

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 118,432

F1 · kind: The exercise of options and sale of the resultant shares in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on February 12, 2021.

F3 · price: The reported price in Column 4 is a weighted average sale price. These shares were sold in multiple transactions at prices ranging from $90.37 to $91.31 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: 0001364954-21-000036 · wf-form4_161860536858201.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 134,949

F1 · kind: The exercise of options and sale of the resultant shares in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on February 12, 2021.

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 $89.16 to $90.00 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: 0001364954-21-000036 · wf-form4_161860536858201.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 138,146

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: 0001364954-21-000028 · wf-form4_161499511503507.xml · nonDerivative · entry 8

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 118,432

F1 · 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: 0001364954-21-000028 · wf-form4_161499511503507.xml · nonDerivative · entry 7

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 118,932

F1 · 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.

F8 · price: This transaction was executed in multiple trades at prices ranging from $96.41 to $96.42; 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: 0001364954-21-000028 · wf-form4_161499511503507.xml · nonDerivative · entry 6

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 119,172

F1 · 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.

F7 · price: This transaction was executed in multiple trades at prices ranging from $95.40 to $96.21; 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: 0001364954-21-000028 · wf-form4_161499511503507.xml · nonDerivative · entry 5

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 123,258

F1 · 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.

F6 · price: This transaction was executed in multiple trades at prices ranging from $91.42 to $91.66; 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: 0001364954-21-000028 · wf-form4_161499511503507.xml · nonDerivative · entry 4

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 124,998

F1 · 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.

F5 · price: This transaction was executed in multiple trades at prices ranging from $90.33 to $91.30; 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: 0001364954-21-000028 · wf-form4_161499511503507.xml · nonDerivative · entry 3

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 133,417

F1 · 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.

F4 · price: This transaction was executed in multiple trades at prices ranging from $89.33 to $90.31; 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: 0001364954-21-000028 · wf-form4_161499511503507.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 153,459

F1 · 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.

F3 · price: This transaction was executed in multiple trades at prices ranging from $88.32 to $89.31; 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: 0001364954-21-000028 · wf-form4_161499511503507.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 160,159

F1 · 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.

F2 · price: This transaction was executed in multiple trades at prices ranging from $87.32 to $88.31; 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: 0001364954-21-000025 · wf-form4_161482509674677.xml · derivative · entry 5

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.

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: 0001364954-21-000025 · wf-form4_161482509674677.xml · nonDerivative · entry 4

FILLMORE JOHN PAUL · CIK 0001760781 · PRESIDENT, CHEGG SKILLS

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 167,937

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

SEC source: 0001364954-21-000025 · 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: 0001364954-21-000027 · 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: 0001364954-20-000230 · 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: 0001364954-20-000230 · 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: 0001364954-20-000188 · wf-form4_159917688437190.xml · nonDerivative · entry 3

FILLMORE JOHN PAUL · CIK 0001760781 · CHIEF STRATEGY OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 135,752

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

SEC source: 0001364954-20-000188 · wf-form4_159917688437190.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · CHIEF STRATEGY OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 137,073

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: 0001364954-20-000188 · wf-form4_159917688437190.xml · nonDerivative · entry 1

FILLMORE JOHN PAUL · CIK 0001760781 · CHIEF STRATEGY OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 138,147

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: 0001364954-20-000139 · wf-form4_159123432054838.xml · nonDerivative · entry 3

FILLMORE JOHN PAUL · CIK 0001760781 · CHIEF STRATEGY OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 139,672

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

SEC source: 0001364954-20-000139 · wf-form4_159123432054838.xml · nonDerivative · entry 2

FILLMORE JOHN PAUL · CIK 0001760781 · CHIEF STRATEGY OFFICER

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 140,993

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.